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Key Documents

A9657

Sigma-Aldrich

DL-Aminoglutethimide

Synonyme(s) :

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

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About This Item

Formule empirique (notation de Hill):
C13H16N2O2
Numéro CAS:
Poids moléculaire :
232.28
Numéro CE :
Numéro MDL:
Code UNSPSC :
51111800
ID de substance PubChem :
Nomenclature NACRES :
NA.77

Source biologique

synthetic

Pureté

≥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

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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
  • 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

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).

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.

Pictogrammes

Exclamation mark

Mention d'avertissement

Warning

Mentions de danger

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


Certificats d'analyse (COA)

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Consulter la Bibliothèque de documents

Arup Maiti et al.
Journal of medicinal chemistry, 50(12), 2799-2806 (2007-05-22)
An efficient and economical synthesis of the naturally occurring aromatase inhibitor abyssinone II was performed. The synthesis features an optimized aromatic prenylation reaction in which an arylcopper intermediate is reacted with prenyl bromide to afford a key intermediate that was
Biphasic regulation of the messenger ribonucleic acid coding for the estrogen receptor by cyclic adenosine 3?: 5?-monophosphate in tumor Leydig cells
Ree A H, et al.
Cancer research, 50(5), 1528-1531 (1990)
Activation of the progesterone-signaling pathway by methyl-beta-cyclodextrin or steroid in Xenopus laevis oocytes involves release of 45-kDa Galphas
Sadler S E, et al.
Developmental Biology, 322(1), 199-207 (2008)
Motoki Tanaka et al.
Neuropharmacology, 62(7), 2373-2387 (2012-03-01)
Both in vivo and in vitro studies have shown that neurosteroids promote learning and memory by modulating synaptic functions in the hippocampus. However, we do not know to what degree endogenously synthesized neurosteroids contribute to the hippocampal synaptic functions. Cytochrome
In vivo alternative assessment of the chemicals that interfere with anterior pituitary POMC expression and interrenal steroidogenesis in POMC: EGFP transgenic zebrafish
Sun L, et al.
Toxicology and Applied Pharmacology, 248(3), 217-225 (2010)

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