Clopidogrel (CED0001290)

Record Information
Version1.0
Creation Date2016-05-25 03:24:39 UTC
Update Date2026-08-19 15:21:12 UTC
Accession NumberCHEM021327
Identification
Common NameClopidogrel
ClassSmall Molecule
Description
Clopidogrel is an organic compound with the formula C16H16ClNO2S and an average molecular weight of 321.82 g/mol. Clopidogrel belongs to the amino acids, peptides, and analogues, a subclass of carboxylic acids and derivatives within the organic compounds. It acts as an antagonist of the P2Y purinoceptor 12 (P2RY12) protein target. The compound is utilized as an antithrombotic agent and is found in or released from ten recorded sources. These include healthcare, pharmaceuticals & veterinary products; drinking water & water supply (drinking water); food, food processing & cookware (preparation of wine or sparkling wine); household cleaning & consumer products (cigar cigarettes, non electric simulated smoking devices, and other smoking requisites); and electrical & electronic equipment (antennas, electrically stimulated smoking devices, magnets, and television systems). The recorded exposure route for clopidogrel is oral. In terms of health effects, clopidogrel is used as a treatment for acute myocardial infarction (PMC3291088), thrombosis (PMC9368651), stroke (PMC6044138, PMC9259378), and ischemic stroke (PMC3148418, PMC8084398, PMC9368651). Additionally, it has a therapeutic effect on thrombosis (PMC11124379) and stroke (PMC3148418).
Contaminant TypeNot Available
Chemical Structure
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 Mass321.822 g/mol
Monoisotopic Mass321.059 g/mol
CAS Registry Number113665-84-2
IUPAC Namemethyl (2S)-2-(2-chlorophenyl)-2-{4H,5H,6H,7H-thieno[3,2-c]pyridin-5-yl}acetate
Traditional Nameclopidogrel
SMILES[H][C@@](N1CCC2=C(C1)C=CS2)(C(=O)OC)C1=CC=CC=C1Cl
InChI IdentifierInChI=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
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Organoleptic EffectsNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted 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
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted GC-MSPredicted GC-MS Spectrumsplash10-03di-3980000000-d577843e19cf599f8a0bNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0229-0967000000-6c51c479e90818ec703bNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0229-0967000000-6c51c479e90818ec703bNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0a4i-2900000000-be6dbedd4a0c4f60d0ddNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0a4i-0900000000-6cfdcd4344e312b9152eNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-03di-0592000000-7840275de971a1c4cd01Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-00di-0039000000-c8efc33e40006dfa1d04Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-053r-0910000000-19b1ace18c36bc486855Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0a4i-0900000000-c7ca4d76836b437c0027Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0230-0935000000-9e8f08289a74a12e1d1bNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0a4i-0900000000-240a5f13f03a49f5ab78Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-00di-0159000000-17a9fe29b343cd5ca501Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-022l-0192000000-f551440009ad0c2d2404Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-08fr-2950000000-aea6a4e495e819b37fdbNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-00di-0059000000-71b4a913e2ab55e93430Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-00dr-0296000000-023d1bb858121c6c9158Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-03di-8940000000-ec8e591212f5c1afd516Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-00di-0189000000-c0c4fea994ad59c6af4cNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-03e9-5290000000-384f9f4c95308bc8487aNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-001i-7790000000-5865fdee9334a4d1d30dNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-00di-0009000000-2bc03219cf962da0b1ffNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-00di-0449000000-3d2799457a93e03f946bNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-01t9-0920000000-0c740a018e7a5007c257Not AvailableView Spectrum
Toxicity Profile
Mechanism of ToxicityNot Available
Carcinogenicity (IARC Classification)Not Available
Minimum Risk LevelNot Available
SymptomsNot Available
TreatmentNot Available
Toxicity Values
Toxicity ValueUnitValue RangeOrganismDose DescriptorRoute of ExposurePredicted or ExperimentalReference
1505.0Log mg/kg[850:2700]RatLD50oralpredictedNot Available
Health Effects
Health EffectRelationshipDirectionReference
ischemic strokeis_treatment_forNot AvailablePMC3148418 , PMC8084398 , PMC9368651
strokehas_therapeutic_effect_onNot AvailablePMC3148418
strokeis_treatment_forNot AvailablePMC6044138 , PMC9259378 , PMC9259378
thrombosisis_treatment_forNot AvailablePMC9368651
thrombosishas_therapeutic_effect_onNot AvailablePMC11124379
acute myocardial infarctionis_treatment_forNot AvailablePMC3291088
pulmonary hypertensionis_treatment_forNot AvailablePMC12221332
tetralogy of Fallotis_treatment_forNot AvailablePMC8543113
Exposure Sources
Source IDSourceSectorReference
115Drinking waterDrinking water & water supplyNot Available
233BrushesPersonal care & cosmeticsNot Available
273Antithrombotic agentsHealthcare, pharmaceuticals & veterinary productsNot Available
506AntennasElectrical & Electronic EquipmentNot Available
518Electrically Stimulated Smoking DevicesElectrical & Electronic EquipmentNot Available
527MagnetsElectrical & Electronic EquipmentNot Available
537Television SystemsElectrical & Electronic EquipmentNot Available
549Preparation Of Wine Or Sparkling WineFood, food processing & cookwareNot Available
556Cigar CigarettesHousehold cleaning & consumer productsNot Available
559Non Electric Simulated Smoking DevicesHousehold cleaning & consumer productsNot Available
560Other Smoking RequisitesHousehold cleaning & consumer productsNot Available
607Rodenticides(1)Agriculture & land managementNot Available
608RodenticidesAgriculture & land managementNot Available
Pathways
4 pathways
Targets
StructureProteinUniProt IDOrganismRelationshipDetails
Cytochrome P450 2B6 structureClick to view 3D structureCytochrome P450 2B6P20813HumansPredicted (SEA)4.35956
Sodium-dependent serotonin transporter structureClick to view 3D structureSodium-dependent serotonin transporterP31645HumansPredicted (SEA)81.8974
P2Y purinoceptor 12 structureClick to view 3D structureP2Y purinoceptor 12Q9H244HumansPredicted (SEA)8.95266
Alpha-2A adrenergic receptor structureClick to view 3D structureAlpha-2A adrenergic receptorP08913HumansPredicted (SEA)420.853
Alpha-2B adrenergic receptor structureClick to view 3D structureAlpha-2B adrenergic receptorP18089HumansPredicted (SEA)298.941
Alpha-2C adrenergic receptor structureClick to view 3D structureAlpha-2C adrenergic receptorP18825HumansPredicted (SEA)333.817
Cytochrome P450 2D6 structureClick to view 3D structureCytochrome P450 2D6P10635HumansPredicted (SEA)1318.38
Sigma non-opioid intracellular receptor 1 structureClick to view 3D structureSigma non-opioid intracellular receptor 1Q99720HumansPredicted (SEA)745.095
5-hydroxytryptamine receptor 1A structureClick to view 3D structure5-hydroxytryptamine receptor 1AP08908HumansPredicted (SEA)1186.34
5-hydroxytryptamine receptor 7 structureClick to view 3D structure5-hydroxytryptamine receptor 7P34969HumansPredicted (SEA)804.961
Cytochrome P450 1A2 structureClick to view 3D structureCytochrome P450 1A2P05177HumansPredicted (SEA)1477.58
Click to view 3D structureProstaglandin F2-alpha receptorP43118Rattus norvegicusPredicted (SEA)10.5096
5-hydroxytryptamine receptor 6 structureClick to view 3D structure5-hydroxytryptamine receptor 6P50406HumansPredicted (SEA)821.387
Cytochrome P450 2C19 structureClick to view 3D structureCytochrome P450 2C19P33261HumansPredicted (SEA)1951.37
Cytochrome P450 3A4 structureClick to view 3D structureCytochrome P450 3A4P08684HumansPredicted (SEA)3869.81
Click to view 3D structure5-hydroxytryptamine receptor 1AP19327Rattus norvegicusPredicted (SEA)1251.04
Click to view 3D structureATP-dependent molecular chaperone HSP82C4YTQ8Candida albicans (strain WO-1) (Yeast)Predicted (SEA)437.513
Click to view 3D structure5-hydroxytryptamine receptor 1BP28564Rattus norvegicusPredicted (SEA)453.861
Alpha-1A adrenergic receptor structureClick to view 3D structureAlpha-1A adrenergic receptorP35348HumansPredicted (SEA)1028.0
Click to view 3D structureAlpha-1B adrenergic receptorP35368HumansPredicted (SEA)842.095
Sodium-dependent dopamine transporter structureClick to view 3D structureSodium-dependent dopamine transporterQ01959HumansPredicted (SEA)1334.57
D(2) dopamine receptor structureClick to view 3D structureD(2) dopamine receptorP14416HumansPredicted (SEA)2298.89
Serine/threonine-protein kinase PLK1 structureClick to view 3D structureSerine/threonine-protein kinase PLK1P53350HumansPredicted (SEA)2294.53
5-hydroxytryptamine receptor 2C structureClick to view 3D structure5-hydroxytryptamine receptor 2CP28335HumansPredicted (SEA)2079.12
Histamine H1 receptor structureClick to view 3D structureHistamine H1 receptorP35367HumansPredicted (SEA)1507.39
Concentrations
Not Available
External Links
DrugBank IDDB00758
HMDB IDHMDB0005011
FooDB IDFDB023584
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN ID3965
PDB IDNot Available
Wikipedia LinkClopidogrel
Chemspider ID54632
ChEBI ID37941
PubChem Compound ID60606
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Bousquet, 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
2. 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.
3. 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.
4. 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.
5. 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.
6. 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.
7. 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.
8. 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.
9. 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.
10. 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.
11. 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.
12. 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.
13. 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.
14. 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.
15. Yende S, Wunderink RG: Effect of clopidogrel on bleeding after coronary artery bypass surgery. Crit Care Med. 2001 Dec;29(12):2271-5.
16. 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.
17. 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.
18. 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.
19. 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.
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.
21. 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.
22. https://www.ncbi.nlm.nih.gov/pubmed/?term=10983738
23. https://www.ncbi.nlm.nih.gov/pubmed/?term=11095576
24. https://www.ncbi.nlm.nih.gov/pubmed/?term=11701941
25. https://www.ncbi.nlm.nih.gov/pubmed/?term=16802846
26. https://www.ncbi.nlm.nih.gov/pubmed/?term=18520712
27. https://www.ncbi.nlm.nih.gov/pubmed/?term=18708826
28. https://www.ncbi.nlm.nih.gov/pubmed/?term=19573725