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 15:16:52 UTC |
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Update Date | 2022-03-07 02:51:58 UTC |
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HMDB ID | HMDB0015397 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | Sunitinib |
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Description | Sunitinib is an oral, small-molecule, multi-targeted receptor tyrosine kinase (RTK) inhibitor that was approved by the FDA for the treatment of renal cell carcinoma (RCC) and imatinib-resistant gastrointestinal stromal tumor (GIST) on January 26, 2006. Sunitinib inhibits cellular signaling by targeting multiple RTKs. These include all platelet-derived growth factor receptors (PDGF-R) and vascular endothelial growth factor receptors (VEGF-R). Sunitinib also inhibits KIT (CD117), the RTK that drives the majority of GISTs. In addition, sunitinib inhibits other RTKs including RET, CSF-1R, and flt3. |
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Structure | CCN(CC)CCNC(=O)C1=C(C)NC(\C=C2/C(=O)NC3=C2C=C(F)C=C3)=C1C InChI=1S/C22H27FN4O2/c1-5-27(6-2)10-9-24-22(29)20-13(3)19(25-14(20)4)12-17-16-11-15(23)7-8-18(16)26-21(17)28/h7-8,11-12,25H,5-6,9-10H2,1-4H3,(H,24,29)(H,26,28)/b17-12- |
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Synonyms | Value | Source |
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SU-11248 | ChEBI | Sunitinibum | ChEBI | Sutent | ChEBI | SU11248 | HMDB | Sunitinib malate | HMDB | 5-(5-Fluoro-2-oxo-1,2-dihydroindolylidenemethyl)-2,4-dimethyl-1H-pyrrole-3-carboxylic acid (2-diethylaminoethyl)amide | HMDB |
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Chemical Formula | C22H27FN4O2 |
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Average Molecular Weight | 398.4738 |
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Monoisotopic Molecular Weight | 398.211804333 |
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IUPAC Name | N-[2-(diethylamino)ethyl]-5-{[(3Z)-5-fluoro-2-oxo-2,3-dihydro-1H-indol-3-ylidene]methyl}-2,4-dimethyl-1H-pyrrole-3-carboxamide |
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Traditional Name | sunitinib |
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CAS Registry Number | 557795-19-4 |
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SMILES | CCN(CC)CCNC(=O)C1=C(C)NC(\C=C2/C(=O)NC3=C2C=C(F)C=C3)=C1C |
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InChI Identifier | InChI=1S/C22H27FN4O2/c1-5-27(6-2)10-9-24-22(29)20-13(3)19(25-14(20)4)12-17-16-11-15(23)7-8-18(16)26-21(17)28/h7-8,11-12,25H,5-6,9-10H2,1-4H3,(H,24,29)(H,26,28)/b17-12- |
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InChI Key | WINHZLLDWRZWRT-ATVHPVEESA-N |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as indolines. Indolines are compounds containing an indole moiety, which consists of pyrrolidine ring fused to benzene to form 2,3-dihydroindole. |
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Kingdom | Organic compounds |
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Super Class | Organoheterocyclic compounds |
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Class | Indoles and derivatives |
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Sub Class | Indolines |
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Direct Parent | Indolines |
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Alternative Parents | |
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Substituents | - Dihydroindole
- Pyrrole-3-carboxamide
- Pyrrole-3-carboxylic acid or derivatives
- Aryl fluoride
- Aryl halide
- Substituted pyrrole
- Benzenoid
- Pyrrole
- Heteroaromatic compound
- Vinylogous amide
- Tertiary amine
- Amino acid or derivatives
- Secondary carboxylic acid amide
- Tertiary aliphatic amine
- Carboxamide group
- Lactam
- Azacycle
- Carboxylic acid derivative
- Amine
- Organofluoride
- Organohalogen compound
- Organonitrogen compound
- Organopnictogen compound
- Organooxygen compound
- Organic oxide
- Carbonyl group
- Organic oxygen compound
- Organic nitrogen compound
- Hydrocarbon derivative
- Aromatic heteropolycyclic compound
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Molecular Framework | Aromatic heteropolycyclic 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 | Not Available | Not Available | Boiling Point | Not Available | Not Available | Water Solubility | 0.031 g/L | Not Available | LogP | 2.5 | Not Available |
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Experimental Chromatographic Properties | Not Available |
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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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Sunitinib,1TMS,isomer #1 | CCN(CC)CCN(C(=O)C1=C(C)[NH]C(/C=C2\C(=O)NC3=CC=C(F)C=C23)=C1C)[Si](C)(C)C | 3452.8 | Semi standard non polar | 33892256 | Sunitinib,1TMS,isomer #1 | CCN(CC)CCN(C(=O)C1=C(C)[NH]C(/C=C2\C(=O)NC3=CC=C(F)C=C23)=C1C)[Si](C)(C)C | 3335.7 | Standard non polar | 33892256 | Sunitinib,1TMS,isomer #1 | CCN(CC)CCN(C(=O)C1=C(C)[NH]C(/C=C2\C(=O)NC3=CC=C(F)C=C23)=C1C)[Si](C)(C)C | 4546.5 | Standard polar | 33892256 | Sunitinib,1TMS,isomer #2 | CCN(CC)CCNC(=O)C1=C(C)N([Si](C)(C)C)C(/C=C2\C(=O)NC3=CC=C(F)C=C23)=C1C | 3544.6 | Semi standard non polar | 33892256 | Sunitinib,1TMS,isomer #2 | CCN(CC)CCNC(=O)C1=C(C)N([Si](C)(C)C)C(/C=C2\C(=O)NC3=CC=C(F)C=C23)=C1C | 3429.0 | Standard non polar | 33892256 | Sunitinib,1TMS,isomer #2 | CCN(CC)CCNC(=O)C1=C(C)N([Si](C)(C)C)C(/C=C2\C(=O)NC3=CC=C(F)C=C23)=C1C | 4484.6 | Standard polar | 33892256 | Sunitinib,1TMS,isomer #3 | CCN(CC)CCNC(=O)C1=C(C)[NH]C(/C=C2\C(=O)N([Si](C)(C)C)C3=CC=C(F)C=C23)=C1C | 3447.4 | Semi standard non polar | 33892256 | Sunitinib,1TMS,isomer #3 | CCN(CC)CCNC(=O)C1=C(C)[NH]C(/C=C2\C(=O)N([Si](C)(C)C)C3=CC=C(F)C=C23)=C1C | 3083.4 | Standard non polar | 33892256 | Sunitinib,1TMS,isomer #3 | CCN(CC)CCNC(=O)C1=C(C)[NH]C(/C=C2\C(=O)N([Si](C)(C)C)C3=CC=C(F)C=C23)=C1C | 4051.5 | Standard polar | 33892256 | Sunitinib,2TMS,isomer #1 | CCN(CC)CCN(C(=O)C1=C(C)N([Si](C)(C)C)C(/C=C2\C(=O)NC3=CC=C(F)C=C23)=C1C)[Si](C)(C)C | 3438.2 | Semi standard non polar | 33892256 | Sunitinib,2TMS,isomer #1 | CCN(CC)CCN(C(=O)C1=C(C)N([Si](C)(C)C)C(/C=C2\C(=O)NC3=CC=C(F)C=C23)=C1C)[Si](C)(C)C | 3457.2 | Standard non polar | 33892256 | Sunitinib,2TMS,isomer #1 | CCN(CC)CCN(C(=O)C1=C(C)N([Si](C)(C)C)C(/C=C2\C(=O)NC3=CC=C(F)C=C23)=C1C)[Si](C)(C)C | 4261.0 | Standard polar | 33892256 | Sunitinib,2TMS,isomer #2 | CCN(CC)CCN(C(=O)C1=C(C)[NH]C(/C=C2\C(=O)N([Si](C)(C)C)C3=CC=C(F)C=C23)=C1C)[Si](C)(C)C | 3323.0 | Semi standard non polar | 33892256 | Sunitinib,2TMS,isomer #2 | CCN(CC)CCN(C(=O)C1=C(C)[NH]C(/C=C2\C(=O)N([Si](C)(C)C)C3=CC=C(F)C=C23)=C1C)[Si](C)(C)C | 3166.5 | Standard non polar | 33892256 | Sunitinib,2TMS,isomer #2 | CCN(CC)CCN(C(=O)C1=C(C)[NH]C(/C=C2\C(=O)N([Si](C)(C)C)C3=CC=C(F)C=C23)=C1C)[Si](C)(C)C | 3820.4 | Standard polar | 33892256 | Sunitinib,2TMS,isomer #3 | CCN(CC)CCNC(=O)C1=C(C)N([Si](C)(C)C)C(/C=C2\C(=O)N([Si](C)(C)C)C3=CC=C(F)C=C23)=C1C | 3448.6 | Semi standard non polar | 33892256 | Sunitinib,2TMS,isomer #3 | CCN(CC)CCNC(=O)C1=C(C)N([Si](C)(C)C)C(/C=C2\C(=O)N([Si](C)(C)C)C3=CC=C(F)C=C23)=C1C | 3240.2 | Standard non polar | 33892256 | Sunitinib,2TMS,isomer #3 | CCN(CC)CCNC(=O)C1=C(C)N([Si](C)(C)C)C(/C=C2\C(=O)N([Si](C)(C)C)C3=CC=C(F)C=C23)=C1C | 3777.5 | Standard polar | 33892256 | Sunitinib,3TMS,isomer #1 | CCN(CC)CCN(C(=O)C1=C(C)N([Si](C)(C)C)C(/C=C2\C(=O)N([Si](C)(C)C)C3=CC=C(F)C=C23)=C1C)[Si](C)(C)C | 3378.1 | Semi standard non polar | 33892256 | Sunitinib,3TMS,isomer #1 | CCN(CC)CCN(C(=O)C1=C(C)N([Si](C)(C)C)C(/C=C2\C(=O)N([Si](C)(C)C)C3=CC=C(F)C=C23)=C1C)[Si](C)(C)C | 3306.8 | Standard non polar | 33892256 | Sunitinib,3TMS,isomer #1 | CCN(CC)CCN(C(=O)C1=C(C)N([Si](C)(C)C)C(/C=C2\C(=O)N([Si](C)(C)C)C3=CC=C(F)C=C23)=C1C)[Si](C)(C)C | 3587.9 | Standard polar | 33892256 | Sunitinib,1TBDMS,isomer #1 | CCN(CC)CCN(C(=O)C1=C(C)[NH]C(/C=C2\C(=O)NC3=CC=C(F)C=C23)=C1C)[Si](C)(C)C(C)(C)C | 3666.9 | Semi standard non polar | 33892256 | Sunitinib,1TBDMS,isomer #1 | CCN(CC)CCN(C(=O)C1=C(C)[NH]C(/C=C2\C(=O)NC3=CC=C(F)C=C23)=C1C)[Si](C)(C)C(C)(C)C | 3519.3 | Standard non polar | 33892256 | Sunitinib,1TBDMS,isomer #1 | CCN(CC)CCN(C(=O)C1=C(C)[NH]C(/C=C2\C(=O)NC3=CC=C(F)C=C23)=C1C)[Si](C)(C)C(C)(C)C | 4552.0 | Standard polar | 33892256 | Sunitinib,1TBDMS,isomer #2 | CCN(CC)CCNC(=O)C1=C(C)N([Si](C)(C)C(C)(C)C)C(/C=C2\C(=O)NC3=CC=C(F)C=C23)=C1C | 3710.1 | Semi standard non polar | 33892256 | Sunitinib,1TBDMS,isomer #2 | CCN(CC)CCNC(=O)C1=C(C)N([Si](C)(C)C(C)(C)C)C(/C=C2\C(=O)NC3=CC=C(F)C=C23)=C1C | 3629.0 | Standard non polar | 33892256 | Sunitinib,1TBDMS,isomer #2 | CCN(CC)CCNC(=O)C1=C(C)N([Si](C)(C)C(C)(C)C)C(/C=C2\C(=O)NC3=CC=C(F)C=C23)=C1C | 4483.1 | Standard polar | 33892256 | Sunitinib,1TBDMS,isomer #3 | CCN(CC)CCNC(=O)C1=C(C)[NH]C(/C=C2\C(=O)N([Si](C)(C)C(C)(C)C)C3=CC=C(F)C=C23)=C1C | 3654.3 | Semi standard non polar | 33892256 | Sunitinib,1TBDMS,isomer #3 | CCN(CC)CCNC(=O)C1=C(C)[NH]C(/C=C2\C(=O)N([Si](C)(C)C(C)(C)C)C3=CC=C(F)C=C23)=C1C | 3298.9 | Standard non polar | 33892256 | Sunitinib,1TBDMS,isomer #3 | CCN(CC)CCNC(=O)C1=C(C)[NH]C(/C=C2\C(=O)N([Si](C)(C)C(C)(C)C)C3=CC=C(F)C=C23)=C1C | 4064.5 | Standard polar | 33892256 | Sunitinib,2TBDMS,isomer #1 | CCN(CC)CCN(C(=O)C1=C(C)N([Si](C)(C)C(C)(C)C)C(/C=C2\C(=O)NC3=CC=C(F)C=C23)=C1C)[Si](C)(C)C(C)(C)C | 3787.9 | Semi standard non polar | 33892256 | Sunitinib,2TBDMS,isomer #1 | CCN(CC)CCN(C(=O)C1=C(C)N([Si](C)(C)C(C)(C)C)C(/C=C2\C(=O)NC3=CC=C(F)C=C23)=C1C)[Si](C)(C)C(C)(C)C | 3818.4 | Standard non polar | 33892256 | Sunitinib,2TBDMS,isomer #1 | CCN(CC)CCN(C(=O)C1=C(C)N([Si](C)(C)C(C)(C)C)C(/C=C2\C(=O)NC3=CC=C(F)C=C23)=C1C)[Si](C)(C)C(C)(C)C | 4325.8 | Standard polar | 33892256 | Sunitinib,2TBDMS,isomer #2 | CCN(CC)CCN(C(=O)C1=C(C)[NH]C(/C=C2\C(=O)N([Si](C)(C)C(C)(C)C)C3=CC=C(F)C=C23)=C1C)[Si](C)(C)C(C)(C)C | 3713.6 | Semi standard non polar | 33892256 | Sunitinib,2TBDMS,isomer #2 | CCN(CC)CCN(C(=O)C1=C(C)[NH]C(/C=C2\C(=O)N([Si](C)(C)C(C)(C)C)C3=CC=C(F)C=C23)=C1C)[Si](C)(C)C(C)(C)C | 3553.0 | Standard non polar | 33892256 | Sunitinib,2TBDMS,isomer #2 | CCN(CC)CCN(C(=O)C1=C(C)[NH]C(/C=C2\C(=O)N([Si](C)(C)C(C)(C)C)C3=CC=C(F)C=C23)=C1C)[Si](C)(C)C(C)(C)C | 3918.9 | Standard polar | 33892256 | Sunitinib,2TBDMS,isomer #3 | CCN(CC)CCNC(=O)C1=C(C)N([Si](C)(C)C(C)(C)C)C(/C=C2\C(=O)N([Si](C)(C)C(C)(C)C)C3=CC=C(F)C=C23)=C1C | 3819.6 | Semi standard non polar | 33892256 | Sunitinib,2TBDMS,isomer #3 | CCN(CC)CCNC(=O)C1=C(C)N([Si](C)(C)C(C)(C)C)C(/C=C2\C(=O)N([Si](C)(C)C(C)(C)C)C3=CC=C(F)C=C23)=C1C | 3624.3 | Standard non polar | 33892256 | Sunitinib,2TBDMS,isomer #3 | CCN(CC)CCNC(=O)C1=C(C)N([Si](C)(C)C(C)(C)C)C(/C=C2\C(=O)N([Si](C)(C)C(C)(C)C)C3=CC=C(F)C=C23)=C1C | 3866.0 | Standard polar | 33892256 | Sunitinib,3TBDMS,isomer #1 | CCN(CC)CCN(C(=O)C1=C(C)N([Si](C)(C)C(C)(C)C)C(/C=C2\C(=O)N([Si](C)(C)C(C)(C)C)C3=CC=C(F)C=C23)=C1C)[Si](C)(C)C(C)(C)C | 3903.1 | Semi standard non polar | 33892256 | Sunitinib,3TBDMS,isomer #1 | CCN(CC)CCN(C(=O)C1=C(C)N([Si](C)(C)C(C)(C)C)C(/C=C2\C(=O)N([Si](C)(C)C(C)(C)C)C3=CC=C(F)C=C23)=C1C)[Si](C)(C)C(C)(C)C | 3840.7 | Standard non polar | 33892256 | Sunitinib,3TBDMS,isomer #1 | CCN(CC)CCN(C(=O)C1=C(C)N([Si](C)(C)C(C)(C)C)C(/C=C2\C(=O)N([Si](C)(C)C(C)(C)C)C3=CC=C(F)C=C23)=C1C)[Si](C)(C)C(C)(C)C | 3779.6 | 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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Predicted GC-MS | Predicted GC-MS Spectrum - Sunitinib GC-MS (Non-derivatized) - 70eV, Positive | splash10-001r-9043000000-f9288d8cb7c447b10d86 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Sunitinib GC-MS (Non-derivatized) - 70eV, Positive | Not Available | 2021-10-12 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Sunitinib GC-MS (Non-derivatized) - 70eV, Positive | Not Available | 2021-10-12 | Wishart Lab | View Spectrum |
MS/MS SpectraSpectrum Type | Description | Splash Key | Deposition Date | Source | View |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Sunitinib 10V, Positive-QTOF | splash10-0002-0419000000-d91569989d4c1e438a58 | 2016-08-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Sunitinib 20V, Positive-QTOF | splash10-1039-4964000000-32cdbd9b3679f4b806d9 | 2016-08-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Sunitinib 40V, Positive-QTOF | splash10-00di-9740000000-14530852543a6132d98b | 2016-08-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Sunitinib 10V, Negative-QTOF | splash10-0002-0019000000-716107e6148bcb3af14c | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Sunitinib 20V, Negative-QTOF | splash10-052b-5398000000-e20fbe1cd3f11ad37acb | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Sunitinib 40V, Negative-QTOF | splash10-0006-9230000000-0d8caf257003c837c3d6 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Sunitinib 10V, Positive-QTOF | splash10-0002-0009000000-c7521df282758983a81b | 2021-10-11 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Sunitinib 20V, Positive-QTOF | splash10-003r-0197000000-fc31f5a3f60673e3fb48 | 2021-10-11 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Sunitinib 40V, Positive-QTOF | splash10-0a4i-0293000000-c9aae10759016725c932 | 2021-10-11 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Sunitinib 10V, Negative-QTOF | splash10-0002-0009000000-f6f1dd2f48935333770c | 2021-10-11 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Sunitinib 20V, Negative-QTOF | splash10-0002-2049000000-fe9e71e910a9eddb2023 | 2021-10-11 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Sunitinib 40V, Negative-QTOF | splash10-052g-6194000000-ce0d447fabdb293e1813 | 2021-10-11 | 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 DB01268 | | details | Urine | Expected but not Quantified | Not Quantified | Not Available | Not Available | Taking drug identified by DrugBank entry DB01268 | | details |
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Abnormal Concentrations |
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| Not Available |
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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 | DB01268 |
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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 | 4486264 |
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KEGG Compound ID | Not Available |
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BioCyc ID | Not Available |
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BiGG ID | Not Available |
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Wikipedia Link | Sunitinib |
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METLIN ID | Not Available |
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PubChem Compound | 5329102 |
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PDB ID | B49 |
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ChEBI ID | 38940 |
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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 | - Demetri GD, van Oosterom AT, Garrett CR, Blackstein ME, Shah MH, Verweij J, McArthur G, Judson IR, Heinrich MC, Morgan JA, Desai J, Fletcher CD, George S, Bello CL, Huang X, Baum CM, Casali PG: Efficacy and safety of sunitinib in patients with advanced gastrointestinal stromal tumour after failure of imatinib: a randomised controlled trial. Lancet. 2006 Oct 14;368(9544):1329-38. [PubMed:17046465 ]
- Motzer RJ, Hutson TE, Tomczak P, Michaelson MD, Bukowski RM, Rixe O, Oudard S, Negrier S, Szczylik C, Kim ST, Chen I, Bycott PW, Baum CM, Figlin RA: Sunitinib versus interferon alfa in metastatic renal-cell carcinoma. N Engl J Med. 2007 Jan 11;356(2):115-24. [PubMed:17215529 ]
- (). FDA label . .
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