Compound: norethindrone
SMILES: O=C1C=C2[C@@H]([C@@H]3[C@H]([C@H]4[C@]([C@](O)(C#C)CC4)(C)CC3)CC2)CC1
InChIKey: VIKNJXKGJWUCNN-XGXHKTLJSA-N
Synonyms: norethindrone, Norethisterone, 68-22-4, Micronor, Norethisteron, Norlutin, 19-Norethisterone, Anovule, Gestest, Micronovum, Norcolut, Norluten, Camila, Noriday, Utovlan, Primolut-N, Micronett, Noralutin, Norethynodrone, Norgestin, Proluteasi, Conludaf, Conludag, Norluton, Triella, Mini-Pe, Norfor, Norpregneninolone, Mini-pill, Nor-QD, Ethinylnortestosterone, Noresthisterone, Norethisteronum, Norethyndron, Noretisterona, Minovlar, Utovlar, Norpregneninlone, 19-Nor-ethindrone, Microneth, Norethin, Gencept, Norpregneninotone, Ethynylnortestosterone, Norcept-E, 17alpha-Ethynyl-19-nortestosterone, Errin, Menzol, Nor-Q.D., Primolut N, 17alpha-Ethinyl-19-nortestosterone, Anhydrohydroxynorprogesterone, 19-Norethinyltestosterone, Ethinyl-19-nortestosterone, NSC-9564, 17alpha-Ethynyl-4-estren-17-ol-3-one, 19-Nor-17-ethinyltestosterone, 17-alpha-Ethynyl-19-nortestosterone, 19-Nor-17-alpha-ethynyltestosterone, 17alpha-Ethinylestra-4-en-17beta-ol-3-one, 17-Hydroxy-19-nor-17alpha-pregn-4-en-20-yn-3-one, 17beta-Hydroxy-19-norpregn-4-en-20-yn-3-one, 17-alpha-Ethynyl-4-estren-17-ol-3-one, 19-Nor-17alpha-ethynyl-17beta-hydroxy-4-androsten-3-one, 17alpha-Ethynyl-17-hydroxy-4-estren-3-one, 19-Nor-17alpa-ethynyltestosterone, Norethindrone (USP), 19-nor-17alpha-Ethynylandrosten-17beta-ol-3-one, 4-Estren-17alpha-ethynyl-17beta-ol-3-one, 17alpha-Ethynyl-19-norandrost-4-en-17beta-ol-3-one, 17-alpha-Ethynyl-17-hydroxy-4-estren-3-one, DTXSID9023380, SC 4640, 17alpha-Ethynyl-17beta-hydroxy-19-norandrost-4-en-3-one, 17-beta-Hydroxy-19-norpregn-4-en-20-yn-3-one, 19-Nortestosterone, 17-ethynyl-, 17-ethynyl-17beta-hydroxyestr-4-en-3-one, 19-Nor-17-alpha-ethynylandrosten-17-beta-ol-3-one, 19-Nor-ethinyl--4,5-testosterone, 17-alpha-Ethynyl-19-norandrost-4-en-17-beta-ol-3-one, 17-Hydroxy-19-nor-17-alpha-pregn-4-en-20-yn-3-one, SC-4640, 19-Nor-17-alpha-ethynyl-17-beta-hydroxy-4-androsten-3-one, Norethindrone [USP], 17alpha-Ethynyl-19-nor-4-androsten-17beta-ol-3-one, T18F433X4S, (17-alpha)-17-Hydroxy-19-norpregn-4-en-20-yn-3-one, 17-alpha-Ethinylestra-4-en-17-beta-ol-3-one, 19-Nor-17alpha-pregn-4-en-20-yn-3-one, 17-hydroxy-, CHEBI:7627, DTXCID303380, (8R,9S,10R,13S,14S,17R)-17-ethynyl-17-hydroxy-13-methyl-1,2,6,7,8,9,10,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-3-one, 17-alpha-Ethinyl-17-beta-hydroxy-delta(sup:4)-estren-3-one, 17-alpha-Ethynyl-17-beta-hydroxy-19-norandrost-4-en-3-one, 17alpha-hydroxy-19-norpregn-4-en-20-yn-3-one, 19-Norpregn-4-en-20-yn-3-one, 17-hydroxy-, (17alpha)-, NORINYL COMPONENT NORETHINDRONE, VYFEMLA COMPONENT NORETHINDRONE, BREVICON COMPONENT NORETHINDRONE, TAYTULLA COMPONENT NORETHINDRONE, (17alpha)-17-ethynyl-17-hydroxyestra-4,8(14),9-trien-3-one, LO MINASTRIN FE COMPONENT NORETHINDRONE, MINASTRIN 24 FE COMPONENT NORETHINDRONE, NorQD, Nor QD, Norethidrone, Affodel, Deblitane, Heather, Incassia, Jencycla, Norlyroc, Orquidea, Sharobel, Emzahh, Lyleq, Lyza, Micronor hrt, Nora Be, (8R,9S,10R,13S,14S,17R)-17-ethynyl-17-hydroxy-13-methyl-1,2,6,7,8,9,10,11,12,14,15,16-dodecahydrocyclopenta(a)phenanthren-3-one, MELEYA, RefChem:55725, (1S,2R,10R,11S,14R,15S)-14-ethynyl-14-hydroxy-15-methyltetracyclo(8.7.0.02,7.011,15)heptadec-6-en-5-one, 200-681-6, 19-Nor-17alpha-ethynyltestosterone, Normapause, 19-Norethindrone, Activella, Norethisterone [INN], Norethindrone (Standard), Anovulatorio, Ciclovulan, Norethadrone, Norethynodron, Estrinor, Synphase, Genora, Milli, Nelova, Nodiol, Noraethisteronum, CHEMBL1162, Synphasic 28, MLS001163874, Brevinor 21, Brevinor 28, Trinovum 21, Noriday 28, Jenest-28, Ethynylmortestosterone, Brevinor-1 21, Brevinor-1 28, Tri-Norinyl, Ovysmen 1 35, Noretisterone [DCIT], Ortho-Novum 1 35, Ortho-Novum 1 50, MFCD00067596, Ortho-Novum 7 7 7, Ovysmen 0.5 35, Ortho 1 35, Ortho 7 7 7, Noretisterone, Norethisteronum [INN-Latin], Noretisterona [INN-Spanish], Nora-BE, (8R,9S,10R,13S,14S,17R)-17-Ethynyl-17-hydroxy-13-methyl-6,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3(2H)-one, Norethisterone [Progestins], (17alpha)-17-hydroxy-19-norpregn-4-en-20-yn-3-one, (14beta,17alpha)-17-Ethynyl-17-Hydroxyestr-4-En-3-One, 17-Ethinyl-19-nortestosterone, Micronor (TN), SMR000499579, CCRIS 484, norethisterone (norethindrone), Primolut-N (TN), Camila (TN), N.E.E., 19-Nor-17-ethinyl testosterone, HSDB 3370, Norethindrone (Norethisterone), EINECS 200-681-6, BRN 1915671, 19-Norpregn-4-en-20-yn-3-one, 17-hydroxy-, (17.alpha.)-, UNII-T18F433X4S, AI3-26422, 17-Ethynyl-19-Nortestosterone, Norethisterone RS, CAS-68-22-4, Norethisterone CRS, Estr-4-en-3-one, 17alpha-ethynyl-17-hydroxy-, NCGC00094738-01, ENT, NET, Prestwick_646, 17-alpha-19-Norpregn-4-en-20-yn-3-one, 17-hydroxy-, 17alpha-Ethinyl-17beta-hydroxy-delta(sup:4)-estren-3-one, Norethisterone (JP18), Prestwick0_000253, Prestwick1_000253, Prestwick2_000253, Prestwick3_000253, NORETHINDRONE [MI], EC 200-681-6, 17alpha-Ethynyl-17beta-hydroxyestr-4-en-3-one, NORETHINDRONE [HSDB], NORETHISTERONE [JAN], SCHEMBL23390, BSPBio_000066, NORETHINDRONE [VANDF], MLS001076679, Norethisterone [EP monograph], SPBio_002285, NORETHINDRONE [USP-RS], NORETHISTERONE [MART.], BPBio1_000074, GTPL2880, orb1308376, orb3139938, NORETHISTERONE [WHO-DD], NORETHISTERONE [WHO-IP], 17-Ethinyl-19-nor-testosterone, HY-B0554R, 19-Nor-17-alpha-pregn-4-en-20-yn-3-one, 17-hydroxy-, MSK2203, HMS1568D08, HMS2090D21, HMS2095D08, HMS2231E18, HMS3259C16, HMS3712D08, NORETHINDRONE [ORANGE BOOK], HY-B0554, 17alpha-pregn-4-en-20-yn-3-one, NORETHINDRONE [USP IMPURITY], NORETHISTERONE [EP IMPURITY], Tox21_111322, Tox21_302427, 19-Norethindrone, >=98%, powder, BDBM50148732, LMST02030097, MSK2203-100A, MSK2203-100M, NORETHINDRONE [USP MONOGRAPH], s4040, AKOS005267172, ARANELLE COMPONENT NORETHINDRONE, NORETHISTERONUM [WHO-IP LATIN], Tox21_111322_1, CCG-220253, DB00717, FN26442, NC00576, FEMCON FE COMPONENT NORETHINDRONE, 17?-ETHYNYL-19-NORTESTOSTERONE, NCGC00179669-01, NCGC00179669-02, NCGC00179669-04, NCGC00255187-01, AC-11100, AC-33117, AS-56451, CPD000499579, Norethisterone for system suitability CRS, NORQUEST FE COMPONENT NORETHINDRONE, SY066763, 17alpha-Ethynyl-17-hydroxyest-4-en-3-one, 17alpha-Ethynyl-3-oxo-4-estren-17beta-ol, CS-0694821, N0449, NS00009098, 17alpha-ethynyl-17-hydroxy-Estr-4-en-3-one, Norethindrone Solution in Methanol, 100ug/mL, Norethisterone 100 microg/mL in Acetonitrile, C05028, C76161, D00182, LEVONORGESTREL IMPURITY U [EP IMPURITY], 17beta-Hydroxy-17alpha-ethynylestr-4-en-3-one, 17-alpha-Ethynyl-17-beta-hydroxy-4-estren-3-one, Norethindrone Solution in Acetonitrile, 100ug/mL, Q421352, SR-01000765382, 17-Hydroxy-19-nor-17?-pregn-4-en-20-yn-3-one, 17alpha-Ethinyl-17alpha-Ethinyl-19-nortestosterone, doi:10.14272/VIKNJXKGJWUCNN-XGXHKTLJSA-N.1, SR-01000765382-3, 13-methyl-17alpha-ethynyl-17-hydroxygon-4-en-3-one, 17-Hydroxy-17-alpha-19-norpregn-4-en-20-yn-3-one, 17-Hydroxy-17alpha-19-norpregn-4-en-20-yn-3-one, 17-hydroxy-19-nor-17alpha-pregn-4-en-20yn-3-one, 19-Norethindrone, VETRANAL(TM), analytical standard, BRD-K92073408-001-03-3, BRD-K92073408-001-16-5, NORETHISTERONE ACETATE IMPURITY A [EP IMPURITY], 17-Hydroxy-(17alpha)-19-Norpregn-4-en-20-yn-3-one, 17-Ethynyl-17-hydroxyestr-4-en-3-one (ACD/Name 4.0), Norethisterone, British Pharmacopoeia (BP) Reference Standard, Norethisterone, European Pharmacopoeia (EP) Reference Standard, Norethindrone, United States Pharmacopeia (USP) Reference Standard, Norethisterone for system suitability, European Pharmacopoeia (EP) Reference Standard, (8R,9S,10R,13S,14S,17R)-17-ethynyl-17-hydroxy-13-methyl-1,2,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-3H-cyclopenta[a]phenanthren-3-one, Levonorgestrel EP Impurity U; Norethindrone; Norethisterone; Norethisterone Acetate EP Impurity A, Norethindrone (Norethisterone), Pharmaceutical Secondary Standard; Certified Reference Material
Theoretical properties:
molecular_formula: C20H26O2
molecular_weight: 298.4 g/mol
exact_mass: 298.193280068 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 1
hydrogen_bond_acceptor_count: 2
rotatable_bond_count: 1
heavy_atom_count: 22
topological_polar_surface_area: 37.3 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
physical_state: White crystalline powder
color: White crystalline powder
odor: ODORLESS
melting_point: 202-208C
solubility: PRACTICALLY INSOL IN WATER; SOL IN CHLOROFORM, ETHER, DIOXANE; SOL @ 25 °C: 1 IN 12.5 PARTS 95% ETHANOL, 1 IN 4 PARTS ACETONE /ACETATE/
vapor_pressure: 3.14x10-7 mmHg
Descriptions:
{"pubchem": "Norethisterone (Norethindrone) can cause cancer according to California Labor Code. It can cause developmental toxicity according to state or federal government labeling requirements.", "chebi": "A 17\u03b2-hydroxy steroid that is testosterone in which the hydrogen at position 17 is replaced by an ethynyl group and in which the methyl group attached to position 10 is replaced by hydrogen.", "chembl": "NORETHINDRONE is a small molecule listed in the ChEMBL database and has reached clinical trial phase 4.0.", "wikipedia": "Norethisterone, also known as norethindrone and sold under the brand name Norlutin among others, is a progestin medication used in birth control pills, menopausal hormone therapy, and for the treatment of gynecological disorders. The medication is available in both low-dose and high-dose formulations and both alone and in combination with an estrogen. It is used by mouth or, as norethisterone enanthate, by injection into muscle.\nSide effects of norethisterone include menstrual irregularities, headaches, nausea, breast tenderness, mood changes, acne, increased hair growth. Norethisterone is a progestin, or a synthetic progestogen, and hence is an agonist of the progesterone receptor, the biological target of progestogens like progesterone. It has weak androgenic and estrogenic activity, mostly at high dosages, and no other important hormonal activity.\nNorethisterone was discovered in 1951 and was one of the first progestins to be developed. It was first introduced for medical use on its own in 1957 and was introduced in combination with an estrogen for use as a birth control pill in 1963. It is sometimes referred to as a \"first-generation\" progestin. Like desogestrel and Norgestrel, Norethisterone is available as a progestogen-only \"mini pill\" for birth control. Norethisterone is marketed widely throughout the world. It is available as a generic medication. In 2023, it was the 136th most commonly prescribed medication in the United States, with more than 4 million prescriptions. It is on the World Health Organization's List of Essential Medicines."}