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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

Signal Word

Warning

Hazard Statements

H315,H319,H335

Hazard Classifications

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

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

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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
R J Santen
Breast cancer research and treatment, 1(3), 183-202 (1981-01-01)
Fifty to sixty percent of postmenopausal women with estrogen receptor positive metastatic breast cancer respond objectively to surgical ablation of the pituitary or adrenal glands. Several investigators have recently developed medical alternatives to surgical ablative therapy for these patients. This
Aminoglutethimide: a "side-effect" turned to therapeutic advantage.
S W Hughss et al.
Postgraduate medical journal, 46(537), 409-416 (1970-07-01)
A L Harris
Experimental cell biology, 53(1), 1-8 (1985-01-01)
Aminoglutethimide is an effective treatment for advanced postmenopausal breast cancer, acting in a novel way. It inhibits peripheral and tumour aromatase, which converts androgens to oestrogens. Marked suppression of oestrone and oestradiol is produced. Aminoglutethimide was used as an inhibitor
A M Brodie et al.
Critical reviews in oncology/hematology, 5(4), 361-396 (1986-01-01)
Approximately one third of human breast carcinomas are hormone dependent and regress upon reduction of circulating estrogen levels. Traditional treatment strategies utilized surgical ablative methods to lower estrogen concentrations as treatment of breast cancer. Currently, investigative emphasis is focused upon
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