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A0496000

Aminoglutethimide

European Pharmacopoeia (EP) Reference Standard

Synonym(s):

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

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About This Item

Empirical Formula (Hill Notation):
C13H16N2O2
CAS Number:
125-84-8
Molecular Weight:
232.28
MDL number:
MFCD00010122
UNSPSC Code:
41116107
PubChem Substance ID:
329770616
NACRES:
NA.24

grade

pharmaceutical primary standard

API family

aminoglutethimide

manufacturer/tradename

EDQM

mp

152-154 °C (lit.)

application(s)

pharmaceutical (small molecule)

format

neat

storage temp.

2-8°C

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) , CYP19A1(1588)

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General description

This product is provided as delivered and specified by the issuing Pharmacopoeia. All information provided in support of this product, including SDS and any product information leaflets have been developed and issued under the Authority of the issuing Pharmacopoeia.For further information and support please go to the website of the issuing Pharmacopoeia.

Application

Aminoglutethimide EP Reference standard, intended for use in laboratory tests only as specifically prescribed in the European Pharmacopoeia.

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).

Packaging

The product is delivered as supplied by the issuing Pharmacopoeia. For the current unit quantity, please visit the EDQM reference substance catalogue.

Other Notes

Sales restrictions may apply.

pictograms

Exclamation mark
GHS07

signalword

Warning

Hazard Classifications

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

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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M A Shaw et al.
Journal of steroid biochemistry, 31(1), 137-146 (1988-07-01)
Aminoglutethimide and ketoconazole, although originally developed as an anticonvulsant and antifungal agent respectively, have both been used to suppress steroid biosynthesis in patients with hormone-sensitive cancer. Aminoglutethimide inhibits several enzymes involved in the synthesis of corticosteroids as well as the
Adrenocortical steroidogenesis and aminoglutethimide I. Biomedical studies.
Y Touitou et al.
Biomedicine / [publiee pour l'A.A.I.C.I.G.], 18(3), 185-191 (1973-05-01)
A L Harris
Breast cancer research and treatment, 6(3), 201-211 (1985-01-01)
Could aminoglutethimide replace adrenalectomy? This question has already been answered in clinical practice in the United Kingdom, for surgical adrenalectomy has declined markedly in frequency as new hormonal therapy has appeared. An optimal assessment of an endocrine therapy can only
E Samojlik et al.
The Journal of clinical investigation, 65(3), 602-612 (1980-03-01)
We evaluated the comparative effects of aminoglutethimide (AG) on androgen and estrogen levels estrone ([E1], estradiol [E2], plasma dehydroepiandrosterone-sulfate [DHEA-S], testosterone [T], dihydrotestosterone [DHT], delta 4-androstenedione [delta 4-A]), follicle-stimulating hormone (FSH), luteinizing hormone (LH), and prolactin in postmenopausal patients with
R J Santen et al.
Pharmacotherapy, 1(2), 95-120 (1981-09-01)
Aminoglutethimide blocks several cytochrome P-450 mediated steroid hydroxylation steps, including those required for conversion of cholesterol to pregnenolone and for the aromatization of androgens to estrogens. Through these actions it blocks adrenal steroidogenesis and the production of estrogens in extraglandular
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