Compound: OXANDROLONE
SMILES: O=C1OC[C@@]2([C@@H]3[C@H]([C@H]4[C@]([C@](O)(C)CC4)(C)CC3)CC[C@H]2C1)C
InChIKey: QSLJIVKCVHQPLV-PEMPUTJUSA-N
Synonyms: OXANDROLONE, Anavar, Lonavar, Vasorome, Oxandrin, Provitar, 53-39-4, Protivar, Oxandrolona, Oxandrolonum, Oxandrolone ciii, SC 11585, SC-11585, 17beta-Hydroxy-17-methyl-2-oxa-5alpha-androstan-3-one, 7H6TM3CT4L, NSC-67068, 8075 CB, CHEBI:7820, (1S,3aS,3bR,5aS,9aS,9bS,11aS)-1-hydroxy-1,9a,11a-trimethyl-2,3,3a,3b,4,5,5a,6,9,9b,10,11-dodecahydroindeno[4,5-h]isochromen-7-one, DTXSID8023399, 2-Oxaandrostan-3-one, 17-hydroxy-17-methyl-, (5alpha,17beta)-, 2-Oxa-5alpha-androstan-3-one, 17beta-hydroxy-17-methyl-, NSC67068, (1S,2S,7S,10R,11S,14S,15S)-14-hydroxy-2,14,15-trimethyl-4-oxatetracyclo(8.7.0.0^(2,7).0^(11,15))heptadecan-5-one, (1S,2S,7S,10R,11S,14S,15S)-14-hydroxy-2,14,15-trimethyl-4-oxatetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-5-one, (1S,3aS,3bR,5aS,9aS,9bS,11aS)-1-hydroxy-1,9a,11a-trimethyl-2,3,3a,3b,4,5,5a,6,9,9b,10,11-dodecahydroindeno(4,5-h)isochromen-7-one, SC11585, RefChem:58389, DTXCID203399, A14AA08, 200-172-9, Ossandrolone [DCIT], Oxandrolonum [INN-Latin], Oxandrolona [INN-Spanish], (4aS,4bS,6aS,7S,9aS,9bR,11aS)-7-hydroxy-4a,6a,7-trimethyltetradecahydroindeno[4,5-h]isochromen-2(1H)-one, Ossandrolone, 17beta-Hydroxy-17alpha-methyl-2-oxa-5alpha-androstan-3-one, Oxandrin (TN), Oxandrolone (1.0 mg/mL in Acetonitrile), 8075 C. B., HSDB 3373, EINECS 200-172-9, NSC 67068, UNII-7H6TM3CT4L, Oxandrolone (JAN/USP/INN), Oxandrin;Anavar, 17-beta-hydroxy-17-methyl-2-oxa-androstan-3-one, Dodecahydro-3-hydroxy-6-(hydroxy-methyl)-3,3a,6-trimethyl-1H-benz(e)indene-7-acetic acid delta-lactone, Oxandrolone [USAN:USP:INN:BAN:JAN], 8075 C.B., OXANDROLONE [MI], OXANDROLONE [INN], OXANDROLONE [JAN], OXANDROLONE [HSDB], OXANDROLONE [USAN], OXANDROLONE [VANDF], OXANDROLONE [MART.], OXANDROLONE [WHO-DD], SCHEMBL148881, GTPL7092, 2-Oxaandrostan-3-one, 17-hydroxy-17-methyl-, (5.alpha.,17.beta.)-, CHEMBL1200436, Oxandrolone, >=98% (HPLC), OXANDROLONE [ORANGE BOOK], OXANDROLONE CIII [USP-RS], 2-Oxa-5-alpha-androstan-3-one, 17-beta-hydroxy-17-methyl-, HMS3712E22, OXANDROLONE [USP MONOGRAPH], HY-B0707, 2-Oxaandrostan-3-one, 17-hydroxy-17-methyl-, (5-alpha,17-beta)-, BDBM50594919, AKOS025401400, CCG-220110, DB00621, AC-14975, FH153287, C07346, D00462, AB01559948-01, Q420859, SR-01000872645, SR-01000872645-1, BRD-K92467929-001-01-1, 17alpha-Methyl-17beta-hydroxy-2-oxa-5alpha-androstan-3-one, (4aS,4bS,6aS,7S,9aS,9bR,11aS)-7-Hydroxy-4a,6a,7-trimethyltetradecahydrocyclopenta[5,6]naphtho[1,2-c]pyran-2(1H)-one
Theoretical properties:
molecular_formula: C19H30O3
molecular_weight: 306.4 g/mol
exact_mass: 306.21949481 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 1
hydrogen_bond_acceptor_count: 3
rotatable_bond_count: 0
heavy_atom_count: 22
topological_polar_surface_area: 46.5 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
physical_state: Crystals
color: Crystals
odor: ODORLESS
solubility: PRACTICALLY INSOL IN WATER; SPARINGLY SOL IN ALC, ACETONE; FREELY SOL IN CHLOROFORM
Descriptions:
{"pubchem": "Oxandrolone is a 17beta-hydroxy steroid, a 3-oxo steroid, an anabolic androgenic steroid and an oxa-steroid. It has a role as an anabolic agent and an androgen.", "chebi": null, "chembl": "OXANDROLONE is a small molecule listed in the ChEMBL database and has reached clinical trial phase 4.0.", "wikipedia": "Oxandrolone is an androgen and synthetic anabolic steroid (AAS) medication to help promote weight gain in various situations, to help offset protein catabolism caused by long-term corticosteroid therapy, to support recovery from severe burns, to treat bone pain associated with osteoporosis, to aid in the development of girls with Turner syndrome, and for other indications. It is taken by mouth. It was sold under the brand names Oxandrin and Anavar, among others.\nThe drug is a synthetic androgen and anabolic steroid, hence is an agonist of the androgen receptor (AR), the biological target of androgens such as testosterone and dihydrotestosterone.\nSide effects of oxandrolone include severe cases of peliosis hepatis, sometimes associated with liver failure and intra-abdominal hemorrhage; liver tumors, sometimes fatal; and blood lipid changes associated with increased risk of atherosclerosis. Additional warnings include the risks associated with cholestatic hepatitis, hypercalcemia in patients with breast cancer, and increased risk for the development of prostatic hypertrophy and prostatic carcinoma in older patients. It has strong anabolic effects and weak androgenic effects, which gave it a mild side effect profile in that regard and made it especially suitable for use in women. Milder side effects in women were increased sexual desire, symptoms of hyperandrogenism such as acne, and symptoms of masculinization such as increased hair growth and voice changes. \nOxandrolone was first described in 1962 and introduced for medical use in 1964. The drug is a controlled substance in many countries, so non-medical use for purposes such as improving physique and performance has been generally illicit.\nIn the United States, the FDA's Endocrinologic and Metabolic Drugs Advisory Committee unanimously concluded in 1984 that there was no evidence of efficacy for oxandrolone. On March 26, 2019, Gemini asked FDA to withdraw approval for all doses of the drug, stating that they were no longer marketing it. FDA notified Gemini and other license holders on December 16, 2022, that it believed that the potential problems with the drug  that the drug were sufficiently serious that it should be removed from the market, citing the 1984 finding of lack of efficacy and the extensive safety warnings and precautions listed on the prescribing information, \"including peliosis hepatis, sometimes associated with liver failure and intra-abdominal hemorrhage; liver cell tumors, sometimes fatal; and blood lipid changes that are known to be associated with increased risk of atherosclerosis\" as well as \"cholestatic hepatitis, hypercalcemia in patients with breast cancer, and increased risk for the development of prostatic hypertrophy and prostatic carcinoma in geriatric patients.\" Gemini and Sandoz requested that the FDA completely withdraw approval for the drug."}