Aminoglutethimide
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MedKoo CAT#: 100051

CAS#: 125-84-8

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.


Chemical Structure

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Aminoglutethimide
CAS# 125-84-8

Theoretical Analysis

MedKoo Cat#: 100051
Name: Aminoglutethimide
CAS#: 125-84-8
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

Price and Availability

Size Price Availability Quantity
500.0mg USD 150.0 Same Day
1.0g USD 250.0 Same Day
2.0g USD 350.0 Same Day
5.0g USD 550.0 Same Day
10.0g USD 950.0 Same Day
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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

Product Data:

Certificate of Analysis:

Safety Data Sheet (SDS):

Biological target: Aminoglutethimide (BA-16038, NSC-330915) is an aromatase inhibitor with an IC50 of 10 μM.
In vitro activity: The effect of aminoglutethimide on cell death induced by overactivation of glutamate receptors in CNS neurons was investigated. In dissociated rat cerebrocortical cell cultures, long-term treatment with aminoglutethimide (10-1000 microM) attenuated NMDA receptor-mediated glutamate cytotoxicity but produced no significant effect on glutamate-induced increases in intracellular Ca2+. Brief as well as long-term pretreatment with aminoglutethimide (30-1000 microM) prevented NMDA receptor-dependent ischemic neuronal injury in organotypic cerebrocortical slice cultures, which was associated with suppression of glutamate release during the ischemic insult. These results indicate that aminoglutethimide, irrelevant to its actions on neurosteroid synthesis, protects CNS neurons from excitotoxic and ischemic injuries. Reference: Br J Pharmacol. 2006 Apr;147(7):729-36. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC1751506/
In vivo activity: Histopathological changes induced by 5-day administration of AG (aminoglutethimide) in mice were investigated. Cytoplasmic vacuoles of various sizes and single cell necrosis were found in zona fasciculata cells in AG-treated mice. Some vacuoles were positive for adipophilin, whereas others were positive for lysosome-associated membrane protein-2 on immunohistochemical staining, indicating they were enlarged lipid droplets and lysosomes, respectively. Electron microscopy revealed enlarged lysosomes containing damaged mitochondria and lamellar bodies in zona fasciculata cells, and they were considered to reflect the intracellular protein degradation processes, mitophagy and lipophagy. These results showed that AG induces excessive lipid accumulation and mitochondrial damage in zona fasciculata cells, which leads to an accelerated lysosomal degradation in mice. Reference: Exp Toxicol Pathol. 2017 Sep 5;69(7):424-429. https://www.sciencedirect.com/science/article/abs/pii/S0940299316302238?via%3Dihub

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMF 10.0 43.05
DMSO 15.0 64.58
DMSO:PBS (pH 7.2) (1:1) 0.5 2.15
Ethanol 8.5 36.59

Preparing Stock Solutions

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.

Recalculate based on batch purity %
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
Formulation protocol: 1. Shirakawa H, Katsuki H, Kume T, Kaneko S, Akaike A. Aminoglutethimide prevents excitotoxic and ischemic injuries in cortical neurons. Br J Pharmacol. 2006 Apr;147(7):729-36. doi: 10.1038/sj.bjp.0706636. PMID: 16474421; PMCID: PMC1751506. 2. 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. PMID: 28410883.
In vitro protocol: 1. Shirakawa H, Katsuki H, Kume T, Kaneko S, Akaike A. Aminoglutethimide prevents excitotoxic and ischemic injuries in cortical neurons. Br J Pharmacol. 2006 Apr;147(7):729-36. doi: 10.1038/sj.bjp.0706636. PMID: 16474421; PMCID: PMC1751506.
In vivo protocol: 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. PMID: 28410883.

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   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.



Additional Information

 
 
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.