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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2006-05-22 15:12:25 UTC
Update Date2022-03-07 02:49:25 UTC
HMDB IDHMDB0005011
Secondary Accession Numbers
  • HMDB05011
Metabolite Identification
Common NameClopidogrel
DescriptionClopidogrel is a potent oral antiplatelet agent often used in the treatment of coronary artery disease, peripheral vascular disease, and cerebrovascular disease. It is marketed by Bristol-Myers Squibb and Sanofi-Aventis under the trade name Plavix. -- Wikipedia ; Clopidogrel is a potent oral antiplatelet agent often used in the treatment of coronary artery disease, peripheral vascular disease, and cerebrovascular disease. It is marketed by Bristol-Myers Squibb and Sanofi-Aventis under the trade name Plavix. It is also marketed in the generic form by Apotex, a large Canadian generic pharmaceutical company, though an injunction to withhold further shipments of their form is in effect while patent issues are dealt with. In 2005 it was the world's second highest selling pharmaceutical with sales of US$5.9 billion.
Structure
Data?1582752339
Synonyms
ValueSource
(+)-ClopidogrelChEBI
ClopidogrelumChEBI
PlavixKegg
(+)-(S)-ClopidogrelHMDB
(S)-ClopidogrelHMDB
Clopidogrel bisulfateHMDB
Clopidogrel bisulphateHMDB
IsocoverHMDB
Clopidogrel sandozHMDB
Clopidogrel hydrochlorideHMDB
BMS Brand 1 OF clopidogrel bisulfateHMDB
Clopidogrel napadisilateHMDB
Clopidogrel, (+)(S)-isomerHMDB
BMS Brand 2 OF clopidogrel bisulfateHMDB
Clopidogrel besylateHMDB
IscoverHMDB
Clopidogrel-mephaHMDB
Clopidogrel besilateHMDB
Clopidogrel mephaHMDB
Chemical FormulaC16H16ClNO2S
Average Molecular Weight321.822
Monoisotopic Molecular Weight321.059027158
IUPAC Namemethyl (2S)-2-(2-chlorophenyl)-2-{4H,5H,6H,7H-thieno[3,2-c]pyridin-5-yl}acetate
Traditional Nameclopidogrel
CAS Registry Number113665-84-2
SMILES
[H][C@@](N1CCC2=C(C1)C=CS2)(C(=O)OC)C1=CC=CC=C1Cl
InChI Identifier
InChI=1S/C16H16ClNO2S/c1-20-16(19)15(12-4-2-3-5-13(12)17)18-8-6-14-11(10-18)7-9-21-14/h2-5,7,9,15H,6,8,10H2,1H3/t15-/m0/s1
InChI KeyGKTWGGQPFAXNFI-HNNXBMFYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as alpha amino acid esters. These are ester derivatives of alpha amino acids.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentAlpha amino acid esters
Alternative Parents
Substituents
  • Alpha-amino acid ester
  • Thienopyridine
  • Chlorobenzene
  • Halobenzene
  • Aralkylamine
  • Aryl chloride
  • Aryl halide
  • Monocyclic benzene moiety
  • Pyridine
  • Benzenoid
  • Heteroaromatic compound
  • Methyl ester
  • Thiophene
  • Carboxylic acid ester
  • Tertiary amine
  • Tertiary aliphatic amine
  • Monocarboxylic acid or derivatives
  • Azacycle
  • Organoheterocyclic compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organochloride
  • Organohalogen compound
  • Hydrocarbon derivative
  • Organic nitrogen compound
  • Carbonyl group
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Amine
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
Process
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.012 g/LALOGPS
logP3.84ALOGPS
logP4.03ChemAxon
logS-4.4ALOGPS
pKa (Strongest Basic)5.14ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area29.54 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity84.93 m³·mol⁻¹ChemAxon
Polarizability33.19 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M+H]+163.1830932474
DeepCCS[M-H]-160.82230932474
DeepCCS[M-2H]-195.00730932474
DeepCCS[M+Na]+170.03830932474
AllCCS[M+H]+170.432859911
AllCCS[M+H-H2O]+167.232859911
AllCCS[M+NH4]+173.432859911
AllCCS[M+Na]+174.232859911
AllCCS[M-H]-171.932859911
AllCCS[M+Na-2H]-171.632859911
AllCCS[M+HCOO]-171.332859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Clopidogrel[H][C@@](N1CCC2=C(C1)C=CS2)(C(=O)OC)C1=CC=CC=C1Cl3343.8Standard polar33892256
Clopidogrel[H][C@@](N1CCC2=C(C1)C=CS2)(C(=O)OC)C1=CC=CC=C1Cl2341.1Standard non polar33892256
Clopidogrel[H][C@@](N1CCC2=C(C1)C=CS2)(C(=O)OC)C1=CC=CC=C1Cl2348.6Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Clopidogrel GC-MS (Non-derivatized) - 70eV, Positivesplash10-03di-3980000000-d577843e19cf599f8a0b2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Clopidogrel GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Clopidogrel GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Clopidogrel LC-ESI-qTof , Positive-QTOFsplash10-0229-0967000000-6c51c479e90818ec703b2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Clopidogrel , positive-QTOFsplash10-0229-0967000000-6c51c479e90818ec703b2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Clopidogrel , positive-QTOFsplash10-0a4i-2900000000-be6dbedd4a0c4f60d0dd2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Clopidogrel 50V, Positive-QTOFsplash10-0a4i-0900000000-6cfdcd4344e312b9152e2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Clopidogrel 20V, Positive-QTOFsplash10-03di-0592000000-7840275de971a1c4cd012021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Clopidogrel 10V, Positive-QTOFsplash10-00di-0039000000-c8efc33e40006dfa1d042021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Clopidogrel 30V, Positive-QTOFsplash10-053r-0910000000-19b1ace18c36bc4868552021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Clopidogrel 40V, Positive-QTOFsplash10-0a4i-0900000000-c7ca4d76836b437c00272021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Clopidogrel 35V, Positive-QTOFsplash10-0230-0935000000-9e8f08289a74a12e1d1b2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Clopidogrel 50V, Positive-QTOFsplash10-0a4i-0900000000-240a5f13f03a49f5ab782021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Clopidogrel 10V, Positive-QTOFsplash10-00di-0159000000-17a9fe29b343cd5ca5012016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Clopidogrel 20V, Positive-QTOFsplash10-022l-0192000000-f551440009ad0c2d24042016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Clopidogrel 40V, Positive-QTOFsplash10-08fr-2950000000-aea6a4e495e819b37fdb2016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Clopidogrel 10V, Negative-QTOFsplash10-00di-0059000000-71b4a913e2ab55e934302016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Clopidogrel 20V, Negative-QTOFsplash10-00dr-0296000000-023d1bb858121c6c91582016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Clopidogrel 40V, Negative-QTOFsplash10-03di-8940000000-ec8e591212f5c1afd5162016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Clopidogrel 10V, Negative-QTOFsplash10-00di-0189000000-c0c4fea994ad59c6af4c2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Clopidogrel 20V, Negative-QTOFsplash10-03e9-5290000000-384f9f4c95308bc8487a2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Clopidogrel 40V, Negative-QTOFsplash10-001i-7790000000-5865fdee9334a4d1d30d2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Clopidogrel 10V, Positive-QTOFsplash10-00di-0009000000-2bc03219cf962da0b1ff2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Clopidogrel 20V, Positive-QTOFsplash10-00di-0449000000-3d2799457a93e03f946b2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Clopidogrel 40V, Positive-QTOFsplash10-01t9-0920000000-0c740a018e7a5007c2572021-09-22Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Membrane (predicted from logP)
Biospecimen LocationsNot Available
Tissue Locations
  • Liver
  • Platelet
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00758
Phenol Explorer Compound IDNot Available
FooDB IDFDB023584
KNApSAcK IDNot Available
Chemspider ID54632
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkClopidogrel
METLIN ID3965
PubChem Compound60606
PDB IDNot Available
ChEBI ID37941
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceBousquet, Andre; Musolino, Andree. Hydroxyacetic ester derivatives, namely (R)-methyl 2-(sulfonyloxy)-2-(chlorophenyl)acetates, preparation method, and use as synthesis intermediates for clopidogrel. PCT Int. Appl. (1999), 35 p
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Eikelboom JW, Hankey GJ, Thom J, Claxton A, Yi Q, Gilmore G, Staton J, Barden A, Norman PE: Enhanced antiplatelet effect of clopidogrel in patients whose platelets are least inhibited by aspirin: a randomized crossover trial. J Thromb Haemost. 2005 Dec;3(12):2649-55. [PubMed:16359503 ]
  2. Contreres JO, Dupuy E, Job B, Habib A, Bryckaert M, Rosa JP, Simoneau G, Herbert JM, Savi P, Levy-Toledano S: Effect of clopidogrel administration to healthy volunteers on platelet phosphorylation events triggered by ADP. Br J Haematol. 2003 Feb;120(4):633-42. [PubMed:12588350 ]
  3. Lev EI, Patel RT, Maresh KJ, Guthikonda S, Granada J, DeLao T, Bray PF, Kleiman NS: Aspirin and clopidogrel drug response in patients undergoing percutaneous coronary intervention: the role of dual drug resistance. J Am Coll Cardiol. 2006 Jan 3;47(1):27-33. Epub 2005 Dec 9. [PubMed:16386660 ]
  4. Savion N, Varon D: Impact--the cone and plate(let) analyzer: testing platelet function and anti-platelet drug response. Pathophysiol Haemost Thromb. 2006;35(1-2):83-8. [PubMed:16855351 ]
  5. van Hecken A, Depre M, Wynants K, Vanbilloen H, Verbruggen A, Arnout J, Vanhove P, Cariou R, De Schepper PJ: Effect of clopidogrel on naproxen-induced gastrointestinal blood loss in healthy volunteers. Drug Metabol Drug Interact. 1998;14(3):193-205. [PubMed:10366994 ]
  6. Craft RM, Chavez JJ, Snider CC, Muenchen RA, Carroll RC: Comparison of modified Thrombelastograph and Plateletworks whole blood assays to optical platelet aggregation for monitoring reversal of clopidogrel inhibition in elective surgery patients. J Lab Clin Med. 2005 Jun;145(6):309-15. [PubMed:15976759 ]
  7. Chen YG, Xu F, Zhang Y, Ji QS, Sun Y, Lu RJ, Li RJ: Effect of aspirin plus clopidogrel on inflammatory markers in patients with non-ST-segment elevation acute coronary syndrome. Chin Med J (Engl). 2006 Jan 5;119(1):32-6. [PubMed:16454979 ]
  8. Hulot JS, Bura A, Villard E, Azizi M, Remones V, Goyenvalle C, Aiach M, Lechat P, Gaussem P: Cytochrome P450 2C19 loss-of-function polymorphism is a major determinant of clopidogrel responsiveness in healthy subjects. Blood. 2006 Oct 1;108(7):2244-7. Epub 2006 Jun 13. [PubMed:16772608 ]
  9. Gansera B, Schmidtler F, Spiliopoulos K, Angelis I, Neumaier-Prauser P, Kemkes BM: Urgent or emergent coronary revascularization using bilateral internal thoracic artery after previous clopidogrel antiplatelet therapy. Thorac Cardiovasc Surg. 2003 Aug;51(4):185-9. [PubMed:14502454 ]
  10. Bauriedel G, Skowasch D, Schneider M, Andrie R, Jabs A, Luderitz B: Antiplatelet effects of angiotensin-converting enzyme inhibitors compared with aspirin and clopidogrel: a pilot study with whole-blood aggregometry. Am Heart J. 2003 Feb;145(2):343-8. [PubMed:12595854 ]
  11. Geiger J, Brich J, Honig-Liedl P, Eigenthaler M, Schanzenbacher P, Herbert JM, Walter U: Specific impairment of human platelet P2Y(AC) ADP receptor-mediated signaling by the antiplatelet drug clopidogrel. Arterioscler Thromb Vasc Biol. 1999 Aug;19(8):2007-11. [PubMed:10446085 ]
  12. Xiao Z, Theroux P: Clopidogrel inhibits platelet-leukocyte interactions and thrombin receptor agonist peptide-induced platelet activation in patients with an acute coronary syndrome. J Am Coll Cardiol. 2004 Jun 2;43(11):1982-8. [PubMed:15172401 ]
  13. Graff J, Harder S, Wahl O, Scheuermann EH, Gossmann J: Anti-inflammatory effects of clopidogrel intake in renal transplant patients: effects on platelet-leukocyte interactions, platelet CD40 ligand expression, and proinflammatory biomarkers. Clin Pharmacol Ther. 2005 Nov;78(5):468-76. Epub 2005 Sep 26. [PubMed:16321613 ]
  14. Evangelista V, Manarini S, Dell'Elba G, Martelli N, Napoleone E, Di Santo A, Lorenzet PS: Clopidogrel inhibits platelet-leukocyte adhesion and platelet-dependent leukocyte activation. Thromb Haemost. 2005 Sep;94(3):568-77. [PubMed:16268474 ]
  15. Ley SJ: Quality care outcomes in cardiac surgery: the role of evidence-based practice. AACN Clin Issues. 2001 Nov;12(4):606-17; quiz 633-5. [PubMed:11759432 ]
  16. Samara WM, Bliden KP, Tantry US, Gurbel PA: The difference between clopidogrel responsiveness and posttreatment platelet reactivity. Thromb Res. 2005;115(1-2):89-94. [PubMed:15567458 ]
  17. Cassar K, Bachoo P, Ford I, Greaves M, Brittenden J: Variability in responsiveness to clopidogrel in patients with intermittent claudication. Eur J Vasc Endovasc Surg. 2006 Jul;32(1):71-5. Epub 2006 Mar 23. [PubMed:16549375 ]
  18. Yende S, Wunderink RG: Effect of clopidogrel on bleeding after coronary artery bypass surgery. Crit Care Med. 2001 Dec;29(12):2271-5. [PubMed:11801823 ]
  19. Malinin A, Pokov A, Swaim L, Kotob M, Serebruany V: Validation of a VerifyNow-P2Y12 cartridge for monitoring platelet inhibition with clopidogrel. Methods Find Exp Clin Pharmacol. 2006 Jun;28(5):315-22. [PubMed:16845449 ]
  20. Quinn MJ, Bhatt DL, Zidar F, Vivekananthan D, Chew DP, Ellis SG, Plow E, Topol EJ: Effect of clopidogrel pretreatment on inflammatory marker expression in patients undergoing percutaneous coronary intervention. Am J Cardiol. 2004 Mar 15;93(6):679-84. [PubMed:15019868 ]

Enzymes

General function:
Involved in monooxygenase activity
Specific function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4-hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Acts as a 1,8-cineole 2-exo-monooxygenase. The enzyme also hydroxylates etoposide.
Gene Name:
CYP3A4
Uniprot ID:
P08684
Molecular weight:
57255.585
General function:
Involved in monooxygenase activity
Specific function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Acts as a 1,4-cineole 2-exo-monooxygenase.
Gene Name:
CYP2B6
Uniprot ID:
P20813
Molecular weight:
56277.81
General function:
Involved in monooxygenase activity
Specific function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics.
Gene Name:
CYP3A5
Uniprot ID:
P20815
Molecular weight:
57108.065
General function:
Involved in binding
Specific function:
Ca(2+)-dependent receptor for myeloid cells that binds to carbohydrates on neutrophils and monocytes. Mediates the interaction of activated endothelial cells or platelets with leukocytes. The ligand recognized is sialyl-Lewis X. Mediates rapid rolling of leukocyte rolling over vascular surfaces during the initial steps in inflammation through interaction with PSGL1
Gene Name:
SELP
Uniprot ID:
P16109
Molecular weight:
90833.1
General function:
Involved in G-protein coupled receptor protein signaling pathway
Specific function:
Receptor for ADP and ATP coupled to G-proteins that inhibit the adenylyl cyclase second messenger system. Not activated by UDP and UTP. Involved in platelets aggregation
Gene Name:
P2RY12
Uniprot ID:
Q9H244
Molecular weight:
39438.4