A9657

DL-Aminoglutethimide

• Synonyme(s) : 3-(4-Aminophenyl)-3-ethyl-2,6-piperidinedione, 3-(p-Aminophenyl)-3-ethylpiperidine-2,6-dione
• Formule empirique (notation de Hill) : C₁₃H₁₆N₂O₂
• Numéro CAS: 125-84-8
• Poids moléculaire : 232.28
• Numéro CE : 204-756-4
• Numéro MDL: MFCD00010122
• Code UNSPSC : 51111800
• ID de substance PubChem : 24278142
• Nomenclature NACRES : NA.77

Propriétés

• Source biologique: synthetic
• Essai: ≥98% (TLC)
• Forme: powder or crystals
• Couleur: white
• Pf: 152-154 °C (lit.)
• Solubilité: 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
• Auteur: Novartis
• Température de stockage: room temp
• Chaîne SMILES: 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)
• Clé InChI: ROBVIMPUHSLWNV-UHFFFAOYSA-N
• Informations sur le gène: 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[1]
• 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[2]
• as an inhibitor of steroidogenic enzymes to study its effects on estrogen receptor (ER) mRNA levels in mouse tumor leydig cell line [3]

Actions biochimiques/physiologiques

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.

Caractéristiques et avantages

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

Conditionnement

Bottomless glass bottle. Contents are inside inserted fused cone.

Informations sur la sécurité

• Pictogrammes: GHS07
• Mention d'avertissement: Warning
• Mentions de danger: H315,H319,H335
• Conseils de prudence: P261 - P264 - P271 - P280 - P302 + P352 - P305 + P351 + P338
• Classification des risques: Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3
• Organes cibles: Respiratory system
• Code de la classe de stockage: 11 - Combustible Solids
• Classe de danger pour l'eau (WGK): WGK 3
• Point d'éclair (°F): Not applicable
• Point d'éclair (°C): Not applicable
• Équipement de protection individuelle: dust mask type N95 (US), Eyeshields, Gloves