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A9657

DL-氨基谷氨酰胺

Name: <SC>DL</SC>-氨基谷氨酰胺
Brand: SIGMA

别名:

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

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关于此项目

经验公式（希尔记法）:

C₁₃H₁₆N₂O₂

化学文摘社编号:

125-84-8

分子量:

232.28

NACRES:

NA.77

PubChem Substance ID:

24278142

UNSPSC Code:

51111800

EC Number:

204-756-4

MDL number:

MFCD00010122

Assay:

≥98% (TLC)

Form:

powder or crystals

Quality level:

200

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biological source

synthetic

Quality Level

200

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

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

Gene Information

human ... CYP11A1(1583), CYP17A1(1586), CYP19A1(1588)
rat ... Cyp19a1(25147)

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).

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

GHS07

signalword

Warning

hcodes

H315,H319,H335

pcodes

P261 - P264 - P271 - P280 - P302 + P352 - P305 + P351 + P338

Hazard Classifications

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

target_organs

Respiratory system

存储类别

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

法规信息

监管及禁止进口产品

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历史批次信息供参考:

分析证书(COA)

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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)

Synthesis and biological evaluation of (+/-)-abyssinone II and its analogues as aromatase inhibitors for chemoprevention of breast cancer.

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

Mechanisms of action of aminoglutethimide as endocrine therapy of breast cancer.

P E Lønning et al.

Drugs, 35(6), 685-710 (1988-06-01)

During the last decade aminoglutethimide has been recognised as a valuable alternative in endocrine therapy for advanced breast cancer. Although some side effects do occur, most often these are initial effects which subside within a few weeks, and cessation of

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)

Aminoglutethimide in the treatment of advanced breast cancer.

R C Stuart-Harris et al.

Cancer treatment reviews, 11(3), 189-204 (1984-09-01)

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全球贸易项目编号

货号	GTIN
A9657-1G	04061826740989
A9657-100MG	04061833412183
A9657-500MG	04061833030585

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