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. Australia requires an import license for this product.

Chemical Structure

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Aminoglutethimide
CAS# 125-84-8
Product data Instruction

Theoretical Analysis

MedKoo Cat#: 100051
Name: Aminoglutethimide
CAS#: 125-84-8
Chemical Formula: C13H16N2O2
Exact Mass: 232.12
Molecular Weight: 232.280
Elemental Analysis: C, 67.22; H, 6.94; N, 12.06; O, 13.78

Price and Availability

Size Price Availability Quantity
500mg USD 150 Same Day
1g USD 250 Same Day
2g USD 450 Same Day
5g USD 950 Same Day
10g USD 1650 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:
Product Data
Certificate of Analysis:
View CoA: current batch, Lot#A7L11F08
Safety Data Sheet (SDS):
View Safety Data Sheet (SDS)
Instruction:
View handling instruction
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 232.280000000000000000000000000000 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.