WARNING: This product is for research use only, not for human or veterinary use.
MedKoo CAT#: 100051
Description: Aminoglutethimide is an anticancer drug that belongs to the family of drugs called nonsteroidal aromatase inhibitors. Aminoglutethimide is used to decrease the production of sex hormones (estrogen in women or testosterone in men) and suppress the growth of tumors that need sex hormones to grow. Aminoglutethimide is 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 and metastatic breast cancer.
MedKoo Cat#: 100051
Chemical Formula: C13H16N2O2
Exact Mass: 232.12118
Molecular Weight: 232.28
Elemental Analysis: C, 67.22; H, 6.94; N, 12.06; O, 13.78
Synonym: Ainoglutethimide; Cytadren; Orimeten; dlAminoglutethimide; pAminoglutethimide; Elipten; Aminoglutetimida; Aminoglutethimidum; Ba16038; Cytadren (TN); Prestwick243; CCRIS 7562; CHEBI:2654; Aminoglutethimidum INNLatin.
IUPAC/Chemical Name: 3-(4-aminophenyl)-3-ethyl-piperidine-2,6-dione
InChi Key: ROBVIMPUHSLWNV-UHFFFAOYSA-N
InChi Code: 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)
SMILES Code: O=C(C(CC)(C1=CC=C(N)C=C1)CC2)NC2=O
Appearance: Solid powder
Purity: >98% (or refer to the Certificate of Analysis)
Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility: Soluble in DMSO, not in water
Shelf Life: >2 years if stored properly
Drug Formulation: This drug may be formulated in DMSO
Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code: 2934.99.9001
The following data is based on the product molecular weight 232.28 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.
|Concentration / Solvent Volume / Mass||1 mg||5 mg||10 mg|
|1 mM||1.15 mL||5.76 mL||11.51 mL|
|5 mM||0.23 mL||1.15 mL||2.3 mL|
|10 mM||0.12 mL||0.58 mL||1.15 mL|
|50 mM||0.02 mL||0.12 mL||0.23 mL|
1: Mutsuga M, Asaoka Y, Imura N, Miyoshi T, Togashi Y. Aminoglutethimide-induced lysosomal changes in adrenal gland in mice. Exp Toxicol Pathol. 2017 Sep 5;69(7):424-429. doi: 10.1016/j.etp.2017.04.004. Epub 2017 Apr 11. PubMed PMID: 28410883.
2: Ng W, Metushi IG, Uetrecht J. Hepatic effects of aminoglutethimide: a model aromatic amine. J Immunotoxicol. 2015 Jan-Mar;12(1):24-32. doi: 10.3109/1547691X.2013.867912. Epub 2013 Dec 19. PubMed PMID: 24350727.
3: Lønning PE, Kvinnsland S. Mechanisms of action of aminoglutethimide as endocrine therapy of breast cancer. Drugs. 1988 Jun;35(6):685-710. Review. PubMed PMID: 3048976.
4: Santen RJ, Misbin RI. Aminoglutethimide: review of pharmacology and clinical use. Pharmacotherapy. 1981 Sep-Oct;1(2):95-120. Review. PubMed PMID: 6765487.
5: Hughss SW, Burley DM. Aminoglutethimide: a "side-effect" turned to therapeutic advantage. Postgrad Med J. 1970 Jul;46(537):409-16. Review. PubMed PMID: 4920933; PubMed Central PMCID: PMC2467063.
Cytadren inhibits the enzymatic conversion of cholesterol to Δ5-pregnenolone, resulting in a decrease in the production of adrenal glucocorticoids, mineralocorticoids, estrogens, and androgens. Cytadren blocks several other steps in steroid synthesis, including the C-11, C-18, and C-21 hydroxylations and the hydroxylations required for the aromatization of androgens to estrogens, mediated through the binding of Cytadren to cytochrome P-450 complexes. A decrease in adrenal secretion of cortisol is followed by an increased secretion of pituitary adrenocorticotropic hormone (ACTH), which will overcome the blockade of adrenocortical steroid synthesis by Cytadren. The compensatory increase in ACTH secretion can be suppressed by the simultaneous administration of hydrocortisone. Since Cytadren increases the rate of metabolism of dexamethasone but not that of hydrocortisone, the latter is preferred as the adrenal glucocorticoid replacement. Although Cytadren inhibits the synthesis of thyroxine by the thyroid gland, the compensatory increase in thyroid-stimulating hormone (TSH) is frequently of sufficient magnitude to overcome the inhibition of thyroid synthesis due to Cytadren. In spite of an increase in TSH, Cytadren has not been associated with increased prolactin secretion. Note: Cytadren was marketed previously as an anticonvulsant but was withdrawn from marketing for that indication in 1966 because of the effects on the adrenal gland.
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.
Cytadren, aminoglutethimide tablets USP, is an inhibitor of adrenocortical steroid synthesis, available as 250-mg tablets for oral administration. Its chemical name is 3-(4-aminophenyl)-3-ethyl-2,6-piperidinedione. Aminoglutethimide USP is a fine, white or creamy white, crystalline powder. It is very slightly soluble in water, and readily soluble in most organic solvents. It forms water- soluble salts with strong acids. Its molecular weight is 232.28. Inactive Ingredients. Cellulose compounds, colloidal silicon dioxide, starch, stearic acid, and talc.
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.