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
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 |
---|---|---|
Identification of the aromatase inhibitor aminoglutethimide in urine by gas chromatography/mass spectrometry. | 2002 |
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Testosterone amplifies excitotoxic damage of cultured oligodendrocytes. | 2004 Mar |
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Implication of glucocorticoid in anti-inflammatory effects of Ro5-4864 in mouse pleurisy induced by carrageenan. | 2006 Mar 13 |
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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
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.
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57288-03-6
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1548995
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DTXSID30972802
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5S1T2OED7F
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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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SUBSTANCE RECORD