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Merck
CN

A9657

Sigma-Aldrich

DL-氨基谷氨酰胺

别名:

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

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About This Item

经验公式(希尔记法):
C13H16N2O2
CAS号:
分子量:
232.28
EC 号:
MDL编号:
UNSPSC代码:
51111800
PubChem化学物质编号:
NACRES:
NA.77

生物来源

synthetic

质量水平

方案

≥98% (TLC)

表单

powder or crystals

颜色

white

mp

152-154 °C (lit.)

溶解性

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

创始人

Novartis

储存温度

room temp

SMILES字符串

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)

InChI key

ROBVIMPUHSLWNV-UHFFFAOYSA-N

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应用

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

生化/生理作用

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.

特点和优势

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

包装

Bottomless glass bottle. Contents are inside inserted fused cone.

象形图

Exclamation mark

警示用语:

Warning

危险声明

危险分类

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

靶器官

Respiratory system

储存分类代码

11 - Combustible Solids

WGK

WGK 3

闪点(°F)

Not applicable

闪点(°C)

Not applicable

个人防护装备

dust mask type N95 (US), Eyeshields, Gloves

法规信息

监管及禁止进口产品

历史批次信息供参考:

分析证书(COA)

Lot/Batch Number

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访问文档库

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
Sandy Lenie et al.
Toxicology letters, 185(3), 143-152 (2009-01-21)
Biologically relevant bioassays are needed to test various endocrine disrupters (EDs). A mouse follicle culture model could allow measuring steroidogenic enzyme function in combination with oocyte growth and meiotic maturation using routine methodology. Three steroidogenesis-disrupting 'model' chemicals were tested; vorozole
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
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)

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