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 02:52:03 UTC |
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HMDB ID | HMDB0015625 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | Prasugrel |
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Description | Prasugrel, a thienopyridine derivative, is a platelet activation and aggregation inhibitor structurally and pharmacologically related to clopidogrel and ticlopidine. Similar to clopidogrel, prasugrel is a prodrug that requires enzymatic transformation in the liver to its active metabolite, R-138727. R-138727 irreversibly binds to P2Y12 type ADP receptors on platelets thereby inhibiting ADP-mediated platelet activation and aggregation. Prasugrel inhibits ADP-mediated platelet aggregation more rapidly, more consistently and to a greater extent (at least 30%) than clopidogrel. The increased potency of prasugrel appears to be due to more efficient conversion to its active metabolite. The relationship, however, between increased platelet aggregation and clinical response has not been determined. Prasugrel carries a higher risk of bleed compared to clopidogrel, which may be a result of its higher potency. Prasugrel was developed by Daiichi Sankyo Co. and is currently marketed in the United States and Canada in cooperation with Eli Lilly and Company for acute coronary syndromes planned for percutaneous coronary intervention (PCI). |
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Structure | CC(=O)OC1=CC2=C(CCN(C2)C(C(=O)C2CC2)C2=CC=CC=C2F)S1 InChI=1S/C20H20FNO3S/c1-12(23)25-18-10-14-11-22(9-8-17(14)26-18)19(20(24)13-6-7-13)15-4-2-3-5-16(15)21/h2-5,10,13,19H,6-9,11H2,1H3 |
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Synonyms | Value | Source |
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5-[2-Cyclopropyl-1-(2-fluorophenyl)-2-oxoethyl]-4,5,6,7-tetrahydrothieno[3,2-c]pyridin-2-yl acetic acid | Generator | CS-747 | HMDB | 747, CS | MeSH, HMDB | HCL, Prasugrel | MeSH, HMDB | Prasugrel HCL | MeSH, HMDB | Effient | MeSH, HMDB | Hydrochloride, prasugrel | MeSH, HMDB | Prasugrel hydrochloride | MeSH, HMDB | Efient | MeSH, HMDB | Prasugrel | MeSH |
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Chemical Formula | C20H20FNO3S |
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Average Molecular Weight | 373.441 |
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Monoisotopic Molecular Weight | 373.114792406 |
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IUPAC Name | 5-[2-cyclopropyl-1-(2-fluorophenyl)-2-oxoethyl]-4H,5H,6H,7H-thieno[3,2-c]pyridin-2-yl acetate |
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Traditional Name | prasugrel |
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CAS Registry Number | 150322-43-3 |
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SMILES | CC(=O)OC1=CC2=C(CCN(C2)C(C(=O)C2CC2)C2=CC=CC=C2F)S1 |
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InChI Identifier | InChI=1S/C20H20FNO3S/c1-12(23)25-18-10-14-11-22(9-8-17(14)26-18)19(20(24)13-6-7-13)15-4-2-3-5-16(15)21/h2-5,10,13,19H,6-9,11H2,1H3 |
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InChI Key | DTGLZDAWLRGWQN-UHFFFAOYSA-N |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as thienopyridines. These are heterocyclic compounds containing a thiophene ring fused to a pyridine ring. Thiophene is 5-membered ring consisting of four carbon atoms and one sulfur atom. Pyridine is a 6-membered ring consisting of five carbon atoms and one nitrogen center. |
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Kingdom | Organic compounds |
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Super Class | Organoheterocyclic compounds |
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Class | Thienopyridines |
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Sub Class | Not Available |
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Direct Parent | Thienopyridines |
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Alternative Parents | |
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Substituents | - Thienopyridine
- 2,3,5-trisubstituted thiophene
- Halobenzene
- Fluorobenzene
- Aralkylamine
- Pyridine
- Aryl fluoride
- Aryl halide
- Benzenoid
- Monocyclic benzene moiety
- Thiophene
- Alpha-aminoketone
- Heteroaromatic compound
- Tertiary aliphatic amine
- Amino acid or derivatives
- Ketone
- Tertiary amine
- Carboxylic acid ester
- Carboxylic acid derivative
- Azacycle
- Monocarboxylic acid or derivatives
- Organonitrogen compound
- Organooxygen compound
- Amine
- Organic nitrogen compound
- Carbonyl group
- Hydrocarbon derivative
- Organic oxide
- Organopnictogen compound
- Organofluoride
- Organic oxygen compound
- Organohalogen 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 | 0.0024 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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Prasugrel,1TMS,isomer #1 | CC(=O)OC1=CC2=C(CCN(C(C(O[Si](C)(C)C)=C3CC3)C3=CC=CC=C3F)C2)S1 | 2886.6 | Semi standard non polar | 33892256 | Prasugrel,1TMS,isomer #1 | CC(=O)OC1=CC2=C(CCN(C(C(O[Si](C)(C)C)=C3CC3)C3=CC=CC=C3F)C2)S1 | 2658.1 | Standard non polar | 33892256 | Prasugrel,1TMS,isomer #1 | CC(=O)OC1=CC2=C(CCN(C(C(O[Si](C)(C)C)=C3CC3)C3=CC=CC=C3F)C2)S1 | 3508.5 | Standard polar | 33892256 | Prasugrel,1TMS,isomer #2 | CC(=O)OC1=CC2=C(CCN(C(=C(O[Si](C)(C)C)C3CC3)C3=CC=CC=C3F)C2)S1 | 2963.7 | Semi standard non polar | 33892256 | Prasugrel,1TMS,isomer #2 | CC(=O)OC1=CC2=C(CCN(C(=C(O[Si](C)(C)C)C3CC3)C3=CC=CC=C3F)C2)S1 | 2674.9 | Standard non polar | 33892256 | Prasugrel,1TMS,isomer #2 | CC(=O)OC1=CC2=C(CCN(C(=C(O[Si](C)(C)C)C3CC3)C3=CC=CC=C3F)C2)S1 | 3479.6 | Standard polar | 33892256 | Prasugrel,1TBDMS,isomer #1 | CC(=O)OC1=CC2=C(CCN(C(C(O[Si](C)(C)C(C)(C)C)=C3CC3)C3=CC=CC=C3F)C2)S1 | 3111.4 | Semi standard non polar | 33892256 | Prasugrel,1TBDMS,isomer #1 | CC(=O)OC1=CC2=C(CCN(C(C(O[Si](C)(C)C(C)(C)C)=C3CC3)C3=CC=CC=C3F)C2)S1 | 2845.8 | Standard non polar | 33892256 | Prasugrel,1TBDMS,isomer #1 | CC(=O)OC1=CC2=C(CCN(C(C(O[Si](C)(C)C(C)(C)C)=C3CC3)C3=CC=CC=C3F)C2)S1 | 3612.1 | Standard polar | 33892256 | Prasugrel,1TBDMS,isomer #2 | CC(=O)OC1=CC2=C(CCN(C(=C(O[Si](C)(C)C(C)(C)C)C3CC3)C3=CC=CC=C3F)C2)S1 | 3173.7 | Semi standard non polar | 33892256 | Prasugrel,1TBDMS,isomer #2 | CC(=O)OC1=CC2=C(CCN(C(=C(O[Si](C)(C)C(C)(C)C)C3CC3)C3=CC=CC=C3F)C2)S1 | 2884.8 | Standard non polar | 33892256 | Prasugrel,1TBDMS,isomer #2 | CC(=O)OC1=CC2=C(CCN(C(=C(O[Si](C)(C)C(C)(C)C)C3CC3)C3=CC=CC=C3F)C2)S1 | 3584.3 | 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 - Prasugrel GC-MS (Non-derivatized) - 70eV, Positive | splash10-03xu-5292000000-363487adeda2803edf87 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Prasugrel GC-MS (Non-derivatized) - 70eV, Positive | Not Available | 2021-10-12 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Prasugrel 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 - Prasugrel , positive-QTOF | splash10-056s-2945000000-7653802e8e3994dc55bc | 2017-09-14 | HMDB team, MONA | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Prasugrel 10V, Positive-QTOF | splash10-02mi-3109000000-5df287f035db2dd8d72e | 2016-08-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Prasugrel 20V, Positive-QTOF | splash10-014i-9012000000-4c525511fe781201418c | 2016-08-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Prasugrel 40V, Positive-QTOF | splash10-014l-9110000000-e5719df9692a6db2952d | 2016-08-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Prasugrel 10V, Negative-QTOF | splash10-05fr-4009000000-9044e8f3f643c0735a0a | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Prasugrel 20V, Negative-QTOF | splash10-0ab9-9148000000-99e7e9c97dd6cac360ac | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Prasugrel 40V, Negative-QTOF | splash10-0596-9280000000-6aa7847fbc28ebfd9358 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Prasugrel 10V, Positive-QTOF | splash10-00di-0009000000-bb206404d6ff5af644df | 2021-10-11 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Prasugrel 20V, Positive-QTOF | splash10-00di-0109000000-7d582aadd109615619c5 | 2021-10-11 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Prasugrel 40V, Positive-QTOF | splash10-0006-9686000000-987d0f1a8e56ddbd1409 | 2021-10-11 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Prasugrel 10V, Negative-QTOF | splash10-00di-0029000000-3ab5ac4bd79d4c163f1e | 2021-10-11 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Prasugrel 20V, Negative-QTOF | splash10-03e9-3093000000-d1df9adedf463fa6bb3f | 2021-10-11 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Prasugrel 40V, Negative-QTOF | splash10-001i-1090000000-8ba5bc2b26647101aa32 | 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 DB06209 | | details | Urine | Expected but not Quantified | Not Quantified | Not Available | Not Available | Taking drug identified by DrugBank entry DB06209 | | 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 | Not Available |
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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 | 5293653 |
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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 | Not Available |
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METLIN ID | Not Available |
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PubChem Compound | 6918456 |
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PDB ID | Not Available |
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ChEBI ID | 87723 |
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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 | - Dovlatova NL, Jakubowski JA, Sugidachi A, Heptinstall S: The reversible P2Y antagonist cangrelor influences the ability of the active metabolites of clopidogrel and prasugrel to produce irreversible inhibition of platelet function. J Thromb Haemost. 2008 Jul;6(7):1153-9. doi: 10.1111/j.1538-7836.2008.03020.x. Epub 2008 Jul 1. [PubMed:18485086 ]
- Tagarakis GI: Ticagrelor and prasugrel: two novel, most-promising antiplatelet agents. Recent Pat Cardiovasc Drug Discov. 2010 Nov;5(3):208-11. [PubMed:20874669 ]
- Jeong YH, Tantry US, Gurbel PA: Importance of potent P2Y(12) receptor blockade in acute myocardial infarction: focus on prasugrel. Expert Opin Pharmacother. 2012 Aug;13(12):1771-96. doi: 10.1517/14656566.2012.704909. Epub 2012 Jul 12. [PubMed:22783896 ]
- Angiolillo DJ: The evolution of antiplatelet therapy in the treatment of acute coronary syndromes: from aspirin to the present day. Drugs. 2012 Nov 12;72(16):2087-116. doi: 10.2165/11640880-000000000-00000. [PubMed:23083110 ]
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