Compound: ETONOGESTREL
SMILES: O=C1C=C2[C@@H]([C@H]3C(=C)C[C@@]4([C@](O)(C#C)CC[C@H]4[C@@H]3CC2)CC)CC1
InChIKey: GCKFUYQCUCGESZ-BPIQYHPVSA-N
Synonyms: ETONOGESTREL, 54048-10-1, Implanon, 3-Oxodesogestrel, 3-Ketodesogestrel, nexplanon, 3-Keto-desogestrel, Org-3236, etonogestrelum, ORG 3236, 304GTH6RNH, (8S,9S,10R,13S,14S,17R)-13-ethyl-17-ethynyl-17-hydroxy-11-methylidene-2,6,7,8,9,10,12,14,15,16-decahydro-1H-cyclopenta[a]phenanthren-3-one, DTXSID9046782, 13-Ethyl-17-hydroxy-11-methylene-18,19-dinor-17alpha-pregn-4-en-20-yn-3-one, DTXCID7026782, CHEBI:50777, (17-alpha)-13-Ethyl-17-hydroxy-11-methylene-18,19-dinorpregn-4-en-20-yn-3-one, 18,19-Dinorpregn-4-en-20-yn-3-one, 13-ethyl-17-hydroxy-11-methylene-, (17-alpha)-, 18,19-Dinor-17alpha-pregn-4-en-20-yn-3-one, 13-ethyl-17-hydroxy-11-methylene-, 3-oxo desogestrel, (1S,2R,10S,11S,14R,15S)-15-ethyl-14-ethynyl-14-hydroxy-17-methylidenetetracyclo(8.7.0.0^(2,7).0^(11,15))heptadec-6-en-5-one, (1S,2R,10S,11S,14R,15S)-15-ethyl-14-ethynyl-14-hydroxy-17-methylidenetetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-en-5-one, (8S,9S,10R,13S,14S,17R)-13-ethyl-17-ethynyl-17-hydroxy-11-methylidene-2,6,7,8,9,10,12,14,15,16-decahydro-1H-cyclopenta(a)phenanthren-3-one, RefChem:56821, G03AC08, MFCD00867863, DESOGESTREL IMPURITY D, 18,19-Dinorpregn-4-en-20-yn-3-one,13-ethyl-17-hydroxy-11-methylene-, (17a)-, (1R,3aS,3bS,9aR,9bS,11aS)-11a-ethyl-1-ethynyl-1-hydroxy-10-methylidene-1H,2H,3H,3aH,3bH,4H,5H,7H,8H,9H,9aH,9bH,10H,11H,11aH-cyclopenta[a]phenanthren-7-one, Implanon (TN), (8S,9S,10R,13S,14S,17R)-13-ethyl-17-ethynyl-17-hydroxy-11-methylene-6,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3(2H)-one, Desogestrel EP Impurity D, Etonogestrel (USAN/INN), UNII-304GTH6RNH, Etonogestrel [USAN:INN:BAN], Nexplanon (TN), NCGC00168777-01, 13-Ethyl-17-hydroxy-11-methylidene-18,19-dinor-17alpha-pregn-4-en-20-yn-3-one (3-Ketodesogestrel), EINECS 258-936-2, Etonogestrel Impurity 9, 17-Ethinyl-17-beta-hydroxy-18-methyl-11-methylene-4-estren-3-one, ETONOGESTREL [MI], ETONOGESTREL [INN], ETONOGESTREL [USAN], (17alpha)-13-Ethyl-17-hydroxy-11-methylene-18,19-dinorpregn-4-en-20-yn-3-one, CHEMBL1531, Etonogestrel [EP monograph], ETONOGESTREL [VANDF], ETONOGESTREL [MART.], ETONOGESTREL [USP-RS], ETONOGESTREL [WHO-DD], SCHEMBL117703, GTPL7590, orb1305313, Etonogestrel, >=98% (HPLC), ETONOGESTREL [ORANGE BOOK], GLXC-90547, HY-B0652, MSK14464, Tox21_112638, BDBM50423516, EBC-26587, s4673, NUVARING COMPONENT ETONOGESTREL, 13-Ethyl-11-methylene-18,19-dinor-17-alpha-pregn-4-en-20-yn-3-one, 17alpha-ethynyl-17beta-hydroxy-11-methylidene-18a-homo-estr-4-en-3-one, AKOS030526156, CCG-267753, DB00294, FE23201, NCGC00168777-04, (8S,9S,10R,13S,14S,17R)-13-ethyl-17-ethynyl-17-hydroxy-11-methylene-2,6,7,8,9,10,12,14,15,16-decahydro-1H-cyclopenta[a]phenanthren-3-one, AS-73246, SY465228, CAS-54048-10-1, DESOGESTREL IMPURITY D [EP IMPURITY], NS00006394, C75537, D04104, EN300-19767790, Q3733839, Etonogestrel, United States Pharmacopeia (USP) Reference Standard, (17a)-13-ethyl-17-hydroxy-11-methylene-18,19-dinorpregn-4-en-20-yn-3-one, 13-Ethyl-11-methylene-18,19-dinor-17alpha-pregn-4-en-20-yn-17-ol-3-one, (1R,3aS,3bS,9aR,9bS,11aS)-11a-Ethyl-1-ethynyl-1-hydroxy-10-methylidene-1,2,3,3a,3b,4,5,8,9,9a,9b,10,11,11a-tetradecahydro-7H-cyclopenta[a]phenanthren-7-one, (8S,9S,10R,13S,14S,17R)-17-ethynyl-17-hydroxy-13-methyl-11-methylene-1,2,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-3H-cyclopenta[a]phenanthren-3-one, 13-Ethyl-17-ethynyl-17-h  ydroxy-11-methylidene-2,6,7,8,9,10,12,13,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-one, 18,19-DINOR-17.ALPHA.-PREGN-4-EN-20-YN-3-ONE, 13-ETHYL-17-HYDROXY-11-METHYLENE-
Theoretical properties:
molecular_formula: C22H28O2
molecular_weight: 324.5 g/mol
exact_mass: 324.208930132 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 1
hydrogen_bond_acceptor_count: 2
rotatable_bond_count: 2
heavy_atom_count: 24
topological_polar_surface_area: 37.3 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
boiling_point: 473.1ºC at 760 mmHg
melting_point: 196-200ºC
solubility: Insoluble
Descriptions:
pubchem: Etonogestrel is a 17beta-hydroxy steroid, a 3-oxo-Delta(4) steroid and a terminal acetylenic compound. It has a role as a contraceptive drug, a female contraceptive drug and a progestin.
chembl: ETONOGESTREL is a small molecule listed in the ChEMBL database and has reached clinical trial phase 4.0.
wikipedia: Etonogestrel is a medication which is used as a means of birth control for women. It is available as an implant placed under the skin of the upper arm under the brand names Nexplanon and Implanon. It is a progestin that is also used in combination with ethinylestradiol, an estrogen, as a vaginal ring under the brand names NuvaRing and Circlet. Etonogestrel is effective as a means of birth control and lasts at least three or four years with some data showing effectiveness for five years. Following removal, fertility quickly returns.
Side effects of etonogestrel include menstrual irregularities, breast tenderness, mood changes, acne, headaches, vaginitis, and others. Etonogestrel is a progestin, or a synthetic progestogen, and hence is an agonist of the progesterone receptor, the biological target of progestogens like progesterone. It works by stopping ovulation, thickening the mucus around the opening of the cervix, and altering the lining of the uterus. It has very weak androgenic and glucocorticoid activity and no other important hormonal activity.
Etonogestrel was patented in 1972 and introduced for medical use in 1998. It became available in the United States in 2006. Etonogestrel implants are approved in more than 90 countries and used by about three million women globally as of 2010.
A closely related and more widely known and used progestin, desogestrel, is a prodrug of etonogestrel in the body.