Record Information |
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Version | 5.0 |
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Status | Expected but not Quantified |
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Creation Date | 2012-09-13 11:51:58 UTC |
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Update Date | 2022-03-07 02:57:14 UTC |
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HMDB ID | HMDB0041991 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | Pitavastatin |
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Description | Most statins are metabolised in part by one or more hepatic cytochrome P450 enzymes, leading to an increased potential for drug interactions and problems with certain foods (such as grapefruit juice). Pitavastatin appears to be a substrate of CYP2C9, and not CYP3A4 (which is a common source of interactions in other statins). As a result, pitavastatin is less likely to interact with drugs that are metabolized via CYP3A4, which might be important for elderly patients who need to take multiple medicines. Pitavastatin (usually as a calcium salt) is a member of the medication class of statins, marketed in the United States under the trade name Livalo. Like other statins, it is an inhibitor of HMG-CoA reductase, the enzyme that catalyses the first step of cholesterol synthesis. It has been available in Japan since 2003, and is being marketed under licence in South Korea and in India. It is likely that pitavastatin will be approved for use in hypercholesterolaemia (elevated levels of cholesterol in the blood) and for the prevention of cardiovascular disease outside South and Southeast Asia as well. |
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Structure | O[C@H](C[C@H](O)\C=C\C1=C(C2=CC=C(F)C=C2)C2=CC=CC=C2N=C1C1CC1)CC(O)=O InChI=1S/C25H24FNO4/c26-17-9-7-15(8-10-17)24-20-3-1-2-4-22(20)27-25(16-5-6-16)21(24)12-11-18(28)13-19(29)14-23(30)31/h1-4,7-12,16,18-19,28-29H,5-6,13-14H2,(H,30,31)/b12-11+/t18-,19-/m1/s1 |
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Synonyms | Value | Source |
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NK 104 | ChEBI | NK-104 | ChEBI | Pitavastatia | ChEBI | Pitavastatine | ChEBI | Pitavastatinum | ChEBI | Pitavastatin calcium | HMDB | Itavastatin | HMDB | Nisvastatin | HMDB | Pitavastatin lactone | HMDB | (e,3R,5S)-7-(2-Cyclopropyl-4-(4-fluorophenyl)quinolin-3-yl)-3,5-dihydroxyhept-6-enoic acid | MeSH | Itavastatin calcium | MeSH |
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Chemical Formula | C25H24FNO4 |
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Average Molecular Weight | 421.4608 |
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Monoisotopic Molecular Weight | 421.168936466 |
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IUPAC Name | (3R,5S,6E)-7-[2-cyclopropyl-4-(4-fluorophenyl)quinolin-3-yl]-3,5-dihydroxyhept-6-enoic acid |
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Traditional Name | pitavastatin |
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CAS Registry Number | 147511-69-1 |
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SMILES | O[C@H](C[C@H](O)\C=C\C1=C(C2=CC=C(F)C=C2)C2=CC=CC=C2N=C1C1CC1)CC(O)=O |
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InChI Identifier | InChI=1S/C25H24FNO4/c26-17-9-7-15(8-10-17)24-20-3-1-2-4-22(20)27-25(16-5-6-16)21(24)12-11-18(28)13-19(29)14-23(30)31/h1-4,7-12,16,18-19,28-29H,5-6,13-14H2,(H,30,31)/b12-11+/t18-,19-/m1/s1 |
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InChI Key | VGYFMXBACGZSIL-MCBHFWOFSA-N |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as phenylquinolines. These are heterocyclic compounds containing a quinoline moiety substituted with a phenyl group. |
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Kingdom | Organic compounds |
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Super Class | Organoheterocyclic compounds |
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Class | Quinolines and derivatives |
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Sub Class | Phenylquinolines |
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Direct Parent | Phenylquinolines |
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Alternative Parents | |
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Substituents | - Phenylquinoline
- 4-phenylpyridine
- Medium-chain hydroxy acid
- Medium-chain fatty acid
- Beta-hydroxy acid
- Fluorobenzene
- Halobenzene
- Halogenated fatty acid
- Heterocyclic fatty acid
- Hydroxy fatty acid
- Aryl fluoride
- Aryl halide
- Monocyclic benzene moiety
- Hydroxy acid
- Fatty acyl
- Fatty acid
- Pyridine
- Unsaturated fatty acid
- Benzenoid
- Heteroaromatic compound
- Secondary alcohol
- Carboxylic acid
- Monocarboxylic acid or derivatives
- Azacycle
- Carboxylic acid derivative
- Organohalogen compound
- Organic oxide
- Organopnictogen compound
- Organic oxygen compound
- Organofluoride
- Organonitrogen compound
- Organooxygen compound
- Alcohol
- Organic nitrogen compound
- Carbonyl group
- 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 | Not Available |
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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 | Not Available | Not Available | LogP | Not Available | Not Available |
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Experimental Chromatographic Properties | Not Available |
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Predicted Molecular Properties | |
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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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Pitavastatin,1TMS,isomer #1 | C[Si](C)(C)O[C@@H](CC(=O)O)C[C@H](O)/C=C/C1=C(C2CC2)N=C2C=CC=CC2=C1C1=CC=C(F)C=C1 | 3606.4 | Semi standard non polar | 33892256 | Pitavastatin,1TMS,isomer #2 | C[Si](C)(C)O[C@H](/C=C/C1=C(C2CC2)N=C2C=CC=CC2=C1C1=CC=C(F)C=C1)C[C@@H](O)CC(=O)O | 3671.9 | Semi standard non polar | 33892256 | Pitavastatin,1TMS,isomer #3 | C[Si](C)(C)OC(=O)C[C@H](O)C[C@H](O)/C=C/C1=C(C2CC2)N=C2C=CC=CC2=C1C1=CC=C(F)C=C1 | 3600.9 | Semi standard non polar | 33892256 | Pitavastatin,2TMS,isomer #1 | C[Si](C)(C)OC(=O)C[C@@H](C[C@H](O)/C=C/C1=C(C2CC2)N=C2C=CC=CC2=C1C1=CC=C(F)C=C1)O[Si](C)(C)C | 3530.0 | Semi standard non polar | 33892256 | Pitavastatin,2TMS,isomer #2 | C[Si](C)(C)O[C@H](/C=C/C1=C(C2CC2)N=C2C=CC=CC2=C1C1=CC=C(F)C=C1)C[C@H](CC(=O)O)O[Si](C)(C)C | 3574.1 | Semi standard non polar | 33892256 | Pitavastatin,2TMS,isomer #3 | C[Si](C)(C)OC(=O)C[C@H](O)C[C@@H](/C=C/C1=C(C2CC2)N=C2C=CC=CC2=C1C1=CC=C(F)C=C1)O[Si](C)(C)C | 3583.4 | Semi standard non polar | 33892256 | Pitavastatin,3TMS,isomer #1 | C[Si](C)(C)OC(=O)C[C@@H](C[C@@H](/C=C/C1=C(C2CC2)N=C2C=CC=CC2=C1C1=CC=C(F)C=C1)O[Si](C)(C)C)O[Si](C)(C)C | 3534.7 | Semi standard non polar | 33892256 | Pitavastatin,1TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)O[C@@H](CC(=O)O)C[C@H](O)/C=C/C1=C(C2CC2)N=C2C=CC=CC2=C1C1=CC=C(F)C=C1 | 3859.1 | Semi standard non polar | 33892256 | Pitavastatin,1TBDMS,isomer #2 | CC(C)(C)[Si](C)(C)O[C@H](/C=C/C1=C(C2CC2)N=C2C=CC=CC2=C1C1=CC=C(F)C=C1)C[C@@H](O)CC(=O)O | 3904.3 | Semi standard non polar | 33892256 | Pitavastatin,1TBDMS,isomer #3 | CC(C)(C)[Si](C)(C)OC(=O)C[C@H](O)C[C@H](O)/C=C/C1=C(C2CC2)N=C2C=CC=CC2=C1C1=CC=C(F)C=C1 | 3852.1 | Semi standard non polar | 33892256 | Pitavastatin,2TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)OC(=O)C[C@@H](C[C@H](O)/C=C/C1=C(C2CC2)N=C2C=CC=CC2=C1C1=CC=C(F)C=C1)O[Si](C)(C)C(C)(C)C | 3981.9 | Semi standard non polar | 33892256 | Pitavastatin,2TBDMS,isomer #2 | CC(C)(C)[Si](C)(C)O[C@H](/C=C/C1=C(C2CC2)N=C2C=CC=CC2=C1C1=CC=C(F)C=C1)C[C@H](CC(=O)O)O[Si](C)(C)C(C)(C)C | 4036.0 | Semi standard non polar | 33892256 | Pitavastatin,2TBDMS,isomer #3 | CC(C)(C)[Si](C)(C)OC(=O)C[C@H](O)C[C@@H](/C=C/C1=C(C2CC2)N=C2C=CC=CC2=C1C1=CC=C(F)C=C1)O[Si](C)(C)C(C)(C)C | 4026.9 | Semi standard non polar | 33892256 | Pitavastatin,3TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)OC(=O)C[C@@H](C[C@@H](/C=C/C1=C(C2CC2)N=C2C=CC=CC2=C1C1=CC=C(F)C=C1)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C | 4148.8 | Semi standard non polar | 33892256 |
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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 - Pitavastatin GC-MS (Non-derivatized) - 70eV, Positive | splash10-0uxr-8149500000-7a528b44f7ab848deb48 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Pitavastatin GC-MS (3 TMS) - 70eV, Positive | splash10-00fr-9313086000-f40b861f3306cfd0bb1f | 2017-10-06 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Pitavastatin 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 - Pitavastatin DI-ESI-qTof , Negative-QTOF | splash10-0006-0095000000-052cbc222b6600555667 | 2017-09-14 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Pitavastatin 35V, Positive-QTOF | splash10-00dl-0097800000-0428ec985244a4e0d2c7 | 2021-09-20 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Pitavastatin 35V, Negative-QTOF | splash10-052f-1049000000-76e0b8e31500a9e32b92 | 2021-09-20 | HMDB team, MONA | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Pitavastatin 10V, Positive-QTOF | splash10-0uki-0017900000-2273fa72cf719982fbb3 | 2017-07-26 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Pitavastatin 20V, Positive-QTOF | splash10-0fe0-3039200000-1c1e957b8189d1f5d719 | 2017-07-26 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Pitavastatin 40V, Positive-QTOF | splash10-00du-9166000000-2131d127f06f3bf43554 | 2017-07-26 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Pitavastatin 10V, Negative-QTOF | splash10-00di-2006900000-04f6a2452db80a3d1aa4 | 2017-07-26 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Pitavastatin 20V, Negative-QTOF | splash10-0pb9-7109200000-ca0e31aa0813197a4a1c | 2017-07-26 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Pitavastatin 40V, Negative-QTOF | splash10-0a4i-9123000000-3e730deb6619e525d76b | 2017-07-26 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Pitavastatin 10V, Positive-QTOF | splash10-00di-0002900000-42e039e37d97dfce014f | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Pitavastatin 20V, Positive-QTOF | splash10-0f79-0039500000-6708d9472d2f46c7e47c | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Pitavastatin 40V, Positive-QTOF | splash10-004j-0092000000-f3c8a3dc91828f12b900 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Pitavastatin 10V, Negative-QTOF | splash10-0kmi-0003900000-c6b2852d17b4214357bb | 2021-09-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Pitavastatin 20V, Negative-QTOF | splash10-08gi-1009000000-aa1023e8d4c1b9896a68 | 2021-09-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Pitavastatin 40V, Negative-QTOF | splash10-0016-7096200000-b42853c789ac3ac44e34 | 2021-09-25 | Wishart Lab | View Spectrum |
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