title: Metabolism of levonorgestrel, norethindrone, and structurally related contraceptive steroids.
abstract: There is limited information on the metabolism of levonorgestrel, norethindrone and structurally related contraceptive steroids. Both levonorgestrel and norethindrone undergo extensive reduction of the alpha, beta-unsaturated ketone in ring A. Levonorgestrel also undergoes hydroxylation at carbons 2 and 16. The metabolites of both compounds circulate predominantly as sulfates. In urine, levonorgestrel metabolites are found primarily in the glucuronide form, whereas norethindrone metabolites are present in approximately equal amounts as sulfates and glucuronides. Of the progestogens structurally related to norethindrone, norethindrone acetate, ethynodiol diacetate, norethindrone enanthate, and perhaps lynestrenol, undergo rapid hydrolysis and are converted to the parent compound and its metabolites. There is no convincing evidence that norethynodrel is converted to norethindrone. Of the progestogens structurally related to levonorgestrel, it appears that neither desogestrel nor gestodene are transformed to the parent compound. However, there is evidence that norgestimate can be, at least partly, converted to levonorgestrel. Further studies on the metabolism of these progestogens are required before we can understand their mechanism of action.
authors: Department of Obstetrics and Gynecology, University of Southern California School of Medicine, Women's Hospital, Los Angeles County/USC Medical Center 90033.
authors: F Z
authors: FZ
authors: Stanczyk
authors: S
authors: S
authors: Roy
mesh_terms: D000818:Animals; D003277:Contraceptives, Oral, Combined / Q000378:metabolism*; D017135:Desogestrel; D005260:Female; D006801:Humans; D016912:Levonorgestrel; D009640:Norethindrone / Q000031:analogs & derivatives / Q000378:metabolism*; D009644:Norgestrel / Q000031:analogs & derivatives / Q000378:metabolism*; D009652:Norpregnenes / Q000378:metabolism
chemical_list: D003277:Contraceptives, Oral, Combined; D009652:Norpregnenes; C033273:Gestodene; D009644:Norgestrel; D016912:Levonorgestrel; D017135:Desogestrel; C017576:norgestimate; D009640:Norethindrone