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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, (S)-

SMILES

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

InChI

InChIKey=ROBVIMPUHSLWNV-ZDUSSCGKSA-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-/m0/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

(S)-Aminoglutethimide is S-isomer of racemate anti-steroid drug Aminoglutethimide, marketed by Novartis for the treatment of Cushing syndrome and other conditions. (S)-Aminoglutethimide was shown to less active than (R)-isomer in inhibiting corticosteroid release in rats, less potent in inhibiting aromatization of testosterone by human placental microsomes.

Approval Year

Targets

Targets

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

Conditions

ConditionModalityTargetsHighest PhaseProduct
PubMed

PubMed

TitleDatePubMed
Identification of the aromatase inhibitor aminoglutethimide in urine by gas chromatography/mass spectrometry.
2002
Testosterone amplifies excitotoxic damage of cultured oligodendrocytes.
2004 Mar
Implication of glucocorticoid in anti-inflammatory effects of Ro5-4864 in mouse pleurisy induced by carrageenan.
2006 Mar 13
Sequential metabolism of 7-dehydrocholesterol to steroidal 5,7-dienes in adrenal glands and its biological implication in the skin.
2009
Patents

Sample Use Guides

(S)-Aminoglutethimide was shown to be 2-3 times less active than R-isomer in inhibiting corticosteroid release in rats when injected iv.
Route of Administration: Intravenous
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, (S)-
Common Name English
(-)-AMINOGLUTETHIMIDE
Common Name English
(-)-(S)-AMINOGLUTETHIMIDE
Common Name English
2,6-PIPERIDINEDIONE, 3-(4-AMINOPHENYL)-3-ETHYL-, (3S)-
Systematic Name English
Code System Code Type Description
CAS
57288-03-6
Created by admin on Sat Dec 16 05:14:44 GMT 2023 , Edited by admin on Sat Dec 16 05:14:44 GMT 2023
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PUBCHEM
1548995
Created by admin on Sat Dec 16 05:14:44 GMT 2023 , Edited by admin on Sat Dec 16 05:14:44 GMT 2023
PRIMARY
EPA CompTox
DTXSID30972802
Created by admin on Sat Dec 16 05:14:44 GMT 2023 , Edited by admin on Sat Dec 16 05:14:44 GMT 2023
PRIMARY
FDA UNII
5S1T2OED7F
Created by admin on Sat Dec 16 05:14:44 GMT 2023 , Edited by admin on Sat Dec 16 05:14:44 GMT 2023
PRIMARY