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DL-Aminoglutethimide

SIGMA/A9657

Synonym: 3-(4-Aminophenyl)-3-ethyl-2,6-piperidinedione; 3-(p-Aminophenyl)-3-ethylpiperidine-2,6-dione

CAS Number: 125-84-8
Empirical Formula (Hill Notation): C13H16N2O2
Molecular Weight: 232.28
EC Number: 204-756-4
MDL Number: MFCD00010122
Linear Formula: C13H16N2O2
Product Type: Chemical

Catalog Number PKG Qty. Price Quantity
45-A9657-100MG 100 mg
$187.00
1/EA
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45-A9657-500MG 500 mg
$635.00
1/EA
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45-A9657-1G 1 g
$1090.00
1/EA
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assay ≥98% (TLC)
biological source synthetic
color white
form powder or crystals
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
mp 152-154 °C (lit.)
originator Novartis
Quality Level 200 
SMILES string CCC1(CCC(=O)NC1=O)c2ccc(N)cc2
solubility 0.1 M HCl: soluble
  45% (w/v) aq 2-hydroxypropyl-β-cyclodextrin: 1.2 mg/mL
  acetonitrile: soluble
  H2O: slightly soluble 0.2 mg/mL
  methanol: soluble
storage temp. room temp
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).
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.
Purity ≥98% (TLC)
mp 152-154 °C (lit.)
Storage Temp. room temp
UNSPSC 51111800

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