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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:00:29 UTC
Update Date2021-09-14 15:46:17 UTC
HMDB IDHMDB0013929
Secondary Accession Numbers
  • HMDB13929
Metabolite Identification
Common Name2-Oxoclopidogrel
Description2-Oxoclopidogrel is a thiolactone intermediate of clopidogrel, an antithrombotic prodrug (PMID: 23249383 ).. Hepatic cytochrome P450 (P450) enzymes catalyze the conversion of clopidogrel to 2-oxo-clopidogrel via CYP3A oxidation. After oxidation, 2-oxoclopidogrel is then subsequently hydrolyzed to the clopidogrel active metabolite known as CAM (PMID: 25970225 ). 2-oxoclopidogrel can form four isomers (H1, H2, H3 and H4) of CAM, in which H4 only found in humans. The H4 isomer exhibits twice the activity of the H2 isomer (PMID: 28602635 ). The H4 isomer blocks adenosine diphosphate (ADP) binding to the P2Y12 receptor which thereby inhibits ADP induced platelet aggregation. 2-oxoclopidogrel is only found in individuals that have used or taken Clopidogrel.
Structure
Data?1582753155
Synonyms
ValueSource
2-oxo-ClopidogrelHMDB
(2S)Methyl 2-(2-chlorophenyl)-2-(2-oxo-7,7a-dihydrothieno(3,2-c)pyridin-5(2H,4H,6H)-yl)acetateHMDB
Chemical FormulaC16H16ClNO3S
Average Molecular Weight337.821
Monoisotopic Molecular Weight337.05394178
IUPAC Namemethyl (2S)-2-(2-chlorophenyl)-2-{2-oxo-2H,4H,5H,6H,7H,7aH-thieno[3,2-c]pyridin-5-yl}acetate
Traditional Namemethyl (2S)-2-(2-chlorophenyl)-2-{2-oxo-4H,6H,7H,7aH-thieno[3,2-c]pyridin-5-yl}acetate
CAS Registry NumberNot Available
SMILES
COC(=O)[C@@H](N1CCC2SC(=O)C=C2C1)C1=CC=CC=C1Cl
InChI Identifier
InChI=1S/C16H16ClNO3S/c1-21-16(20)15(11-4-2-3-5-12(11)17)18-7-6-13-10(9-18)8-14(19)22-13/h2-5,8,13,15H,6-7,9H2,1H3/t13?,15-/m0/s1
InChI KeyJBSAZVIMJUOBNB-WUJWULDRSA-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
  • Piperidine
  • Benzenoid
  • Methyl ester
  • Carbothioic s-lactone
  • 2,5-dihydrothiophene
  • Tertiary aliphatic amine
  • Thiocarboxylic acid ester
  • Tertiary amine
  • Carboxylic acid ester
  • Thiocarboxylic acid or derivatives
  • Azacycle
  • Organoheterocyclic compound
  • Monocarboxylic acid or derivatives
  • Organic oxide
  • Organohalogen compound
  • Organopnictogen compound
  • Organochloride
  • Organic oxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Amine
  • Organooxygen compound
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
Process
RoleNot Available
Physical Properties
StateNot Available
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 Solubility0.053 g/LALOGPS
logP2.75ALOGPS
logP2.87ChemAxon
logS-3.8ALOGPS
pKa (Strongest Acidic)8.28ChemAxon
pKa (Strongest Basic)4.51ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area46.61 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity88.01 m³·mol⁻¹ChemAxon
Polarizability33.85 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M+H]+174.30530932474
DeepCCS[M-H]-171.94730932474
DeepCCS[M-2H]-206.22630932474
DeepCCS[M+Na]+181.33830932474
AllCCS[M+H]+174.232859911
AllCCS[M+H-H2O]+171.232859911
AllCCS[M+NH4]+177.032859911
AllCCS[M+Na]+177.832859911
AllCCS[M-H]-175.032859911
AllCCS[M+Na-2H]-174.832859911
AllCCS[M+HCOO]-174.732859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
2-OxoclopidogrelCOC(=O)[C@@H](N1CCC2SC(=O)C=C2C1)C1=CC=CC=C1Cl3807.3Standard polar33892256
2-OxoclopidogrelCOC(=O)[C@@H](N1CCC2SC(=O)C=C2C1)C1=CC=CC=C1Cl2646.2Standard non polar33892256
2-OxoclopidogrelCOC(=O)[C@@H](N1CCC2SC(=O)C=C2C1)C1=CC=CC=C1Cl2675.5Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 2-Oxoclopidogrel GC-MS (Non-derivatized) - 70eV, Positivesplash10-004i-0190000000-489b988baa99d3ba5ff12017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2-Oxoclopidogrel GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Oxoclopidogrel 10V, Positive-QTOFsplash10-000i-0119000000-8a5e7008cac66b2674212016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Oxoclopidogrel 20V, Positive-QTOFsplash10-059i-0196000000-26909a713c5535a89bf52016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Oxoclopidogrel 40V, Positive-QTOFsplash10-004j-4590000000-bc0e44783d88160ecf932016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Oxoclopidogrel 10V, Negative-QTOFsplash10-000i-0009000000-9bddc2d228e1e448d9142016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Oxoclopidogrel 20V, Negative-QTOFsplash10-0f7c-0159000000-6c8164efb2cd0531f5ed2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Oxoclopidogrel 40V, Negative-QTOFsplash10-03dl-6791000000-0473925e521b6029585b2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Oxoclopidogrel 10V, Negative-QTOFsplash10-000i-0049000000-adb4e0342f064419581d2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Oxoclopidogrel 20V, Negative-QTOFsplash10-0059-5192000000-e19d0ffa95f84bc891562021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Oxoclopidogrel 40V, Negative-QTOFsplash10-001i-9682000000-aef34ebc8a3f6b9a9ce62021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Oxoclopidogrel 10V, Positive-QTOFsplash10-000i-0009000000-584cee3804a36ce3f8212021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Oxoclopidogrel 20V, Positive-QTOFsplash10-000i-0229000000-10f9eb47c9a85cda38862021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Oxoclopidogrel 40V, Positive-QTOFsplash10-03fr-0944000000-9d423bbf8f92a15c9fd82021-09-22Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Extracellular
Biospecimen Locations
  • Blood
  • Urine
Tissue Locations
  • Kidney
  • Liver
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID28518812
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound56848893
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Zhu Y, Zhou J: In vitro biotransformation studies of 2-oxo-clopidogrel: multiple thiolactone ring-opening pathways further attenuate prodrug activation. Chem Res Toxicol. 2013 Jan 18;26(1):179-90. doi: 10.1021/tx300460k. Epub 2012 Dec 28. [PubMed:23249383 ]
  2. Dansette PM, Levent D, Hessani A, Mansuy D: Bioactivation of clopidogrel and prasugrel: factors determining the stereochemistry of the thiol metabolite double bond. Chem Res Toxicol. 2015 Jun 15;28(6):1338-45. doi: 10.1021/acs.chemrestox.5b00133. Epub 2015 May 21. [PubMed:25970225 ]
  3. Lyngby JG, Court MH, Lee PM: Validation of a method for quantitation of the clopidogrel active metabolite, clopidogrel, clopidogrel carboxylic acid, and 2-oxo-clopidogrel in feline plasma. J Vet Cardiol. 2017 Aug;19(4):384-395. doi: 10.1016/j.jvc.2017.03.004. Epub 2017 Jun 9. [PubMed:28602635 ]

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
References
  1. Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [PubMed:19515014 ]
  2. Saw J, Steinhubl SR, Berger PB, Kereiakes DJ, Serebruany VL, Brennan D, Topol EJ: Lack of adverse clopidogrel-atorvastatin clinical interaction from secondary analysis of a randomized, placebo-controlled clopidogrel trial. Circulation. 2003 Aug 26;108(8):921-4. Epub 2003 Aug 18. [PubMed:12925453 ]
  3. Neubauer H, Gunesdogan B, Hanefeld C, Spiecker M, Mugge A: Lipophilic statins interfere with the inhibitory effects of clopidogrel on platelet function--a flow cytometry study. Eur Heart J. 2003 Oct;24(19):1744-9. [PubMed:14522569 ]
  4. Lau WC, Gurbel PA, Watkins PB, Neer CJ, Hopp AS, Carville DG, Guyer KE, Tait AR, Bates ER: Contribution of hepatic cytochrome P450 3A4 metabolic activity to the phenomenon of clopidogrel resistance. Circulation. 2004 Jan 20;109(2):166-71. Epub 2004 Jan 5. [PubMed:14707025 ]
  5. Mukherjee D, Kline-Rogers E, Fang J, Munir K, Eagle KA: Lack of clopidogrel-CYP3A4 statin interaction in patients with acute coronary syndrome. Heart. 2005 Jan;91(1):23-6. [PubMed:15604326 ]
  6. Poulsen TS, Vinholt P, Mickley H, Korsholm L, Kristensen SR, Damkier P: Existence of a clinically relevant interaction between clopidogrel and HMG-CoA reductase inhibitors? Re-evaluating the evidence. Basic Clin Pharmacol Toxicol. 2005 Feb;96(2):103-10. [PubMed:15679472 ]
  7. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
  8. Clarke TA, Waskell LA: The metabolism of clopidogrel is catalyzed by human cytochrome P450 3A and is inhibited by atorvastatin. Drug Metab Dispos. 2003 Jan;31(1):53-9. [PubMed:12485953 ]
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. This enzyme contributes to the wide pharmacokinetics variability of the metabolism of drugs such as S-warfarin, diclofenac, phenytoin, tolbutamide and losartan.
Gene Name:
CYP2C9
Uniprot ID:
P11712
Molecular weight:
55627.365
References
  1. Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [PubMed:19515014 ]
  2. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
General function:
Involved in monooxygenase activity
Specific function:
Responsible for the metabolism of a number of therapeutic agents such as the anticonvulsant drug S-mephenytoin, omeprazole, proguanil, certain barbiturates, diazepam, propranolol, citalopram and imipramine.
Gene Name:
CYP2C19
Uniprot ID:
P33261
Molecular weight:
55944.565
References
  1. Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [PubMed:19515014 ]
  2. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
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
References
  1. Walsky RL, Astuccio AV, Obach RS: Evaluation of 227 drugs for in vitro inhibition of cytochrome P450 2B6. J Clin Pharmacol. 2006 Dec;46(12):1426-38. [PubMed:17101742 ]
  2. Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [PubMed:19515014 ]
  3. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
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
References
  1. Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [PubMed:19515014 ]
  2. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
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. Most active in catalyzing 2-hydroxylation. Caffeine is metabolized primarily by cytochrome CYP1A2 in the liver through an initial N3-demethylation. Also acts in the metabolism of aflatoxin B1 and acetaminophen. Participates in the bioactivation of carcinogenic aromatic and heterocyclic amines. Catalizes the N-hydroxylation of heterocyclic amines and the O-deethylation of phenacetin.
Gene Name:
CYP1A2
Uniprot ID:
P05177
Molecular weight:
58406.915
References
  1. Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [PubMed:19515014 ]
  2. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
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. In the epoxidation of arachidonic acid it generates only 14,15- and 11,12-cis-epoxyeicosatrienoic acids. It is the principal enzyme responsible for the metabolism the anti-cancer drug paclitaxel (taxol).
Gene Name:
CYP2C8
Uniprot ID:
P10632
Molecular weight:
55824.275
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
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
References
  1. Dorsam RT, Murugappan S, Ding Z, Kunapuli SP: Clopidogrel: interactions with the P2Y12 receptor and clinical relevance. Hematology. 2003 Dec;8(6):359-65. [PubMed:14668029 ]
  2. Herbert JM, Savi P: P2Y12, a new platelet ADP receptor, target of clopidogrel. Semin Vasc Med. 2003 May;3(2):113-22. [PubMed:15199474 ]
  3. Taubert D, Kastrati A, Harlfinger S, Gorchakova O, Lazar A, von Beckerath N, Schomig A, Schomig E: Pharmacokinetics of clopidogrel after administration of a high loading dose. Thromb Haemost. 2004 Aug;92(2):311-6. [PubMed:15269827 ]
  4. Wang L, Jacobsen SE, Bengtsson A, Erlinge D: P2 receptor mRNA expression profiles in human lymphocytes, monocytes and CD34+ stem and progenitor cells. BMC Immunol. 2004 Aug 3;5:16. [PubMed:15291969 ]
  5. Wihlborg AK, Wang L, Braun OO, Eyjolfsson A, Gustafsson R, Gudbjartsson T, Erlinge D: ADP receptor P2Y12 is expressed in vascular smooth muscle cells and stimulates contraction in human blood vessels. Arterioscler Thromb Vasc Biol. 2004 Oct;24(10):1810-5. Epub 2004 Aug 12. [PubMed:15308557 ]
  6. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]
  7. Gladding P, Webster M, Zeng I, Farrell H, Stewart J, Ruygrok P, Ormiston J, El-Jack S, Armstrong G, Kay P, Scott D, Gunes A, Dahl ML: The pharmacogenetics and pharmacodynamics of clopidogrel response: an analysis from the PRINC (Plavix Response in Coronary Intervention) trial. JACC Cardiovasc Interv. 2008 Dec;1(6):620-7. doi: 10.1016/j.jcin.2008.09.008. [PubMed:19463375 ]
  8. Savi P, Zachayus JL, Delesque-Touchard N, Labouret C, Herve C, Uzabiaga MF, Pereillo JM, Culouscou JM, Bono F, Ferrara P, Herbert JM: The active metabolite of Clopidogrel disrupts P2Y12 receptor oligomers and partitions them out of lipid rafts. Proc Natl Acad Sci U S A. 2006 Jul 18;103(29):11069-74. Epub 2006 Jul 11. [PubMed:16835302 ]
  9. van Gestel MA, Heemskerk JW, Slaaf DW, Heijnen VV, Reneman RS, oude Egbrink MG: In vivo blockade of platelet ADP receptor P2Y12 reduces embolus and thrombus formation but not thrombus stability. Arterioscler Thromb Vasc Biol. 2003 Mar 1;23(3):518-23. Epub 2003 Jan 23. [PubMed:12615691 ]