Compound: DIMETHISTERONE
SMILES: O=C1C=C2[C@]([C@@H]3[C@H]([C@H]4[C@]([C@](O)(C#CC)CC4)(C)CC3)C[C@@H]2C)(C)CC1
InChIKey: LVHOURKCKUYIGK-RGUJTQARSA-N
Synonyms: DIMETHISTERONE, Dimethisteron, Secrosteron, Dimethisterone anhydrous, 79-64-1, Dimetisterona, Dimethisteronum, Dimetisterone, (6S,8R,9S,10R,13S,14S,17S)-17-hydroxy-6,10,13-trimethyl-17-prop-1-ynyl-2,6,7,8,9,11,12,14,15,16-decahydro-1H-cyclopenta[a]phenanthren-3-one, OIC9M646C5, DTXSID5057834, DTXCID6031623, Androst-4-en-3-one, 17-hydroxy-6-methyl-17-(1-propynyl)-, (6alpha,17beta)-, (6S,8R,9S,10R,13S,14S,17S)-17-hydroxy-6,10,13-trimethyl-17-prop-1-ynyl-2,6,7,8,9,11,12,14,15,16-decahydro-1H-cyclopenta(a)phenanthren-3-one, RefChem:134181, 201-215-4, K4MZ02M175, Lutogan, Dimetisterone [DCIT], Dimethisterone [INN], Dimethisteronum [INN-Latin], Dimetisterona [INN-Spanish], 6-alpha,21-Dimethylethisterone, EINECS 201-215-4, P-5048, Dimethisterone [Progestins], UNII-OIC9M646C5, 6-alpha-Methyl-17-(1-propynyl)testosterone, 6-alpha-Methyl-17-alpha-propynyltestosterone, 6alpha,21-Dimethyl-17alpha-ethinyltestosterone, 6alpha,21-Dimethyl-17alpha-ethinyl testosterone, 17-alpha-Ethynyl-6-alpha,21-dimethyltestosterone, 6-alpha,21-Dimethyl-17-alpha-ethinyltestosterone, 17-beta-Hydroxy-6-alpha-methyl-17-(1-propynyl)androst-4-en-3-one, 17-alpha-Ethynyl-17-hydroxy-6-alpha,21-dimethylandrost-4-en-3-one, 17-alpha-Pregn-4-en-20-yn-3-one, 6-alpha,21-dimethyl-17-hydroxy-, 6-alpha,21-Dimethyl-17-beta-hydroxy-17-alpha-pregn-4-en-20-yn-3-one, (6-alpha,17-beta)-17-Hydroxy-6-methyl-17-(1-propynyl)-androst-4-en-3-one, DIMETHISTERONE [MI], Androst-4-en-3-one, 17-hydroxy-6-methyl-17-(1-propynyl)-, (6-alpha,17-beta)-, SCHEMBL146840, CHEBI:4606, DIMETHISTERONE [WHO-DD], CHEMBL2106347, LVHOURKCKUYIGK-RGUJTQARSA-N, Tox21_113973, Androst-4-en-3-one, 17-beta-hydroxy-6-alpha-methyl-17-(1-propynyl)-, CAS-79-64-1, NCGC00274271-01, NS00038048, C07628, Q5277305, Androst-4-en-3-one,17-hydroxy-6-methyl-17-(1-propynyl)-,(6a,17b)-, (1S,3aS,3bR,5S,9aR,9bS,11aS)-1-Hydroxy-5,9a,11a-trimethyl-1-(prop-1-yn-1-yl)-1,2,3,3a,3b,4,5,8,9,9a,9b,10,11,11a-tetradecahydro-7H-cyclopenta[a]phenanthren-7-one
Theoretical properties:
molecular_formula: C23H32O2
molecular_weight: 340.5 g/mol
exact_mass: 340.240230259 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 1
hydrogen_bond_acceptor_count: 2
rotatable_bond_count: 1
heavy_atom_count: 25
topological_polar_surface_area: 37.3 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
Descriptions:
pubchem: Dimethisterone is a 3-hydroxy steroid. It has a role as an androgen.
wikipedia: Dimethisterone, formerly sold under the brand names Lutagan and Secrosteron among others, is a progestin medication which was used in birth control pills and in the treatment of gynecological disorders but is now no longer available. It was used both alone and in combination with an estrogen. It is taken by mouth.
Side effects of dimethisterone are similar to those of other progestins. When used in combination with high doses of an estrogen, an increased risk of endometrial cancer can occur. Dimethisterone 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 antimineralocorticoid activity and no other important hormonal activity.
Dimethisterone was first described and was introduced for medical use in 1959. It started being used in birth control pills in 1965. However, due to its low potency and consequent inability to prevent the increased risk of endometrial cancer with estrogens, dimethisterone was soon discontinued for such purposes.