Compound: allylestrenol
SMILES: O[C@@]1([C@@]2([C@H]([C@H]3[C@@H]([C@@H]4C(=CCCC4)CC3)CC2)CC1)C)CC=C
InChIKey: ATXHVCQZZJYMCF-XUDSTZEESA-N
Synonyms: allylestrenol, 432-60-0, Gestanin, Allyloestrenol, Orageston, Perselin, Organon, Alilestrenol, 17alpha-Allylestr-4-en-17beta-ol, Allilestrenolo, Allylestrenolum, DTXSID9022574, I47VB5DZ8O, NSC-37723, 17-(2-Propenyl)estr-4-en-17-ol, 17-Hydroxy-17-alpha-allyl-4-estrene, 17-alpha-Allyl-17-beta-hydroxy-4-estrene, 17-alpha-Allyl-3-deoxy-19-nortestosterone, 19-norpregn-4-ene-20-yn-17beta-ol, DTXCID902574, NSC37723, RefChem:554916, G03DC01, 207-082-9, Gestanon, Gestanol, Turinal, Gestanyn, Estrenol, allyl-, MFCD00198957, 17alpha-Allyl-4-estren-17beta-ol, (8R,9S,10R,13S,14S,17R)-13-methyl-17-prop-2-enyl-2,3,6,7,8,9,10,11,12,14,15,16-dodecahydro-1H-cyclopenta[a]phenanthren-17-ol, Estr-4-en-17-ol, 17-(2-propenyl)-, (17b)-, 17-allylestr-4-en-17-beta-ol, 17.alpha.-Allylestr-4-en-17.beta.-ol, Allyloestrenolum, 17-alpha-Allylestr-4-en-17-beta-ol, 17alpha-Allylestrenol, Allilestrenolo [DCIT], Gestanon-r, Alilestrenol [INN-Spanish], Allylestrenolum [INN-Latin], Perselin (TN), 17.alpha.-Allylestrenol, 17alpha-Allyl-4-destrene-17beta-ol, 17alpha-Allyl-4-oestrene-17beta-ol, Allylestrenol (JAN/INN), 17-alpha-Allyl-4-oestrene-17-beta-ol, 17alpha-Allyl-17beta-hydroxy-4-estrene, 17alpha-Allyl-3-deoxy-19-nortestosterone, Allyl estrenol, CCRIS 9068, 17-alpha-Allylhydroxy-19-nor-4-androstene, 3-Deoxy-17-alpha-allyl-19-nortestosterone, ATXHVCQZZJYMCF-XUDSTZEESA-N, NCGC00159497-02, 21-Methylene-19-nor-17-alpha-preg-4-en-17-ol, EINECS 207-082-9, Estr-4-en-17beta-ol, 17-allyl-, 17-alpha-Allyl-17-beta-hydroxy-delta(sup 4)-estren, 17alpha-Allyl-19-nor-delta-4-androstene-17beta-ol, NSC 37723, Estr-4-en-17-ol, 17-(2-propenyl)-, (17beta)-, BRN 3148038, 17.alpha.-Allyl-4-estren-17.beta.-ol, 17.alpha.-Allyl-4-destrene-17.beta.-ol, 17.alpha.-Allyl-4-oestrene-17.beta.-ol, ESTR-4-EN-17-beta-OL, 17-ALLYL-, 17.alpha.-Allyl-3-deoxy-19-nortestosterone, 17.alpha.-Allyl-17.beta.-hydroxy-4-estrene, ALLYLESTRENOL [MI], UNII-I47VB5DZ8O, ALLYLESTRENOL [INN], ALLYLESTRENOL [JAN], (17beta)-17-prop-2-en-1-ylestr-4-en-17-ol, ALLYLESTRENOL [MART.], SCHEMBL329623, 19-Nor-17-alpha-preg-4-en-17-ol, 21-methylene-, ALLYLESTRENOL [WHO-DD], Allylestrenol [INN:BAN:JAN], orb1305318, CHEMBL3185133, SCHEMBL17891654, CHEBI:31189, 17.alpha.-Allyl-17-.beta.-hydroxy-.delta.(sup 4)-estren, Tox21_111718, LMST02030125, s5219, AKOS015964938, DB01431, DS-8255, Estr-4-en-17-ol, (17.beta.)-, FA55289, Estr-4-en-17.beta.-ol, 17-allyl-, CAS-432-60-0, HY-17375, SY108284, 3-deketo-17alpha-allyl-19-nortestosterone, A2570, CS-0006769, NS00031328, WLN: L E5 B666 MUTJ E1 FQ F2U1, D01374, 4-06-00-04143 (Beilstein Handbook Reference), Q531965, SR-01000883956, SR-01000883956-1, BRD-K12872829-001-01-0, (1R,3aS,3bR,9aR,9bS,11aS)-11a-Methyl-1-(prop-2-en-1-yl)-2,3,3a,3b,4,5,7,8,9,9a,9b,10,11,11a-tetradecahydro-1H-cyclopenta[a]phenanthren-1-ol, (8R,9S,10R,13S,14S,17R)-17-allyl-13-methyl-2,3,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-ol, (8R,9S,10R,13S,14S,17R)-17-allyl-13-methyl-2,3,6,7,8,9,10,11,12,14,15,16-dodecahydro-1H-cyclopenta[a]phenanthren-17-ol, 13-Methyl-17-prop-2-enyl-2,3,6,7,8,9,1,11,12,14,15,16-dodecahydro-1H-cyclopenta[a]phenanthren-17-ol
Theoretical properties:
molecular_formula: C21H32O
molecular_weight: 300.5 g/mol
exact_mass: 300.245315640 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 1
hydrogen_bond_acceptor_count: 1
rotatable_bond_count: 2
heavy_atom_count: 22
topological_polar_surface_area: 20.2 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
solubility: 5.58e-04 g/L
Descriptions:
pubchem: Allylestrenol is a steroid. It derives from a hydride of an estrane.
chembl: ALLYLESTRENOL is a small molecule listed in the ChEMBL database and has reached clinical trial phase 2.0.
wikipedia: Allylestrenol, sold under the brand names Gestanin and Turinal among others, is a progestin medication which is used to treat recurrent and threatened miscarriage and to prevent premature labor in pregnant women. However, except in the case of proven progesterone deficiency, its use for such purposes is no longer recommended. A Cochrane review in 2025 found that it had little to no effect in subsequent pregnancy outcomes for women with unexplained, recurrent miscarriage.  It is also used in Japan to treat benign prostatic hyperplasia (BPH) in men. The medication is used alone and is not formulated in combination with an estrogen. It is taken by mouth.
Side effects of allylestrenol are few and have not been well-defined, but are assumed to be similar to those of related medications. Allylestrenol 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 no other important hormonal activity. The medication is a prodrug of 17α-allyl-19-nortestosterone (3-ketoallylestrenol) in the body.
Allylestrenol was first described in 1958 and was introduced for medical use by 1961. It has been marketed widely throughout the world in the past, but today its availability and usage are relatively limited. It remains available in a few European countries and in a number of Asian countries.