Record Information |
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Version | 5.0 |
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Status | Expected but not Quantified |
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Creation Date | 2012-09-06 15:16:49 UTC |
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Update Date | 2022-03-07 02:51:38 UTC |
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HMDB ID | HMDB0014501 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | Aminoglutethimide |
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Description | Aminoglutethimide, also known as cytadren or orimeten, belongs to the class of organic compounds known as aniline and substituted anilines. These are organic compounds containing an aminobenzene moiety. Aminoglutethimide is a drug which is used for the suppression of adrenal function in selected patients with cushing's syndrome, malignant neoplasm of the female breast, and carcinoma in situ of the breast. Aminoglutethimide is a strong basic compound (based on its pKa). Aminoglutethimide is a potentially toxic compound. A dicarboximide that is a six-membered cyclic compound having ethyl and 4-aminophenyl substituents at the 3-position. |
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Structure | CCC1(CCC(=O)NC1=O)C1=CC=C(N)C=C1 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) |
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Synonyms | Value | Source |
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2-(p-Aminophenyl)-2-ethylglutarimide | ChEBI | 3-Ethyl-3-(p-aminophenyl)-2,6-dioxopiperidine | ChEBI | alpha-(p-Aminophenyl)-alpha-ethylglutarimide | ChEBI | Aminoglutethimidum | ChEBI | Aminoglutetimida | ChEBI | DL-Aminoglutethimide | ChEBI | p-Aminoglutethimide | ChEBI | Cytadren | Kegg | a-(p-Aminophenyl)-a-ethylglutarimide | Generator | Α-(p-aminophenyl)-α-ethylglutarimide | Generator | Ciba vision brand OF aminoglutethimide | HMDB | Novartis brand OF aminoglutethimide | HMDB | Orimeten | HMDB |
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Chemical Formula | C13H16N2O2 |
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Average Molecular Weight | 232.2783 |
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Monoisotopic Molecular Weight | 232.121177766 |
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IUPAC Name | 3-(4-aminophenyl)-3-ethylpiperidine-2,6-dione |
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Traditional Name | aminoglutethimide |
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CAS Registry Number | 125-84-8 |
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SMILES | CCC1(CCC(=O)NC1=O)C1=CC=C(N)C=C1 |
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InChI Identifier | 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) |
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InChI Key | ROBVIMPUHSLWNV-UHFFFAOYSA-N |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as aniline and substituted anilines. These are organic compounds containing an aminobenzene moiety. |
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Kingdom | Organic compounds |
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Super Class | Benzenoids |
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Class | Benzene and substituted derivatives |
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Sub Class | Aniline and substituted anilines |
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Direct Parent | Aniline and substituted anilines |
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Alternative Parents | |
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Substituents | - Aniline or substituted anilines
- Tetrahydropyridine
- Hydropyridine
- Amino acid or derivatives
- N-acylimine
- Lactim
- Organoheterocyclic compound
- Organic 1,3-dipolar compound
- Propargyl-type 1,3-dipolar organic compound
- Carboxylic acid derivative
- Azacycle
- Organopnictogen compound
- Amine
- Organic oxygen compound
- Primary amine
- Organooxygen compound
- Organonitrogen compound
- Organic nitrogen compound
- Carbonyl group
- Hydrocarbon derivative
- Organic oxide
- Aromatic heteromonocyclic compound
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Molecular Framework | Aromatic heteromonocyclic compounds |
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External Descriptors | |
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Ontology |
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Physiological effect | Not Available |
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Disposition | |
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Process | Not Available |
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Role | Not Available |
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Physical Properties |
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State | Solid |
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Experimental Molecular Properties | Property | Value | Reference |
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Melting Point | 149 - 150 °C | Not Available | Boiling Point | Not Available | Not Available | Water Solubility | 0.37 g/L | Not Available | LogP | 1.3 | Not Available |
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Experimental Chromatographic Properties | Experimental Collision Cross Sections |
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Predicted Molecular Properties | | Show more...
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Predicted Chromatographic Properties | Predicted Collision Cross SectionsPredicted Kovats Retention IndicesUnderivatizedDerivatizedDerivative Name / Structure | SMILES | Kovats RI Value | Column Type | Reference |
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Aminoglutethimide,1TMS,isomer #1 | CCC1(C2=CC=C(N[Si](C)(C)C)C=C2)CCC(=O)NC1=O | 2416.9 | Semi standard non polar | 33892256 | Aminoglutethimide,1TMS,isomer #1 | CCC1(C2=CC=C(N[Si](C)(C)C)C=C2)CCC(=O)NC1=O | 2416.2 | Standard non polar | 33892256 | Aminoglutethimide,1TMS,isomer #1 | CCC1(C2=CC=C(N[Si](C)(C)C)C=C2)CCC(=O)NC1=O | 2983.5 | Standard polar | 33892256 | Aminoglutethimide,1TMS,isomer #2 | CCC1(C2=CC=C(N)C=C2)CCC(=O)N([Si](C)(C)C)C1=O | 2208.3 | Semi standard non polar | 33892256 | Aminoglutethimide,1TMS,isomer #2 | CCC1(C2=CC=C(N)C=C2)CCC(=O)N([Si](C)(C)C)C1=O | 2261.4 | Standard non polar | 33892256 | Aminoglutethimide,1TMS,isomer #2 | CCC1(C2=CC=C(N)C=C2)CCC(=O)N([Si](C)(C)C)C1=O | 2971.3 | Standard polar | 33892256 | Aminoglutethimide,2TMS,isomer #1 | CCC1(C2=CC=C(N([Si](C)(C)C)[Si](C)(C)C)C=C2)CCC(=O)NC1=O | 2378.2 | Semi standard non polar | 33892256 | Aminoglutethimide,2TMS,isomer #1 | CCC1(C2=CC=C(N([Si](C)(C)C)[Si](C)(C)C)C=C2)CCC(=O)NC1=O | 2529.0 | Standard non polar | 33892256 | Aminoglutethimide,2TMS,isomer #1 | CCC1(C2=CC=C(N([Si](C)(C)C)[Si](C)(C)C)C=C2)CCC(=O)NC1=O | 2898.5 | Standard polar | 33892256 | Aminoglutethimide,2TMS,isomer #2 | CCC1(C2=CC=C(N[Si](C)(C)C)C=C2)CCC(=O)N([Si](C)(C)C)C1=O | 2321.8 | Semi standard non polar | 33892256 | Aminoglutethimide,2TMS,isomer #2 | CCC1(C2=CC=C(N[Si](C)(C)C)C=C2)CCC(=O)N([Si](C)(C)C)C1=O | 2359.7 | Standard non polar | 33892256 | Aminoglutethimide,2TMS,isomer #2 | CCC1(C2=CC=C(N[Si](C)(C)C)C=C2)CCC(=O)N([Si](C)(C)C)C1=O | 2674.1 | Standard polar | 33892256 | Aminoglutethimide,3TMS,isomer #1 | CCC1(C2=CC=C(N([Si](C)(C)C)[Si](C)(C)C)C=C2)CCC(=O)N([Si](C)(C)C)C1=O | 2260.6 | Semi standard non polar | 33892256 | Aminoglutethimide,3TMS,isomer #1 | CCC1(C2=CC=C(N([Si](C)(C)C)[Si](C)(C)C)C=C2)CCC(=O)N([Si](C)(C)C)C1=O | 2496.9 | Standard non polar | 33892256 | Aminoglutethimide,3TMS,isomer #1 | CCC1(C2=CC=C(N([Si](C)(C)C)[Si](C)(C)C)C=C2)CCC(=O)N([Si](C)(C)C)C1=O | 2537.6 | Standard polar | 33892256 | Aminoglutethimide,1TBDMS,isomer #1 | CCC1(C2=CC=C(N[Si](C)(C)C(C)(C)C)C=C2)CCC(=O)NC1=O | 2631.9 | Semi standard non polar | 33892256 | Aminoglutethimide,1TBDMS,isomer #1 | CCC1(C2=CC=C(N[Si](C)(C)C(C)(C)C)C=C2)CCC(=O)NC1=O | 2689.2 | Standard non polar | 33892256 | Aminoglutethimide,1TBDMS,isomer #1 | CCC1(C2=CC=C(N[Si](C)(C)C(C)(C)C)C=C2)CCC(=O)NC1=O | 3082.7 | Standard polar | 33892256 | Aminoglutethimide,1TBDMS,isomer #2 | CCC1(C2=CC=C(N)C=C2)CCC(=O)N([Si](C)(C)C(C)(C)C)C1=O | 2434.1 | Semi standard non polar | 33892256 | Aminoglutethimide,1TBDMS,isomer #2 | CCC1(C2=CC=C(N)C=C2)CCC(=O)N([Si](C)(C)C(C)(C)C)C1=O | 2535.4 | Standard non polar | 33892256 | Aminoglutethimide,1TBDMS,isomer #2 | CCC1(C2=CC=C(N)C=C2)CCC(=O)N([Si](C)(C)C(C)(C)C)C1=O | 3027.2 | Standard polar | 33892256 | Aminoglutethimide,2TBDMS,isomer #1 | CCC1(C2=CC=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C2)CCC(=O)NC1=O | 2863.4 | Semi standard non polar | 33892256 | Aminoglutethimide,2TBDMS,isomer #1 | CCC1(C2=CC=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C2)CCC(=O)NC1=O | 3013.2 | Standard non polar | 33892256 | Aminoglutethimide,2TBDMS,isomer #1 | CCC1(C2=CC=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C2)CCC(=O)NC1=O | 3017.4 | Standard polar | 33892256 | Aminoglutethimide,2TBDMS,isomer #2 | CCC1(C2=CC=C(N[Si](C)(C)C(C)(C)C)C=C2)CCC(=O)N([Si](C)(C)C(C)(C)C)C1=O | 2765.5 | Semi standard non polar | 33892256 | Aminoglutethimide,2TBDMS,isomer #2 | CCC1(C2=CC=C(N[Si](C)(C)C(C)(C)C)C=C2)CCC(=O)N([Si](C)(C)C(C)(C)C)C1=O | 2864.0 | Standard non polar | 33892256 | Aminoglutethimide,2TBDMS,isomer #2 | CCC1(C2=CC=C(N[Si](C)(C)C(C)(C)C)C=C2)CCC(=O)N([Si](C)(C)C(C)(C)C)C1=O | 2838.4 | Standard polar | 33892256 | Aminoglutethimide,3TBDMS,isomer #1 | CCC1(C2=CC=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C2)CCC(=O)N([Si](C)(C)C(C)(C)C)C1=O | 2972.1 | Semi standard non polar | 33892256 | Aminoglutethimide,3TBDMS,isomer #1 | CCC1(C2=CC=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C2)CCC(=O)N([Si](C)(C)C(C)(C)C)C1=O | 3177.6 | Standard non polar | 33892256 | Aminoglutethimide,3TBDMS,isomer #1 | CCC1(C2=CC=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C2)CCC(=O)N([Si](C)(C)C(C)(C)C)C1=O | 2796.2 | Standard polar | 33892256 |
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Spectra |
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| GC-MS SpectraSpectrum Type | Description | Splash Key | Deposition Date | Source | View |
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Experimental GC-MS | GC-MS Spectrum - Aminoglutethimide EI-B (Non-derivatized) | splash10-0ue9-5960000000-f9b33cb2d18e6b01ae76 | 2017-09-12 | HMDB team, MONA, MassBank | View Spectrum | Experimental GC-MS | GC-MS Spectrum - Aminoglutethimide EI-B (Non-derivatized) | splash10-0ue9-5960000000-f9b33cb2d18e6b01ae76 | 2018-05-18 | HMDB team, MONA, MassBank | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Aminoglutethimide GC-MS (Non-derivatized) - 70eV, Positive | splash10-01q9-0930000000-1559858da10d4930e919 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Aminoglutethimide GC-MS (Non-derivatized) - 70eV, Positive | Not Available | 2021-10-12 | Wishart Lab | View Spectrum | MS | Mass Spectrum (Electron Ionization) | splash10-0f89-3950000000-013571ce504af9a2d603 | 2014-09-20 | Not Available | View Spectrum |
MS/MS SpectraSpectrum Type | Description | Splash Key | Deposition Date | Source | View |
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Experimental LC-MS/MS | LC-MS/MS Spectrum - Aminoglutethimide LC-ESI-qTof , Positive-QTOF | splash10-0540-2960000000-949d8dddc3981b8c3e63 | 2017-09-14 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Aminoglutethimide LC-ESI-qTof , Positive-QTOF | splash10-0uxr-0905000000-155a653652a8dc132b5c | 2017-09-14 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Aminoglutethimide LC-ESI-qTof , Positive-QTOF | splash10-001j-3910000000-d92bbd37c74ab8b7828d | 2017-09-14 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Aminoglutethimide , positive-QTOF | splash10-0540-1970000000-fc41c032a79d79173387 | 2017-09-14 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Aminoglutethimide , positive-QTOF | splash10-0540-2960000000-949d8dddc3981b8c3e63 | 2017-09-14 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Aminoglutethimide , positive-QTOF | splash10-001j-3910000000-d92bbd37c74ab8b7828d | 2017-09-14 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Aminoglutethimide 30V, Positive-QTOF | splash10-00di-0910000000-2af28058ce65d2c2b40e | 2021-09-20 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Aminoglutethimide 15V, Positive-QTOF | splash10-00di-0920000000-a50aa2833e911342e507 | 2021-09-20 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Aminoglutethimide 45V, Positive-QTOF | splash10-00di-0900000000-d172683054220fdf2313 | 2021-09-20 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Aminoglutethimide 60V, Positive-QTOF | splash10-05fr-0900000000-3564a0e475748f410e23 | 2021-09-20 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Aminoglutethimide 30V, Negative-QTOF | splash10-014i-0290000000-99e0c515559b4638490a | 2021-09-20 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Aminoglutethimide 15V, Negative-QTOF | splash10-0159-0090000000-22908f241db3fc37cdbc | 2021-09-20 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Aminoglutethimide 75V, Positive-QTOF | splash10-0a59-0900000000-6a7e540e50c50942e829 | 2021-09-20 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Aminoglutethimide 90V, Positive-QTOF | splash10-001i-0900000000-3c4030cf08f3c992fdac | 2021-09-20 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Aminoglutethimide 90V, Negative-QTOF | splash10-0006-0900000000-8be298c9d42d7769f129 | 2021-09-20 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Aminoglutethimide 75V, Negative-QTOF | splash10-0006-0900000000-a290024caadd7d64fe8f | 2021-09-20 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Aminoglutethimide 45V, Negative-QTOF | splash10-00kf-0940000000-ce0f2ff21762621367e5 | 2021-09-20 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Aminoglutethimide 60V, Negative-QTOF | splash10-0006-0900000000-24977ebbbf8d80633142 | 2021-09-20 | HMDB team, MONA | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Aminoglutethimide 10V, Positive-QTOF | splash10-00lr-0190000000-bd92b28e06f9a2c94ab1 | 2016-08-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Aminoglutethimide 20V, Positive-QTOF | splash10-00lr-0590000000-2ecccc66bf459b9dff9b | 2016-08-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Aminoglutethimide 40V, Positive-QTOF | splash10-00l2-2900000000-486145b0245b40ea818c | 2016-08-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Aminoglutethimide 10V, Negative-QTOF | splash10-001i-0090000000-b5c20a34adc0796f60c2 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Aminoglutethimide 20V, Negative-QTOF | splash10-01q9-1190000000-e50243f982300e3ad740 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Aminoglutethimide 40V, Negative-QTOF | splash10-0006-9410000000-a3860f54f1f49a280fb8 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Aminoglutethimide 10V, Negative-QTOF | splash10-001i-0090000000-62df4688c2e6b97f190f | 2021-09-24 | Wishart Lab | View Spectrum |
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Biological Properties |
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Cellular Locations | |
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Biospecimen Locations | |
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Tissue Locations | Not Available |
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Pathways | |
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Normal Concentrations |
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Blood | Expected but not Quantified | Not Quantified | Not Available | Not Available | Taking drug identified by DrugBank entry DB00357 | | details | Urine | Expected but not Quantified | Not Quantified | Not Available | Not Available | Taking drug identified by DrugBank entry DB00357 | | details |
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Abnormal Concentrations |
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| Not Available |
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Predicted Concentrations |
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Blood | 0.000 uM | Adult (>18 years old) | Both | Normal | Predicted based on drug qualities | Blood | 0.000 umol/mmol creatinine | Adult (>18 years old) | Both | Normal | Predicted based on drug qualities |
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Associated Disorders and Diseases |
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Disease References | None |
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Associated OMIM IDs | None |
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External Links |
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DrugBank ID | DB00357 |
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Phenol Explorer Compound ID | Not Available |
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FooDB ID | Not Available |
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KNApSAcK ID | Not Available |
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Chemspider ID | 2060 |
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KEGG Compound ID | C07617 |
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BioCyc ID | Not Available |
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BiGG ID | Not Available |
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Wikipedia Link | Aminoglutethimide |
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METLIN ID | Not Available |
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PubChem Compound | 2145 |
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PDB ID | Not Available |
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ChEBI ID | 2654 |
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Food Biomarker Ontology | Not Available |
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VMH ID | Not Available |
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MarkerDB ID | Not Available |
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Good Scents ID | Not Available |
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References |
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Synthesis Reference | Not Available |
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Material Safety Data Sheet (MSDS) | Not Available |
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General References | Not Available |
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