Progesterone - wikipedia Progesterone This article is about progesterone as a hormone. For its use as a medication, see Progesterone ( medication ). Progesterone Names IUPAC name ( 8S, 9S, 10R, 13S, 14S, 17S ) - 17 - acetyl - 10, 13 - dimethyl - 1, 2, 6, 7, 8, 9, 11, 12, 14, 15, 16, 17 - dodecahydrocyclopenta ( a ) phenanthren - 3 - one Other names Pregn - 4 - ene - 3, 20 - dione Identifiers CAS Number 57 - 83 - 0 3D model ( JSmol ) Interactive image ChEBI CHEBI : 17026 ChemSpider 5773 DrugBank DB00396 ECHA InfoCard 100.000. 318 KEGG C00410 PubChem CID 5994 UNII 4G7DS2Q64Y InChI InChI = 1S / C21H30O2 / c1 - 13 ( 22 ) 17 - 6 - 7 - 18 - 16 - 5 - 4 - 14 - 12 - 15 ( 23 ) 8 - 10 - 20 ( 14, 2 ) 19 ( 16 ) 9 - 11 - 21 ( 17, 18 ) 3 / h12, 16 - 19H, 4 - 11H2, 1 - 3H3 / t16 -, 17 +, 18 -, 19 -, 20 -, 21 + / m0 / s1 Key : RJKFOVLPORLFTN - LEKSSAKUSA - N SMILES CC ( = O ) ( C@H ) 1CC ( C @ @ H ) 2 ( C @ @ ) 1 ( CC ( C@H ) 3 ( C@H ) 2CCC4 = CC ( = O ) CC ( C @ ) 34C ) C Properties Chemical formula Molar mass 314.469 g / mol Melting point 126 Pharmacology ATC code G03DA04 ( WHO ) Routes of administration By mouth, topical / transdermal, vaginal, intramuscular injection, subcutaneous injection, subcutaneous implant Pharmacokinetics : Bioavailability OMP : < 10 % Protein binding Albumin : 80 % CBG : 18 % SHBG : < 1 % Free : 1 -- 2 % Metabolism Hepatic ( CYP2C19, CYP3A4, CYP2C9, 5α - reductase, 3α - HSD, 17α - hydroxylase, 21 - hydroxylase, 20α - HSD ) Biological half - life OMP : 16 -- 18 hours IM : 22 -- 26 hours SC : 13 -- 18 hours Excretion Renal Except where otherwise noted, data are given for materials in their standard state ( at 25 ° C ( 77 ° F ), 100 kPa ). N verify ( what is ? ) Infobox references Progesterone is an endogenous steroid and progestogen sex hormone involved in the menstrual cycle, pregnancy, and embryogenesis of humans and other species. It belongs to a group of steroid hormones called the progestogens, and is the major progestogen in the body. Progesterone is also a crucial metabolic intermediate in the production of other endogenous steroids, including the sex hormones and the corticosteroids, and plays an important role in brain function as a neurosteroid. Contents 1 Biological activity 2 Biological function 2.1 Hormonal interactions 2.2 Reproductive system 2.3 Breasts 2.3. 1 Lobuloalveolar development 2.3. 2 Ductal development 2.3. 3 Breast cancer risk 2.4 Skin health 2.5 Sexuality 2.5. 1 Sex drive 2.5. 2 Homosexuality 2.6 Nervous system 2.7 Aging 2.8 Brain damage 2.8. 1 Proposed mechanism 2.9 Addiction 2.10 Other effects 3 Biochemistry 3.1 Biosynthesis 3.2 Distribution 3.3 Metabolism 3.4 Levels 3.5 Sources 3.5. 1 Animal 3.5. 2 Plants 4 Medical use 5 Chemistry 5.1 Synthesis 5.1. 1 Semisynthesis 1 5.1. 1.1 Semisynthesis 2 5.1. 2 Total synthesis 6 History 7 References 8 External links Biological activity Progesterone is the most important progestogen in the body, the result of its action as a potent agonist of the nuclear progesterone receptor ( nPR ) ( with an affinity of K = 1 nM ). In addition, progesterone is an agonist of the more recently discovered membrane progesterone receptors ( mPRs ), as well as a ligand of the PGRMC1 ( progesterone receptor membrane component 1 ). Moreover, progesterone is also known to be an antagonist of the sigma σ receptor, a negative allosteric modulator of nicotinic acetylcholine receptors, and a potent antagonist of the mineralocorticoid receptor ( MR ). Progesterone prevents MR activation by binding to this receptor with an affinity exceeding even those of aldosterone and glucocorticoids such as cortisol and corticosterone, and produces antimineralocorticoid effects, such as natriuresis, at physiological concentrations. In addition, progesterone binds to and behaves as a partial agonist of the glucocorticoid receptor ( GR ), albeit with very low potency ( EC > 100-fold less relative to cortisol ). Progesterone, through its neurosteroid active metabolites such as 5α - dihydroprogesterone and allopregnanolone, acts indirectly as a positive allosteric modulator of the GABA receptor. Progesterone and some of its metabolites, such as 5β - dihydroprogesterone, are agonists of the pregnane X receptor ( PXR ), albeit weakly so ( EC > 10 μM ). In accordance, progesterone induces several hepatic cytochrome P450 enzymes, such as CYP3A4, especially during pregnancy when concentrations are much higher than usual. Perimenopausal women have been found to have greater CYP3A4 activity relative to men and postmenopausal women, and it has been inferred that this may be due to the higher progesterone levels present in perimenopausal women. Progesterone modulates the activity of CatSper ( cation channels of sperm ) voltage - gated Ca channels. Since eggs release progesterone, sperm may use progesterone as a homing signal to swim toward eggs ( chemotaxis ). As a result, it has been suggested that substances that block the progesterone binding site on CatSper channels could potentially be used in male contraception. Biological function Hormonal interactions Progesterone has a number of physiological effects that are amplified in the presence of estrogens. Estrogens through estrogen receptors ( ERs ) induce or upregulate the expression of the PR. One example of this is in breast tissue, where estrogens allow progesterone to mediate lobuloalveolar development. Elevated levels of progesterone potently reduce the sodium - retaining activity of aldosterone, resulting in natriuresis and a reduction in extracellular fluid volume. Progesterone withdrawal, on the other hand, is associated with a temporary increase in sodium retention ( reduced natriuresis, with an increase in extracellular fluid volume ) due to the compensatory increase in aldosterone production, which combats the blockade of the mineralocorticoid receptor by the previously elevated level of progesterone. Reproductive system Micrograph showing changes to the endometrium due to progesterone ( decidualization ) H&E stain. Progesterone has key effects via non-genomic signalling on human sperm as they migrate through the female tract before fertilization occurs, though the receptor ( s ) as yet remain unidentified. Detailed characterisation of the events occurring in sperm in response to progesterone has elucidated certain events including intracellular calcium transients and maintained changes, slow calcium oscillations, now thought to possibly regulate motility. It is produced by the ovaries. Interestingly, progesterone has also been shown to demonstrate effects on octopus spermatozoa. Progesterone is sometimes called the `` hormone of pregnancy '', and it has many roles relating to the development of the fetus : Progesterone converts the endometrium to its secretory stage to prepare the uterus for implantation. At the same time progesterone affects the vaginal epithelium and cervical mucus, making it thick and impenetrable to sperm. Progesterone is anti-mitogenic in endometrial epithelial cells, and as such, mitigates the tropic effects of estrogen. If pregnancy does not occur, progesterone levels will decrease, leading, in the human, to menstruation. Normal menstrual bleeding is progesterone - withdrawal bleeding. If ovulation does not occur and the corpus luteum does not develop, levels of progesterone may be low, leading to anovulatory dysfunctional uterine bleeding. During implantation and gestation, progesterone appears to decrease the maternal immune response to allow for the acceptance of the pregnancy. Progesterone decreases contractility of the uterine smooth muscle. In addition progesterone inhibits lactation during pregnancy. The fall in progesterone levels following delivery is one of the triggers for milk production. A drop in progesterone levels is possibly one step that facilitates the onset of labor. The fetus metabolizes placental progesterone in the production of adrenal steroids. Breasts See also : Breast development § Biochemistry Lobuloalveolar development Progesterone plays an important role in breast development in women. In conjunction with prolactin, it mediates lobuloalveolar maturation of the mammary glands during pregnancy to allow for milk production and thus lactation and breastfeeding of offspring following parturition ( childbirth ). Estrogen induces expression of the PR in breast tissue and hence progesterone is dependent on estrogen to mediate lobuloalveolar development. It has been found that RANKL is a critical downstream mediator of progesterone - induced lobuloalveolar maturation. RANKL knockout mice show an almost identical mammary phenotype to PR knockout mice, including normal mammary ductal development but complete failure of the development of lobuloalveolar structures. Ductal development Though to a far lesser extent than estrogen, which is the major mediator of mammary ductal development ( via the ERα ), progesterone has been found to be involved in ductal development of the mammary glands to some extent as well. PR knockout mice or mice treated with the PR antagonist mifepristone show delayed although otherwise normal mammary ductal development at puberty. In addition, mice modified to have overexpression of PRA display ductal hyperplasia, and progesterone induces ductal growth in the mouse mammary gland. Progesterone mediates ductal development mainly via induction of the expression of amphiregulin, the same growth factor that estrogen primarily induces the expression of to mediate ductal development. These animal findings suggest that, while not essential for full mammary ductal development, progesterone seems to play a potentiating or accelerating role in estrogen - mediated mammary ductal development. Breast cancer risk Progesterone also appears to be involved in the pathophysiology of breast cancer, though its role, and whether it is a promoter or inhibitor of breast cancer risk, has not been fully elucidated. In any case, while most synthetic progestins like medroxyprogesterone acetate have been found to significantly increase the risk of breast cancer in postmenopausal women in combination with estrogen as a component of hormone replacement therapy, the combination of natural progesterone ( or the atypical progestin dydrogesterone ) with estrogen has been found not to do so. Skin Health The estrogen receptor, as well as the progesterone receptor, have been detected in the skin, including in keratinocytes and fibroblasts. At menopause and thereafter, decreased levels of female sex hormones result in atrophy, thinning, and increased wrinkling of the skin and a reduction in skin elasticity, firmness, and strength. These skin changes constitute an acceleration in skin aging and are the result of decreased collagen content, irregularities in the morphology of epidermal skin cells, decreased ground substance between skin fibers, and reduced capillaries and blood flow. The skin also becomes more dry during menopause, which is due to reduced skin hydration and surface lipids ( sebum production ). Along with chronological aging and photoaging, estrogen deficiency in menopause is one of the three main factors that predominantly influences skin aging. HRT, consisting of systemic treatment with estrogen alone or in combination with a progestogen, has well - documented and considerable beneficial effects on the skin of postmenopausal women. These benefits include increased skin collagen content, skin thickness and elasticity, and skin hydration and surface lipids. Topical estrogen has been found to have similar beneficial effects on the skin. In addition, a study has found that topical 2 % progesterone cream significantly increases skin elasticity and firmness and observably decreases wrinkles in peri - and postmenopausal women. Skin hydration and surface lipids, on the other hand, did not significantly change with topical progesterone. These findings suggest that progesterone, like estrogen, also has beneficial effects on the skin, and may be independently protective against skin aging. Sexuality Sex drive See also : Sexual motivation and hormones Progesterone and its neurosteroid active metabolite allopregnanolone appear to be importantly involved in sex drive in females. Homosexuality Dr. Diana Fleischman, of the University of Portsmouth, and colleagues examined the relationship between progesterone and sexual attitudes. Their research was published in the Archives of Sexual Behavior. They found that women who have higher levels of progesterone are more likely to be open to the idea of engaging in sexual behaviour with other women. This pattern is particularly dramatic in men who have high levels of progesterone. Nervous system Progesterone, like pregnenolone and dehydroepiandrosterone ( DHEA ), belongs to an important group of endogenous steroids called neurosteroids. It can be metabolized within all parts of the central nervous system. Neurosteroids are neuromodulators, and are neuroprotective, neurogenic, and regulate neurotransmission and myelination. The effects of progesterone as a neurosteroid are mediated predominantly through its interactions with non-nuclear PRs, namely the mPRs and PGRMC1, as well as certain other receptors, such as the σ and nACh receptors. Aging Since most progesterone in males is created during testicular production of testosterone, and most in females by the ovaries, the shutting down ( whether by natural or chemical means ), or removal, of those inevitably causes a considerable reduction in progesterone levels. Previous concentration upon the role of progestogens in female reproduction, when progesterone was simply considered a `` female hormone '', obscured the significance of progesterone elsewhere in both sexes. The tendency for progesterone to have a regulatory effect, the presence of progesterone receptors in many types of body tissue, and the pattern of deterioration ( or tumor formation ) in many of those increasing in later years when progesterone levels have dropped, is prompting widespread research into the potential value of maintaining progesterone levels in both males and females. Brain damage See also : Progesterone ( medication ) § Brain damage Previous studies have shown that progesterone supports the normal development of neurons in the brain, and that the hormone has a protective effect on damaged brain tissue. It has been observed in animal models that females have reduced susceptibility to traumatic brain injury and this protective effect has been hypothesized to be caused by increased circulating levels of estrogen and progesterone in females. Proposed mechanism The mechanism of progesterone protective effects may be the reduction of inflammation that follows brain trauma and hemorrhage. Damage incurred by traumatic brain injury is believed to be caused in part by mass depolarization leading to excitotoxicity. One way in which progesterone helps to alleviate some of this excitotoxicity is by blocking the voltage - dependent calcium channels that trigger neurotransmitter release. It does so by manipulating the signaling pathways of transcription factors involved in this release. Another method for reducing the excitotoxicity is by up - regulating the GABA, a widespread inhibitory neurotransmitter receptor. Progesterone has also been shown to prevent apoptosis in neurons, a common consequence of brain injury. It does so by inhibiting enzymes involved in the apoptosis pathway specifically concerning the mitochondria, such as activated caspase 3 and cytochrome c. Not only does progesterone help prevent further damage, it has also been shown to aid in neuroregeneration. One of the serious effects of traumatic brain injury includes edema. Animal studies show that progesterone treatment leads to a decrease in edema levels by increasing the concentration of macrophages and microglia sent to the injured tissue. This was observed in the form of reduced leakage from the blood brain barrier in secondary recovery in progesterone treated rats. In addition, progesterone was observed to have antioxidant properties, reducing the concentration of oxygen free radicals faster than without. There is also evidence that the addition of progesterone can also help re myelinate damaged axons due to trauma, restoring some lost neural signal conduction. Another way progesterone aids in regeneration includes increasing the circulation of endothelial progenitor cells in the brain. This helps new vasculature to grow around scar tissue which helps repair the area of insult. Addiction See also : Progesterone ( medication ) § Addiction Progesterone enhances the function of serotonin receptors in the brain, so an excess or deficit of progesterone has the potential to result in significant neurochemical issues. This provides an explanation for why some people resort to substances that enhance serotonin activity such as nicotine, alcohol, and cannabis when their progesterone levels fall below optimal levels. Sex differences in hormone levels may induce women to respond differently than men to nicotine. When women undergo cyclic changes or different hormonal transition phases ( menopause, pregnancy, adolescence ), there are changes in their progesterone levels. Therefore, females have an increased biological vulnerability to nicotine 's reinforcing effects compared to males and progesterone may be used to counter this enhanced vulnerability. This information supports the idea that progesterone can affect behavior. Similar to nicotine, cocaine also increases the release of dopamine in the brain. The neurotransmitter is involved in the reward center and is one of the main neurotransmitters involved with substance abuse and reliance. In a study of cocaine users, it was reported that progesterone reduced craving and the feeling of being stimulated by cocaine. Thus, progesterone was suggested as an agent that decreases cocaine craving by reducing the dopaminergic properties of the drug. Other effects Progesterone also has a role in skin elasticity and bone strength, in respiration, in nerve tissue and in female sexuality, and the presence of progesterone receptors in certain muscle and fat tissue may hint at a role in sexually dimorphic proportions of those. During pregnancy, progesterone is said to decrease irritability. During pregnancy, progesterone helps to suppress immune responses of the mother to fetal antigens, which prevents rejection of the fetus. Progesterone raises epidermal growth factor - 1 ( EGF - 1 ) levels, a factor often used to induce proliferation, and used to sustain cultures, of stem cells. Progesterone increases core temperature ( thermogenic function ) during ovulation. Progesterone reduces spasm and relaxes smooth muscle. Bronchi are widened and mucus regulated. ( PRs are widely present in submucosal tissue. ) Progesterone acts as an antiinflammatory agent and regulates the immune response. Progesterone reduces gall - bladder activity. Progesterone normalizes blood clotting and vascular tone, zinc and copper levels, cell oxygen levels, and use of fat stores for energy. Progesterone may affect gum health, increasing risk of gingivitis ( gum inflammation ). Progesterone appears to prevent endometrial cancer ( involving the uterine lining ) by regulating the effects of estrogen. Progesterone plays an important role in the signaling of insulin release and pancreatic function, and may affect the susceptibility to diabetes or gestational diabetes. Progesterone may play a role in male behavior, such as in male aggression towards infants. Biochemistry Biosynthesis Steroidogenesis, showing progesterone among the progestogens in yellow area. In mammals, progesterone, like all other steroid hormones, is synthesized from pregnenolone, which itself is derived from cholesterol. Cholesterol undergoes double oxidation to produce 22R - hydroxycholesterol and then 20α, 22R - dihydroxycholesterol. This vicinal diol is then further oxidized with loss of the side chain starting at position C22 to produce pregnenolone. This reaction is catalyzed by cytochrome P450scc. The conversion of pregnenolone to progesterone takes place in two steps. First, the 3β - hydroxyl group is oxidized to a keto group and second, the double bond is moved to C4, from C5 through a keto / enol tautomerization reaction. This reaction is catalyzed by 3β - hydroxysteroid dehydrogenase / δ - isomerase. Progesterone in turn is the precursor of the mineralocorticoid aldosterone, and after conversion to 17α - hydroxyprogesterone, of cortisol and androstenedione. Androstenedione can be converted to testosterone, estrone, and estradiol. Pregnenolone and progesterone can also be synthesized by yeast. Distribution Progesterone binds extensively to plasma proteins, including albumin ( 50 -- 54 % ) and transcortin ( 43 -- 48 % ). It has similar affinity for albumin relative to the PR. Metabolism The metabolism of progesterone is rapid and extensive and occurs mainly in the liver, though enzymes that metabolize progesterone are also expressed widely in the brain, skin, and various other extrahepatic tissues. Progesterone has a terminal half - life of only approximately 5 minutes in circulation. The metabolism of progesterone is complex, and it may form as many as 35 different unconjugated metabolites when it is ingested orally. Progesterone is highly susceptible to enzymatic reduction via reductases and hydroxysteroid dehydrogenases due to its double bond ( between the C4 and C5 positions ) and its two ketones ( at the C3 and C20 positions ). The major metabolic pathway of progesterone is reduction by 5α - reductase and 5β - reductase into the dihydrogenated 5α - dihydroprogesterone and 5β - dihydroprogesterone, respectively. This is followed by the further reduction of these metabolites via 3α - hydroxysteroid dehydrogenase and 3β - hydroxysteroid dehydrogenase into the tetrahydrogenated allopregnanolone, pregnanolone, isopregnanolone, and epipregnanolone. Subsequently, 20α - hydroxysteroid dehydrogenase and 20β - hydroxysteroid dehydrogenase reduce these metabolites to form the corresponding hexahydrogenated pregnanediols ( eight different isomers in total ), which are then conjugated via glucuronidation and / or sulfation, released from the liver into circulation, and excreted by the kidneys into the urine. The major metabolite of progesterone in the urine is the 3α, 5β, 20α isomer of pregnanediol glucuronide, which has been found to constitute 15 to 30 % of an injection of progesterone. Other metabolites of progesterone formed by the enzymes in this pathway include 3α - dihydroprogesterone, 3β - dihydroprogesterone, 20α - dihydroprogesterone, and 20β - dihydroprogesterone, as well as various combination products of the enzymes aside from those already mentioned. Progesterone can also first be hydroxylated ( see below ) and then reduced. Relatively small portions of progesterone are hydroxylated via 17α - hydroxylase ( CYP17A1 ) and 21 - hydroxylase ( CYP21A2 ) into 17α - hydroxyprogesterone and 11 - deoxycorticosterone ( 21 - hydroxyprogesterone ), respectively, and pregnanetriols are formed secondarily to 17α - hydroxylation. In addition, progesterone can be hydroxylated in the liver by other cytochrome P450 enzymes which are not steroid - specific. 6β - Hydroxylation, which is catalyzed mainly by CYP3A4, is the major transformation, and is responsible for approximately 70 % of cytochrome P450 - mediated progesterone metabolism. Other routes include 6α -, 16α -, and 16β - hydroxylation. However, treatment of women with ketoconazole, a strong CYP3A4 inhibitor, had minimal effects on progesterone levels, producing only a slight and non-significant increase, and this suggests that cytochrome P450 enzymes play only a small role in progesterone metabolism. Levels Person type Reference range for blood test Lower limit Upper limit Unit Female - menstrual cycle ( see diagram below ) Female - postmenopausal < 0.2 ng / mL < 0.6 nmol / L Female on oral contraceptives 0.34 0.92 ng / mL 2.9 nmol / L Males ≥ 16 years 0.27 0.9 ng / mL 0.86 2.9 nmol / L Female or male 1 -- 9 years 0.1 4.1 or 4.5 ng / mL 0.3 13 nmol / L In women, progesterone levels are relatively low during the preovulatory phase of the menstrual cycle, rise after ovulation, and are elevated during the luteal phase, as shown in diagram below. Progesterone levels tend to be < 2 ng / ml prior to ovulation, and > 5 ng / ml after ovulation. If pregnancy occurs, human chorionic gonadotropin is released maintaining the corpus luteum allowing it to maintain levels of progesterone. Between 7 -- 9 weeks the placenta begins to produce progesterone in place of the corpus luteum, this process is named the luteal - placental shift. After the luteal - placental shift progesterone levels start to rise further and may reach 100 -- 200 ng / ml at term. Whether a decrease in progesterone levels is critical for the initiation of labor has been argued and may be species - specific. After delivery of the placenta and during lactation, progesterone levels are very low. Progesterone levels are relatively low in children and postmenopausal women. Adult males have levels similar to those in women during the follicular phase of the menstrual cycle. Blood test results should always be interpreted using the reference ranges provided by the laboratory that performed the results. Example reference ranges are listed below. Progesterone levels during the menstrual cycle. The ranges denoted By biological stage may be used in closely monitored menstrual cycles in regard to other markers of its biological progression, with the time scale being compressed or stretched to how much faster or slower, respectively, the cycle progresses compared to an average cycle. The ranges denoted Inter-cycle variability are more appropriate to use in non-monitored cycles with only the beginning of menstruation known, but where the woman accurately knows her average cycle lengths and time of ovulation, and that they are somewhat averagely regular, with the time scale being compressed or stretched to how much a woman 's average cycle length is shorter or longer, respectively, than the average of the population. The ranges denoted Inter-woman variability are more appropriate to use when the average cycle lengths and time of ovulation are unknown, but only the beginning of menstruation is given. Sources Animal Progesterone is produced in high amounts in the ovaries ( by the corpus luteum ) from the onset of puberty to menopause, and is also produced in smaller amounts by the adrenal glands after the onset of adrenarche in both males and females. To a lesser extent, progesterone is produced in nervous tissue, especially in the brain, and in adipose ( fat ) tissue, as well. During human pregnancy, progesterone is produced in increasingly high amounts by the ovaries and placenta. At first, the source is the corpus luteum that has been `` rescued '' by the presence of human chorionic gonadotropin ( hCG ) from the conceptus. However, after the 8th week, production of progesterone shifts to the placenta. The placenta utilizes maternal cholesterol as the initial substrate, and most of the produced progesterone enters the maternal circulation, but some is picked up by the fetal circulation and used as substrate for fetal corticosteroids. At term the placenta produces about 250 mg progesterone per day. An additional animal source of progesterone is milk products. After consumption of milk products the level of bioavailable progesterone goes up. Plants In at least one plant, Juglans regia, progesterone has been detected. In addition, progesterone - like steroids are found in Dioscorea mexicana. Dioscorea mexicana is a plant that is part of the yam family native to Mexico. It contains a steroid called diosgenin that is taken from the plant and is converted into progesterone. Diosgenin and progesterone are also found in other Dioscorea species, as well as in other plants that are not closely related, such as fenugreek. Another plant that contains substances readily convertible to progesterone is Dioscorea pseudojaponica native to Taiwan. Research has shown that the Taiwanese yam contains saponins -- steroids that can be converted to diosgenin and thence to progesterone. Many other Dioscorea species of the yam family contain steroidal substances from which progesterone can be produced. Among the more notable of these are Dioscorea villosa and Dioscorea polygonoides. One study showed that the Dioscorea villosa contains 3.5 % diosgenin. Dioscorea polygonoides has been found to contain 2.64 % diosgenin as shown by gas chromatography - mass spectrometry. Many of the Dioscorea species that originate from the yam family grow in countries that have tropical and subtropical climates. Medical use Main article : Progesterone ( medication ) Progesterone is used as a medication, mainly in hormone replacement therapy. Chemistry A sample of progesterone. See also : List of neurosteroids Progesterone is a pregnane ( C21 ) steroid and is also known as pregn - 4 - ene - 3, 20 - dione. It has a double bond ( 4 - ene ) between the C4 and C5 positions and two ketone groups ( 3, 20 - dione ), one at the C3 position and the other at the C20 position. Like all unconjugated steroid hormones, progesterone is lipophilic and hydrophobic. Synthesis Semisynthesis 1 An economical semisynthesis of progesterone from the plant steroid diosgenin isolated from yams was developed by Russell Marker in 1940 for the Parke - Davis pharmaceutical company. This synthesis is known as the Marker degradation. Additional semisyntheses of progesterone have also been reported starting from a variety of steroids. For the example, cortisone can be simultaneously deoxygenated at the C - 17 and C - 21 position by treatment with iodotrimethylsilane in chloroform to produce 11 - keto - progesterone ( ketogestin ), which in turn can be reduced at position - 11 to yield progesterone. The Marker semisynthesis of progesterone from diosgenin. Semisynthesis 2 Progesterone can also be made from the stigmasterol found in soybean oil also. c.f. Percy Julian. Stigmasterol to progesterone synthesis. Total synthesis The Johnson total synthesis of progesterone. A total synthesis of progesterone was reported in 1971 by W.S. Johnson. The synthesis begins with reacting the phosphonium salt 7 with phenyl lithium to produce the phosphonium ylide 8. The ylide 8 is reacted with an aldehyde to produce the alkene 9. The ketal protecting groups of 9 are hydrolyzed to produce the diketone 10, which in turn is cyclized to form the cyclopentenone 11. The ketone of 11 is reacted with methyl lithium to yield the tertiary alcohol 12, which in turn is treated with acid to produce the tertiary cation 13. The key step of the synthesis is the π - cation cyclization of 13 in which the B -, C -, and D - rings of the steroid are simultaneously formed to produce 14. This step resembles the cationic cyclization reaction used in the biosynthesis of steroids and hence is referred to as biomimetic. In the next step the enol orthoester is hydrolyzed to produce the ketone 15. The cyclopentene A-ring is then opened by oxidizing with ozone to produce 16. Finally, the diketone 17 undergoes an intramolecular aldol condensation by treating with aqueous potassium hydroxide to produce progesterone. History The hormonal action of progesterone was discovered in 1929, following that of estrogen in 1923. By 1931 -- 1932, nearly pure crystalline material of high progestational activity had been isolated from the corpus luteum of animals, and by 1934, pure crystalline progesterone had been refined and obtained and the chemical structure of progesterone was determined. This was achieved by Adolf Butenandt at the Chemisches Institut of Technical University in Gdańsk, who extracted this new compound from several thousand liters of urine. Chemical synthesis of progesterone from stigmasterol and pregnanediol was accomplished later that year. Up to this point, progesterone, known generically as corpus luteum hormone, had been being referred to by several groups by different names, including corporin, lutein, luteosterone, and progestin. In 1935, at the time of the Second International Conference on the Standardization of Sex Hormones in London, England, a compromise was made between the groups and the name progesterone ( progestational steroidal ketone ) was created. References Jump up ^ Adler N, Pfaff D, Goy RW ( 6 Dec 2012 ). Handbook of Behavioral Neurobiology Volume 7 Reproduction ( 1st ed. ). New York : Plenum Press. p. 189. ISBN 978 - 1 - 4684 - 4834 - 4. Retrieved 4 July 2015. Jump up ^ `` progesterone ( CHEBI : 17026 ) ''. ChEBI. European Molecular Biology Laboratory - EBI. Retrieved 4 July 2015. ^ Jump up to : Stanczyk FZ ( September 2002 ). `` Pharmacokinetics and potency of progestins used for hormone replacement therapy and contraception ''. Reviews in Endocrine & Metabolic Disorders. 3 ( 3 ) : 211 -- 24. PMID 12215716. doi : 10.1023 / A : 1020072325818. ^ Jump up to : Simon JA, Robinson DE, Andrews MC, Hildebrand JR, Rocci ML, Blake RE, Hodgen GD ( July 1993 ). `` The absorption of oral micronized progesterone : the effect of food, dose proportionality, and comparison with intramuscular progesterone ''. Fertility and Sterility. 60 ( 1 ) : 26 -- 33. PMID 8513955. doi : 10.1016 / S0015 - 0282 ( 16 ) 56031 - 2. Jump up ^ Fritz MA, Speroff L ( 28 March 2012 ). Clinical Gynecologic Endocrinology and Infertility. Lippincott Williams & Wilkins. pp. 44 --. ISBN 978 - 1 - 4511 - 4847 - 3. Jump up ^ Marshall WJ, Marshall WJ, Bangert SK ( 2008 ). Clinical Chemistry. Elsevier Health Sciences. pp. 192 --. ISBN 0 - 7234 - 3455 - 7. Jump up ^ Yamazaki H, Shimada T ( October 1997 ). `` Progesterone and testosterone hydroxylation by cytochromes P450 2C19, 2C9, and 3A4 in human liver microsomes ''. Archives of Biochemistry and Biophysics. 346 ( 1 ) : 161 -- 9. PMID 9328296. doi : 10.1006 / abbi. 1997.0302. Jump up ^ McKay GA, Walters MR ( 6 February 2013 ). Lecture Notes : Clinical Pharmacology and Therapeutics. John Wiley & Sons. p. 33. ISBN 978 - 1 - 118 - 34489 - 7. Jump up ^ Zutshi ( 1 January 2005 ). Hormones in Obstetrics and Gynaecology. Jaypee Brothers Publishers. p. 74. ISBN 978 - 81 - 8061 - 427 - 9. ^ Jump up to : Cometti B ( November 2015 ). `` Pharmaceutical and clinical development of a novel progesterone formulation ''. Acta Obstetricia et Gynecologica Scandinavica. 94 Suppl 161 : 28 -- 37. PMID 26342177. doi : 10.1111 / aogs. 12765. ^ Jump up to : King TL, Brucker MC ( 25 October 2010 ). Pharmacology for Women 's Health. Jones & Bartlett Publishers. pp. 372 -- 373. ISBN 978 - 1 - 4496 - 5800 - 7. ^ Jump up to : Baulieu E, Schumacher M ( 2000 ). `` Progesterone as a neuroactive neurosteroid, with special reference to the effect of progesterone on myelination ''. Steroids. 65 ( 10 - 11 ) : 605 -- 12. PMID 11108866. doi : 10.1016 / s0039 - 128x ( 00 ) 00173 - 2. ^ Jump up to : Josimovich J ( 11 November 2013 ). Gynecologic Endocrinology. Springer Science & Business Media. pp. 9, 25 -- 29. ISBN 978 - 1 - 4613 - 2157 - 6. Jump up ^ Thomas P, Pang Y ( 2012 ). `` Membrane progesterone receptors : evidence for neuroprotective, neurosteroid signaling and neuroendocrine functions in neuronal cells ''. Neuroendocrinology. 96 ( 2 ) : 162 -- 71. PMC 3489003. PMID 22687885. doi : 10.1159 / 000339822. Jump up ^ Meyer C, Schmid R, Schmieding K, Falkenstein E, Wehling M ( February 1998 ). `` Characterization of high affinity progesterone - binding membrane proteins by anti-peptide antiserum ''. Steroids. 63 ( 2 ) : 111 -- 6. PMID 9516722. doi : 10.1016 / s0039 - 128x ( 97 ) 00143 - 8. Jump up ^ Maurice T, Urani A, Phan VL, Romieu P ( November 2001 ). `` The interaction between neuroactive steroids and the sigma1 receptor function : behavioral consequences and therapeutic opportunities ''. Brain Research. Brain Research Reviews. 37 ( 1 - 3 ) : 116 -- 32. PMID 11744080. doi : 10.1016 / s0165 - 0173 ( 01 ) 00112 - 6. Jump up ^ Johannessen M, Fontanilla D, Mavlyutov T, Ruoho AE, Jackson MB ( February 2011 ). `` Antagonist action of progesterone at σ - receptors in the modulation of voltage - gated sodium channels ''. American Journal of Physiology. Cell Physiology. 300 ( 2 ) : C328 -- 37. PMC 3043630. PMID 21084640. doi : 10.1152 / ajpcell. 00383.2010. ^ Jump up to : Rupprecht R, Reul JM, van Steensel B, Spengler D, Söder M, Berning B, Holsboer F, Damm K ( October 1993 ). `` Pharmacological and functional characterization of human mineralocorticoid and glucocorticoid receptor ligands ''. European Journal of Pharmacology. 247 ( 2 ) : 145 -- 54. PMID 8282004. doi : 10.1016 / 0922 - 4106 ( 93 ) 90072 - H. Jump up ^ Elger W, Beier S, Pollow K, Garfield R, Shi SQ, Hillisch A ( 2003 ). `` Conception and pharmacodynamic profile of drospirenone ''. Steroids. 68 ( 10 - 13 ) : 891 -- 905. PMID 14667981. doi : 10.1016 / j. steroids. 2003.08. 008. Jump up ^ Attardi BJ, Zeleznik A, Simhan H, Chiao JP, Mattison DR, Caritis SN ( 2007 ). `` Comparison of progesterone and glucocorticoid receptor binding and stimulation of gene expression by progesterone, 17 - alpha hydroxyprogesterone caproate, and related progestins ''. Am. J. Obstet. Gynecol. 197 ( 6 ) : 599. e1 -- 7. PMC 2278032. PMID 18060946. doi : 10.1016 / j. ajog. 2007.05. 024. Jump up ^ Lei K, Chen L, Georgiou EX, Sooranna SR, Khanjani S, Brosens JJ, Bennett PR, Johnson MR ( 2012 ). `` Progesterone acts via the nuclear glucocorticoid receptor to suppress IL - 1β - induced COX - 2 expression in human term myometrial cells ''. PloS One. 7 ( 11 ) : e50167. PMC 3509141. PMID 23209664. doi : 10.1371 / journal. pone. 0050167. Jump up ^ Paul SM, Purdy RH ( March 1992 ). `` Neuroactive steroids ''. FASEB Journal. 6 ( 6 ) : 2311 -- 22. PMID 1347506. Jump up ^ Kliewer SA, Goodwin B, Willson TM ( 2002 ). `` The nuclear pregnane X receptor : a key regulator of xenobiotic metabolism ''. Endocr. Rev. 23 ( 5 ) : 687 -- 702. PMID 12372848. doi : 10.1210 / er. 2001 - 0038. Jump up ^ Lehmann JM, McKee DD, Watson MA, Willson TM, Moore JT, Kliewer SA ( 1998 ). `` The human orphan nuclear receptor PXR is activated by compounds that regulate CYP3A4 gene expression and cause drug interactions ''. J. Clin. Invest. 102 ( 5 ) : 1016 -- 23. PMC 508967. PMID 9727070. doi : 10.1172 / JCI3703. Jump up ^ Meanwell NA ( 8 December 2014 ). Tactics in Contemporary Drug Design. Springer. pp. 161 --. ISBN 978 - 3 - 642 - 55041 - 6. ^ Jump up to : Legato MJ, Bilezikian JP ( 2004 ). Principles of Gender - specific Medicine. Gulf Professional Publishing. pp. 146 --. ISBN 978 - 0 - 12 - 440906 - 4. Jump up ^ Lemke TL, Williams DA ( 24 January 2012 ). Foye 's Principles of Medicinal Chemistry. Lippincott Williams & Wilkins. pp. 164 --. ISBN 978 - 1 - 60913 - 345 - 0. Jump up ^ Estrogens -- Advances in Research and Application : 2013 Edition : ScholarlyBrief. ScholarlyEditions. 21 June 2013. pp. 4 --. ISBN 978 - 1 - 4816 - 7550 - 5. Jump up ^ Strünker T, Goodwin N, Brenker C, Kashikar ND, Weyand I, Seifert R, Kaupp UB ( March 2011 ). `` The CatSper channel mediates progesterone - induced Ca2+ influx in human sperm ''. Nature. 471 ( 7338 ) : 382 -- 6. PMID 21412338. doi : 10.1038 / nature09769. Lay summary -- Nature News. Jump up ^ Lishko PV, Botchkina IL, Kirichok Y ( March 2011 ). `` Progesterone activates the principal Ca2+ channel of human sperm ''. Nature. 471 ( 7338 ) : 387 -- 91. PMID 21412339. doi : 10.1038 / nature09767. Jump up ^ Kastner P, Krust A, Turcotte B, Stropp U, Tora L, Gronemeyer H, Chambon P ( May 1990 ). `` Two distinct estrogen - regulated promoters generate transcripts encoding the two functionally different human progesterone receptor forms A and B ''. The EMBO Journal. 9 ( 5 ) : 1603 -- 14. PMC 551856. PMID 2328727. ^ Jump up to : Hallam SZ, Osuch JR ( 1 January 2006 ). Hormones and Breast Cancer in Post-Menopausal Women. IOS Press. p. 69. ISBN 978 - 1 - 58603 - 653 - 9. ^ Jump up to : Johnson LR ( 2003 ). Essential Medical Physiology. Academic Press. p. 770. ISBN 978 - 0 - 12 - 387584 - 6. ^ Jump up to : Coad J, Dunstall M ( 2011 ). Anatomy and Physiology for Midwives, with Pageburst online access, 3 : Anatomy and Physiology for Midwives. Elsevier Health Sciences. p. 413. ISBN 0 - 7020 - 3489 - 4. Jump up ^ Landau RL, Bergenstal DM, Lugibihl K, Kascht ME ( October 1955 ). `` The metabolic effects of progesterone in man ''. The Journal of Clinical Endocrinology and Metabolism. 15 ( 10 ) : 1194 -- 215. PMID 13263410. doi : 10.1210 / jcem - 15 - 10 - 1194. Jump up ^ Correia JN, Conner SJ, Kirkman - Brown JC ( May 2007 ). `` Non-genomic steroid actions in human spermatozoa. `` Persistent tickling from a laden environment '' ``. Seminars in Reproductive Medicine. 25 ( 3 ) : 208 -- 19. PMID 17447210. doi : 10.1055 / s - 2007 - 973433. Jump up ^ Kirkman - Brown JC, Bray C, Stewart PM, Barratt CL, Publicover SJ ( June 2000 ). `` Biphasic elevation of ( Ca ( 2 + ) ) ( i ) in individual human spermatozoa exposed to progesterone ''. Developmental Biology. 222 ( 2 ) : 326 -- 35. PMID 10837122. doi : 10.1006 / dbio. 2000.9729. Jump up ^ Kirkman - Brown JC, Barratt CL, Publicover SJ ( March 2004 ). `` Slow calcium oscillations in human spermatozoa ''. The Biochemical Journal. 378 ( Pt 3 ) : 827 -- 32. PMC 1223996. PMID 14606954. doi : 10.1042 / BJ20031368. Jump up ^ Harper CV, Barratt CL, Publicover SJ ( October 2004 ). `` Stimulation of human spermatozoa with progesterone gradients to simulate approach to the oocyte. Induction of ( Ca ( 2 + ) ) ( i ) oscillations and cyclical transitions in flagellar beating ''. The Journal of Biological Chemistry. 279 ( 44 ) : 46315 -- 25. PMID 15322137. doi : 10.1074 / jbc. M401194200. Jump up ^ Marieb, Elaine ( 2013 ). Anatomy & physiology. Benjamin - Cummings. p. 903. ISBN 9780321887603. Jump up ^ Tosti E, Di Cosmo A, Cuomo A, Di Cristo C, Gragnaniello G ( May 2001 ). `` Progesterone induces activation in Octopus vulgaris spermatozoa ''. Molecular Reproduction and Development. 59 ( 1 ) : 97 -- 105. PMID 11335951. doi : 10.1002 / mrd. 1011. ^ Jump up to : Bowen R ( 2000 - 08 - 06 ). `` Placental Hormones ''. Retrieved 2008 - 03 - 12. Jump up ^ Patel B, Elguero S, Thakore S, Dahoud W, Bedaiwy M, Mesiano S ( 2014 ). `` Role of nuclear progesterone receptor isoforms in uterine pathophysiology ''. Human Reproduction Update. 21 ( 2 ) : 155 -- 73. PMC 4366574. PMID 25406186. doi : 10.1093 / humupd / dmu056. Jump up ^ Macias H, Hinck L ( 2012 ). `` Mammary gland development ''. Wiley Interdisciplinary Reviews. Developmental Biology. 1 ( 4 ) : 533 -- 57. PMC 3404495. PMID 22844349. doi : 10.1002 / wdev. 35. ^ Jump up to : Hilton HN, Graham JD, Clarke CL ( September 2015 ). `` Minireview : Progesterone Regulation of Proliferation in the Normal Human Breast and in Breast Cancer : A Tale of Two Scenarios ? ''. Molecular Endocrinology. 29 ( 9 ) : 1230 -- 42. PMID 26266959. doi : 10.1210 / me. 2015 - 1152. Jump up ^ Strauss JF, Barbieri RL ( 13 September 2013 ). Yen and Jaffe 's Reproductive Endocrinology. Elsevier Health Sciences. pp. 236 --. ISBN 978 - 1 - 4557 - 2758 - 2. Jump up ^ Scaling AL, Prossnitz ER, Hathaway HJ ( June 2014 ). `` GPER mediates estrogen - induced signaling and proliferation in human breast epithelial cells and normal and malignant breast ''. Hormones & Cancer. 5 ( 3 ) : 146 -- 60. PMC 4091989. PMID 24718936. doi : 10.1007 / s12672 - 014 - 0174 - 1. ^ Jump up to : Aupperlee MD, Leipprandt JR, Bennett JM, Schwartz RC, Haslam SZ ( 2013 ). `` Amphiregulin mediates progesterone - induced mammary ductal development during puberty ''. Breast Cancer Research. 15 ( 3 ) : R44. PMC 3738150. PMID 23705924. doi : 10.1186 / bcr3431. Jump up ^ Kuhl H, Schneider HP ( August 2013 ). `` Progesterone -- promoter or inhibitor of breast cancer ''. Climacteric. 16 Suppl 1 : 54 -- 68. PMID 23336704. doi : 10.3109 / 13697137.2013. 768806. Jump up ^ Fournier A, Berrino F, Clavel - Chapelon F ( 2008 ). `` Unequal risks for breast cancer associated with different hormone replacement therapies : results from the E3N cohort study ''. Breast Cancer Res. Treat. 107 ( 1 ) : 103 -- 11. PMC 2211383. PMID 17333341. doi : 10.1007 / s10549 - 007 - 9523 - x. Jump up ^ Campagnoli C, Clavel - Chapelon F, Kaaks R, Peris C, Berrino F ( July 2005 ). `` Progestins and progesterone in hormone replacement therapy and the risk of breast cancer ''. The Journal of Steroid Biochemistry and Molecular Biology. 96 ( 2 ) : 95 -- 108. PMC 1974841. PMID 15908197. doi : 10.1016 / j. jsbmb. 2005.02. 014. ^ Jump up to : Raine - Fenning NJ, Brincat MP, Muscat - Baron Y ( 2003 ). `` Skin aging and menopause : implications for treatment ''. Am J Clin Dermatol. 4 ( 6 ) : 371 -- 8. PMID 12762829. doi : 10.2165 / 00128071 - 200304060 - 00001. ^ Jump up to : Holzer G, Riegler E, Hönigsmann H, Farokhnia S, Schmidt JB, Schmidt B ( 2005 ). `` Effects and side - effects of 2 % progesterone cream on the skin of peri - and postmenopausal women : results from a double - blind, vehicle - controlled, randomized study ''. Br. J. Dermatol. 153 ( 3 ) : 626 -- 34. PMID 16120154. doi : 10.1111 / j. 1365 - 2133.2005. 06685. x. Jump up ^ King SR ( 9 November 2012 ). Neurosteroids and the Nervous System. Springer Science & Business Media. pp. 44 -- 46. ISBN 978 - 1 - 4614 - 5559 - 2. Jump up ^ Homosexuality may help us bond University of Portsmouth UoP News Jump up ^ Having homosexual thoughts ' is an essential part of human evolution ' study suggests The Telegraph Jump up ^ Homosexuality May Have Evolved In Humans Because It Helps Us Bond, Scientists Say Huff Post ^ Jump up to : Hanukoglu I, Karavolas HJ, Goy RW ( 1977 ). `` Progesterone metabolism in the pineal, brain stem, thalamus and corpus callosum of the female rat. ''. Brain Res. 125 ( 2 ) : 313 -- 24. PMID 558037. doi : 10.1016 / 0006 - 8993 ( 77 ) 90624 - 2. CS1 maint : Multiple names : authors list ( link ) Jump up ^ Schumacher M, Guennoun R, Robert F, Carelli C, Gago N, Ghoumari A, Gonzalez Deniselle MC, Gonzalez SL, Ibanez C, Labombarda F, Coirini H, Baulieu EE, De Nicola AF ( June 2004 ). `` Local synthesis and dual actions of progesterone in the nervous system : neuroprotection and myelination ''. Growth Hormone & IGF Research. 14 Suppl A : S18 -- 33. PMID 15135772. doi : 10.1016 / j. ghir. 2004.03. 007. Jump up ^ Roof RL, Hall ED ( May 2000 ). `` Gender differences in acute CNS trauma and stroke : neuroprotective effects of estrogen and progesterone ''. Journal of Neurotrauma. 17 ( 5 ) : 367 -- 88. PMID 10833057. doi : 10.1089 / neu. 2000.17. 367. Jump up ^ Pan DS, Liu WG, Yang XF, Cao F ( October 2007 ). `` Inhibitory effect of progesterone on inflammatory factors after experimental traumatic brain injury ''. Biomedical and Environmental Sciences. 20 ( 5 ) : 432 -- 8. PMID 18188998. Jump up ^ Jiang C, Zuo F, Wang Y, Wan J, Yang Z, Lu H, Chen W, Zang W, Yang Q, Wang J ( June 2016 ). `` Progesterone exerts neuroprotective effects and improves long - term neurologic outcome after intracerebral hemorrhage in middle - aged mice. ''. Neurobiology of aging. 42 : 13 -- 24. PMC 4857017. PMID 27143417. doi : 10.1016 / j. neurobiolaging. 2016.02. 029. ^ Jump up to : Luoma JI, Stern CM, Mermelstein PG ( August 2012 ). `` Progesterone inhibition of neuronal calcium signaling underlies aspects of progesterone - mediated neuroprotection ''. The Journal of Steroid Biochemistry and Molecular Biology. 131 ( 1 - 2 ) : 30 -- 6. PMC 3303940. PMID 22101209. doi : 10.1016 / j. jsbmb. 2011.11. 002. ^ Jump up to : Stein DG ( March 2008 ). `` Progesterone exerts neuroprotective effects after brain injury ''. Brain Research Reviews. 57 ( 2 ) : 386 -- 97. PMC 2699575. PMID 17826842. doi : 10.1016 / j. brainresrev. 2007.06. 012. Jump up ^ Espinoza TR, Wright DW ( 2011 ). `` The role of progesterone in traumatic brain injury ''. The Journal of Head Trauma Rehabilitation. 26 ( 6 ) : 497 -- 9. PMID 22088981. doi : 10.1097 / HTR. 0b013e31823088fa. Jump up ^ Herson PS, Koerner IP, Hurn PD ( May 2009 ). `` Sex, sex steroids, and brain injury ''. Seminars in Reproductive Medicine. 27 ( 3 ) : 229 -- 39. PMC 2675922. PMID 19401954. doi : 10.1055 / s - 0029 - 1216276. Jump up ^ Li Z, Wang B, Kan Z, Zhang B, Yang Z, Chen J, Wang D, Wei H, Zhang JN, Jiang R ( January 2012 ). `` Progesterone increases circulating endothelial progenitor cells and induces neural regeneration after traumatic brain injury in aged rats ''. Journal of Neurotrauma. 29 ( 2 ) : 343 -- 53. PMC 3261789. PMID 21534727. doi : 10.1089 / neu. 2011.1807. ^ Jump up to : Lynch WJ, Sofuoglu M ( December 2010 ). `` Role of progesterone in nicotine addiction : evidence from initiation to relapse ''. Experimental and Clinical Psychopharmacology. 18 ( 6 ) : 451 -- 61. PMC 3638762. PMID 21186920. doi : 10.1037 / a0021265. Jump up ^ Cosgrove KP, Esterlis I, McKee SA, Bois F, Seibyl JP, Mazure CM, Krishnan - Sarin S, Staley JK, Picciotto MR, O'Malley SS ( April 2012 ). `` Sex differences in availability of β2 * - nicotinic acetylcholine receptors in recently abstinent tobacco smokers ''. Archives of General Psychiatry. 69 ( 4 ) : 418 -- 27. PMC 3508698. PMID 22474108. doi : 10.1001 / archgenpsychiatry. 2011.1465. Jump up ^ Mello NK, Knudson IM, Kelly M, Fivel PA, Mendelson JH ( October 2011 ). `` Effects of progesterone and testosterone on cocaine self - administration and cocaine discrimination by female rhesus monkeys ''. Neuropsychopharmacology. 36 ( 11 ) : 2187 -- 99. PMC 3176575. PMID 21796112. doi : 10.1038 / npp. 2011.130. Jump up ^ Sriram, D ( 2007 ). Medicinal Chemistry. New Delhi : Dorling Kindersley India Pvt. Ltd. p. 432. ISBN 81 - 317 - 0031 - 3. ^ Jump up to : Blackburn S ( 14 April 2014 ). Maternal, Fetal, & Neonatal Physiology. Elsevier Health Sciences. pp. 92 --. ISBN 978 - 0 - 323 - 29296 - 2. Jump up ^ Faivre, E.J. ; Lange, C.A. ( 30 October 2006 ). `` Progesterone Receptors Upregulate Wnt - 1 To Induce Epidermal Growth Factor Receptor Transactivation and c - Src - Dependent Sustained Activation of Erk1 / 2 Mitogen - Activated Protein Kinase in Breast Cancer Cells ''. Molecular and Cellular Biology. 27 ( 2 ) : 466 -- 480. doi : 10.1128 / MCB. 01539 - 06. Jump up ^ Physiology : 5 / 5ch9 / s5ch9_13 - Essentials of Human Physiology Jump up ^ Hould FS, Fried GM, Fazekas AG, Tremblay S, Mersereau WA ( December 1988 ). `` Progesterone receptors regulate gallbladder motility ''. The Journal of Surgical Research. 45 ( 6 ) : 505 -- 12. PMID 3184927. doi : 10.1016 / 0022 - 4804 ( 88 ) 90137 - 0. Jump up ^ `` Hormones and Oral Health ''. WebMD. Jump up ^ Picard F, Wanatabe M, Schoonjans K, Lydon J, O'Malley BW, Auwerx J ( November 2002 ). `` Progesterone receptor knockout mice have an improved glucose homeostasis secondary to beta - cell proliferation ''. Proceedings of the National Academy of Sciences of the United States of America. 99 ( 24 ) : 15644 -- 8. PMC 137770. PMID 12438645. doi : 10.1073 / pnas. 202612199. Jump up ^ Brănişteanu DD, Mathieu C ( March 2003 ). `` Progesterone in gestational diabetes mellitus : guilty or not guilty ? ''. Trends in Endocrinology and Metabolism. 14 ( 2 ) : 54 -- 6. PMID 12591170. doi : 10.1016 / S1043 - 2760 ( 03 ) 00003 - 1. Jump up ^ Schneider JS, Stone MK, Wynne - Edwards KE, Horton TH, Lydon J, O'Malley B, Levine JE ( March 2003 ). `` Progesterone receptors mediate male aggression toward infants ''. Proceedings of the National Academy of Sciences of the United States of America. 100 ( 5 ) : 2951 -- 6. PMC 151447. PMID 12601162. doi : 10.1073 / pnas. 0130100100. Jump up ^ Häggström, Mikael ; Richfield, David ( 2014 ). `` Diagram of the pathways of human steroidogenesis ''. WikiJournal of Medicine. 1 ( 1 ). ISSN 2002 - 4436. doi : 10.15347 / wjm / 2014.005. Jump up ^ Bewick PM ( 2002 ). Medicinal natural products : a biosynthetic approach. New York : Wiley. p. 244. ISBN 0 - 471 - 49641 - 3. Jump up ^ Duport C, Spagnoli R, Degryse E, Pompon D ( February 1998 ). `` Self - sufficient biosynthesis of pregnenolone and progesterone in engineered yeast ''. Nature Biotechnology. 16 ( 2 ) : 186 -- 9. PMID 9487528. doi : 10.1038 / nbt0298 - 186. Jump up ^ Progesterone - Drugs.com, retrieved 2015 - 08 - 23 ^ Jump up to : Tommaso Falcone ; William W. Hurd ( 2007 ). Clinical Reproductive Medicine and Surgery. Elsevier Health Sciences. pp. 22 --. ISBN 0 - 323 - 03309 - 1. ^ Jump up to : Perry T. Cupps ( 20 February 1991 ). Reproduction in Domestic Animals. Elsevier. pp. 101 --. ISBN 978 - 0 - 08 - 057109 - 6. ^ Jump up to : Stanczyk FZ ( 2003 ). `` All progestins are not created equal ''. Steroids. 68 ( 10 - 13 ) : 879 -- 90. PMID 14667980. doi : 10.1016 / j. steroids. 2003.08. 003. Jump up ^ Frank J. Dowd ; Bart Johnson ; Angelo Mariotti ( 3 September 2016 ). Pharmacology and Therapeutics for Dentistry. Elsevier Health Sciences. pp. 448 --. ISBN 978 - 0 - 323 - 44595 - 5. ^ Jump up to : Kuhl H ( 2005 ). `` Pharmacology of estrogens and progestogens : influence of different routes of administration ''. Climacteric. 8 Suppl 1 : 3 -- 63. PMID 16112947. doi : 10.1080 / 13697130500148875. ^ Jump up to : Tony M. Plant ; Anthony J. Zeleznik ( 15 November 2014 ). Knobil and Neill 's Physiology of Reproduction. Academic Press. pp. 304 --. ISBN 978 - 0 - 12 - 397769 - 4. ^ Jump up to : Nanette F. Santoro ; Genevieve Neal - Perry ( 11 September 2010 ). Amenorrhea : A Case - Based, Clinical Guide. Springer Science & Business Media. pp. 13 --. ISBN 978 - 1 - 60327 - 864 - 5. Jump up ^ Reddy DS ( 2010 ). `` Neurosteroids : endogenous role in the human brain and therapeutic potentials ''. Progress in Brain Research. 186 : 113 -- 37. PMC 3139029. PMID 21094889. doi : 10.1016 / B978 - 0 - 444 - 53630 - 3.00008 - 7. ^ Jump up to : Etienne - Emile Baulieu ; Paul A. Kelly ( 30 November 1990 ). Hormones : From Molecules to Disease. Springer Science & Business Media. pp. 401 --. ISBN 978 - 0 - 412 - 02791 - 8. Jump up ^ Beranič N, Gobec S, Rižner TL ( 2011 ). `` Progestins as inhibitors of the human 20 - ketosteroid reductases, AKR1C1 and AKR1C3 ''. Chem. Biol. Interact. 191 ( 1 - 3 ) : 227 -- 33. PMID 21182831. doi : 10.1016 / j. cbi. 2010.12. 012. Jump up ^ James M. Greenblatt ; Kelly Brogan ( 27 April 2016 ). Integrative Therapies for Depression : Redefining Models for Assessment, Treatment and Prevention. CRC Press. pp. 201 --. ISBN 978 - 1 - 4987 - 0230 - 0. Jump up ^ Charles Graham ( 2 December 2012 ). Reproductive Biology of the Great Apes : Comparative and Biomedical Perspectives. Elsevier. pp. 179 --. ISBN 978 - 0 - 323 - 14971 - 6. ^ Jump up to : Carla de Azevedo Piccinato ( 2008 ). Regulation of Steroid Metabolism and the Hepatic Transcriptome by Estradiol and Progesterone. ProQuest. pp. 24 -- 25. ISBN 978 - 1 - 109 - 04632 - 8. Jump up ^ Akalin S ( 1991 ). `` Effects of ketoconazole in hirsute women ''. Acta Endocrinol. 124 ( 1 ) : 19 -- 22. PMID 1825737. doi : 10.1530 / acta. 0.1240019. ^ Jump up to : Progesterone Reference Ranges, Performed at the Clinical Center at the National Institutes of Health, Bethesda MD, 03Feb09 ^ Jump up to : Converted from mass values using molar mass of 314.46 g / mol Jump up ^ Csapo AI, Pulkkinen MU, Wiest WG ( 1973 ). `` Effects of lutectomy and progestreone replacement therapy in early pregnancy patients ''. Am J Obstet Gynecol. 115 : 759 -- 65. Jump up ^ NIH Clinical Center ( 2004 - 08 - 16 ). `` Progesterone Historical Reference Ranges ''. United States National Institutes of Health. Retrieved 2008 - 03 - 12. Jump up ^ Häggström, Mikael ( 2014 ). `` Reference ranges for estradiol, progesterone, luteinizing hormone and follicle - stimulating hormone during the menstrual cycle ''. WikiJournal of Medicine. 1 ( 1 ). ISSN 2002 - 4436. doi : 10.15347 / wjm / 2014.001. Jump up ^ Goodson III WH, Handagama P, Moore II DH, Dairkee S ( 2007 - 12 - 13 ). `` Milk products are a source of dietary progesterone ''. 30th Annual San Antonio Breast Cancer Symposium. pp. abstract # 2028. Retrieved 2008 - 03 - 12. Jump up ^ Pauli GF, Friesen JB, Gödecke T, Farnsworth NR, Glodny B ( March 2010 ). `` Occurrence of progesterone and related animal steroids in two higher plants ''. Journal of Natural Products. 73 ( 3 ) : 338 -- 45. PMID 20108949. doi : 10.1021 / np9007415. Jump up ^ Applezweig N ( May 1969 ). `` Steroids ''. Chemical Week. 104 : 57 -- 72. PMID 12255132. Jump up ^ Noguchi E, Fujiwara Y, Matsushita S, Ikeda T, Ono M, Nohara T ( September 2006 ). `` Metabolism of tomato steroidal glycosides in humans ''. Chemical & Pharmaceutical Bulletin. 54 ( 9 ) : 1312 -- 4. PMID 16946542. doi : 10.1248 / cpb. 54.1312. Jump up ^ Yang DJ, Lu TJ, Hwang LS ( October 2003 ). `` Isolation and identification of steroidal saponins in Taiwanese yam cultivar ( Dioscorea pseudojaponica Yamamoto ) ''. Journal of Agricultural and Food Chemistry. 51 ( 22 ) : 6438 -- 44. PMID 14558759. doi : 10.1021 / jf030390j. Jump up ^ Hooker E ( 2004 ). `` Final report of the amended safety assessment of Dioscorea Villosa ( Wild Yam ) root extract ''. International Journal of Toxicology. 23 Suppl 2 : 49 -- 54. PMID 15513824. doi : 10.1080 / 10915810490499055. Jump up ^ Niño J, Jiménez DA, Mosquera OM, Correa YM ( 2007 ). `` Diosgenin quantification by HPLC in a Dioscorea polygonoides tuber collection from colombian flora ''. Journal of the Brazilian Chemical Society. 18 ( 5 ) : 1073 -- 1076. doi : 10.1590 / S0103 - 50532007000500030. Jump up ^ Myoda T, Nagai T, Nagashima T ( 2005 ). Properties of starches in yam ( Dioscorea spp. ) tuber. Current Topics in Food Science and Technology. pp. 105 -- 114. ISBN 81 - 308 - 0003 - 9. ^ Jump up to : Marker RE, Krueger J ( 1940 ). `` Sterols. CXII. Sapogenins. XLI. The Preparation of Trillin and its Conversion to Progesterone ''. J. Am. Chem. Soc. 62 ( 12 ) : 3349 -- 3350. doi : 10.1021 / ja01869a023. Jump up ^ Numazawa M, Nagaoka M, Kunitama Y ( September 1986 ). `` Regiospecific deoxygenation of the dihydroxyacetone moiety at C - 17 of corticoid steroids with iodotrimethylsilane ''. Chemical & Pharmaceutical Bulletin. 34 ( 9 ) : 3722 -- 6. PMID 3815593. doi : 10.1248 / cpb. 34.3722. Jump up ^ Heyl FW ( 1950 ). `` Progesterone from 3 - Acetoxybisnor - 5 - cholenaldehyde and 3 - Ketobisnor - 4 - cholenaldehyde ''. Journal of the American Chemical Society. 72 ( 6 ) : 2617 -- 2619. doi : 10.1021 / ja01162a076. Jump up ^ Slomp G ( 1958 ). `` Ozonolysis. II. 1 The Effect of Pyridine on the Ozonolysis of 4, 22 - Stigmastadien - 3 - one 2 ''. Journal of the American Chemical Society. 80 ( 4 ) : 915 -- 921. doi : 10.1021 / ja01537a041. Jump up ^ Sundararaman P, Djerassi C ( October 1977 ). `` A convenient synthesis of progesterone from stigmasterol ''. The Journal of Organic Chemistry. 42 ( 22 ) : 3633 -- 4. PMID 915584. doi : 10.1021 / jo00442a044. Jump up ^ `` Nova Transcripts : Forgotten Genius ''. PBS.org. February 6, 2007. Jump up ^ `` Giants of the Past ''. lipidlibrary.aocs.org. ^ Jump up to : Johnson WS, Gravestock MB, McCarry BE ( August 1971 ). `` Acetylenic bond participation in biogenetic - like olefinic cyclizations. II. Synthesis of dl - progesterone ''. Journal of the American Chemical Society. 93 ( 17 ) : 4332 -- 4. PMID 5131151. doi : 10.1021 / ja00746a062. ^ Jump up to : Coutinho EM, Segal SJ ( 1999 ). Is Menstruation Obsolete ?. Oxford University Press. pp. 31 --. ISBN 978 - 0 - 19 - 513021 - 8. Jump up ^ Walker A ( 7 March 2008 ). The Menstrual Cycle. Routledge. pp. 49 --. ISBN 978 - 1 - 134 - 71411 - 7. Jump up ^ Piosik R ( 2003 ). `` Adolf Butenandt und sein Wirken an der Technischen Hochschule Danzig ''. Chemkon. 10 ( 3 ) : 135 -- 138. doi : 10.1002 / ckon. 200390038. Jump up ^ Ginsburg B ( 6 December 2012 ). Premenstrual Syndrome : Ethical and Legal Implications in a Biomedical Perspective. Springer Science & Business Media. pp. 274 --. ISBN 978 - 1 - 4684 - 5275 - 4. Jump up ^ Sir Humphry Davy Rolleston ( 1936 ). The Endocrine Organs in Health and Disease : With an Historical Review. Oxford University Press, H. Milford. p. 406. Jump up ^ Allen WM ( October 1970 ). `` Progesterone : how did the name originate ? ''. Southern Medical Journal. 63 ( 10 ) : 1151 -- 5. PMID 4922128. doi : 10.1097 / 00007611 - 197010000 - 00012. External links Progesterone MS Spectrum Progesterone at the US National Library of Medicine Medical Subject Headings ( MeSH ) Kimball JW ( 2007 - 05 - 27 ). `` Progesterone ''. Kimball 's Biology Pages. Retrieved 2008 - 06 - 18. Hormones Endocrine glands Hypothalamic - pituitary Hypothalamus GnRH TRH Dopamine CRH GHRH Somatostatin ( GHIH ) MCH Posterior pituitary Oxytocin Vasopressin Anterior pituitary FSH LH TSH Prolactin POMC CLIP ACTH MSH Endorphins Lipotropin GH Adrenal axis Adrenal cortex aldosterone cortisol cortisone DHEA DHEA - S androstenedione Adrenal medulla epinephrine norepinephrine Thyroid Thyroid hormone Calcitonin Thyroid axis Parathyroid PTH Gonadal axis Testis testosterone AMH inhibin Ovary estradiol progesterone activin and inhibin relaxin ( pregnancy ) Placenta hCG HPL estrogen progesterone Pancreas glucagon insulin amylin somatostatin pancreatic polypeptide Pineal gland melatonin N, N - dimethyltryptamine 5 - methoxy - N, N - dimethyltryptamine Other Thymus Thymosins Thymosin α1 Beta thymosins Thymopoietin Thymulin Digestive system Stomach gastrin ghrelin Duodenum CCK Incretins GIP GLP - 1 secretin motilin VIP Ileum enteroglucagon peptide YY Liver / other Insulin - like growth factor IGF - 1 IGF - 2 Adipose tissue leptin adiponectin resistin Skeleton Osteocalcin Kidney JGA ( renin ) peritubular cells EPO calcitriol prostaglandin Heart Natriuretic peptide ANP BNP Endogenous steroids Precursors Cholesterol 22R - Hydroxycholesterol 20α, 22R - Dihydroxycholesterol Pregnenolone 11β - Hydroxypregnenolone 17α - Hydroxypregnenolone 21 - Hydroxypregnenolone 17α, 21 - Dihydroxypregnenolone 11β, 17α, 21 - Trihydroxypregnenolone Corticosteroids Glucocorticoids 3α, 5α - Tetrahydrocorticosterone 5α - Dihydrocorticosterone 11 - Deoxycorticosterone 11 - Deoxycortisol 11 - Ketoprogesterone 21 - Deoxycortisol 21 - Deoxycortisone Corticosterone Cortisol Cortisone 17α - Hydroxypregnenolone 17α - Hydroxyprogesterone Pregnenolone Progesterone Mineralocorticoids 5α - Dihydroaldosterone 11 - Dehydrocorticosterone ( 11 - oxocorticosterone, 17 - deoxycortisone ) 11 - Deoxycortisol 11 - Deoxycorticosterone 11β - Hydroxyprogesterone ( 21 - deoxycorticosterone ) 18 - Hydroxy - 11 - deoxycorticosterone 18 - Hydroxycorticosterone 18 - Hydroxyprogesterone Aldosterone Corticosterone Cortisol Sex steroids Androgens 11 - Ketodihydrotestosterone 11 - Ketotestosterone 7β - Hydroxyepiandrosterone 11β - Hydroxyandrostenedione Adrenosterone ( 11 - ketoandrostenedione ) Androstenediol Androstenedione Androsterone Dehydroandrosterone DHEA DHEA sulfate Dihydrotestosterone Epiandrosterone Epitestosterone 16α - Hydroxyandrostenedione 16α - Hydroxy - DHEA 16α - Hydroxy - DHEA sulfate Testosterone Metabolites : 3α - Androstanediol 3α - Androstanediol glucuronide 3β - Androstanediol 3α, 5β - Androstanediol 3β, 5β - Androstanediol 5β - Androstanedione 5β - Dihydrotestosterone Androstanetriols Androstenediol sulfate Androsterone glucuronide Androsterone sulfate Dihydrotestosterone glucuronide Dihydrotestosterone sulfate Etiocholanolone Etiocholanolone glucuronide Epietiocholanolone Testosterone glucuronide Testosterone sulfate Estrogens Estranes : Estetrol Estradiol Estrone Estriol 16β - Epiestriol ( 16β - hydroxyestradiol ) 17α - Epiestriol ( 16α - hydroxy - 17α - estradiol ) 16β, 17α - Epiestriol ( 16β - hydroxy - 17α - estradiol ) 2 - Hydroxyestradiol 2 - Hydroxyestriol 2 - Hydroxyestrone 4 - Hydroxyestradiol 4 - Hydroxyestriol 4 - Hydroxyestrone 4 - Methoxyestradiol 16α - Hydroxyestrone Others : 27 - Hydroxycholesterol 3α - Androstanediol 3β - Androstanediol 4 - Androstenedione 5 - Androstenediol DHEA DHEA sulfate 7 - Keto - DHEA 7α - Hydroxy - DHEA 16α - Hydroxy - DHEA Metabolites : 2 - Methoxyestradiol 2 - Methoxyestrone 4 - Methoxyestrone Estradiol glucuronide Estradiol sulfate Estrone glucuronide Estrone sulfate Estriol glucuronide Estriol sulfate Lipoidal estradiol ( e.g., estradiol stearate, estradiol palmitate ) Progestogens Progesterone 16α - Hydroxyprogesterone 17α - Hydroxyprogesterone 20α - Dihydroprogesterone 5α - Dihydroprogesterone 11 - Deoxycorticosterone 5α - DHDOC Metabolites : Allopregnanediol Pregnanediol Pregnanediol glucuronide Pregnanetriol Neurosteroids Cholestanes : 24S - Hydroxycholesterol Cholesterol Pregnanes : 3α - Dihydroprogesterone 3β - Dihydroprogesterone 5α - Dihydrocorticosterone 5α - Dihydroprogesterone 5β - Dihydroprogesterone Allopregnanolone Corticosterone DHC DHDOC Deoxycorticosterone Epipregnanolone Isopregnanolone Pregnanolone Pregnenolone Pregnenolone sulfate Progesterone THB THDOC Androstanes : 3α - Androstanediol 3α - Androstenol 7 - Keto - DHEA 7α - Hydroxy - DHEA 7β - Hydroxy - DHEA 7α - Hydroxyepiandrosterone 7β - Hydroxyepiandrosterone Androsterone DHEA DHEA sulfate Etiocholanolone Pheromones : 3α - Androstenol 3β - Androstenol Androstadienol Androstadienone Androstenone Androsterone Estratetraenol Others Vitamin D: 7 - Dehydrocholesterol Calcidiol / Calcifediol Calcitriol Cholecalciferol Others : 7α - Hydroxycholesterol 11α - Hydroxyprogesterone 11β - Hydroxyprogesterone Cholesterol sulfate Progestogens and antiprogestogens Progestogens ( and progestins ) PR agonists Progesterone derivatives : Progesterone Quingestrone Retroprogesterone derivatives : Dydrogesterone Trengestone 17α - Hydroxyprogesterone ( and closely related ) derivatives : Acetomepregenol ( mepregenol diacetate ) Algestone Algestone acetophenide ( dihydroxyprogesterone acetophenide ) Anagestone acetate Chlormadinone acetate Cyproterone acetate Delmadinone acetate Flugestone acetate ( flurogestone acetate ) Flumedroxone acetate Hydroxyprogesterone Hydroxyprogesterone acetate Hydroxyprogesterone caproate Hydroxyprogesterone heptanoate Medroxyprogesterone Medroxyprogesterone acetate Megestrol acetate Melengestrol acetate Osaterone acetate Pentagestrone acetate Other 17α - substituted ( besides hydroxylated ) derivatives : Haloprogesterone Medrogestone Proligestone 19 - Norprogesterone ( including 17α - substituted ) derivatives : Demegestone Gestonorone caproate ( gestronol hexanoate ) Nomegestrol acetate Norgestomet Promegestone Segesterone acetate ( nestorone ) Trimegestone 17α - Ethynyltestosterone derivatives : Danazol Dimethisterone Ethisterone 19 - Nortestosterone ( including 17α - substituted ) derivatives : Estranes : Dienogest Etynodiol diacetate Gestrinone Lynestrenol Norethisterone ( norethindrone ) Norethisterone acetate Norethisterone enanthate Noretynodrel Norgestrienone Quingestanol acetate Tibolone ; Gonanes : Desogestrel Etonogestrel Gestodene Levonorgestrel Norelgestromin Norgestimate Norgestrel ; Others : Allylestrenol Altrenogest Norgesterone Normethandrone ( methylestrenolone ) Norvinisterone Oxendolone Spirolactone derivatives : Drospirenone Others : Anabolic -- androgenic steroids ( e.g., nandrolone and esters, trenbolone and esters, norethandrolone, normethandrone, others ) Antiprogestogens SPRMs Asoprisnil Telapristone Ulipristal acetate PR antagonists Aglepristone Mifepristone Valproic acid WHO - EM Withdrawn from market Clinical trials : Phase III Never to phase III See also Progesterone receptor modulators Androgens and antiandrogens Estrogens and antiestrogens List of progestogens Mineralocorticoids and antimineralocorticoids ( H02 ) Mineralocorticoids Desoxycortone ( desoxycorticosterone ) Desoxycortone esters Hydrocortisone ( cortisol ) Hydrocortisone esters Fludrocortisone Fludrocortisone acetate Methylprednisolone Methylprednisolone esters Prednisolone Prednisolone esters Prednisone Prednisone esters Antimineralocorticoids Steroidal : Canrenoate potassium ( potassium canrenoate ) Canrenone Drospirenone Dydrogesterone Eplerenone Gestodene Medrogestone Progesterone Spironolactone Trimegestone Nonsteroidal : Amlodipine Apararenone Benidipine Esaxerenone Felodipine Finerenone Nifedipine Nimodipine Nitrendipine Synthesis modifiers Acetoxolone Aminoglutethimide Carbenoxolone Enoxolone Ketoconazole Metyrapone Mitotane Trilostane WHO - EM Withdrawn from market Clinical trials : Phase III Never to phase III See also Mineralocorticoid receptor modulators Glucocorticoids and antiglucocorticoids List of corticosteroids Biological activity GABA receptor positive modulators Alcohols Brometone Butanol Chloralodol Chlorobutanol ( cloretone ) Ethanol ( alcohol ) ( alcoholic drink ) Ethchlorvynol Isobutanol Isopropanol Menthol Methanol Methylpentynol Pentanol Petrichloral Propanol tert - Butanol ( 2M2P ) tert - Pentanol ( 2M2B ) Tribromoethanol Trichloroethanol Triclofos Trifluoroethanol Barbiturates ( - ) - DMBB Allobarbital Alphenal Amobarbital Aprobarbital Barbexaclone Barbital Benzobarbital Benzylbutylbarbiturate Brallobarbital Brophebarbital Butabarbital / Secbutabarbital Butalbital Buthalital Butobarbital Butallylonal Carbubarb Crotylbarbital Cyclobarbital Cyclopentobarbital Difebarbamate Enallylpropymal Ethallobarbital Eterobarb Febarbamate Heptabarb Heptobarbital Hexethal Hexobarbital Metharbital Methitural Methohexital Methylphenobarbital Narcobarbital Nealbarbital Pentobarbital Phenallymal Phenobarbital Phetharbital Primidone Probarbital Propallylonal Propylbarbital Proxibarbital Reposal Secobarbital Sigmodal Spirobarbital Talbutal Tetrabamate Tetrabarbital Thialbarbital Thiamylal Thiobarbital Thiobutabarbital Thiopental Thiotetrabarbital Valofane Vinbarbital Vinylbital Benzodiazepines 2 - Oxoquazepam 3 - Hydroxyphenazepam Adinazolam Alprazolam Arfendazam Avizafone Bentazepam Bretazenil Bromazepam Brotizolam Camazepam Carburazepam Chlordiazepoxide Ciclotizolam Cinazepam Cinolazepam Clazolam Climazolam Clobazam Clonazepam Clonazolam Cloniprazepam Clorazepate Clotiazepam Cloxazolam CP - 1414S Cyprazepam Delorazepam Demoxepam Diazepam Diclazepam Doxefazepam Elfazepam Estazolam Ethyl carfluzepate Ethyl dirazepate Ethyl loflazepate Etizolam EVT - 201 FG - 8205 Fletazepam Flubromazepam Flubromazolam Fludiazepam Flunitrazepam Flunitrazolam Flurazepam Flutazolam Flutemazepam Flutoprazepam Fosazepam Gidazepam Halazepam Haloxazolam Iclazepam Imidazenil Irazepine Ketazolam Lofendazam Lopirazepam Loprazolam Lorazepam Lormetazepam Meclonazepam Medazepam Menitrazepam Metaclazepam Mexazolam Midazolam Motrazepam N - Desalkylflurazepam Nifoxipam Nimetazepam Nitrazepam Nitrazepate Nitrazolam Nordazepam Nortetrazepam Oxazepam Oxazolam Phenazepam Pinazepam Pivoxazepam Prazepam Premazepam Proflazepam Pyrazolam QH - II - 66 Quazepam Reclazepam Remimazolam Rilmazafone Ripazepam Ro48 - 6791 Ro48 - 8684 SH - 053 - R - CH3 - 2 ′ F Sulazepam Temazepam Tetrazepam Tolufazepam Triazolam Triflubazam Triflunordazepam ( Ro5 - 2904 ) Tuclazepam Uldazepam Zapizolam Zolazepam Zomebazam Carbamates Carisbamate Carisoprodol Clocental Cyclarbamate Difebarbamate Emylcamate Ethinamate Febarbamate Felbamate Hexapropymate Lorbamate Mebutamate Meprobamate Nisobamate Pentabamate Phenprobamate Procymate Styramate Tetrabamate Tybamate Flavonoids 6 - Methylapigenin Ampelopsin ( dihydromyricetin ) Apigenin Baicalein Baicalin Catechin EGC EGCG Hispidulin Linarin Luteolin Rc - OMe Skullcap constituents ( e.g., baicalin ) Wogonin Imidazoles Etomidate Metomidate Propoxate Kava constituents 10 - Methoxyyangonin 11 - Methoxyyangonin 11 - Hydroxyyangonin Desmethoxyyangonin 11 - Methoxy - 12 - hydroxydehydrokavain 7, 8 - Dihydroyangonin Kavain 5 - Hydroxykavain 5, 6 - Dihydroyangonin 7, 8 - Dihydrokavain 5, 6, 7, 8 - Tetrahydroyangonin 5, 6 - Dehydromethysticin Methysticin 7, 8 - Dihydromethysticin Yangonin Monoureides Acecarbromal Apronal ( apronalide ) Bromisoval Carbromal Capuride Ectylurea Neuroactive steroids Acebrochol Allopregnanolone ( brexanolone ) Alfadolone Alfaxalone 3α - Androstanediol Androstenol Androsterone Certain anabolic - androgenic steroids Cholesterol DHDOC 3α - DHP 5α - DHP 5β - DHP DHT Etiocholanolone Ganaxolone Hydroxydione Minaxolone ORG - 20599 ORG - 21465 P1 - 185 Pregnanolone ( eltanolone ) Progesterone Renanolone SAGE - 105 SAGE - 217 SAGE - 324 SAGE - 516 SAGE - 689 SAGE - 872 Testosterone THDOC Nonbenzodiazepines β - Carbolines : Abecarnil Gedocarnil Harmane SL - 651,498 ZK - 93423 Cyclopyrrolones : Eszopiclone Pagoclone Pazinaclone Suproclone Suriclone Zopiclone Imidazopyridines : Alpidem DS - 1 Necopidem Saripidem Zolpidem Pyrazolopyrimidines : Divaplon Fasiplon Indiplon Lorediplon Ocinaplon Panadiplon Taniplon Zaleplon Others : Adipiplon CGS - 8216 CGS - 9896 CGS - 13767 CGS - 20625 CL - 218,872 CP - 615,003 CTP - 354 ELB - 139 GBLD - 345 JM - 1232 L - 838,417 Lirequinil ( Ro41 - 3696 ) NS - 2664 NS - 2710 NS - 11394 Pipequaline ROD - 188 RWJ - 51204 SB - 205,384 SX - 3228 TGSC01AA TP - 003 TPA - 023 TP - 13 U-89843A U-90042 Viqualine Y - 23684 Phenols Fospropofol Propofol Thymol Piperidinediones Glutethimide Methyprylon Piperidione Pyrithyldione Pyrazolopyridines Cartazolate Etazolate ICI - 190,622 Tracazolate Quinazolinones Afloqualone Cloroqualone Diproqualone Etaqualone Mebroqualone Mecloqualone Methaqualone Methylmethaqualone Nitromethaqualone SL - 164 Volatiles / gases Acetone Acetophenone Acetylglycinamide chloral hydrate Aliflurane Benzene Butane Butylene Centalun Chloral Chloral betaine Chloral hydrate Chloroform Cryofluorane Desflurane Dichloralphenazone Dichloromethane Diethyl ether Enflurane Ethyl chloride Ethylene Fluroxene Gasoline Halopropane Halothane Isoflurane Kerosine Methoxyflurane Methoxypropane Nitric oxide Nitrogen Nitrous oxide Norflurane Paraldehyde Propane Propylene Roflurane Sevoflurane Synthane Teflurane Toluene Trichloroethane ( methyl chloroform ) Trichloroethylene Vinyl ether Others / unsorted 3 - Hydroxybutanal α - EMTBL AA - 29504 Avermectins ( e.g., ivermectin ) Bromide compounds ( e.g., lithium bromide, potassium bromide, sodium bromide ) Carbamazepine Chloralose Chlormezanone Clomethiazole DEABL Dihydroergolines ( e.g., dihydroergocryptine, dihydroergosine, dihydroergotamine, ergoloid ( dihydroergotoxine ) ) DS2 Efavirenz Etazepine Etifoxine Fenamates ( e.g., flufenamic acid, mefenamic acid, niflumic acid, tolfenamic acid ) Fluoxetine Flupirtine Hopantenic acid Lanthanum Lavender oil Lignans ( e.g., 4 - O - methylhonokiol, honokiol, magnolol, obovatol ) Loreclezole Menthyl isovalerate ( validolum ) Monastrol Niacin Nicotinamide ( niacinamide ) Org 25,435 Phenytoin Propanidid Retigabine ( ezogabine ) Safranal Seproxetine Stiripentol Sulfonylalkanes ( e.g., sulfonmethane ( sulfonal ), tetronal, trional ) Terpenoids ( e.g., borneol ) Topiramate Valerian constituents ( e.g., isovaleric acid, isovaleramide, valerenic acid, valerenol ) Unsorted benzodiazepine site positive modulators : α - Pinene MRK - 409 ( MK - 0343 ) TCS - 1105 TCS - 1205 See also : Receptor / signaling modulators GABA receptor modulators GABA metabolism / transport modulators Glucocorticoid receptor modulators GR Agonists Cortisol - like and related ( 16 - unsubstituted ) : 3α, 5α - Tetrahydrocorticosterone 5α - Dihydrocorticosterone 9α - Fluorocortisone ( alfluorone ) 11 - Dehydrocorticosterone ( 11 - oxocorticosterone, 17 - deoxycortisone ) 11 - Dehydrocorticosterone acetate 11 - Deoxycorticosterone ( desoxycortone, deoxycortone, desoxycorticosterone ) Desoxycortone esters 11 - Deoxycortisol ( cortodoxone, cortexolone ) Cortifen ( cortiphen, kortifen ) Cortodoxone acetate 21 - Deoxycortisol Δ - Prednisolone Δ - Prednisolone 21 - acetate Amebucort Chloroprednisone Chloroprednisone acetate Cloprednol Cloprednol acetate Corticosterone Corticosterone acetate Corticosterone benzoate Cortisol ( hydrocortisone ) Benzodrocortisone ( hydrocortisone benzoate ) Hydrocortamate ( hydrocortisone diethylaminoacetate ) Hydrocortisone esters Cortisone Cortisone acetate Deprodone Deprodone propionate Dichlorisone Dichlorisone acetate Dichlorisone diacetate Difluprednate Endrisone ( endrysone ) Etiprednol Etiprednol dicloacetate ( etiprednol dichloroacetate ) Fludrocortisone ( fludrocortone ) Fludrocortisone acetate Fluorometholone Fluorometholone acetate Fluperolone Fluperolone acetate Fluprednisolone Fluprednisolone esters Halopredone Halopredone acetate ( halopredone diacetate ) Isoflupredone ( 9α - fluoroprednisolone ) Isoflupredone acetate Loteprednol Loteprednol etabonate Mazipredone ( depersolone ) Medrysone Methylprednisolone Methylprednisolone esters Prebediolone Prebediolone acetate Prednisolone Prednazate Prednazoline Prednicarbate ( prednisolone ethylcarbonate propionate ) Prednimustine Prednisolamate ( prednisolone diethylaminoacetate ) Prednisolone esters Prednisone Prednisone esters Pregnenolone Pregnenolone acetate Pregnenolone succinate ( pregnenolone hemisuccinate ) Resocortol Tipredane Tixocortol Butixocort ( tixocortol butyrate ) Butixocort propionate Tixocortol pivalate Methasones and related ( 16 - substituted ) : 16α - Methyl - 11 - oxoprednisolone Alclometasone Alclometasone dipropionate Amelometasone Beclometasone ( beclomethasone ) Beclometasone esters Betamethasone ( betametasone ) Betamethasone esters Cortobenzolone ( betamethasone salicylate ) Ciclometasone ( ciclomethasone, cyclomethasone ) Clobetasol Clobetasol propionate Clobetasone Clobetasone butyrate Clocortolone Clocortolone esters Cloticasone Cloticasone propionate Cormetasone ( cormethasone ) Cormetasone acetate Descinolone Desoximetasone ( desoxymethasone ) Dexamethasone ( dexametasone ) Dexamethasone esters Diflorasone Diflorasone diacetate Diflucortolone Diflucortolone pivalate Diflucortolone valerate Dimesone Dimesone acetate Doxibetasol ( doxybetasol ) Fluclorolone Flumetasone ( flumethasone ) Flumetasone acetate Flumetasone pivalate Fluocinolone Fluocortin Fluocortin butyl ( fluocortin butylate ) Fluocortolone Fluocortolone esters Fluprednidene ( fluprednylidene ) Fluprednidene acetate Fluticasone Fluticasone furoate Fluticasone propionate Halocortolone Halometasone Icometasone Icometasone enbutate ( icometasone butyrate acetate ) Isoprednidene Locicortolone ( locicortone ) Locicortolone dicibate ( locicortone dicibate ) Meclorisone Meclorisone dibutyrate Meprednisone ( methylprednisone ) Meprednisone acetate Meprednisone hydrogen succinate ( methylprednisone hemisuccinate ) Mometasone Mometasone furoate Paramethasone Paramethasone acetate Paramethasone disodium phosphate Paramethasone phosphate Prednylidene Prednylidene diethylaminoacetate Rimexolone Ticabesone Ticabesone propionate Timobesone Timobesone acetate Triamcinolone Triamcinolone diacetate Ulobetasol ( halobetasol ) Ulobetasol propionate Vamorolone Cyclic ketals ( 16, 17 - cyclized ) : Acrocinonide ( triamcinolone acroleinide ) Amcinafal ( triamcinolone pentanonide ) Amcinafide ( triamcinolone acetophenide ) Amcinonide ( triamcinolone acetate cyclopentanonide ) Budesonide Ciclesonide Cicortonide Deflazacort ( azacort ) Descinolone acetonide Desonide ( hydroxyprednisolone acetonide ) Desonide disodium phosphate Desonide pivalate Dexbudesonide Drocinonide Drocinonide phosphate Fluazacort Fluclorolone acetonide ( flucloronide ) Fludroxycortide ( flurandrenolone, flurandrenolide ) Flumoxonide Flunisolide Flunisolide acetate Fluocinolone acetonide Ciprocinonide ( fluocinolone acetonide cyclopropylcarboxylate ) Fluocinonide ( fluocinolide, fluocinolone acetonide acetate ) Procinonide ( fluocinolone acetonide propionate ) Formocortal Halcinonide Itrocinonide Rofleponide Rofleponide palmitate Tralonide Triamcinolone acetonide Flupamesone ( triamcinolone acetonide metembonate ) Triamcinolone acetonide esters Triamcinolone aminobenzal benzamidoisobutyrate ( TBI - PAB ) Triclonide Others / atypical ( other expanded steroid ring systems, homosteroids, and non-pregnane steroids ) : Cortisuzol Cortivazol Domoprednate Naflocort Nicocortonide Nicocortonide acetate Nivacortol ( nivazol ) Oxisopred RU - 28362 Non-corticosteroids with some glucocorticoid activity : 15β - Hydroxycyproterone acetate 17α - Hydroxyprogesterone Chlormadinone acetate Cyproterone Cyproterone acetate Delmadinone acetate Flugestone Flugestone acetate ( flurogestone acetate ) Fluoxymesterone Gestodene Medrogestone Medroxyprogesterone acetate Megestrol acetate Metribolone Norgestomet Osaterone acetate Progesterone Promegestone Quingestrone Segesterone acetate ( nestorone ) Tetrahydrogestrinone Nonsteroidal glucocorticoids : AZD - 5423 GSK - 9027 Mixed ( SEGRMs ) Dagrocorat Fosdagrocorat Mapracorat Antagonists 7α - Hydroxy - DHEA 17α - Methylprogesterone Aglepristone Asoprisnil Asoprisnil ecamate C108297 C113176 CORT - 108297 Cyproterone acetate Guggulsterone Ketoconazole Lilopristone LLY - 2707 Miconazole Mifepristone Onapristone ORG - 34116 ORG - 34517 ( SCH - 900636 ) ORG - 34850 Pregnenolone 16α - carbonitrile Relacorilant ( CORT - 125134 ) RTI 3021 -- 012 RTI 3021 -- 022 Telapristone Tibolone Toripristone Ulipristal acetate See also Receptor / signaling modulators Glucocorticoids and antiglucocorticoids Mineralocorticoid receptor modulators List of corticosteroids Mineralocorticoid receptor modulators MR Agonists 11 - Dehydrocorticosterone ( 11 - oxocorticosterone, 17 - deoxycortisone ) 11 - Dehydrocorticosterone acetate 11 - Deoxycorticosterone ( desoxycortone, deoxycortone, desoxycorticosterone ) Desoxycortone esters 11 - Deoxycortisol ( cortodoxone, cortexolone ) Cortifen ( cortiphen, kortifen ) Cortodoxone acetate 11β - Hydroxyprogesterone 16α, 18 - Dihydroxy - 11 - deoxycorticosterone 17α - Hydroxyaldosterone 18 - Hydroxy - 11 - deoxycorticosterone 19 - Norprogesterone Aldosterone Corticosterone Corticosterone acetate Corticosterone benzoate Cortisol ( hydrocortisone ) Benzodrocortisone ( hydrocortisone benzoate ) Hydrocortamate ( hydrocortisone diethylaminoacetate ) Hydrocortisone esters Cortisone Cortisone acetate Fludrocortisone ( fludrocortone ) Fludrocortisone acetate Mometasone Mometasone furoate Prednisolone Prednazate Prednazoline Prednicarbate ( prednisolone ethylcarbonate propionate ) Prednimustine Prednisolamate ( prednisolone diethylaminoacetate ) Prednisolone esters Prednisone Prednisone esters Antagonists Steroidal : 6β - Hydroxy - 7α - thiomethylspironolactone 7α - Thiomethylspironolactone ( SC - 26519 ) 7α - Thioprogesterone ( SC - 8365 ) 7α - Thiospironolactone ( SC - 24813 ) 16α - Hydroxyprogesterone 17α - Hydroxyprogesterone 18 - Deoxyaldosterone Canrenoate potassium ( potassium canrenoate ) Canrenoic acid ( canrenoate ) Canrenone ( canrenoate y - lactone ) Dicirenone Dimethisterone Drospirenone Dydrogesterone Eplerenone Gestodene Guggulsterone Medrogestone Mespirenone Mexrenoate potassium Mexrenoic acid ( mexrenoate ) Mexrenone Oxprenoic acid ( oxprenoate ) Oxprenoate potassium ( RU - 28318 ) Pregnenolone Progesterone Prorenoate potassium Prorenoic acid ( prorenoate ) Prorenone RO - 14 - 9012 RU - 26752 SC - 5233 ( spirolactone ) SC - 8109 SC - 11927 ( CS - 1 ) SC - 19886 SC - 27169 Spirorenone Spironolactone Spiroxasone Tibolone Trimegestone ZK - 91587 ZK - 97894 Nonsteroidal : Amlodipine Apararenone Benidipine BR - 4628 Esaxerenone Felodipine Finerenone Nifedipine Nimodipine Nitrendipine PF - 03882845 SM - 368229 See also Receptor / signaling modulators Mineralocorticoids and antimineralocorticoids Glucocorticoid receptor modulators List of corticosteroids Nicotinic acetylcholine receptor modulators nAChRs Agonists : 5 - HIAA A-84,543 A-366,833 A-582,941 A-867,744 ABT - 202 ABT - 418 ABT - 560 ABT - 894 Acetylcholine Altinicline Anabasine Anatoxin - a AR - R17779 Bephenium hydroxynaphthoate Butinoline Butyrylcholine Carbachol Choline Cotinine Cytisine Decamethonium Desformylflustrabromine Dianicline Dimethylphenylpiperazinium Epibatidine Epiboxidine Ethanol ( alcohol ) Ethoxysebacylcholine EVP - 4473 EVP - 6124 Galantamine GTS - 21 Ispronicline Ivermectin Levamisole Lobeline MEM - 63,908 ( RG - 3487 ) Morantel Nicotine ( tobacco ) NS - 1738 PHA - 543,613 PHA - 709,829 PNU - 120,596 PNU - 282,987 Pozanicline Pyrantel Rivanicline RJR - 2429 Sazetidine A SB - 206553 Sebacylcholine SIB - 1508Y SIB - 1553A SSR - 180,711 Suberyldicholine Suxamethonium ( succinylcholine ) Suxethonium ( succinyldicholine ) TC - 1698 TC - 1734 TC - 1827 TC - 2216 TC - 5214 TC - 5619 TC - 6683 Tebanicline Tribendimidine Tropisetron UB - 165 Varenicline WAY - 317,538 XY - 4083 Antagonists : 18 - MAC 18 - MC α - Neurotoxins ( e.g., α - bungarotoxin, α - cobratoxin, α - conotoxin, many others ) ABT - 126 Alcuronium Allopregnanolone Amantadine Anatruxonium AQW051 Atracurium Barbiturates ( e.g., pentobarbital, sodium thiopental ) BNC - 210 Bungarotoxins ( e.g., α - bungarotoxin, κ - bungarotoxin ) Bupropion BW - A444 Candocuronium iodide ( chandonium iodide ) Chlorisondamine Cisatracurium Coclaurine Coronaridine Curare Cyclopropane Dacuronium bromide Decamethonium Dehydronorketamine Desflurane Dextromethorphan Dextropropoxyphene Dextrorphan Diadonium DHβE Dihydrochandonium Dimethyltubocurarine ( metocurine ) Dioscorine Dipyrandium Dizocilpine ( MK - 801 ) Doxacurium Encenicline Enflurane Erythravine Esketamine Fazadinium Gallamine Gantacurium chloride Halothane Hexafluronium Hexamethonium ( benzohexonium ) Hydroxybupropion Hydroxynorketamine Ibogaine Isoflurane Ketamine Kynurenic acid Laudanosine Laudexium ( laudolissin ) Levacetylmethadol Levomethadone Malouetine ME - 18 - MC Mecamylamine Memantine Methadone Methorphan ( racemethorphan ) Methyllycaconitine Metocurine Mivacurium Morphanol ( racemorphan ) Neramexane Nitrous oxide Norketamine Pancuronium bromide Pempidine Pentamine Pentolinium Phencyclidine Pipecuronium bromide Progesterone Promegestone Radafaxine Rapacuronium bromide Reboxetine Rocuronium bromide Sevoflurane Stercuronium iodide Surugatoxin Thiocolchicoside Toxiferine Tramadol Trimetaphan camsilate ( trimethaphan camsylate ) Tropeinium Tubocurarine Vanoxerine Vecuronium bromide Xenon Precursors ( and prodrugs ) Acetyl - coA Adafenoxate Choline ( lecithin ) Citicoline Cyprodenate Dimethylethanolamine Glycerophosphocholine Meclofenoxate ( centrophenoxine ) Phosphatidylcholine Phosphatidylethanolamine Phosphorylcholine Pirisudanol See also : Receptor / signaling modulators Muscarinic acetylcholine receptor modulators Acetylcholine metabolism / transport modulators Progesterone receptor modulators PR Agonists Progesterone derivatives : 5α - Dihydroprogesterone 9α - Bromo - 11 - ketoprogesterone 11 - Dehydroprogesterone 11 - Deoxycorticosterone 16α - Hydroxyprogesterone 20α - Dihydroprogesterone Dimepregnen Diosgenin P1 - 185 Progesterone Quingestrone Retroprogesterone derivatives : Dydrogesterone Retroprogesterone Ro 6 - 3129 Trengestone 17α - Substituted progesterone derivatives : 6α - Methyl - 17α - bromoprogesterone 15β - Hydroxycyproterone acetate 17α - Hydroxyprogesterone ( hydroxyprogesterone ) 17α - Methylprogesterone Acetomepregenol ( mepregenol diacetate ) Algestone Algestone acetonide Algestone acetophenide Anagestone Anagestone acetate Butagest ( buterol ) Chlormadinone Chlormadinone acetate Cismadinone Cismadinone acetate Clogestone Clogestone acetate Clomegestone Clomegestone acetate Cyproterone acetate Delmadinone Delmadinone acetate Edogestrone Flugestone Flugestone acetate Flumedroxone Flumedroxone acetate Gestaclone Haloprogesterone Hydromadinone Hydromadinone acetate Hydroxyprogesterone acetate Hydroxyprogesterone caproate ( hydroxyprogesterone hexanoate ) Hydroxyprogesterone heptanoate ( hydroxyprogesterone enanthate ) Mecigestone ( pentarane B) Medrogestone Medroxyprogesterone Medroxyprogesterone acetate Megestrol Megestrol acetate Melengestrol Melengestrol acetate Mometasone Mometasone furoate Osaterone Osaterone acetate Pentagestrone Pentagestrone acetate Pentarane A Proligestone 19 - Norprogesterone derivatives : 19 - Norprogesterone Amadinone Amadinone acetate Demegestone Gestadienol Gestadienol acetate Gestonorone caproate ( gestronol hexanoate ) Gestronol ( gestonorone ) Nomegestrol Nomegestrol acetate Norgestomet ORG - 2058 Oxogestone Oxogestone phenpropionate ( xinogestone ) Promegestone Segesterone Segesterone acetate ( nestorone ) Trimegestone Testosterone derivatives : Progestins : 6, 6 - Difluoronorethisterone 6, 6 - Difluoronorethisterone acetate Allylestrenol Altrenogest Chloroethynylnorgestrel Cingestol Danazol Desogestrel Dienogest Ethisterone Ethynerone Etonogestrel Etynodiol Etynodiol diacetate Gestodene Gestrinone Levonorgestrel Levonorgestrel butanoate Lynestrenol Metynodiol Metynodiol diacetate Norelgestromin Norethisterone ( norethindrone ) Norethisterone acetate Norethisterone acetate oxime Norethisterone enanthate Noretynodrel Norgesterone Norgestimate Norgestrel Norgestrienone Norvinisterone Oxendolone Quingestanol Quingestanol acetate Tibolone Tigestol Tosagestin ; Anabolic -- androgenic steroids : 11β - Methyl - 19 - nortestosterone 11β - Methyl - 19 - nortestosterone dodecylcarbonate 19 - Nor - 5 - androstenediol 19 - Nor - 5 - androstenedione Bolandiol Bolandiol dipropionate Bolandione Dimethisterone Dienedione Dienolone Dimethandrolone Dimethandrolone buciclate Dimethandrolone dodecylcarbonate Dimethandrolone undecanoate Dimethyltrienolone Ethyldienolone Ethylestrenol ( ethylnandrol ) Methyldienolone Metribolone ( R - 1881 ) Methoxydienone ( methoxygonadiene ) Mibolerone Nandrolone Nandrolone esters ( e.g., nandrolone decanoate, nandrolone phenylpropionate ) Norethandrolone Normethandrone ( methylestrenolone, normethandrolone, normethisterone ) Tetrahydrogestrinone Trenbolone ( trienolone ) Trestolone Trestolone acetate Spirolactone derivatives : Canrenoic acid Canrenone Drospirenone Mespirenone Potassium canrenoate SC - 5233 ( spirolactone ) SC - 8109 Spironolactone Spirorenone Nonsteroidal : 3, 8 - Dihydrodiligustilide LG - 100128 Riligustilide RWJ - 26819 RWJ - 49853 RWJ - 60130 Tanaproget ZM - 182345 Mixed ( SPRMs ) Steroidal : Asoprisnil Asoprisnil ecamate Guggulsterone J1042 LG - 120838 Mifepristone ORG - 31710 ORG - 33628 Telapristone Ulipristal acetate Vilaprisan ZK - 137316 Nonsteroidal : Apigenin Kaempferol LG - 120920 Naringenin PRA - 910 Syringic acid Antagonists Steroidal : Aglepristone Lilopristone Lonaprisan Onapristone RTI 3021 -- 022 Toripristone Zanoterone Nonsteroidal : LG001447 LG - 100127 LG - 100128 LG - 120830 LG - 121046 Valproic acid ZM - 150271 ZM - 172406 mPR ( PAQR ) Agonists 5α - Dihydroprogesterone 5β - Dihydroprogesterone 11 - Deoxycortisone ( 21 - hydroxyprogesterone ) 11 - Deoxycortisol ( 17α, 21 - dihydroxyprogesterone ) 17α - Hydroxyprogesterone Allopregnanolone Mifepristone Pregnenolone Progesterone Antagonists Mifepristone See also Receptor / signaling modulators Progestogens and antiprogestogens Androgen receptor modulators Estrogen receptor modulators List of progestogens Sigma receptor modulators σ Agonists : 3 - PPP 4 - PPBP 5 - MeO - DMT Alazocine ( SKF - 10047 ) Amantadine ANAVEX2 - 73 Arketamine BD - 737 BD - 1052 Captodiame Citalopram CGRP Cloperastine Cocaine Cutamesine ( SA - 4503 ) Cyclazocine Dehydroepiandrosterone ( DHEA ) ( prasterone ) Dehydroepiandrosterone sulfate ( DHEA - S ) ( prasterone sulfate ) Dextrallorphan Dextromethorphan ( DXM ) Dextrorphan ( DXO ) Dimemorfan Dimethyltryptamine ( DMT ) Ditolylguanidine ( DTG ) Donepezil Eliprodil Escitalopram Fabomotizole ( afobazole ) Fluoxetine Fluvoxamine Ifenprodil Igmesine ( JO - 1784 ) IPAB Ketamine L - 687384 MDMA ( midomafetamine ) Memantine Methamphetamine Methoxetamine Methylphenidate Nepinalone Neuropeptide Y Noscapine OPC - 14523 Opipramol Pentazocine Pentoxyverine ( carbetapentane ) PRE-084 Pregnenolone Pregnenolone sulfate Pridopidine Racemethorphan ( methorphan ) Racemorphan ( morphanol ) UMB - 23 UMB - 82 Antagonists : 3 - PPP AC - 927 BD - 1008 BD - 1031 BD - 1047 BD - 1060 BD - 1063 BD - 1067 BMY - 14802 ( BMS - 181100 ) CM - 156 Dup - 734 E-5842 E-52862 ( S1RA ) Haloperidol LR - 132 LR - 172 MS - 377 NE - 100 NPC - 16377 Panamesine ( EMD - 57455 ) PD - 144418 Pentazocine Progesterone Rimcazole ( BW - 234U ) Sertraline SR - 31742A Allosteric modulators : Phenytoin ; Positive : Methylphenylpiracetam SOMCL - 668 Unknown / unsorted : 3 - Methoxydextrallorphan 3 - MeO - PCP 4C - T - 2 4 - IBP 4 - IPBS 4 - MeO - PCP 5 - MeO - DALT 5 - MeO - DiPT Amitriptyline Azidopamil Chlorpromazine Clemastine Clomipramine Clorgiline D - Deprenyl DiPT DPT Ibogaine Imipramine KCR - 12 - 83.1 Nemonapride Noribogaine RHL - 033 RS - 67,333 RTI - 55 Saffron Safinamide Selegiline Spipethiane Trifluoperazine W - 18 YKP10A σ Agonists : 3 - PPP Arketamine BD - 1047 BD1063 Ditolylguanidine ( DTG ) DKR - 1005 DKR - 1051 Haloperidol Ifenprodil Ketamine MDMA ( midomafetamine ) Methamphetamine OPC - 14523 Opipramol PB - 28 Phencyclidine Siramesine ( Lu 28 - 179 ) UKH - 1114 Antagonists : AC - 927 BD - 1008 BD - 1067 CM - 156 CT - 1812 LR - 172 MIN - 101 Panamesine ( EMD - 57455 ) SAS - 0132 Unknown / unsorted : 3 - Methoxydextrallorphan 3 - MeO - PCE 4 - MeO - PCP 5 - MeO - DALT 5 - MeO - DiPT Clemastine DiPT DPT Ibogaine Nemonapride Nepinalone Noribogaine Pentazocine RS - 67,333 Safinamide TMA UMB - 23 UMB - 82 W - 18 Unsorted Agonists : Berberine Ethylketazocine Fourphit Metaphit Nalbuphine Naluzotan Tapentadol Tenocyclidine Antagonists : AHD1 AZ66 Lamotrigine Naloxone SM - 21 UMB - 100 UMB - 101 UMB - 103 UMB - 116 YZ - 011 YZ - 069 YZ - 185 Allosteric modulators : SKF - 83959 Unknown / unsorted : 18 - Methoxycoronaridine BMY - 13980 Butaclamol Caramiphen Carvotroline Chlorphenamine ( chlorpheniramine ) Chlorpromazine Cinnarizine Cinuperone Clocapramine Dezocine EMD - 59983 Hypericin ( St. John 's wort ) Fluphenazine Gevotroline ( WY - 47384 ) Mepyramine ( pyrilamine ) Molindone Perphenazine Pimozide Proadifen Promethazine Propranolol Quinidine Remoxipride SL 82.0715 SR - 31747A Tiospirone ( BMY - 13859 ) Venlafaxine See also : Receptor / signaling modulators Xenobiotic - sensing receptor modulators CAR Agonists : 6, 7 - Dimethylesculetin Amiodarone Artemisinin Benfuracarb Carbamazepine Carvedilol Chlorpromazine Chrysin CITCO Clotrimazole Cyclophosphamide Cypermethrin DHEA ( prasterone ) Efavirenz Ellagic acid Griseofulvin Methoxychlor Mifepristone Nefazodone Nevirapine Nicardipine Octicizer Permethrin Phenobarbital Phenytoin Pregnanedione ( 5β - dihydroprogesterone ) Reserpine TCPOBOP Telmisartan Tolnaftate Troglitazone Valproic acid Antagonists : 3, 17β - Estradiol 3α - Androstanol 3α - Androstenol 3β - Androstanol 17 - Androstanol AITC Ethinylestradiol Meclizine Nigramide J Okadaic acid PK - 11195 S - 07662 T - 0901317 PXR Agonists : 17α - Hydroxypregnenolone 17α - Hydroxyprogesterone Δ - Androstenedione Δ - Androstenediol Δ - Androstenedione AA - 861 Allopregnanediol Allopregnanedione ( 5α - dihydroprogesterone ) Allopregnanolone ( brexanolone ) Alpha - Lipoic acid Ambrisentan AMI - 193 Amlodipine besylate Antimycotics Artemisinin Aurothioglucose Bile acids Bithionol Bosentan Bumecaine Cafestol Cephaloridine Cephradine Chlorpromazine Ciglitazone Clindamycin Clofenvinfos Chloroxine Clotrimazole Colforsin Corticosterone Cyclophosphamide Cyproterone acetate Demecolcine Dexamethasone DHEA ( prasterone ) DHEA - S ( prasterone sulfate ) Dibunate sodium Diclazuril Dicloxacillin Dimercaprol Dinaline Docetaxel Docusate calcium Dodecylbenzenesulfonic acid Dronabinol Droxidopa Eburnamonine Ecopipam Enzacamene Epothilone B Erythromycin Famprofazone Febantel Felodipine Fenbendazole Fentanyl Flucloxacillin Fluorometholone Griseofulvin Guggulsterone Haloprogin Hetacillin potassium Hyperforin Hypericum perforatum ( St John 's wort ) Indinavir sulfate Lasalocid sodium Levothyroxine Linolenic acid LOE - 908 Loratadine Lovastatin Meclizine Methacycline Methylprednisolone Metyrapone Mevastatin Mifepristone Nafcillin Nicardipine Nicotine Nifedipine Nilvadipine Nisoldipine Norelgestromin Omeprazole Orlistat Oxatomide Paclitaxel Phenobarbital Piperine Plicamycin Prednisolone Pregnanediol Pregnanedione ( 5β - dihydroprogesterone ) Pregnanolone Pregnenolone Pregnenolone 16α - carbonitrile Proadifen Progesterone Quingestrone Reserpine Reverse triiodothyronine Rifampicin Rifaximin Rimexolone Riodipine Ritonavir Simvastatin Sirolimus Spironolactone Spiroxatrine SR - 12813 Suberoylanilide Sulfisoxazole Suramin Tacrolimus Tenylidone Terconazole Testosterone isocaproate Tetracycline Thiamylal sodium Thiothixene Thonzonium bromide Tianeptine Troglitazone Troleandomycin Tropanyl 3, 5 - dimethulbenzoate Zafirlukast Zeranol Antagonists : Ketoconazole Sesamin See also Receptor / signaling modulators Nuclear receptor modulators Retrieved from `` https://en.wikipedia.org/w/index.php?title=Progesterone&oldid=800199431 '' Categories : 11β - Hydroxysteroid dehydrogenase inhibitors Antimineralocorticoids Diketones GABAA receptor positive allosteric modulators Glucocorticoids Glycine receptor antagonists Neurosteroids Hepatotoxins Hormones of the hypothalamus - pituitary - adrenal axis Hormones of the hypothalamus - pituitary - gonad axis Hormones of the hypothalamic - pituitary - prolactin axis Hormones of the ovary Hormones of the placenta Hormones of the suprarenal cortex Hormones of the brain Hormones of the pregnant female Human female endocrine system Human hormones Pregnane X receptor agonists Pregnanes Progestogens Sex hormones Sigma antagonists Steroid hormones Total synthesis Hidden categories : CS1 maint : Multiple names : authors list Articles without InChI source ECHA InfoCard ID from Wikidata Articles with changed KEGG identifier Articles with changed InChI identifier Articles containing unverified chemical infoboxes All articles with unsourced statements Articles with unsourced statements from June 2016 Articles with unsourced statements from April 2014 Articles containing links to copyright violations Talk Contents About Wikipedia Беларуская Български Bosanski Català Čeština Dansk Deutsch ދިވެހިބަސް Ελληνικά Español Euskara فارسی Français Gaeilge Galego 한국어 Հայերեն Bahasa Indonesia Italiano עברית Lietuvių Magyar Македонски മലയാളം Nederlands 日本 語 Norsk Occitan Oʻzbekcha / ўзбекча Polski Português Română Русский Scots Simple English Slovenščina کوردی Српски / srpski Srpskohrvatski / српскохрватски Suomi Svenska Türkçe Українська Tiếng Việt 中文 Edit links This page was last edited on 12 September 2017, at 01 : 36. 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Question: where does the progesterone that helps maintain the pregnancy come from
Answer: the ovaries