Compound: DESOGESTREL
SMILES: O[C@]1(C#C)[C@@]2([C@H]([C@H]3[C@@H]([C@@H]4C(=CCCC4)CC3)C(C2)=C)CC1)CC
InChIKey: RPLCPCMSCLEKRS-BPIQYHPVSA-N
Synonyms: DESOGESTREL, 54024-22-5, Cerazette, Desogestrelum, Org-2969, ORG 2969, 13-Ethyl-11-methylene-18,19-dinor-17alpha-pregn-4-en-20-yn-17-ol, (8S,9S,10R,13S,14S,17R)-13-ethyl-17-ethynyl-11-methylidene-1,2,3,6,7,8,9,10,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-17-ol, DTXSID6022898, 81K9V7M3A3, CHEBI:4453, DTXCID702898, VOLNEA COMPONENT DESOGESTREL, BEKYREE COMPONENT DESOGESTREL, ENSKYCE COMPONENT DESOGESTREL, PIMTREA COMPONENT DESOGESTREL, VIORELE COMPONENT DESOGESTREL, ISIBLOOM COMPONENT DESOGESTREL, 13-ethyl-11-methylene-18,19-dinorpregn-4-en-20-yn-17alpha-ol, 18,19-Dinorpregn-4-en-20-yn-17-ol, 13-ethyl-11-methylene-, (17alpha)-, Cerelle, Desomono, Feanolla, Zelleta, Nacrez, Aizea, (8S,9S,10R,13S,14S,17R)-13-ethyl-17-ethynyl-11-methylidene-1,2,3,6,7,8,9,10,12,14,15,16-dodecahydrocyclopenta(a)phenanthren-17-ol, RefChem:585820, 13-Ethyl-11-methylene-18,19-dinor-17 alpha-pregn-4-en-20-yn-17-ol, Org2969, G03AC09, 13 Ethyl 11 methylene 18,19 dinor 17 alpha pregn 4 en 20 yn 17 ol, alpha-pregn-4-en-20-yn-17-ol, 13-Ethyl-11-methylene-18,19-dinor-17, 258-929-4, desogen, Mircette, Desogestrelum [INN-Latin], MFCD00869346, C22H30O, NCGC00167449-01, (8S,9S,10R,13S,14S,17R)-13-ethyl-17-ethynyl-11-methylene-2,3,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-ol, 13-ethyl-17-ethynyl-11-methylene-1,2,3,6,7,8,9,10,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-17-ol;(17alpha)-13-Ethyl-11-methylene-1819-dinorpregn-4-en-20-yn-17-o, HSDB 3593, SR-01000883959, EINECS 258-929-4, Desogestrel (USAN/INN), UNII-81K9V7M3A3, Desogestrel [USAN:INN:BAN], Desogestrel?, Desogestrel CRS, 18,19-Dinorpregn-4-en-20-yn-17-ol, 13-ethyl-11-methylene-, (17.alpha.)-, Desogestrel (Standard), Desogestrel 100 microg/mL in Acetonitrile, DESOGESTREL [MI], DESOGESTREL [INN], DESOGESTREL [JAN], DESOGESTREL [HSDB], DESOGESTREL [USAN], DESOGESTREL [VANDF], CHEMBL1533, DESOGESTREL [MART.], SCHEMBL41341, DESOGESTREL [USP-RS], DESOGESTREL [WHO-DD], GTPL7065, orb1300437, DESOGESTREL [ORANGE BOOK], 17alpha-ethynyl-11-methylidene-18a-homo-estr-4-en-17beta-ol, DESOGESTREL [EP MONOGRAPH], DESOGESTREL [USP MONOGRAPH], KARIVA COMPONENT DESOGESTREL, DESOGEN COMPONENT DESOGESTREL, MSK10877, VELIVET COMPONENT DESOGESTREL, Tox21_112453, AC-308, BDBM50423510, CYCLESSA COMPONENT DESOGESTREL, EBC-26734, HY-12516R, LMST02030104, MIRCETTE COMPONENT DESOGESTREL, s4638, (17alpha)-13-Ethyl-11-methylene-18,19-dinorpregn-4-en-20-yn-17-ol, AKOS015963198, Desogestrel for system suitability CRS, CCG-267585, CS-3686, DB00304, ORTHO-CEPT COMPONENT DESOGESTREL, (1R,3aS,3bS,9aR,9bS,11aS)-11a-ethyl-1-ethynyl-10-methylidene-1H,2H,3H,3aH,3bH,4H,5H,7H,8H,9H,9aH,9bH,10H,11H,11aH-cyclopenta[a]phenanthren-1-ol, (8S,9S,10R,13S,14S,17R)-13-ethyl-17-ethynyl-11-methylene-1,2,3,6,7,8,9,10,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-17-ol, AS-13022, HY-12516, CAS-54024-22-5, D4163, NS00003854, C07629, C15951, D02367, Desogestrel, VETRANAL(TM), analytical standard, EN300-23839418, Q415304, SR-01000883959-1, SR-01000883959-2, BRD-K46061689-001-01-9, 17alpha-ethynyl-13beta-ethyl-11-methylene-4-gonen-17-ol, Desogestrel, European Pharmacopoeia (EP) Reference Standard, 13-ethyl-11-methylene-18,19-dinor-17a-pregn-4-en-20-yn-17-ol, Desogestrel, United States Pharmacopeia (USP) Reference Standard, Desogestrel, Pharmaceutical Secondary Standard; Certified Reference Material, Desogestrel for system suitability, European Pharmacopoeia (EP) Reference Standard, (1R,3aS,3bS,9aR,9bS,11aS)-11a-Ethyl-1-ethynyl-10-methylidene-2,3,3a,3b,4,5,7,8,9,9a,9b,10,11,11a-tetradecahydro-1H-cyclopenta[a]phenanthren-1-ol, 13-ethyl-17-ethynyl-11-methylene-1,2,3,6,7,8,9,10,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-17-ol;(17|_)-13-Ethyl-11-methylene-18 pound not19-dinorpregn-4-en-20-yn-17-o
Theoretical properties:
molecular_formula: C22H30O
molecular_weight: 310.5 g/mol
exact_mass: 310.229665576 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 1
hydrogen_bond_acceptor_count: 1
rotatable_bond_count: 2
heavy_atom_count: 23
topological_polar_surface_area: 20.2 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
physical_state: Crystals
color: Crystals
boiling_point: 428ºC
melting_point: 109-110ºC
solubility: <1 mg/ml
Descriptions:
pubchem: Desogestrel is a 17beta-hydroxy steroid and a terminal acetylenic compound. It has a role as a contraceptive drug, a synthetic oral contraceptive and a progestin.
chembl: DESOGESTREL is a small molecule listed in the ChEMBL database and has reached clinical trial phase 4.0.
wikipedia: Desogestrel is a progestin medication which is used in birth control pills. It is also used in the treatment of menopausal symptoms in women. The medication is available and used alone or in combination with an estrogen. It is taken by mouth.
Side effects of desogestrel include menstrual irregularities, headaches, nausea, breast tenderness, mood changes, acne, increased hair growth, and others. Desogestrel 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 very weak androgenic and glucocorticoid activity and no other important hormonal activity. The medication is a prodrug of etonogestrel (3-ketodesogestrel) in the body.
Desogestrel was discovered in 1972 and was introduced for medical use in Europe in 1981. It became available in the United States in 1992. Desogestrel is sometimes referred to as a "third-generation" progestin. Like norethisterone and Norgestrel, Desogestrel is widely available as a progestogen-only "mini pill" for birth control. Desogestrel is marketed widely throughout the world. It is available as a generic medication. In 2020, the version with ethinylestradiol was the 120th most commonly prescribed medication in the United States, with more than 5 million prescriptions.