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Details

Stereochemistry ABSOLUTE
Molecular Formula C13H16N2O2
Molecular Weight 232.2783
Optical Activity UNSPECIFIED
Defined Stereocenters 1 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of AMINOGLUTETHIMIDE, (R)-

SMILES

CC[C@@]1(CCC(=O)NC1=O)C2=CC=C(N)C=C2

InChI

InChIKey=ROBVIMPUHSLWNV-CYBMUJFWSA-N
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)/t13-/m1/s1

HIDE SMILES / InChI

Description
Curator's Comment: description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/1175729 | https://www.ncbi.nlm.nih.gov/pubmed/446416

(R)-Aminoglutethimide is R-isomer of racemate anti-steroid drug Aminoglutethimide, marketed by Novartis for the treatment of Cushing syndrome and other conditions. (R)-Aminoglutethimide was shown to more active than (S)-isomer in inhibiting corticosteroid release in rats, more potent in inhibiting aromatization of testosterone by human placental microsomes. (R)-Aminoglutethimide was investigated in a clinical trial against breast cancer, where it was found to enhance the clearance rate of plasma estrone sulfate.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Target ID: P11511
Gene ID: 1588.0
Gene Symbol: CYP19A1
Target Organism: Homo sapiens (Human)
19.0 µM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
The absolute configuration of the enantiomers of glutethimide and aminoglutethimide.
1975 Sep 15
Stereoselective inhibition of aromatase by enantiomers of aminoglutethimide.
1979 Jul
Patents

Patents

Sample Use Guides

In a clinical trial against breast cancer, (R)-Aminoglutethimide was administered orally four times a day at doses 125 mg.
Route of Administration: Oral
In Vitro Use Guide
To measure inhibition of placental aromatase, [1beta,2beta-3H]testosterone (107dpm) and 10 uM unlabeled testosterone was incubated with approximately 10 mg microsomal protein in 0.05 M sodium phosphate buffer (pH 7.4). Each tube was preincubated for 2 min at 25°C in a shaking water bath. The NADPH-generating system, consisting of 1 mM NADPH, 10 mM glucose-6-phosphate, and 1 U glucose-6-phosphate dehydrogenase, was added to start the reaction. Aminoglutethimide was added in 20 ul ethanol and an equal volume of ethanol was added to the control incubation tubes. Aliquots were withdrawn at 0, 5, 10, 15, and 20 min, and the reaction was terminated by the addition of 0.3 ml cold 1 mM HgCls and 1 ml 1% aqueous suspension of Norit A charcoal to each tube. After 20 min, the tubes were centrifuged to separate the charcoal-adsorbed steroids, and radioactivity associated with tritiated water was measured.
Name Type Language
AMINOGLUTETHIMIDE, (R)-
Common Name English
(+)-AMINOGLUTETHIMIDE
Systematic Name English
2,6-PIPERIDINEDIONE, 3-(4-AMINOPHENYL)-3-ETHYL-, (R)-
Systematic Name English
(+)-R-AMINOGLUTETHIMIDE
Systematic Name English
Code System Code Type Description
PUBCHEM
86488
Created by admin on Sat Dec 16 09:46:57 GMT 2023 , Edited by admin on Sat Dec 16 09:46:57 GMT 2023
PRIMARY
FDA UNII
LUC985IS6T
Created by admin on Sat Dec 16 09:46:57 GMT 2023 , Edited by admin on Sat Dec 16 09:46:57 GMT 2023
PRIMARY
CAS
55511-44-9
Created by admin on Sat Dec 16 09:46:57 GMT 2023 , Edited by admin on Sat Dec 16 09:46:57 GMT 2023
PRIMARY
EPA CompTox
DTXSID501318980
Created by admin on Sat Dec 16 09:46:57 GMT 2023 , Edited by admin on Sat Dec 16 09:46:57 GMT 2023
PRIMARY