Compound: ethisterone
SMILES: O=C1C=C2[C@]([C@@H]3[C@H]([C@H]4[C@]([C@](O)(C#C)CC4)(C)CC3)CC2)(C)CC1
InChIKey: CHNXZKVNWQUJIB-CEGNMAFCSA-N
Synonyms: ethisterone, 434-03-7, Aethisteron, Etisterona, Nugestoral, Syngestrotabs, Trosinone, Pregneninolone, Ora-Lutin, Ethynyltestosterone, 17alpha-Ethynyltestosterone, Aethisteronum, Ethisteronum, Progestolets, Anhydrohydroxyprogesterone, Anhydroxyprogesterone, Prodroxan, Produxan, Progestab, Pranone, Etisterone, Praegninum, Progestoral, 17alpha-Ethinyltestosterone, 17alpha-Ethinyl testosterone, DTXSID2023016, P201BVY1MJ, NSC-9565, 17alpha-Ethynyl-17beta-hydroxyandrost-4-en-3-one, 17-beta-Hydroxy-17-alpha-ethynyl-4-androsten-3-one, DTXCID003016, (8R,9S,10R,13S,14S,17R)-17-ethynyl-17-hydroxy-10,13-dimethyl-2,6,7,8,9,11,12,14,15,16-decahydro-1H-cyclopenta[a]phenanthren-3-one, CHEBI:34749, 17-Ethynyl-17beta-hydroxyandrost-4-en-3-one, Pregn-4-en-20-yn-3-one, 17-hydroxy-, (17alpha)-, NSC9565, 17 alpha Ethynyltestosterone, 17 alpha-Ethynyltestosterone, (8R,9S,10R,13S,14S,17R)-17-ethynyl-17-hydroxy-10,13-dimethyl-2,6,7,8,9,11,12,14,15,16-decahydro-1H-cyclopenta(a)phenanthren-3-one, RefChem:138413, G03DC04, 207-096-5, Ethinone, Pregnin, MFCD00003656, MLS000069396, CHEMBL241694, (17alpha)-17-hydroxypregn-4-en-20-yn-3-one, 17-Ethinyltestosterone, SMR000058320, 17-hydroxy-17alpha-pregn-4-en-20-yn-3-one, (8R,9S,10R,13S,14S,17R)-17-ethynyl-17-hydroxy-10,13-dimethyl-1,2,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-3H-cyclopenta[a]phenanthren-3-one, (8R,9S,10R,13S,14S,17R)-17-ethynyl-17-hydroxy-10,13-dimethyl-6,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3(2H)-one, Ethinyl testosterone, Etisterone [DCIT], 17-Ethinyl testosterone, Ethisteronum [INN-Latin], Etisterona [INN-Spanish], UNII-P201BVY1MJ, 17-alpha-Ethynyltestosterone, Ethisterone [INN:BAN:NF], Pregneninolone;, Ethnyltestosterone;, NCGC00095023-01, NCGC00159363-02, CAS-434-03-7, Ethynyltestosterone;, NSC 9565, EINECS 207-096-5, Ethisterone anhydrohydroxyprogesterone, BRN 1889895, 17-Ethynyl-17.beta.-hydroxyandrost-4-en-3-one, 17-Ethynyltestosterone;, 17?-Ethynyltestosterone, AI3-26421, ETHISTERONE [MI], Opera_ID_1078, Prestwick3_000261, ETHISTERONE [INN], EC 207-096-5, 17-Hydroxy-17-alpha-pregn-4-en-20-yn-3-one, ETHISTERONE [MART.], SCHEMBL24475, BSPBio_000102, ETHISTERONE [USP-RS], ETHISTERONE [WHO-DD], 4-08-00-01225 (Beilstein Handbook Reference), Androst-4-en-3-one, 17alpha-ethynyl-17-hydroxy-, MLS001076282, BPBio1_000114, orb1310743, orb3025575, Ethisterone, >=99% (HPLC), HMS2090E14, HMS2095F04, HMS2234J08, HMS3712F04, HY-B0487, MSK10473, Tox21_111393, Tox21_111604, Tox21_302324, BBL028141, BDBM50198711, s2611, STK801873, AKOS005622724, Tox21_111604_1, AC-2170, CCG-220261, FE22865, 17?-Hydroxypregn-4-en-20-yn-3-one, NCGC00021466-03, NCGC00021466-05, NCGC00021466-06, NCGC00255184-01, 17alpha-hydroxypregn-4-en-20-yn-3-one, AS-13381, SY075636, AB00490005, E0040, NS00007266, AB00384255-11, AB00384255-13, AB00384255_14, Ethisterone, VETRANAL(TM), analytical standard, 17alpha-Pregn-4-en-20-yn-3-one, 17-hydroxy-, SR-01000002984, 17-alpha-Pregn-4-en-20-yn-3-one, 17-hydroxy-, 17alpha-ethynyl-17beta-hydroxy-androst-4-en-3-one, Q5403717, SR-01000002984-2, BRD-K03981224-001-02-9, BRD-K03981224-001-19-3, Pregn-4-en-20-yn-3-one, 17-hydroxy-, (17-alpha)-, (8R,10R,13S,17R)-17-Ethynyl-17-hydroxy-10,13-dimethyl-1,2,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-cyclopenta[a]phenanthren-3-one, (8R,9S,10R,13S,14S,17S)-17-ethynyl-17-hydroxy-10,13-dimethyl-1,7,8,10,11,12,13,15,16,17-decahydro-2H-cyclopenta[a]phenanthren-3(6H,9H,14H)-one
Theoretical properties:
molecular_formula: C21H28O2
molecular_weight: 312.4 g/mol
exact_mass: 312.208930132 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 1
hydrogen_bond_acceptor_count: 2
rotatable_bond_count: 1
heavy_atom_count: 23
topological_polar_surface_area: 37.3 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
Descriptions:
pubchem: Ethisterone is a 17beta-hydroxy steroid that is testosterone in which the 17beta hydrogen is replaced by an ethynyl group. Ethisterone was the first orally active progestin and is a metabolite of danazol. It has a role as a drug metabolite and a progestin. It is a tertiary alcohol, a 17beta-hydroxy steroid, a 3-oxo-Delta(4) steroid and a terminal acetylenic compound. It is functionally related to a testosterone.
chebi: A 17β-hydroxy steroid that is testosterone in which the 17β hydrogen is replaced by an ethynyl group. Ethisterone was the first orally active progestin and is a metabolite of danazol.
chembl: ETHISTERONE is a small molecule listed in the ChEMBL database and has reached clinical trial phase 3.0.
wikipedia: Ethisterone, also known as ethinyltestosterone, pregneninolone, and anhydrohydroxyprogesterone and formerly sold under the brand names Proluton C and Pranone among others, is a progestin medication which was used in the treatment of gynecological disorders but is now no longer available. It was used alone and was not formulated in combination with an estrogen. The medication is taken by mouth.
Side effects of ethisterone include masculinization among others. Ethisterone 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 some androgenic and anabolic activity and no other important hormonal activity.
Ethisterone was discovered in 1938 and was introduced for medical use in Germany in 1939 and in the United States in 1945. It was the second progestogen to be marketed, following injected progesterone in 1934, and was both the first orally active progestogen and the first progestin to be introduced. Ethisterone was followed by the improved and much more widely used and known progestin norethisterone in 1957.