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A9657

Sigma-Aldrich

DL-Aminoglutethimide

Sinonimo/i:

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

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About This Item

Formula empirica (notazione di Hill):
C13H16N2O2
Numero CAS:
125-84-8
Peso molecolare:
232.28
Numero CE:
204-756-4
Numero MDL:
MFCD00010122
Codice UNSPSC:
51111800
ID PubChem:
24278142
NACRES:
NA.77
Prezzi e disponibilità al momento non sono disponibili

Origine biologica

synthetic

Saggio

≥98% (TLC)

Stato

powder or crystals

Colore

white

Punto di fusione

152-154 °C (lit.)

Solubilità

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

Ideatore

Novartis

Temperatura di conservazione

room temp

Stringa SMILE

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)
ROBVIMPUHSLWNV-UHFFFAOYSA-N

Informazioni sul gene

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

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Applicazioni

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]

Azioni biochim/fisiol

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.

Caratteristiche e vantaggi

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

Confezionamento

Bottomless glass bottle. Contents are inside inserted fused cone.

Applicazioni

N° Catalogo
Descrizione
Determinazione del prezzo

Pittogrammi

Exclamation mark
GHS07

Avvertenze

Warning

Indicazioni di pericolo

H315,H319,H335

Classi di pericolo

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

Organi bersaglio

Respiratory system

Codice della classe di stoccaggio

11 - Combustible Solids

Classe di pericolosità dell'acqua (WGK)

WGK 3

Punto d’infiammabilità (°F)

Not applicable

Punto d’infiammabilità (°C)

Not applicable

Dispositivi di protezione individuale

dust mask type N95 (US), Eyeshields, Gloves

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Certificati d'analisi (COA)

Lot/Batch Number
BCCJ6494
BCCB1342
BCBD0757V
BCBN4336V
BCBH1519V

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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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