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 02:52:05 UTC |
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HMDB ID | HMDB0015705 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | Ivacaftor |
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Description | Ivacaftor is only found in individuals that have used or taken this drug. It is a drug for the treatment of cystic fibrosis, developed by Vertex Pharmaceuticals and the Cystic Fibrosis Foundation.Cystic fibrosis is caused by any one of several defects in a protein, cystic fibrosis transmembrane conductance regulator, which regulates fluid flow within cells and affects the components of sweat, digestive fluids, and mucus. The defect, which is caused by a mutation in the individual's DNA, can be in any of several locations along the protein, each of which interferes with a different function of the protein. One mutation, G551D, lets the CFTR protein reach the epithelial cell surface, but doesn't let it transport chloride through the ion channel. Ivacaftor is a potentiator of the CFTR protein. The CFTR protein is a chloride channel present at the surface of epithelial cells in multiple organs. Ivacaftor facilitates increased chloride transport by potentiating the channel-open probability (or gating) of the G551D-CFTR protein. |
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Structure | CC(C)(C)C1=CC(=C(O)C=C1NC(=O)C1=CNC2=CC=CC=C2C1=O)C(C)(C)C InChI=1S/C24H28N2O3/c1-23(2,3)16-11-17(24(4,5)6)20(27)12-19(16)26-22(29)15-13-25-18-10-8-7-9-14(18)21(15)28/h7-13,27H,1-6H3,(H,25,28)(H,26,29) |
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Synonyms | Value | Source |
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Ivacaftorum | ChEBI | Kalydeco | ChEBI | VX-770 | ChEBI | N-(2,4-Di-tert-butyl-5-hydroxyphenyl)-4-oxo-1,4-dihydroquinoline-3-carboxamide | HMDB | N-(2,4-Bis(1,1-dimethylethyl)-5-hydroxyphenyl)-4-oxo-1,4-dihydroquinoline-3-carboxamide | HMDB |
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Chemical Formula | C24H28N2O3 |
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Average Molecular Weight | 392.4907 |
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Monoisotopic Molecular Weight | 392.209992772 |
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IUPAC Name | N-(2,4-di-tert-butyl-5-hydroxyphenyl)-4-oxo-1,4-dihydroquinoline-3-carboxamide |
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Traditional Name | ivacaftor |
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CAS Registry Number | 873054-44-5 |
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SMILES | CC(C)(C)C1=CC(=C(O)C=C1NC(=O)C1=CNC2=CC=CC=C2C1=O)C(C)(C)C |
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InChI Identifier | InChI=1S/C24H28N2O3/c1-23(2,3)16-11-17(24(4,5)6)20(27)12-19(16)26-22(29)15-13-25-18-10-8-7-9-14(18)21(15)28/h7-13,27H,1-6H3,(H,25,28)(H,26,29) |
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InChI Key | PURKAOJPTOLRMP-UHFFFAOYSA-N |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as aromatic anilides. These are aromatic compounds containing an anilide group in which the carboxamide group is substituted with an aromatic group. They have the general structure RNC(=O)R', where R= benzene, and R = aryl group. |
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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 | Anilides |
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Direct Parent | Aromatic anilides |
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Alternative Parents | |
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Substituents | - Aromatic anilide
- Quinoline-3-carboxamide
- Dihydroquinolone
- Quinoline
- Dihydroquinoline
- Phenylpropane
- Pyridine carboxylic acid or derivatives
- 1-hydroxy-2-unsubstituted benzenoid
- Phenol
- Pyridine
- Heteroaromatic compound
- Vinylogous amide
- Carboxamide group
- Secondary carboxylic acid amide
- Azacycle
- Organoheterocyclic compound
- Carboxylic acid derivative
- Organic nitrogen compound
- Hydrocarbon derivative
- Organooxygen compound
- Organonitrogen compound
- Organic oxide
- Organopnictogen compound
- Organic oxygen compound
- 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 | 0.002 g/L | Not Available | LogP | Not Available | 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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Ivacaftor,1TMS,isomer #1 | CC(C)(C)C1=CC(C(C)(C)C)=C(O[Si](C)(C)C)C=C1NC(=O)C1=C[NH]C2=CC=CC=C2C1=O | 3522.5 | Semi standard non polar | 33892256 | Ivacaftor,1TMS,isomer #2 | CC(C)(C)C1=CC(C(C)(C)C)=C(N(C(=O)C2=C[NH]C3=CC=CC=C3C2=O)[Si](C)(C)C)C=C1O | 3261.1 | Semi standard non polar | 33892256 | Ivacaftor,1TMS,isomer #3 | CC(C)(C)C1=CC(C(C)(C)C)=C(NC(=O)C2=CN([Si](C)(C)C)C3=CC=CC=C3C2=O)C=C1O | 3492.3 | Semi standard non polar | 33892256 | Ivacaftor,2TMS,isomer #1 | CC(C)(C)C1=CC(C(C)(C)C)=C(N(C(=O)C2=C[NH]C3=CC=CC=C3C2=O)[Si](C)(C)C)C=C1O[Si](C)(C)C | 3230.7 | Semi standard non polar | 33892256 | Ivacaftor,2TMS,isomer #1 | CC(C)(C)C1=CC(C(C)(C)C)=C(N(C(=O)C2=C[NH]C3=CC=CC=C3C2=O)[Si](C)(C)C)C=C1O[Si](C)(C)C | 3291.2 | Standard non polar | 33892256 | Ivacaftor,2TMS,isomer #1 | CC(C)(C)C1=CC(C(C)(C)C)=C(N(C(=O)C2=C[NH]C3=CC=CC=C3C2=O)[Si](C)(C)C)C=C1O[Si](C)(C)C | 3481.6 | Standard polar | 33892256 | Ivacaftor,2TMS,isomer #2 | CC(C)(C)C1=CC(C(C)(C)C)=C(O[Si](C)(C)C)C=C1NC(=O)C1=CN([Si](C)(C)C)C2=CC=CC=C2C1=O | 3549.1 | Semi standard non polar | 33892256 | Ivacaftor,2TMS,isomer #2 | CC(C)(C)C1=CC(C(C)(C)C)=C(O[Si](C)(C)C)C=C1NC(=O)C1=CN([Si](C)(C)C)C2=CC=CC=C2C1=O | 3316.6 | Standard non polar | 33892256 | Ivacaftor,2TMS,isomer #2 | CC(C)(C)C1=CC(C(C)(C)C)=C(O[Si](C)(C)C)C=C1NC(=O)C1=CN([Si](C)(C)C)C2=CC=CC=C2C1=O | 3563.5 | Standard polar | 33892256 | Ivacaftor,2TMS,isomer #3 | CC(C)(C)C1=CC(C(C)(C)C)=C(N(C(=O)C2=CN([Si](C)(C)C)C3=CC=CC=C3C2=O)[Si](C)(C)C)C=C1O | 3299.0 | Semi standard non polar | 33892256 | Ivacaftor,2TMS,isomer #3 | CC(C)(C)C1=CC(C(C)(C)C)=C(N(C(=O)C2=CN([Si](C)(C)C)C3=CC=CC=C3C2=O)[Si](C)(C)C)C=C1O | 3336.5 | Standard non polar | 33892256 | Ivacaftor,2TMS,isomer #3 | CC(C)(C)C1=CC(C(C)(C)C)=C(N(C(=O)C2=CN([Si](C)(C)C)C3=CC=CC=C3C2=O)[Si](C)(C)C)C=C1O | 3520.1 | Standard polar | 33892256 | Ivacaftor,3TMS,isomer #1 | CC(C)(C)C1=CC(C(C)(C)C)=C(N(C(=O)C2=CN([Si](C)(C)C)C3=CC=CC=C3C2=O)[Si](C)(C)C)C=C1O[Si](C)(C)C | 3310.7 | Semi standard non polar | 33892256 | Ivacaftor,3TMS,isomer #1 | CC(C)(C)C1=CC(C(C)(C)C)=C(N(C(=O)C2=CN([Si](C)(C)C)C3=CC=CC=C3C2=O)[Si](C)(C)C)C=C1O[Si](C)(C)C | 3334.4 | Standard non polar | 33892256 | Ivacaftor,3TMS,isomer #1 | CC(C)(C)C1=CC(C(C)(C)C)=C(N(C(=O)C2=CN([Si](C)(C)C)C3=CC=CC=C3C2=O)[Si](C)(C)C)C=C1O[Si](C)(C)C | 3394.0 | Standard polar | 33892256 | Ivacaftor,1TBDMS,isomer #1 | CC(C)(C)C1=CC(C(C)(C)C)=C(O[Si](C)(C)C(C)(C)C)C=C1NC(=O)C1=C[NH]C2=CC=CC=C2C1=O | 3718.3 | Semi standard non polar | 33892256 | Ivacaftor,1TBDMS,isomer #2 | CC(C)(C)C1=CC(C(C)(C)C)=C(N(C(=O)C2=C[NH]C3=CC=CC=C3C2=O)[Si](C)(C)C(C)(C)C)C=C1O | 3521.0 | Semi standard non polar | 33892256 | Ivacaftor,1TBDMS,isomer #3 | CC(C)(C)C1=CC(C(C)(C)C)=C(NC(=O)C2=CN([Si](C)(C)C(C)(C)C)C3=CC=CC=C3C2=O)C=C1O | 3710.5 | Semi standard non polar | 33892256 | Ivacaftor,2TBDMS,isomer #1 | CC(C)(C)C1=CC(C(C)(C)C)=C(N(C(=O)C2=C[NH]C3=CC=CC=C3C2=O)[Si](C)(C)C(C)(C)C)C=C1O[Si](C)(C)C(C)(C)C | 3681.9 | Semi standard non polar | 33892256 | Ivacaftor,2TBDMS,isomer #1 | CC(C)(C)C1=CC(C(C)(C)C)=C(N(C(=O)C2=C[NH]C3=CC=CC=C3C2=O)[Si](C)(C)C(C)(C)C)C=C1O[Si](C)(C)C(C)(C)C | 3635.9 | Standard non polar | 33892256 | Ivacaftor,2TBDMS,isomer #1 | CC(C)(C)C1=CC(C(C)(C)C)=C(N(C(=O)C2=C[NH]C3=CC=CC=C3C2=O)[Si](C)(C)C(C)(C)C)C=C1O[Si](C)(C)C(C)(C)C | 3667.8 | Standard polar | 33892256 | Ivacaftor,2TBDMS,isomer #2 | CC(C)(C)C1=CC(C(C)(C)C)=C(O[Si](C)(C)C(C)(C)C)C=C1NC(=O)C1=CN([Si](C)(C)C(C)(C)C)C2=CC=CC=C2C1=O | 3909.9 | Semi standard non polar | 33892256 | Ivacaftor,2TBDMS,isomer #2 | CC(C)(C)C1=CC(C(C)(C)C)=C(O[Si](C)(C)C(C)(C)C)C=C1NC(=O)C1=CN([Si](C)(C)C(C)(C)C)C2=CC=CC=C2C1=O | 3660.3 | Standard non polar | 33892256 | Ivacaftor,2TBDMS,isomer #2 | CC(C)(C)C1=CC(C(C)(C)C)=C(O[Si](C)(C)C(C)(C)C)C=C1NC(=O)C1=CN([Si](C)(C)C(C)(C)C)C2=CC=CC=C2C1=O | 3731.6 | Standard polar | 33892256 | Ivacaftor,2TBDMS,isomer #3 | CC(C)(C)C1=CC(C(C)(C)C)=C(N(C(=O)C2=CN([Si](C)(C)C(C)(C)C)C3=CC=CC=C3C2=O)[Si](C)(C)C(C)(C)C)C=C1O | 3706.6 | Semi standard non polar | 33892256 | Ivacaftor,2TBDMS,isomer #3 | CC(C)(C)C1=CC(C(C)(C)C)=C(N(C(=O)C2=CN([Si](C)(C)C(C)(C)C)C3=CC=CC=C3C2=O)[Si](C)(C)C(C)(C)C)C=C1O | 3649.8 | Standard non polar | 33892256 | Ivacaftor,2TBDMS,isomer #3 | CC(C)(C)C1=CC(C(C)(C)C)=C(N(C(=O)C2=CN([Si](C)(C)C(C)(C)C)C3=CC=CC=C3C2=O)[Si](C)(C)C(C)(C)C)C=C1O | 3689.3 | Standard polar | 33892256 | Ivacaftor,3TBDMS,isomer #1 | CC(C)(C)C1=CC(C(C)(C)C)=C(N(C(=O)C2=CN([Si](C)(C)C(C)(C)C)C3=CC=CC=C3C2=O)[Si](C)(C)C(C)(C)C)C=C1O[Si](C)(C)C(C)(C)C | 3891.2 | Semi standard non polar | 33892256 | Ivacaftor,3TBDMS,isomer #1 | CC(C)(C)C1=CC(C(C)(C)C)=C(N(C(=O)C2=CN([Si](C)(C)C(C)(C)C)C3=CC=CC=C3C2=O)[Si](C)(C)C(C)(C)C)C=C1O[Si](C)(C)C(C)(C)C | 3808.9 | Standard non polar | 33892256 | Ivacaftor,3TBDMS,isomer #1 | CC(C)(C)C1=CC(C(C)(C)C)=C(N(C(=O)C2=CN([Si](C)(C)C(C)(C)C)C3=CC=CC=C3C2=O)[Si](C)(C)C(C)(C)C)C=C1O[Si](C)(C)C(C)(C)C | 3634.8 | 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 - Ivacaftor GC-MS (Non-derivatized) - 70eV, Positive | splash10-00di-0739000000-1b41f2c7ddedd90d43c8 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Ivacaftor GC-MS (1 TMS) - 70eV, Positive | splash10-006y-3351900000-dc90833dbef87cc492c0 | 2017-10-06 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Ivacaftor GC-MS (Non-derivatized) - 70eV, Positive | Not Available | 2021-10-12 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Ivacaftor 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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Experimental LC-MS/MS | LC-MS/MS Spectrum - Ivacaftor LC-ESI-qTof , Positive-QTOF | splash10-03gj-1891400000-9f74f1c76f8bde03b286 | 2017-09-14 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Ivacaftor , positive-QTOF | splash10-0079-1809000000-c0147e018d786aee606b | 2017-09-14 | HMDB team, MONA | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Ivacaftor 10V, Positive-QTOF | splash10-0006-0009000000-86c4c1172d1bee0ab8cf | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Ivacaftor 20V, Positive-QTOF | splash10-00dl-0918000000-00798a3656e171f62c81 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Ivacaftor 40V, Positive-QTOF | splash10-0006-0911000000-2fefa753407d0181cec3 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Ivacaftor 10V, Negative-QTOF | splash10-0006-0409000000-9aa079aa9d35e2f8ab13 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Ivacaftor 20V, Negative-QTOF | splash10-0006-0900000000-30095278d7b7875589bf | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Ivacaftor 40V, Negative-QTOF | splash10-0006-0900000000-fc85de7523217af66c4c | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Ivacaftor 10V, Positive-QTOF | splash10-0079-0509000000-16aa918207aec379d615 | 2021-10-11 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Ivacaftor 20V, Positive-QTOF | splash10-00di-0900000000-383766b2b3690775474c | 2021-10-11 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Ivacaftor 40V, Positive-QTOF | splash10-0ck9-2619000000-2307c51d7b28f4ff118f | 2021-10-11 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Ivacaftor 10V, Negative-QTOF | splash10-0006-0009000000-d21896041c7a6bff6e47 | 2021-10-12 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Ivacaftor 20V, Negative-QTOF | splash10-0006-0309000000-696199233265215e456f | 2021-10-12 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Ivacaftor 40V, Negative-QTOF | splash10-0006-1913000000-a31f02ed83400d9b16dd | 2021-10-12 | 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 DB08820 | | details | Urine | Expected but not Quantified | Not Quantified | Not Available | Not Available | Taking drug identified by DrugBank entry DB08820 | | 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 | DB08820 |
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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 | 17347474 |
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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 | Ivacaftor |
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METLIN ID | Not Available |
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PubChem Compound | 16220172 |
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PDB ID | Not Available |
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ChEBI ID | 66901 |
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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 | - Accurso FJ, Rowe SM, Clancy JP, Boyle MP, Dunitz JM, Durie PR, Sagel SD, Hornick DB, Konstan MW, Donaldson SH, Moss RB, Pilewski JM, Rubenstein RC, Uluer AZ, Aitken ML, Freedman SD, Rose LM, Mayer-Hamblett N, Dong Q, Zha J, Stone AJ, Olson ER, Ordonez CL, Campbell PW, Ashlock MA, Ramsey BW: Effect of VX-770 in persons with cystic fibrosis and the G551D-CFTR mutation. N Engl J Med. 2010 Nov 18;363(21):1991-2003. doi: 10.1056/NEJMoa0909825. [PubMed:21083385 ]
- Ramsey BW, Davies J, McElvaney NG, Tullis E, Bell SC, Drevinek P, Griese M, McKone EF, Wainwright CE, Konstan MW, Moss R, Ratjen F, Sermet-Gaudelus I, Rowe SM, Dong Q, Rodriguez S, Yen K, Ordonez C, Elborn JS: A CFTR potentiator in patients with cystic fibrosis and the G551D mutation. N Engl J Med. 2011 Nov 3;365(18):1663-72. doi: 10.1056/NEJMoa1105185. [PubMed:22047557 ]
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