Aminoglutethimide
Group of stereoisomers / From Wikipedia, the free encyclopedia
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Aminoglutethimide (AG), sold under the brand names Elipten, Cytadren, and Orimeten among others, is a medication which has been used in the treatment of seizures, Cushing's syndrome, breast cancer, and prostate cancer, among other indications.[2][3][4][5][6][7] It has also been used by bodybuilders, athletes, and other men for muscle-building and performance- and physique-enhancing purposes.[7][1] AG is taken by mouth three or four times per day.[8][4]
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Trade names | Elipten, Cytadren, Orimeten, numerous others |
Other names | AG; AGI; Ba 16038; Ciba 16038; ND-1966; 2-(p-Aminophenyl)-2-ethylglutarimide |
AHFS/Drugs.com | Consumer Drug Information |
MedlinePlus | a604039 |
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Routes of administration | By mouth |
Drug class | Aromatase inhibitor; Antiestrogen; Steroidogenesis inhibitor; Antiglucocorticoid |
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Bioavailability | Rapid, complete[1] |
Metabolism | Liver (minimal; acetylation)[1] |
Elimination half-life | 12.5 hours[1] |
Excretion | Urine (34–54%, unchanged)[1] |
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ECHA InfoCard | 100.004.325 |
Chemical and physical data | |
Formula | C13H16N2O2 |
Molar mass | 232.283 g·mol−1 |
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Chirality | Racemic mixture |
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Side effects of AG include lethargy, somnolence, dizziness, headache, appetite loss, skin rash, hypertension, liver damage, and adrenal insufficiency, among others.[4] AG is both an anticonvulsant and a steroidogenesis inhibitor.[3][4] In terms of the latter property, it inhibits enzymes such as cholesterol side-chain cleavage enzyme (CYP11A1, P450scc) and aromatase (CYP19A1), thereby inhibiting the conversion of cholesterol into steroid hormones and blocking the production of androgens, estrogens, and glucocorticoids, among other endogenous steroids.[4] As such, AG is an aromatase inhibitor and adrenal steroidogenesis inhibitor, including both an androgen synthesis inhibitor and a corticosteroid synthesis inhibitor.[9][10][11][6][7]
AG was introduced for medical use, as an anticonvulsant, in 1960.[12][13] It was withdrawn in 1966 due to toxicity.[12][13] Its steroidogenesis-inhibiting properties were discovered serendipitously and it was subsequently repurposed for use in the treatment of Cushing's syndrome, breast cancer, and prostate cancer from 1969 and thereafter.[9][13][6] However, although used in the past, it has mostly been superseded by newer agents with better efficacy and lower toxicity such as ketoconazole, abiraterone acetate, and other aromatase inhibitors.[4][9] It remains marketed only in a few countries.[14][7]