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
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
| Molecular Formula | C13H16N2O2 |
| Molecular Weight | 232.2783 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ABSOLUTE |
| Additional Stereochemistry | No |
| Defined Stereocenters | 1 / 1 |
| E/Z Centers | 0 |
| Optical Activity | UNSPECIFIED |
DescriptionCurator'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
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
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
Target ID: P11511 Gene ID: 1588.0 Gene Symbol: CYP19A1 Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/446416 |
370.0 µM [IC50] | ||
Target ID: CHEMBL2033 Sources: https://www.ncbi.nlm.nih.gov/pubmed/1613747 |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
PubMed
| Title | Date | PubMed |
|---|---|---|
| Sequential metabolism of 7-dehydrocholesterol to steroidal 5,7-dienes in adrenal glands and its biological implication in the skin. | 2009 |
|
| Implication of glucocorticoid in anti-inflammatory effects of Ro5-4864 in mouse pleurisy induced by carrageenan. | 2006-03-13 |
|
| Testosterone amplifies excitotoxic damage of cultured oligodendrocytes. | 2004-03 |
|
| Ectopic ACTH-syndrome due to a thymic carcinoid tumor. | 2002-05-23 |
|
| Identification of the aromatase inhibitor aminoglutethimide in urine by gas chromatography/mass spectrometry. | 2002 |
Patents
Sample Use Guides
In Vivo Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/1175729
(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
Sources: https://www.ncbi.nlm.nih.gov/pubmed/446416
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.
| Substance Class |
Chemical
Created
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admin
on
Edited
Mon Mar 31 21:27:57 GMT 2025
by
admin
on
Mon Mar 31 21:27:57 GMT 2025
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| Record UNII |
5S1T2OED7F
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| Record Status |
Validated (UNII)
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5S1T2OED7F
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| Related Record | Type | Details | ||
|---|---|---|---|---|
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RACEMATE -> ENANTIOMER |