Details of the Drug
General Information of Drug (ID: DMOL54H)
Drug Name |
Clopidogrel
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Synonyms |
clopidogrel; 113665-84-2; (S)-Clopidogrel; Plavix; Clopidogrel [INN:BAN]; (+)-(S)-Clopidogrel; (+)-Clopidogrel; UNII-A74586SNO7; HSDB 7430; CLOPIDOGREL SULFATE; CHEBI:37941; GKTWGGQPFAXNFI-HNNXBMFYSA-N; A74586SNO7; CPD000550475; Zyllt; Clopidogrel (TN); SR-25990C; Plavix (TN); methyl (2S)-(2-chlorophenyl)(6,7-dihydrothieno[3,2-c]pyridin-5(4H)-yl)ethanoate; Clopidogrelum; Thrombo; Clopidogrel BMS; Clopidogrel Hexal; Clopidogrel Acino; methyl (2S)-2-(2-chlorophenyl)-2-{4H,5H,6H,7H-thieno[3,2-c]pyridin-5-yl}acetate; PM-103; Clopidogrel (captisol-enabled); Clopidogrel (captisol-enabled), The Medicines Co; Clopidogrel (captisol-enabled, cardiovascular disease), Cydex; Clopidogrel (captisol-enabled, cardiovascular disease), Prism Pharmaceuticals
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Indication |
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Drug Type |
Small molecular drug
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Structure | ||||||||||||||||||||
3D MOL | 2D MOL | |||||||||||||||||||
#Ro5 Violations (Lipinski): 0 | Molecular Weight (mw) | 321.8 | ||||||||||||||||||
Topological Polar Surface Area (xlogp) | 3.8 | |||||||||||||||||||
Rotatable Bond Count (rotbonds) | 4 | |||||||||||||||||||
Hydrogen Bond Donor Count (hbonddonor) | 0 | |||||||||||||||||||
Hydrogen Bond Acceptor Count (hbondacc) | 4 | |||||||||||||||||||
ADMET Property |
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Chemical Identifiers |
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Cross-matching ID | ||||||||||||||||||||
Molecular Interaction Atlas of This Drug
Drug Therapeutic Target (DTT) |
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Drug Transporter (DTP) |
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Drug-Metabolizing Enzyme (DME) |
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Molecular Interaction Atlas (MIA) | ||||||||||||||||||||||||||||||||||||||||||||||||||||
Drug-Drug Interaction (DDI) Information of This Drug
Coadministration of a Drug Treating the Same Disease as Clopidogrel
Coadministration of a Drug Treating the Disease Different from Clopidogrel (Comorbidity)
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Drug Inactive Ingredient(s) (DIG) and Formulation(s) of This Drug
References
1 | URL: http://www.guidetopharmacology.org Nucleic Acids Res. 2015 Oct 12. pii: gkv1037. The IUPHAR/BPS Guide to PHARMACOLOGY in 2016: towards curated quantitative interactions between 1300 protein targets and 6000 ligands. (Ligand id: 7150). | ||||
---|---|---|---|---|---|
2 | Trusted, scientifically sound profiles of drug programs, clinical trials, safety reports, and company deals, written by scientists. Springer. 2015. Adis Insight (drug id 800029432) | ||||
3 | URL: http://www.guidetopharmacology.org Nucleic Acids Res. 2015 Oct 12. pii: gkv1037. The IUPHAR/BPS Guide to PHARMACOLOGY in 2016: towards curated quantitative interactions between 1300 protein targets and 6000 ligands. (Target id: 328). | ||||
4 | BDDCS applied to over 900 drugs | ||||
5 | Trend Analysis of a Database of Intravenous Pharmacokinetic Parameters in Humans for 1352 Drug Compounds | ||||
6 | Estimating the safe starting dose in phase I clinical trials and no observed effect level based on QSAR modeling of the human maximum recommended daily dose | ||||
7 | P2Y12, a new platelet ADP receptor, target of clopidogrel. Semin Vasc Med. 2003 May;3(2):113-22. | ||||
8 | Impact of P-glycoprotein on clopidogrel absorption. Clin Pharmacol Ther. 2006 Nov;80(5):486-501. | ||||
9 | 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. | ||||
10 | Cytochrome P450 3A inhibition by ketoconazole affects prasugrel and clopidogrel pharmacokinetics and pharmacodynamics differently. Clin Pharmacol Ther. 2007 May;81(5):735-41. | ||||
11 | Impact of the CYP2C19 gene polymorphism on clopidogrel personalized drug regimen and the clinical outcomes. Clin Lab. 2016 Sep 1;62(9):1773-1780. | ||||
12 | Clinical pharmacokinetics and pharmacodynamics of clopidogrel. Clin Pharmacokinet. 2015 Feb;54(2):147-66. | ||||
13 | Clopidogrel pathway. Pharmacogenet Genomics. 2010 Jul;20(7):463-5. | ||||
14 | Expression levels and activation of a PXR variant are directly related to drug resistance in osteosarcoma cell lines. Cancer. 2007 Mar 1;109(5):957-65. | ||||
15 | Contribution of human hepatic cytochrome P450 isoforms to regioselective hydroxylation of steroid hormones. Xenobiotica. 1998 Jun;28(6):539-47. | ||||
16 | Comprehensive evaluation of tamoxifen sequential biotransformation by the human cytochrome P450 system in vitro: prominent roles for CYP3A and CYP2D6. J Pharmacol Exp Ther. 2004 Sep;310(3):1062-75. | ||||
17 | Isoform-specific regulation of cytochromes P450 expression by estradiol and progesterone. Drug Metab Dispos. 2013 Feb;41(2):263-9. | ||||
18 | Metabolic interactions between acetaminophen (paracetamol) and two flavonoids, luteolin and quercetin, through in-vitro inhibition studies. J Pharm Pharmacol. 2017 Dec;69(12):1762-1772. | ||||
19 | Potent mechanism-based inhibition of CYP3A4 by imatinib explains its liability to interact with CYP3A4 substrates. Br J Pharmacol. 2012 Apr;165(8):2787-98. | ||||
20 | Effects of morin on the pharmacokinetics of etoposide in rats. Biopharm Drug Dispos. 2007 Apr;28(3):151-6. | ||||
21 | The metabolism of zidovudine by human liver microsomes in vitro: formation of 3'-amino-3'-deoxythymidine. Biochem Pharmacol. 1994 Jul 19;48(2):267-76. | ||||
22 | Roles of cytochromes P450 1A2, 2A6, and 2C8 in 5-fluorouracil formation from tegafur, an anticancer prodrug, in human liver microsomes. Drug Metab Dispos. 2000 Dec;28(12):1457-63. | ||||
23 | Effects of polyunsaturated fatty acids on prostaglandin synthesis and cyclooxygenase-mediated DNA adduct formation by heterocyclic aromatic amines in human adenocarcinoma colon cells. Mol Carcinog. 2004 Jul;40(3):180-8. | ||||
24 | Endoxifen and other metabolites of tamoxifen inhibit human hydroxysteroid sulfotransferase 2A1 (hSULT2A1). Drug Metab Dispos. 2014 Nov;42(11):1843-50. | ||||
25 | Cytochrome P450 1A2 (CYP1A2) activity and risk factors for breast cancer: a cross-sectional study. Breast Cancer Res. 2004;6(4):R352-65. | ||||
26 | PharmGKB summary: pathways of acetaminophen metabolism at the therapeutic versus toxic doses. Pharmacogenet Genomics. 2015 Aug;25(8):416-26. | ||||
27 | The effect of apigenin on pharmacokinetics of imatinib and its metabolite N-desmethyl imatinib in rats. Biomed Res Int. 2013;2013:789184. | ||||
28 | The influence of metabolic gene polymorphisms on urinary 1-hydroxypyrene concentrations in Chinese coke oven workers. Sci Total Environ. 2007 Aug 1;381(1-3):38-46. | ||||
29 | Identification of P450 enzymes involved in metabolism of verapamil in humans. Naunyn Schmiedebergs Arch Pharmacol. 1993 Sep;348(3):332-7. | ||||
30 | Metabolism and metabolic inhibition of xanthotoxol in human liver microsomes. Evid Based Complement Alternat Med. 2016;2016:5416509. | ||||
31 | Drug related genetic polymorphisms affecting adverse reactions to methotrexate, vinblastine, doxorubicin and cisplatin in patients with urothelial cancer. J Urol. 2008 Dec;180(6):2389-95. | ||||
32 | Human prostate CYP3A5: identification of a unique 5'-untranslated sequence and characterization of purified recombinant protein. Biochem Biophys Res Commun. 1999 Jul 14;260(3):676-81. | ||||
33 | Polymorphisms in cytochrome P4503A5 (CYP3A5) may be associated with race and tumor characteristics, but not metabolism and side effects of tamoxifen in breast cancer patients. Cancer Lett. 2005 Jan 10;217(1):61-72. | ||||
34 | Drug Interactions Flockhart Table | ||||
35 | Induction of hepatic CYP2E1 by a subtoxic dose of acetaminophen in rats: increase in dichloromethane metabolism and carboxyhemoglobin elevation. Drug Metab Dispos. 2007 Oct;35(10):1754-8. | ||||
36 | Urinary 6 beta-hydroxycortisol excretion in rheumatoid arthritis. Br J Rheumatol. 1997 Jan;36(1):54-8. | ||||
37 | Clinical pharmacokinetics of imatinib. Clin Pharmacokinet. 2005;44(9):879-94. | ||||
38 | Kinetics and regulation of cytochrome P450-mediated etoposide metabolism. Drug Metab Dispos. 2004 Sep;32(9):993-1000. | ||||
39 | Differential mechanism-based inhibition of CYP3A4 and CYP3A5 by verapamil. Drug Metab Dispos. 2005 May;33(5):664-71. | ||||
40 | Progesterone and testosterone hydroxylation by cytochromes P450 2C19, 2C9, and 3A4 in human liver microsomes. Arch Biochem Biophys. 1997 Oct 1;346(1):161-9. | ||||
41 | Tamoxifen inhibits cytochrome P450 2C9 activity in breast cancer patients. J Chemother. 2006 Aug;18(4):421-4. | ||||
42 | Characterization of the oxidative metabolites of 17beta-estradiol and estrone formed by 15 selectively expressed human cytochrome p450 isoforms. Endocrinology. 2003 Aug;144(8):3382-98. | ||||
43 | Summary of information on human CYP enzymes: human P450 metabolism data. Drug Metab Rev. 2002 Feb-May;34(1-2):83-448. | ||||
44 | Drug-drug interactions with imatinib: an observational study. Medicine (Baltimore). 2016 Oct;95(40):e5076. | ||||
45 | Drug interactions with calcium channel blockers: possible involvement of metabolite-intermediate complexation with CYP3A. Drug Metab Dispos. 2000 Feb;28(2):125-30. | ||||
46 | New insights into the structural features and functional relevance of human cytochrome P450 2C9. Part I. Curr Drug Metab. 2009 Dec;10(10):1075-126. | ||||
47 | A potential role for the estrogen-metabolizing cytochrome P450 enzymes in human breast carcinogenesis. Breast Cancer Res Treat. 2003 Dec;82(3):191-7. | ||||
48 | A mechanistic approach to antiepileptic drug interactions. Ann Pharmacother. 1998 May;32(5):554-63. | ||||
49 | Effect of tamoxifen on the enzymatic activity of human cytochrome CYP2B6. J Pharmacol Exp Ther. 2002 Jun;301(3):945-52. | ||||
50 | Hepatic metabolism of diclofenac: role of human CYP in the minor oxidative pathways. Biochem Pharmacol. 1999 Sep 1;58(5):787-96. | ||||
51 | Insights into CYP2B6-mediated drug-drug interactions. Acta Pharm Sin B. 2016 Sep;6(5):413-425. | ||||
52 | Drugs that may have potential CYP2B6 interactions. | ||||
53 | Involvement of human cytochrome P450 2B6 in the omega- and 4-hydroxylation of the anesthetic agent propofol. Xenobiotica. 2007 Jul;37(7):717-24. | ||||
54 | Nicotine and 4-(methylnitrosamino)-1-(3-pyridyl)-butanone metabolism by cytochrome P450 2B6. Drug Metab Dispos. 2005 Dec;33(12):1760-4. | ||||
55 | PharmGKB summary: phenytoin pathway. Pharmacogenet Genomics. 2012 Jun;22(6):466-70. | ||||
56 | Application of the relative activity factor approach in scaling from heterologously expressed cytochromes p450 to human liver microsomes: studies on amitriptyline as a model substrate. J Pharmacol Exp Ther. 2001 Apr;297(1):326-37. | ||||
57 | High-dose rabeprazole/amoxicillin therapy as the second-line regimen after failure to eradicate H. pylori by triple therapy with the usual doses of a proton pump inhibitor, clarithromycin and amoxicillin. Hepatogastroenterology. 2003 Nov-Dec;50(54):2274-8. | ||||
58 | Cytochrome P450 pharmacogenetics and cancer. Oncogene. 2006 Mar 13;25(11):1679-91. | ||||
59 | CYP2C19*17 is associated with decreased breast cancer risk. Breast Cancer Res Treat. 2009 May;115(2):391-6. | ||||
60 | Cytochromes of the P450 2C subfamily are the major enzymes involved in the O-demethylation of verapamil in humans. Naunyn Schmiedebergs Arch Pharmacol. 1995 Dec;353(1):116-21. | ||||
61 | Diclofenac and its derivatives as tools for studying human cytochromes P450 active sites: particular efficiency and regioselectivity of P450 2Cs. Biochemistry. 1999 Oct 26;38(43):14264-70. | ||||
62 | Organic anion-transporting polypeptide B (OATP-B) and its functional comparison with three other OATPs of human liver. Gastroenterology. 2001 Feb;120(2):525-33. | ||||
63 | Possible involvement of multiple human cytochrome P450 isoforms in the liver metabolism of propofol. Br J Anaesth. 1998 Jun;80(6):788-95. | ||||
64 | Human intestinal transporter database: QSAR modeling and virtual profiling of drug uptake, efflux and interactions. Pharm Res. 2013 Apr;30(4):996-1007. | ||||
65 | MDR1 (ABCB1) G1199A (Ser400Asn) polymorphism alters transepithelial permeability and sensitivity to anticancer agents. Cancer Chemother Pharmacol. 2009 Jun;64(1):183-8. | ||||
66 | Mammalian drug efflux transporters of the ATP binding cassette (ABC) family in multidrug resistance: A review of the past decade. Cancer Lett. 2016 Jan 1;370(1):153-64. | ||||
67 | Folate transporter expression decreases in the human placenta throughout pregnancy and in pre-eclampsia. Pregnancy Hypertens. 2012 Apr;2(2):123-31. | ||||
68 | Comparative studies on in vitro methods for evaluating in vivo function of MDR1 P-glycoprotein. Pharm Res. 2001 Dec;18(12):1660-8. | ||||
69 | Antiestrogens and steroid hormones: substrates of the human P-glycoprotein. Biochem Pharmacol. 1994 Jul 19;48(2):287-92. | ||||
70 | Association of genetic polymorphisms in the influx transporter SLCO1B3 and the efflux transporter ABCB1 with imatinib pharmacokinetics in patients with chronic myeloid leukemia. Ther Drug Monit. 2011 Apr;33(2):244-50. | ||||
71 | Hughes B: 2009 FDA drug approvals. Nat Rev Drug Discov. 2010 Feb;9(2):89-92. | ||||
72 | Clinical pipeline report, company report or official report of AstraZeneca (2009). | ||||
73 | Rapid and reversible modulation of platelet function in man by a novel P2Y(12) ADP-receptor antagonist, INS50589. Platelets. 2007 Aug;18(5):346-56. | ||||
74 | Elinogrel, a reversible P2Y12 receptor antagonist for the treatment of acute coronary syndrome and prevention of secondary thrombotic events. Curr Opin Investig Drugs. 2010 Mar;11(3):340-8. | ||||
75 | Pharmacological characterization of the human P2Y11 receptor. Br J Pharmacol. 1999 Nov;128(6):1199-206. | ||||
76 | Molecular cloning of the platelet P2T(AC) ADP receptor: pharmacological comparison with another ADP receptor, the P2Y(1) receptor. Mol Pharmacol. 2001 Sep;60(3):432-9. | ||||
77 | Stereoselective inhibition of human platelet aggregation by R-138727, the active metabolite of CS-747 (prasugrel, LY640315), a novel P2Y12 receptor inhibitor. Thromb Haemost. 2005 Sep;94(3):593-8. | ||||
78 | Cerner Multum, Inc. "UK Summary of Product Characteristics.". | ||||
79 | Canadian Pharmacists Association. | ||||
80 | Itkonen MK, Tornio A, Neuvonen M, Neuvonen PJ, Niemi M, Backman JT "Clopidogrel Markedly Increases the Plasma Concentrations of the CYP2C8 Substrate Pioglitazone." Drug Metab Dispos (2016):. [PMID: 27260150] | ||||
81 | Agencia Espaola de Medicamentos y Productos Sanitarios Healthcare "Centro de informacion online de medicamentos de la AEMPS - CIMA.". | ||||
82 | Clarke TA, Waskell LA "The metabolism of clopidogrel is catalyzed by human cytochrome P450 3A and is inhibited by atorvastatin." Drug Metab Dispos 31 (2003): 53-9. [PMID: 12485953] | ||||
83 | Collet JP, Hulot JS, Pena A, et al. "Cytochrome P450 2C19 polymorphism in young patients treated with clopidogrel after myocardial infarction: a cohort study." Lancet 373 (2009): 309-17. [PMID: 19108880] | ||||
84 | Eggleston W, Clark KH, Marraffa JM "Loperamide abuse associated with cardiac dysrhythmia and death." Ann Emerg Med 69 (2017): 83-6. [PMID: 27140747] | ||||
85 | Product Information. Tykerb (lapatinib). Novartis Pharmaceuticals, East Hanover, NJ. | ||||
86 | Product Information. Tukysa (tucatinib). Seattle Genetics Inc, Bothell, WA. | ||||
87 | Cerner Multum, Inc. "Australian Product Information.". | ||||
88 | Alderman CP, Moritz CK, Ben-Tovim DI "Abnormal platelet aggregation associated with fluoxetine therapy." Ann Pharmacother 26 (1992): 1517-9. [PMID: 1482806] | ||||
89 | Anand S, Yusuf S, Xie C, et al. "Oral anticoagulant and antiplatelet therapy and peripheral arterial disease." N Engl J Med 357 (2007): 217-27. [PMID: 17634457] | ||||
90 | Product Information. Ofev (nintedanib). Boehringer Ingelheim, Ridgefield, CT. | ||||
91 | Price AJ, Frcpath DO "Is there a clinical interaction between low molecular weight heparin and non-steroidal analgesics after total hip replacement?" Ann R Coll Surg Engl 77 (1995): 395. [PMID: 7486773] | ||||
92 | Product Information. Xarelto (rivaroxaban). Bayer Inc, Toronto, IA. | ||||
93 | Product Information. Panhematin (hemin). Recordati Rare Diseases Inc, Lebanon, NJ. | ||||
94 | Heck AM, DeWitt BA, Lukes AL "Potential interactions between alternative therapies and warfarin." Am J Health Syst Pharm 57 (2000): 1221-7 quiz 1228-30. [PMID: 10902065] | ||||
95 | Product Information. Plavix (clopidogrel). Bristol-Myers Squibb, Princeton, NJ. | ||||
96 | Product Information. Acular (ketorolac). Allergan Inc, Irvine, CA. | ||||
97 | Product Information. Dexilant (dexlansoprazole). Takeda Pharmaceuticals America, Lincolnshire, IL. | ||||
98 | Product Information. Aptivus (tipranavir). Boehringer-Ingelheim, Ridgefield, CT. | ||||
99 | Product Information. Viberzi (eluxadoline). Actavis Pharma, Inc., Parsippany, NJ. | ||||
100 | Caruso V, Iacoviello L, Di Castelnuovo A, et.al "Thrombotic complications in childhood acute lymphoblastic leukemia: a meta-analysis of 17 prospective studies comprising 1752 pediatric patients." Blood 108 (2006): 2216-22. [PMID: 16804111] | ||||
101 | Product Information. Calquence (acalabrutinib). Astra-Zeneca Pharmaceuticals, Wilmington, DE. | ||||
102 | Product Information. Iclusig (ponatinib). Ariad Pharmaceuticals Inc, Cambridge, MA. | ||||
103 | Product Information. Sprycel (dasatinib). Bristol-Myers Squibb, Princeton, NJ. | ||||
104 | Product Information. Brukinsa (zanubrutinib). BeiGene USA, Inc, San Mateo, CA. | ||||
105 | Klinkhardt U, Kirchmaier CM, Westrup D, Graff J, Mahnel R, Breddin HK, Harder S "Ex vivo-in vitro interaction between aspirin, clopidogrel, and the glycoprotein IIb/IIIa inhibitors abciximab and SR121566A." Clin Pharmacol Ther 67 (2000): 305-13. [PMID: 10741635] | ||||
106 | Product Information. Xtandi (enzalutamide). Astellas Pharma US, Inc, Deerfield, IL. | ||||
107 | Product Information. Flolan (epoprostenol). Glaxo Wellcome, Research Triangle Park, NC. | ||||
108 | Abebe W "Herbal medication: potential for adverse interactions with analgesic drugs." J Clin Pharm Ther 27 (2002): 391-401. [PMID: 12472978] | ||||
109 | Bergmann TK, Filppula AM, Launiainen T, Nielsen F, Backman J, Brosen K "Neurotoxicity and low paclitaxel clearance associated with concomitant clopidogrel therapy in a 60 year old Caucasian woman with ovarian carcinoma." Br J Clin Pharmacol (2015):. [PMID: 26446447] | ||||
110 | Product Information. Bevyxxa (betrixaban). Portola Pharmaceuticals, South San Francisco, CA. | ||||
111 | Ohyama K, Nakajima M, Suzuki M, Shimada N, Yamazaki H, Yokoi T "Inhibitory effects of amiodarone and its N-deethylated metabolite on human cytochrome P450 activities: Prediction of in vivo drug interactions." Br J Clin Pharmacol 49 (2000): 244-53. [PMID: 10718780] | ||||