Substance
ID:180863
Names and Identifiers
Synonyms
3-(p-Aminophenyl)-3-ethylpiperidine-2,6-dione3-(4-Aminophenyl)-3-ethyl-2,6-piperidinedioneDL-Aminoglutethimide
IUPAC Traditional name
aminoglutethimide
IUPAC name
3-(4-aminophenyl)-3-ethylpiperidine-2,6-dione
Properties
Physical Property
Solubility
methanol: soluble
45% (w/v) aq 2-hydroxypropyl-β-cyclodextrin: soluble1.2 mg/mL
H2O: slightly soluble0.2 mg/mL
acetonitrile: soluble
0.1 M HCl: soluble
Melting Point
152-154 °C(lit.)
Apperance
white
Safety Information
Personal Protective Equipment
dust mask type N95 (US), Eyeshields, Gloves
GHS Precautionary statements
P261-P305+P351+P338
Risk Statements
36/37/38
German water hazard class
3
GHS Pictograms
Acute toxicity (oral, dermal, inhalation), category 4
Skin irritation, category 2
Eye irritation, category 2
Skin sensitisation, category 1
Specific Target Organ Toxicity – Single exposure, category 3
RTECS
MA4026950
GHS Signal Word
Warning
GHS Hazard statements
H315-H319-H335
Safety Statements
26-36
European Hazard Symbols
Irritant (Xi)Pharmacology Properties
Gene Information
human ... CYP17A1(1586), CYP19A1(1588)rat ... Cyp19a1(25147)
Molecule Details
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).
Other Notes
Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. A9657.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.
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).
Other Notes
Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. A9657.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.
Molecular Spectra
No Data Available
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References
No Data Available
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