Back أمينوغلوتيثيميد Arabic آمینوقلوتتیمید AZB Aminoglwtethimid Welsh Aminoglutethimid German آمینوگلوتتیمید Persian Aminoglutetimidi Finnish Aminoglutetimid Hungarian Amminoglutetimide Italian Aminoglutetymid Polish Aminoglutetimida Portuguese

Aminoglutethimide

Aminoglutethimide
Clinical data
Trade namesElipten, Cytadren, Orimeten, numerous others
Other namesAG; AGI; Ba 16038; Ciba 16038; ND-1966; 2-(p-Aminophenyl)-2-ethylglutarimide
AHFS/Drugs.comConsumer Drug Information
MedlinePlusa604039
Pregnancy
category
  • AU: D
Routes of
administration		By mouth
Drug classAromatase inhibitor; Antiestrogen; Steroidogenesis inhibitor; Antiglucocorticoid
ATC code
Pharmacokinetic data
BioavailabilityRapid, complete[1]
MetabolismLiver (minimal; acetylation)[1]
Elimination half-life12.5 hours[1]
ExcretionUrine (34–54%, unchanged)[1]
Identifiers
  • (RS)-3-(4-aminophenyl)-3-ethyl-piperidine-2,6-dione
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.004.325 Edit this at Wikidata
Chemical and physical data
FormulaC13H16N2O2
Molar mass232.283 g·mol−1
3D model (JSmol)
ChiralityRacemic mixture
  • O=C1NC(=O)CCC1(c2ccc(N)cc2)CC
  • InChI=1S/C13H16N2O2/c1-2-13(8-7-11(16)15-12(13)17)9-3-5-10(14)6-4-9/h3-6H,2,7-8,14H2,1H3,(H,15,16,17) checkY
  • Key:ROBVIMPUHSLWNV-UHFFFAOYSA-N checkY
  (verify)

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]

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]

  1. ^ a b c d e Cite error: The named reference TindallSedrak2013 was invoked but never defined (see the help page).
  2. ^ Milne GW (2018). Drugs: Synonyms and Properties: Synonyms and Properties. Taylor & Francis. pp. 1182–. ISBN 978-1-351-78989-9.
  3. ^ a b Morton IK, Hall JM (2012). Concise Dictionary of Pharmacological Agents: Properties and Synonyms. Springer Science & Business Media. pp. 14–. ISBN 978-94-011-4439-1.
  4. ^ a b c d e f Friedlander TW, Ryan CJ (2010). "Adrenal Androgen Synthesis Inhibitor Therapies in Castrate-Resistant Prostate Cancer". In Figg WD, Chau CH, Small EJ (eds.). Drug Management of Prostate Cancer. Springer Science & Business Media. pp. 91–96. ISBN 978-1-60327-829-4.
  5. ^ Gross BA, Mindea SA, Pick AJ, Chandler JP, Batjer HH (2007). "Medical management of Cushing disease". Neurosurgical Focus. 23 (3): 1–6. doi:10.3171/foc.2007.23.3.12. PMID 17961023.
  6. ^ a b c Cite error: The named reference Osborne2012 was invoked but never defined (see the help page).
  7. ^ a b c d William Llewellyn (2011). Anabolics. Molecular Nutrition Llc. pp. 770–. ISBN 978-0-9828280-1-4.
  8. ^ Cite error: The named reference WilkesBarton-Burke2013 was invoked but never defined (see the help page).
  9. ^ a b c Cite error: The named reference Patrick2013 was invoked but never defined (see the help page).
  10. ^ Cite error: The named reference SmithWilliams2005 was invoked but never defined (see the help page).
  11. ^ Cite error: The named reference Ebadi2007 was invoked but never defined (see the help page).
  12. ^ a b Cite error: The named reference Sneader2005 was invoked but never defined (see the help page).
  13. ^ a b c Cite error: The named reference HarrapDavis2012 was invoked but never defined (see the help page).
  14. ^ "List of Aromatase inhibitors". Drugs.com.

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