Compound: dydrogesterone
SMILES: O=C1C=C2C=C[C@H]3[C@H]4[C@]([C@@H](C(=O)C)CC4)(C)CC[C@H]3[C@]2(C)CC1
InChIKey: JGMOKGBVKVMRFX-HQZYFCCVSA-N
Synonyms: dydrogesterone, 152-62-5, Isopregnenone, Hydrogesterone, Duphaston, Gynorest, Hydrogestrone, Gestatron, Retrone, Diphaston, Dufaston, Duvaron, Terolut, Prodel, 10alpha-Isopregnenone, Retro-6-dehydroprogesterone, Didrogesterone, Dydrogesteronum, delta(6)-Retroprogesterone, didrogesterona, 6-Dehydro-retro-progesterone, delta(sup 6)-Retroprogesterone, 9beta,10alpha-Pregna-4,6-diene-3,20-dione, Retroprogesterone, 6-dehydro-, NSC-92336, 6-Dehydro-9beta,10alpha-progesterone, (8S,9R,10S,13S,14S,17S)-17-acetyl-10,13-dimethyl-1,2,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthren-3-one, DTXSID1022974, 90I02KLE8K, (9-beta,10-alpha)-Pregna-4,6-diene-3,20-dione, Pregna-4,6-diene-3,20-dione, (9beta,10alpha)-, 9-beta,10-alpha-Pregna-4,6-diene-3,20-dione, DTXCID702974, CHEBI:31527, Dehydrogesterone, NSC92336, 6-Dehydro-9 beta-10 alpha-progesterone, dibrogesterone, 6 Dehydro 9 beta 10 alpha progesterone, Duphaston-hrt, (1R,2S,10S,11S,14S,15S)-14-acetyl-2,15-dimethyltetracyclo(8.7.0.0^(2,7).0^(11,15))heptadeca-6,8-dien-5-one, (1R,2S,10S,11S,14S,15S)-14-acetyl-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-6,8-dien-5-one, (8S,9R,10S,13S,14S,17S)-17-acetyl-10,13-dimethyl-1,2,8,9,11,12,14,15,16,17-decahydrocyclopenta(a)phenanthren-3-one, RefChem:57304, G03DB01, 205-806-8, Didrogesterone [DCIT], Dydrogesteronum [INN-Latin], Dydrogesterona [INN-Spanish], 6-Dehydroretroprogesterone, (9beta,10alpha)-pregna-4,6-diene-3,20-dione, MLS002153947, (8S,9R,10S,13S,14S,17S)-17-acetyl-10,13-dimethyl-1,2,8,9,10,11,12,13,14,15,16,17-dodecahydro-3H-cyclopenta[a]phenanthren-3-one, Dydrogesterona, NSC 92336, Duphaston (TN), Gynorest (TN), (8S,9R,10S,13S,14S,17S)-17-acetyl-10,13-dimethyl-8,9,10,11,12,13,14,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-3(2H)-one, CAS-152-62-5, CCRIS 9069, HSDB 3321, MLS002695106, EINECS 205-806-8, 9-beta,10alpha-Pregna-4,6-diene-3,20-dione, UNII-90I02KLE8K, Dydrogesterone; 9beta,10alpha-Pregna-4,6-diene-3,20-dione, Dydrogesterone?, Dydrogesterone CRS, NCGC00016413-01, MFCD00867864, Dydrogesterone [USAN:USP:INN:BAN:JAN], 6-Dehydro-9.beta.,10.alpha.-progesterone, Prestwick0_000671, Prestwick1_000671, Prestwick2_000671, Prestwick3_000671, Dydrogesterone (Standard), DYDROGESTERONE [MI], Pregna-4,6-diene-3,20-dione, (9b,10a)-, .DELTA.6-Retroprogesterone, DYDROGESTERONE [INN], DYDROGESTERONE [JAN], SCHEMBL37703, BSPBio_000761, DYDROGESTERONE [HSDB], DYDROGESTERONE [USAN], SPBio_002682, DYDROGESTERONE [MART.], BPBio1_000839, GTPL2878, HY-B0257AR, orb1304602, Pregna-4,6-diene-3,20-dione, (9-beta,10-alpha)-, DYDROGESTERONE [USP-RS], DYDROGESTERONE [WHO-DD], CHEMBL1200853, HY-B0257A, 9.beta.,6-diene-3,20-dione, MSK8567, Dydrogesterone (JP18/USP/INN), HMS1570G03, HMS2097G03, HMS2230C10, HMS3714G03, 9-.beta.,6-diene-3,20-dione, DYDROGESTERONE [ORANGE BOOK], Tox21_110429, DYDROGESTERONE [EP MONOGRAPH], EBC-26745, MSK8567-100M, s4097, DYDROGESTERONE [USP MONOGRAPH], AKOS015895532, Tox21_110429_1, CCG-220671, DB00378, FD22631, GS-6735, NCGC00179445-01, NCGC00179445-03, NCGC00179445-04, (1S,3aS,3bS,9aS,9bR,11aS)-1-acetyl-9a,11a-dimethyl-1H,2H,3H,3aH,3bH,7H,8H,9H,9aH,9bH,10H,11H,11aH-cyclopenta[a]phenanthren-7-one, SMR001233286, SY392723, (9b,10a)-Pregna-4,6-diene-3,20-dione, AB00513884, NS00009687, D01217, Dydrogesterone Solution in Methanol, 100ug/mL, H10151, Pregna-4,20-dione, (9.beta.,10.alpha.)-, AB00513884_04, EN300-19767791, SR-01000841256, Q4161380, SR-01000841256-2, BRD-K68620903-001-03-1, BRD-K68620903-001-09-8, BRD-K68620903-001-11-4, PREGNA-4,6-DIENE-3,20-DIONE, (9.BETA.,10.ALPHA.)
Theoretical properties:
molecular_formula: C21H28O2
molecular_weight: 312.4 g/mol
exact_mass: 312.208930132 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 0
hydrogen_bond_acceptor_count: 2
rotatable_bond_count: 1
heavy_atom_count: 23
topological_polar_surface_area: 34.1 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
physical_state: Crystals from acetone + hexane
color: Crystals from acetone + hexane
odor: Odorless
melting_point: 168-169
solubility: Soluble in acetone, chloroform (1 in 2), ethanol (1 in 40) and diethyl ether (1 in 200); slightly soluble in fixed oils; sparingly soluble in methanol.
Descriptions:
pubchem: Dydrogesterone is a 20-oxo steroid and a 3-oxo-Delta(4) steroid. It has a role as a progestin.
chembl: DYDROGESTERONE is a small molecule listed in the ChEMBL database and has reached clinical trial phase 4.0.
wikipedia: Dydrogesterone, sold under the brand name Duphaston among others, is a progestin medication which is used for a variety of indications, including threatened or recurrent miscarriage during pregnancy, dysfunctional bleeding, infertility due to luteal insufficiency, dysmenorrhea, endometriosis, secondary amenorrhea, irregular cycles, premenstrual syndrome, and as a component of menopausal hormone therapy. It is taken by mouth.
Side effects of dydrogesterone include menstrual irregularities, headache, nausea, breast tenderness, and others. Dydrogesterone is a progestin, or a synthetic progestogen, and hence is an agonist of the progesterone receptor, the biological target of progestogens like progesterone. The medication is an atypical progestogen and does not inhibit ovulation. It has weak antimineralocorticoid activity and no other important hormonal activity.
Dydrogesterone was developed in the 1950s and introduced for medical use in 1961. It is available widely throughout Europe, no longer available in the United Kingdom, since 2008 and is also marketed in Australia and elsewhere in the world. The medication was previously available in the United States, but it has been discontinued in that country.