A9657

DL-Aminoglutethimid

• Synonym(e): 3-(4-Aminophenyl)-3-ethyl-2,6-piperidinedione, 3-(p-Aminophenyl)-3-ethylpiperidine-2,6-dione
• Empirische Formel (Hill-System): C₁₃H₁₆N₂O₂
• CAS-Nummer: 125-84-8
• Molekulargewicht: 232.28
• EG-Nummer: 204-756-4
• MDL-Nummer: MFCD00010122
• UNSPSC-Code: 51111800
• PubChem Substanz-ID: 24278142
• NACRES: NA.77

Eigenschaften

• Biologische Quelle: synthetic
• Assay: ≥98% (TLC)
• Form: powder or crystals
• Farbe: white
• mp (Schmelzpunkt): 152-154 °C (lit.)
• Löslichkeit: 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
• Ersteller: Novartis
• Lagertemp.: 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)
• InChIKey: ROBVIMPUHSLWNV-UHFFFAOYSA-N
• Angaben zum Gen: human ... CYP11A1(1583) , CYP17A1(1586) , CYP19A1(1588) ; rat ... Cyp19a1(25147)

Beschreibung

Anwendung

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]

Biochem./physiol. Wirkung

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.

Leistungsmerkmale und Vorteile

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

Verpackung

Bottomless glass bottle. Contents are inside inserted fused cone.

Sicherheitshinweise

• Piktogramme: GHS07
• Signalwort: Warning
• H-Sätze: H315,H319,H335
• P-Sätze: P261 - P264 - P271 - P280 - P302 + P352 - P305 + P351 + P338
• Gefahreneinstufungen: Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3
• Zielorgane: Respiratory system
• Lagerklassenschlüssel: 11 - Combustible Solids
• WGK: WGK 3
• Flammpunkt (°F): Not applicable
• Flammpunkt (°C): Not applicable
• Persönliche Schutzausrüstung: dust mask type N95 (US), Eyeshields, Gloves