A9657

DL-Aminoglutethimide

• Synonym(s): 3-(4-Aminophenyl)-3-ethyl-2,6-piperidinedione, 3-(p-Aminophenyl)-3-ethylpiperidine-2,6-dione
• Empirical Formula (Hill Notation): C₁₃H₁₆N₂O₂
• CAS Number: 125-84-8
• Molecular Weight: 232.28
• NACRES: NA.77
• PubChem Substance ID: 24278142
• UNSPSC Code: 51111800
• EC Number: 204-756-4
• MDL number: MFCD00010122
• Assay: ≥98% (TLC)
• Form: powder or crystals

Properties

• biological source: synthetic
• Quality Segment: 200
• assay: ≥98% (TLC)
• form: powder or crystals
• color: white
• mp: 152-154 °C (lit.)
• solubility: H₂O: slightly soluble 0.2 mg/mL, 45% (w/v) aq 2-hydroxypropyl-β-cyclodextrin: 1.2 mg/mL, 0.1 M HCl: soluble, acetonitrile: soluble, methanol: soluble
• originator: Novartis
• storage temp.: room temp
• SMILES string: CCC1(CCC(=O)NC1=O)c2ccc(N)cc2
• 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)
• InChI key: ROBVIMPUHSLWNV-UHFFFAOYSA-N
• Gene Information: human ... CYP11A1(1583), CYP17A1(1586), CYP19A1(1588) ; rat ... Cyp19a1(25147)

Description

Application

DL-Aminoglutethimide has been used:

• as a steroid synthesis inhibitor to study its effects on steroid synthesis in amphibian Xenopus laevis oocytes
• as an adrenostatic compound to study its effects on full form Enhanced green fluorescent protein (EGFP) andproopiomelanocortin (POMC) expression in the anterior domain of zebrafish pituitary corticotrophs
• as an inhibitor of steroidogenic enzymes to study its effects on estrogen receptor (ER) mRNA levels in mouse tumor leydig cell line

Biochem/physiol Actions

DL-Aminoglutethimide is a derivative of the sedative glutethimide. Originally introduced as an anticonvulsant, it was found to cause adrenal insufficiency. Blocks adrenal steroidogenesis by inhibiting the enzymatic conversion of cholesterol to pregnenolone. It also blocks the peripheral conversion (aromatization) of androgenic precursors to estrogens. The D-isomer is 30 times more potent at inhibiting aromatase activity, whereas the L-isomer is more potent at inhibiting cholesterol side-chain cleavage (steroidogenesis).

Derivative of the sedative glutethimide. Originally introduced as an anticonvulsant, it was found to cause adrenal insufficiency. Blocks adrenal steroidogenesis by inhibiting the enzymatic conversion of cholesterol to pregnenolone.

Features and Benefits

This compound was developed by Novartis. To browse the list of other pharma-developed compounds and Approved Drugs/Drug Candidates, click here.

Packaging

Bottomless glass bottle. Contents are inside inserted fused cone.

Safety Information

• Pictograms: GHS07
• Signal Word: Warning
• Hazard Codes: H315,H319,H335
• Precautionary Statements: P261 - P264 - P271 - P280 - P302 + P352 - P305 + P351 + P338
• Hazard Classifications: Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3
• Target Organs: Respiratory system
• Storage Class: 11 - Combustible Solids
• WGK: WGK 3
• Flash Point (°F): Not applicable
• Flash Point (°C): Not applicable
• PPE (personal protective equipment): dust mask type N95 (US), Eyeshields, Gloves