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A9657

Sigma-Aldrich

DL-Aminoglutethimide

Synonym(s):

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

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MYR 375.00

MYR 375.00


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1 L
MYR 375.00

About This Item

Empirical Formula (Hill Notation):
C13H16N2O2
CAS Number:
Molecular Weight:
232.28
EC Number:
MDL number:
UNSPSC Code:
51111800
PubChem Substance ID:
NACRES:
NA.77

MYR 375.00


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biological source

synthetic

Quality Level

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

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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]

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.

Pictograms

Exclamation mark

Signal Word

Warning

Hazard Statements

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Haibo Han et al.
Nature communications, 6, 8271-8271 (2015-10-01)
Tumour-initiating cells (TICs) are advocated to constitute the sustaining force to maintain and renew fully established malignancy; however, the molecular mechanisms responsible for these properties are elusive. We previously demonstrated that voltage-gated calcium channel α2δ1 subunit marks hepatocellular carcinoma (HCC)
Wei Zhao et al.
Cancer cell, 23(4), 541-556 (2013-04-20)
The identification and targeted therapy of cells involved in hepatocellular carcinoma (HCC) recurrence remain challenging. Here, we generated a monoclonal antibody against recurrent HCC, 1B50-1, that bound the isoform 5 of the α2δ1 subunit of voltage-gated calcium channels and identified
Claudia S Bauer et al.
Current opinion in neurobiology, 20(5), 563-571 (2010-06-29)
The classical roles of α(2)δ proteins are as accessory calcium channel subunits, enhancing channel trafficking. They were thought to have type-I transmembrane topology, but we find that they can form GPI-anchored proteins. Moreover α(2)δ-1 and α(2)δ-3 have been shown to
D E Iles et al.
Human molecular genetics, 3(6), 969-975 (1994-06-01)
Malignant hyperthermia susceptibility (MHS) is an autosomal dominant disorder of skeletal muscle which manifests as a potentially fatal hypermetabolic crisis triggered by commonly used anaesthetic agents. The demonstration of genetic heterogeneity in MHS prompted the investigation of the roles played
L Schleithoff et al.
Genomics, 61(2), 201-209 (1999-10-27)
CACNA2 encodes the alpha(2)/delta subunit of the human voltage-gated calcium channels and is located in the candidate region of malignant hyperthermia susceptibility type 3 (MHS3). We determined the structural organization of CACNA2 by isolation of overlapping genomic DNA clones from

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