Aminoglutethimide

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Aminoglutethimide
Aminoglutethimide.svg
Systematic (IUPAC) name
(RS)-3-(4-aminophenyl)-3-ethyl-piperidine-2,6-dione
Clinical data
AHFS/Drugs.com Consumer Drug Information
MedlinePlus a604039
Pregnancy cat. D (AU) D (US)
Legal status ?
Routes Oral
Pharmacokinetic data
Bioavailability >95%
Metabolism Hepatic
Half-life 12.5 ± 1.6 hours
Excretion Renal
Identifiers
CAS number 125-84-8 YesY
ATC code L02BG01
PubChem CID 2145
DrugBank DB00357
ChemSpider 2060 YesY
UNII 0O54ZQ14I9 YesY
KEGG D00574 YesY
ChEBI CHEBI:2654 YesY
ChEMBL CHEMBL488 YesY
Chemical data
Formula C13H16N2O2 
Mol. mass 232.278 g/mol
 YesY (what is this?)  (verify)

Aminoglutethimide is an anti-steroid drug marketed under the tradename Cytadren by Novartis around the world. It blocks the production of steroids derived from cholesterol and is clinically used in the treatment of Cushing's syndrome[1] and metastatic breast cancer. It is also used by body builders.

Mechanism[edit]

Aminoglutethimide has two mechanisms of action:

  1. It blocks aromatase[2] in the generation of estrogens from androstenedione and testosterone.
  2. It blocks the conversion of cholesterol to pregnenolone by inhibiting the enzyme P450scc and consequently decreases synthesis of all hormonally active steroids.

At low doses, aminogluthethimide is only an effective inhibitor of aromatase, but at higher doses, it effectively blocks P450scc as well.

Side effects[edit]

Its side effects are skin rash, hepatotoxicity, inhibition of cortisol in the human body, and it may also cause hypothyroidism[citation needed]. Since cortisol helps break down muscle, aminoglutethimide is used by bodybuilders in a steroid cycle.

Clinical uses[edit]

Aminoglutethimide is indicated in conjunction with other drugs for the suppression of adrenal function in patients with Cushing's syndrome.

It is also a 2nd or 3rd line choice for the treatment of hormone sensitive (estrogen and progesterone) metastatic breast cancer.

Abuse[edit]

Aminoglutethimide is abused by body builders and other steroid users to lower circulating levels of cortisol in the body and prevent muscle loss. Cortisol is catabolic to protein in muscle and effective blockade of P450scc by aminogluthethimide at high doses prevents muscle loss.[citation needed]

References[edit]

  1. ^ Gross BA, Mindea SA, Pick AJ, Chandler JP, Batjer HH (2007). "Medical management of Cushing disease". Neurosurgical focus 23 (3): E10. doi:10.3171/foc.2007.23.3.12. PMID 17961023. 
  2. ^ Siraki AG, Bonini MG, Jiang J, Ehrenshaft M, Mason RP (July 2007). "Aminoglutethimide-induced protein free radical formation on myeloperoxidase: a potential mechanism of agranulocytosis". Chemical research in toxicology 20 (7): 1038–45. doi:10.1021/tx6003562. PMC 2073000. PMID 17602675. 

External links[edit]

See also[edit]