Clopidogrel

Not to be confused with Clopidol.

Clopidogrel
Skeletal formula
Ball-and-stick model clopidogrel
Clinical data
Pronunciation/kləˈpɪdəɡrɛl, kloʊ-/[1]
Trade namesPlavix, Iscover, others[2]
AHFS/Drugs.comMonograph
MedlinePlusa601040
License data
Pregnancy
category
Routes of
administration		By mouth
ATC code
Legal status
Legal status
Pharmacokinetic data
Bioavailability>50%
Protein binding94–98%
MetabolismLiver
Onset of action2 hours[10]
Elimination half-life7–8 hours (inactive metabolite)
Duration of action5 days[10]
Excretion50% Kidney
46% bile duct
Identifiers
  • (+)-(S)-methyl 2-(2-chlorophenyl)-2-(6,7-dihydrothieno[3,2-c]pyridin-5(4H)-yl)acetate
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
PDB ligand
CompTox Dashboard (EPA)
ECHA InfoCard100.127.841 Edit this at Wikidata
Chemical and physical data
FormulaC16H16ClNO2S
Molar mass321.82 g·mol−1
3D model (JSmol)
  • COC(=O)[C@H](c1ccccc1Cl)N2CCc3c(ccs3)C2
  • 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 checkY
  • Key:GKTWGGQPFAXNFI-HNNXBMFYSA-N checkY
  (verify)

Clopidogrel, sold under the brand name Plavix among others, is an antiplatelet medication used to reduce the risk of heart disease and stroke in those at high risk.[10] It is also used together with aspirin in heart attacks and following the placement of a coronary artery stent (dual antiplatelet therapy).[10] It is taken by mouth.[10] Its effect starts about two hours after intake and lasts for five days.[10]

Common side effects include headache, nausea, easy bruising, itching, and heartburn.[10] More severe side effects include bleeding and thrombotic thrombocytopenic purpura.[10] While there is no evidence of harm from use during pregnancy, such use has not been well studied.[3] Clopidogrel is in the thienopyridine-class of antiplatelets.[10] It works by irreversibly inhibiting a receptor called P2Y12 on platelets.[10]

Clopidogrel was patented in 1982, and approved for medical use in 1997.[6][11] It is on the World Health Organization's List of Essential Medicines.[12] In 2022, it was the 47th most commonly prescribed medication in the United States, with more than 13 million prescriptions.[13][14] It is available as a generic medication.[10]

  1. ^ "Clopidogrel". Lexico Dictionaries. Archived from the original on 25 October 2019. Retrieved 26 October 2019.
  2. ^ Cite error: The named reference brands was invoked but never defined (see the help page).
  3. ^ a b "Clopidogrel (Plavix) Use During Pregnancy". Drugs.com. Archived from the original on 21 December 2016. Retrieved 14 December 2016.
  4. ^ "FDA-sourced list of all drugs with black box warnings (Use Download Full Results and View Query links.)". nctr-crs.fda.gov. FDA. Retrieved 22 October 2023.
  5. ^ "Plavix Summary of Product Characteristics (SmPC)". (emc). 23 January 2023. Retrieved 15 January 2024.
  6. ^ a b Cite error: The named reference Plavix FDA label was invoked but never defined (see the help page).
  7. ^ "Plavix- clopidogrel tablet, film coated". DailyMed. 22 September 2022. Retrieved 15 January 2024.
  8. ^ "Plavix EPAR". European Medicines Agency (EMA). 14 July 1998. Retrieved 15 January 2024.
  9. ^ "Iscover EPAR". European Medicines Agency (EMA). 14 July 1998. Retrieved 15 August 2024.
  10. ^ a b c d e f g h i j k "Clopidogrel Bisulfate". The American Society of Health-System Pharmacists. Archived from the original on 21 December 2016. Retrieved 8 December 2016.
  11. ^ Fischer J, Ganellin CR (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 453. ISBN 9783527607495. Archived from the original on 20 December 2016.
  12. ^ World Health Organization (2023). The selection and use of essential medicines 2023: web annex A: World Health Organization model list of essential medicines: 23rd list (2023). Geneva: World Health Organization. hdl:10665/371090. WHO/MHP/HPS/EML/2023.02.
  13. ^ "The Top 300 of 2022". ClinCalc. Archived from the original on 30 August 2024. Retrieved 30 August 2024.
  14. ^ "Clopidogrel Drug Usage Statistics, United States, 2013 - 2022". ClinCalc. Retrieved 30 August 2024.