Clopidogrel (CHEM021327)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-25 03:24:39 UTC
Update Date2026-04-13 20:35:36 UTC
Accession NumberCHEM021327
Identification
Common NameClopidogrel
ClassSmall Molecule
DescriptionClopidogrel is a prodrug of a platelet inhibitor used to reduce the risk of myocardial infarction and stroke. Clopidogrel is indicated to reduce the risk of myocardial infarction for patients with non-ST elevated acute coronary syndrome (ACS), patients with ST-elevated myocardial infarction, and in recent MI, stroke, or established peripheral arterial disease, It has been shown to be superior to in reducing cardiovascular outcomes in patients with cardiovascular disease and provides additional benefit to patients with acute coronary syndromes already taking aspirin. Clopidogrel was granted FDA approval on 17 November 1997.
Contaminant Sources
  • FooDB Chemicals
  • STOFF IDENT Compounds
  • Suspected Compounds - Waste Water
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
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
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot 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
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-03di-3980000000-d577843e19cf599f8a0bSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-0229-0967000000-6c51c479e90818ec703bSpectrum
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-0229-0967000000-6c51c479e90818ec703bSpectrum
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-0a4i-2900000000-be6dbedd4a0c4f60d0ddSpectrum
LC-MS/MSLC-MS/MS Spectrum - 50V, Positivesplash10-0a4i-0900000000-6cfdcd4344e312b9152eSpectrum
LC-MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-03di-0592000000-7840275de971a1c4cd01Spectrum
LC-MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-00di-0039000000-c8efc33e40006dfa1d04Spectrum
LC-MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-053r-0910000000-19b1ace18c36bc486855Spectrum
LC-MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-0900000000-c7ca4d76836b437c0027Spectrum
LC-MS/MSLC-MS/MS Spectrum - 35V, Positivesplash10-0230-0935000000-9e8f08289a74a12e1d1bSpectrum
LC-MS/MSLC-MS/MS Spectrum - 50V, Positivesplash10-0a4i-0900000000-240a5f13f03a49f5ab78Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-0159000000-17a9fe29b343cd5ca501Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-022l-0192000000-f551440009ad0c2d2404Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-08fr-2950000000-aea6a4e495e819b37fdbSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0059000000-71b4a913e2ab55e93430Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00dr-0296000000-023d1bb858121c6c9158Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-03di-8940000000-ec8e591212f5c1afd516Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0189000000-c0c4fea994ad59c6af4cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03e9-5290000000-384f9f4c95308bc8487aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-001i-7790000000-5865fdee9334a4d1d30dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-0009000000-2bc03219cf962da0b1ffSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-0449000000-3d2799457a93e03f946bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-01t9-0920000000-0c740a018e7a5007c257Spectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
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