Compound: mestranol
SMILES: O(c1cc2c([C@@H]3[C@H]([C@H]4[C@]([C@](O)(C#C)CC4)(C)CC3)CC2)cc1)C
InChIKey: IMSSROKUHAOUJS-MJCUULBUSA-N
Synonyms: mestranol, 72-33-3, Norquen, Ovastol, Menophase, EE3ME, Mestranolum, Ethynylestradiol 3-methyl ether, 3-Methoxyethynylestradiol, 3-Methylethynylestradiol, Ethynylestradiol methyl ether, Mestranolo, Compound 33355, 3-Methoxy-17alpha-ethynylestradiol, Ethinylestradiol 3-methyl ether, Ethynyloestradiol 3-methyl ether, EE3-ME, 17alpha-Ethynylestradiol 3-methyl ether, 3-Methoxy-17alpha-ethinylestradiol, 17-Ethynylestradiol 3-methyl ether, 3-Methoxy-17alpha-ethinyloestradiol, 17-Ethynyloestradiol 3-methyl ether, 17alpha-Ethynylestradiol methyl ether, EEI3ME, DTXSID0020814, 17alpha-Ethinylestradiol 3-methyl ether, 17alpha-Ethynyloestradiol 3-methyl ether, EE-3ME, B2V233XGE7, 17-Ethynyl-3-methoxy-1,3,5(10)-oestratien-17-beta-ol, NSC-84032, (8R,9S,13S,14S,17R)-17-ethynyl-3-methoxy-13-methyl-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthren-17-ol, 3-Methoxy-19-nor-17alpha-pregna-1,3,5(10)-trien-20-yn-17-ol, 19-Norpregna-1,3,5(10)-trien-20-yn-17-ol, 3-methoxy-, (17alpha)-, DTXCID20814, CHEBI:6784, (17alpha)-3-Methoxy-19-norpregna-1,3,5(10)-trien-20-yn-17-ol, Ethinyl Estradiol 3 Methyl Ether, Ethinyl Estradiol 3-Methyl Ether, (1S,10R,11S,14R,15S)-14-ethynyl-5-methoxy-15-methyltetracyclo(8.7.0.0^(2,7).0^(11,15))heptadeca-2(7),3,5-trien-14-ol, (1S,10R,11S,14R,15S)-14-ethynyl-5-methoxy-15-methyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-2(7),3,5-trien-14-ol, (8R,9S,13S,14S,17R)-17-ethynyl-3-methoxy-13-methyl-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta(a)phenanthren-17-ol, RefChem:811181, (1S,10R,11S,14R,15S)-14-ethynyl-5-methoxy-15-methyltetracyclo(8.7.0.02,7.011,15)heptadeca-2(7),3,5-trien-14-ol, 200-777-8, Devocin, EE(sub3)ME, Inostral, 3-O-Methylethynylestradiol, 3-Methylethynyloestradiol, 3-Methoxyethynyloestradiol, SC 4725, (8R,9S,13S,14S,17R)-17-Ethynyl-3-methoxy-13-methyl-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthren-17-ol, component of Norinyl, component of Ortho-Novum, delta-MVE, Ethinyloestradiol 3-methyl ether, MLS000028595, component of Ovulen, component of Norquen, MFCD00003689, Inostral (steroid), Mestranolo [DCIT], NCGC00093347-02, SMR000059128, (17beta)-17-ethynyl-3-(methyloxy)estra-1,3,5(10)-trien-17-ol, Mestranolum [INN-Latin], Caswell No. 547A, .delta.-MVE, 17alpha-Ethinyl estradiol 3-methyl ether, 17-Ethynyl-3-methoxyestra-1,3,5(10)-trien-17-ol, 3-Methoxy-17alpha-ethynyloestradiol, 3-Methoxy-17-alpha-ethinylestradiol, 3-Methoxy-17-alpha-ethynylestradiol, 3-Methoxy-17-alpha-ethinyloestradiol, 3-Methoxy-17-alpha-ethynyloestradiol, CCRIS 377, 17-alpha-Ethynyloestradiol methyl ether, 8027 C. B., 3-Methoxy-17-ethynyloestradiol-17-beta, Mestranol [Steroidal oestrogens], 17alpha-Ethinyl oestradiol 3-methyl ether, HSDB 3588, 17-alpha-Ethinyl estradiol 3-methyl ether, 17-alpha-Ethinyl oestradiol 3-methyl ether, EINECS 200-777-8, NSC 84032, EPA Pesticide Chemical Code 115401, 17beta-Estradiol, 17-ethynyl-, 3-(methyl ether), BRN 2625905, UNII-B2V233XGE7, NSC84032, AI3-51798, ethynylestradiol-3-methyl ether, 3-Methoxy-17alpha-ethynyl-1,3,5(10)-estratrien-17beta-ol, Mestranol CRS, 19-Norpregna-1,3,5(10)-trien-20-yn-17-ol, 3-methoxy-, (17.alpha.)-, 3-Methoxy-17alpha-ethynyl-1,3,5(10)-oestratrien-17beta-ol, 17-alpha-Ethynyl-3-methoxy-1,3,5(10)-estratrien-17-beta-ol, 3-Methoxy-17-alpha-ethynyl-1,3,5(10)-estratrien-17-beta-ol, 3-Methoxy-17-alpha-ethynyl-1,3,5(10)-oestratrien-17-beta-ol, CAS-72-33-3, IMSSROKUHAOUJS-MJCUULBUSA-N, 3-Methoxy-17-alpha-19-norpregna-1,3,5(10)-trien-20-yn-17-ol, 3-Methoxy-19-nor-17-alpha-pregna-1,3,5(10)-trien-20-yn-17-ol, Prestwick_966, Mestranol, 99%, Mestranol (Standard), Mestranol [USAN:USP:INN:BAN:JAN], Estra-1,3,5(10)-trien-17beta-ol, 17-ethynyl-3-methoxy-, MESTRANOL [INN], MESTRANOL [JAN], Opera_ID_872, MESTRANOL [MI], MESTRANOL [HSDB], MESTRANOL [USAN], 17alpha-19-Norpregna-1,3,5(10)-trien-20-yn-17-ol, 3-methoxy-, Estra-1,3,5(10)-trien-17-beta-ol, 17-alpha-ethynyl-3-methoxy-, Prestwick0_000846, Prestwick1_000846, Prestwick2_000846, Prestwick3_000846, MESTRANOL [VANDF], (+)-17-alpha-Ethynyl-17-beta-hydroxy-3-methoxy-1,3,5(10)-estratriene, (17-alpha)-3-Methoxy-19-norpregna-1,3,5(10)-trien-20-yn-17-ol, 17-ethynyl-3-methoxyestra-1(10),2,4-trien-17-ol, EE3 ME, MESTRANOL [MART.], (+)-17-alpha-Ethynyl-17-beta-hydroxy-3-methoxy-1,3,5(10)-oestratriene, 17-alpha-Ethynyl-3-methoxy-17-beta-hydroxy-delta-1,3,5(10)-estratriene, 17-alpha-Ethynyl-3-methoxy-17-beta-hydroxy-delta-1,3,5(10)-oestratriene, 3,17-beta-Dihydroxy-17-alpha-ethynyl-1,3,5(10)-estratriene-3-methyl ether, MESTRANOL [USP-RS], MESTRANOL [WHO-DD], SCHEMBL41391, BSPBio_000831, MLS001077321, MLS001424224, BIDD:ER0199, SPBio_002752, Mestranol (JP18/USP/INN), BPBio1_000915, GTPL7087, MESTRANOL [ORANGE BOOK], 17-ethynyl-3-methoxyestra-1(10),2,4-trien-17beta-ol, CHEMBL1201151, MESTRANOL [EP MONOGRAPH], SCHEMBL31004875, ENOVID COMPONENT MESTRANOL, HY-B0390R, OVULEN COMPONENT MESTRANOL, 17-ethynyl-3-methoxyoestra-1(10),2,4-trien-17beta-ol, 3-Methoxy-17a-ethyn ylestradiol, MESTRANOL [USP MONOGRAPH], MSK8586, 3-Methoxy-19-norpregna-1,3,5(10)-trien-20-yn-17beta-ol, HMS1570J13, HMS2051J22, HMS2097J13, HMS2230L20, HMS3714J13, HY-B0390, Tox21_111200, Tox21_301837, 17-alpha-19-Norpregna-1,3,5(10)-trien-20-yn-17-ol, 3-methoxy-, 19-Nor-17alpha-pregna-1,3,5(10)-trien-20-yn-17-ol, 3-methoxy-, EBC-07794, MSK8586-100A, SBB066071, AKOS005267152, Tox21_111200_1, CCG-101067, DB01357, FM25119, NC00317, NCGC00093347-03, NCGC00093347-05, NCGC00093347-07, NCGC00179410-01, NCGC00255342-01, AC-13293, AS-56063, NS00009656, S2125, Mestranol Solution in Acetonitrile, 100ug/mL, Mestranol, VETRANAL(TM), analytical standard, C07618, C76306, D00575, Q904308, SR-01000695429, SR-01000695429-4, BRD-K31920458-001-03-8, BRD-K31920458-001-23-6, Z1557501642, 17a-Ethynyl-3-methoxy-17b-hydroxy-1,3,5(10)-estratriene, Mestranol, European Pharmacopoeia (EP) Reference Standard, (17beta)-17-ethynyl-3-methoxyestra-1(10),2,4-trien-17-ol, Mestranol, United States Pharmacopeia (USP) Reference Standard, (17a)-3-Methoxy-19-norpregna-1,3,5(10)-trien-20-yn-17-ol, 17.Alpha.-19-Norpregna-1,3,5(10)-trien-20-yn-17-ol, 3-meth, 3-Methoxy-17alpha-19-norpregna-1,3,5(10)-trien-20-yn-17-ol, (+)-17alpha-Ethynyl-17beta-hydroxy-3-methoxy-1,3,5(10)-estratriene, (+)-17alpha-Ethynyl-17beta-hydroxy-3-methoxy-1,3,5(10)-oestratriene, (+ )-17.alpha.-Ethynyl-17.beta.-hydroxy-3-methoxy-1,3, 5(10)-oestratriene, (+)-17.alpha.-Ethynyl-17.beta.-hydroxy-3-methoxy-1,3, 5(10)-estratriene, 3-METHOXY-19-NOR-17.ALPHA.-PREGNA-1,3,5(10)-TRIEN-20-YN-17-OL., (1S,11S,15S,10R,14R)-14-ethynyl-5-methoxy-15-methyltetracyclo[8.7.0.0<2,7>.0<1 1,15>]heptadeca-2(7),3,5-trien-14-ol, (8R,13S,17R)-17-Ethynyl-3-methoxy-13-methyl-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthren-17-ol
Theoretical properties:
molecular_formula: C21H26O2
molecular_weight: 310.4 g/mol
exact_mass: 310.193280068 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 1
hydrogen_bond_acceptor_count: 2
rotatable_bond_count: 2
heavy_atom_count: 23
topological_polar_surface_area: 29.5 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
physical_state: Crystals from methanol or acetone
color: Crystals from methanol or acetone
solubility: In double-distilled water, 0.32 mg/L
vapor_pressure: 9.75x10-9
Descriptions:
pubchem: Mestranol can cause cancer according to an independent committee of scientific and health experts.
chebi: A terminal acetylenic compound that is (17α)-17-ethynylestra-1(10),2,4-triene substituted by a methoxy group at position 3 and a hydroxy group at position 17.
chembl: MESTRANOL is a small molecule listed in the ChEMBL database and has reached clinical trial phase 4.0.
wikipedia: Mestranol, sold under the brand names Enovid, Norinyl, and Ortho-Novum among others, is an estrogen medication which has been used in birth control pills, menopausal hormone therapy, and the treatment of menstrual disorders. It is formulated in combination with a progestin and is not available alone. It is taken by mouth.
Side effects of mestranol include nausea, breast tension, edema, and breakthrough bleeding among others. It is an estrogen, or an agonist of the estrogen receptors, the biological target of estrogens like estradiol. Mestranol is a prodrug of ethinylestradiol in the body.
Mestranol was discovered in 1956 and was introduced for medical use in 1957. It was the estrogen component in the first birth control pill. In 1969, mestranol was replaced by ethinylestradiol in most birth control pills, although mestranol continues to be used in a few birth control pills even today. Mestranol remains available only in a few countries, including the United States, United Kingdom, Japan, and Chile.