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USDailyMed:Warfarin AU:D B01AA03(WHO)QB01AA03(WHO) AU:S4(Prescription only)CA:℞-onlyUK:POM(Prescription only)US:℞-only (RS)-4-Hydroxy-3-(3-oxo-1-phenylbutyl)- 2H-chromen-2-one 81-81-2Yas salt:129-06-6 54678486as salt:16204922 6853 DB00682Nas salt:DBSALT000278 10442445Yas salt:17333193 5Q7ZVV76EIas salt:6153CWM0CL D08682Yas salt:D00564 CHEBI:10033Yas salt:CHEBI:10034 ChEMBL1464Nas salt:ChEMBL1200879 RWF (PDBe,RCSB PDB)as salt: SWF (PDBe,RCSB PDB) Interactive image CC(=O)CC(C\1=C(/O)c2ccccc2OC/1=O)c3ccccc3 InChI=1S/C19H16O4/c1-12(20)11-15(13-7-3-2-4-8-13)17-18(21)14-9-5-6-10-16(14)23-19(17)22/h2-10,15,21H,11H2,1H3YKey:PJVWKTKQMONHTI-UHFFFAOYSA-NY Warfarin, sold under the brand nameCoumadinamong others, is used as ananticoagulant medication.It is commonly used to preventdeep vein thrombosisandpulmonary embolism, and to protect againststrokein people who haveatrial fibrillation,valvular heart disease, orartificial heart valves.Warfarin may sometimes be prescribed following aST-segment elevation myocardial infarctionandorthopedic surgery.It is usually taken by mouth, but may also‍‍‍‍‍‍​​​‍​​​​​​ be administeredintravenously. The commonside effect, a natural consequence of reduced clotting, isbleeding.Less common side effects may include areas oftissue damage, andpurple toes syndrome.Use is not recommended duringpregnancy.The effects of warfarin are typically monitored by checkingprothrombin time(INR) every one to four weeks.Many other medications anddietary factorscan interact with warfarin, either increasing or decreasing its effectiveness.The effects of warfarin may be reversed withphytomenadione(vitamin K1),fresh frozen plasma, orprothrombin complex concentrate. Warfarin decreasesblood clottingby blockingvitamin K epoxide reductase, anenzymethat reactivatesvitamin K1.Without sufficient active vitamin K1, the plasma concentrations ofclotting factorsII, VII, IX, and X are reduced and thus have decreased clotting ability.The anticlottingprotein Candprotein Sare also inhibited, but to a lesser degree.It is wrongly described as a "vitamin K antagonist". This term is incorrect. Warfarin does not antagonize the action of vitamin K1, but rather antagonizes vitamin K1 recycling, depleting active vitamin K1. A few days are required for full effect to occur, and these effects can last for up to five days.Because the mechanism involves enzymes such asVKORC1, patients on warfarin withpolymorphisms of the enzymesmay require adjustments in therapy if the genetic variant that they have is more readily inhibited by warfarin, thus requiring lower doses. Warfarin first came into large-scale commercial use in 1948 as arat poison.It was formally approved as a medication to treat blood clots in humans by the U.S.Food and Drug Administrationin 1954.In 1955, warfarin's reputation as a safe and acceptable treatment forcoronary artery disease,arterial plaques, andischemic strokeswas bolstered when PresidentDwight D. Eisenhowerwas treated with warfarin following a highly publicized heart attack.It is on theWorld Health Organization's List of Essential Medicines.Warfarin is available as ageneric medicationand is sold under many brand names.In 2023, it was the 116th most commonly prescribed medication in the United States, with more than 5million prescriptions.