Warfarin

Synonyms :
4-Hydroxy-3-(3-oxo-1-phenylbutyl)coumarin, Coumafene, Zoocoumarin

Status : approved

Category

Anticoagulants

Therapeutic Classification

ANTITHROMBOTIC AGENTS

BLOOD AND BLOOD FORMING ORGANS
ANTITHROMBOTIC AGENTS
ANTITHROMBOTIC AGENTS
Rodenticides

Description

Warfarin is an anticoagulant drug normally used to prevent blood clot formation as well as migration. Although originally marketed as a pesticide (d-Con, Rodex, among others), Warfarin has since become the most frequently prescribed oral anticoagulant in North America. Warfarin has several properties that should be noted when used medicinally, including its ability to cross the placental barrier during pregnancy which can result in fetal bleeding, spontaneous abortion, preterm birth, stillbirth, and neonatal death. Additional adverse effects such as necrosis, purple toe syndrome, osteoporosis, valve and artery calcification, and drug interactions have also been documented with warfarin use. Warfarin does not actually affect blood viscosity, rather, it inhibits vitamin-k dependent synthesis of biologically active forms of various clotting factors in addition to several regulatory factors.

Used

For the treatment of retinal vascular occlusion, pulmonary embolism, cardiomyopathy, atrial fibrillation and flutter, cerebral embolism, transient cerebral ischaemia, arterial embolism and thrombosis.

Mechanism Of Action

Warfarin inhibits vitamin K reductase, resulting in depletion of the reduced form of vitamin K (vitamin KH2). As vitamin K is a cofactor for the carboxylation of glutamate residues on the N-terminal regions of vitamin K-dependent proteins, this limits the gamma-carboxylation and subsequent activation of the vitamin K-dependent coagulant proteins. The synthesis of vitamin K-dependent coagulation factors II, VII, IX, and X and anticoagulant proteins C and S is inhibited. Depression of three of the four vitamin K-dependent coagulation factors (factors II, VII, and X) results in decreased prothrombin levels and a decrease in the amount of thrombin generated and bound to fibrin. This reduces the thrombogenicity of clots.

Dosage

Form Route Strength
Injection, powder, lyophilized, for solution intravenous 2 mg/mL
Powder for solution intravenous 5 mg
Tablet oral 1 mg
Tablet oral 10 mg
Tablet oral 2 mg
Tablet oral 2.5 mg
Tablet oral 3 mg
Tablet oral 4 mg
Tablet oral 5 mg
Tablet oral 6 mg
Tablet oral 7.5 mg
Tablet oral 10.0 mg
Tablet oral 3.0 mg
Tablet oral 4.0 mg
Tablet oral 5.0 mg

Pharmacodynamics

Warfarin, a coumarin anticoagulant, is a racemic mixture of two active isomers. It is used in the prevention and treatment of thromboembolic disease including venous thrombosis, thromboembolism, and pulmonary embolism as well as for the prevention of ischemic stroke in patients with atrial fibrillation (AF).

Toxic Effect

LD50=374 (orally in mice)

Metabolism

Metabolized stereo- and regio-selectively by hepatic microsomal enzymes. S-warfarin is predominantly metabolized by cytochrome P450 (CYP) 2C9 to yield the 6- and 7-hydroxylated metabolites. R-warfarin is metabolized by CYP1A1, 1A2, and 3A4 to yield 6-, 8-, and 10-hydroxylated metabolites. Hydroxylated metabolites may be further conjugated prior to excretion into bile and urine. UGT1A1 appears to be responsible for producing the 6-O-glucuronide of warfarin, with a possibly contribution from UGT1A10. Five UGT1As may be involved in the formation of 7-O-glucuronide warfarin. S-warfarin has higher potency than R-warfarin and genetic polymorphisms in CYP2C9 may dramatically decrease clearance of and increase toxicity of the medication.

Absorption

Rapidly absorbed following oral administration with considerable interindividual variations. Also absorbed percutaneously.

Half Life

R-warfarin t1/2=37-89 hours; S-warfarin t1/2=21-43 hours.

Protein Binding

99% bound primarily to albumin

Elimination Route

The elimination of warfarin is almost entirely by metabolism. Very little warfarin is excreted unchanged in urine. The metabolites are principally excreted into the urine; and to a lesser extent into the bile.

Clearance

* 0.065 +/- 0.025 mL/min/kg [CYP2C9 Genotype *1/*1] * 0.041 +/- 0.021 [CYP2C9 Genotype *1/*2 or *1/*3] * 0.020 +/- 0.011 [CYP2C9 Genotype *2/*2, *2/*3, or *3/*3]

Volume of Distribution

* 0.14 L/kg

Chemical Classification

This compound belongs to the class of organic compounds known as 4-hydroxycoumarins. These are coumarins that contain one or more hydroxyl groups attached to C4-position the coumarin skeleton.

4-hydroxycoumarins

Organic compounds

Phenylpropanoids and polyketides

Coumarins and derivatives

Hydroxycoumarins

Salt : Warfarin sodium

Chemical Name

4-Hydroxy-3-(3-oxo-1-phenylbutyl)coumarin

Brands

name Dosage form Country
Apo-warfarin tablet Canada
Apo-warfarin tablet Canada
Apo-warfarin tablet Canada
Apo-warfarin tablet Canada
Apo-warfarin tablet Canada
Apo-warfarin tablet Canada
Apo-warfarin tablet Canada
Coumadin tablet US
Coumadin tablet US
Coumadin tablet US
Coumadin tablet US
Coumadin tablet US
Coumadin tablet US
Coumadin tablet US
Coumadin tablet US
Coumadin tablet US
Coumadin tablet US
Coumadin tablet US
Coumadin tablet US
Coumadin tablet US
Coumadin tablet US
Coumadin tablet US
Coumadin tablet US
Coumadin tablet US
Coumadin tablet US
Coumadin tablet US
Coumadin tablet US
Coumadin powder for solution Canada
Coumadin tablet US
Coumadin tablet US
Coumadin tablet US
Coumadin tablet US
Coumadin tablet US
Coumadin tablet US
Coumadin tablet US
Coumadin tablet US
Coumadin tablet US
Coumadin tablet US
Coumadin tablet US
Coumadin injection, powder, lyophilized, for solution US
Coumadin tablet US
Coumadin tablet US
Coumadin tablet US
Coumadin tablet US
Coumadin tablet US
Coumadin tablet US
Coumadin tablet US
Coumadin tablet US
Coumadin tablet US
Coumadin tablet US
Coumadin tablet US
Coumadin tablet US
Coumadin tablet US
Coumadin tablet US
Coumadin tablet US
Coumadin tablet US
Coumadin Tab 10mg tablet Canada
Coumadin Tab 1mg tablet Canada
Coumadin Tab 2.5mg tablet Canada
Coumadin Tab 2mg tablet Canada
Coumadin Tab 3mg tablet Canada
Coumadin Tab 4mg tablet Canada
Coumadin Tab 5mg tablet Canada
Coumadin Tab 6 mg tablet Canada
Jantoven tablet US
Jantoven tablet US
Jantoven tablet US
Jantoven tablet US
Jantoven tablet US
Jantoven tablet US
Jantoven tablet US
Jantoven tablet US
Jantoven tablet US
Jantoven tablet US
Jantoven tablet US
Jantoven tablet US
Jantoven tablet US
Jantoven tablet US
Jantoven tablet US
Jantoven tablet US
Jantoven tablet US
Jantoven tablet US
Jantoven tablet US
Jantoven tablet US
Jantoven tablet US
Jantoven tablet US
Jantoven tablet US
Jantoven tablet US
Mylan-warfarin tablet Canada
Mylan-warfarin tablet Canada
Mylan-warfarin tablet Canada
Mylan-warfarin tablet Canada
Mylan-warfarin tablet Canada
Mylan-warfarin tablet Canada
Mylan-warfarin tablet Canada
Mylan-warfarin tablet Canada
Mylan-warfarin tablet Canada
Novo-warfarin tablet Canada
Novo-warfarin tablet Canada
Novo-warfarin tablet Canada
Novo-warfarin tablet Canada
Novo-warfarin tablet Canada
Novo-warfarin tablet Canada
Novo-warfarin tablet Canada
Novo-warfarin tablet Canada
Novo-warfarin tablet Canada
Nu-warfarin tablet Canada
Nu-warfarin tablet Canada
Nu-warfarin tablet Canada
Nu-warfarin tablet Canada
Nu-warfarin tablet Canada
Nu-warfarin tablet Canada
Nu-warfarin tablet Canada
Taro-warfarin tablet Canada
Taro-warfarin tablet Canada
Taro-warfarin tablet Canada
Taro-warfarin tablet Canada
Taro-warfarin tablet Canada
Taro-warfarin tablet Canada
Taro-warfarin tablet Canada
Taro-warfarin tablet Canada
Taro-warfarin tablet Canada
Warfarin tablet Canada
Warfarin tablet Canada
Warfarin tablet Canada
Warfarin tablet Canada
Warfarin tablet Canada
Warfarin tablet Canada
Warfarin tablet Canada
Warfarin tablet Canada
Warfarin tablet Canada
Warfarin Sodium tablet US
Warfarin Sodium tablet US
Warfarin Sodium tablet US
Warfarin Sodium tablet US
Warfarin Sodium tablet US
Warfarin Sodium tablet US
Warfarin Sodium tablet US
Warfarin Sodium tablet US
Warfarin Sodium tablet US
Warfarin Sodium tablet US
Warfarin Sodium tablet US
Warfarin Sodium tablet US
Warfarin Sodium tablet US
Warfarin Sodium tablet US
Warfarin Sodium tablet US
Warfarin Sodium tablet US
Warfarin Sodium tablet US
Warfarin Sodium tablet US
Warfarin Sodium tablet US
Warfarin Sodium tablet US
Warfarin Sodium tablet US
Warfarin Sodium tablet US
Warfarin Sodium tablet US
Warfarin Sodium tablet US
Warfarin Sodium tablet US
Warfarin Sodium tablet US
Warfarin Sodium tablet US
Warfarin Sodium tablet US
Warfarin Sodium tablet US
Warfarin Sodium tablet US
Warfarin Sodium tablet US
Warfarin Sodium tablet US
Warfarin Sodium tablet US
Warfarin Sodium tablet US
Warfarin Sodium tablet US
Warfarin Sodium tablet US
Warfarin Sodium tablet US
Warfarin Sodium tablet US
Warfarin Sodium tablet US
Warfarin Sodium tablet US
Warfarin Sodium tablet US
Warfarin Sodium tablet US
Warfarin Sodium tablet US
Warfarin Sodium tablet US
Warfarin Sodium tablet US
Warfarin Sodium tablet US
Warfarin Sodium tablet US
Warfarin Sodium tablet US
Warfarin Sodium tablet US
Warfarin Sodium tablet US
Warfarin Sodium tablet US
Warfarin Sodium tablet US
Warfarin Sodium tablet US
Warfarin Sodium tablet US
Warfarin Sodium tablet US
Warfarin Sodium tablet US
Warfarin Sodium tablet US
Warfarin Sodium tablet US
Warfarin Sodium tablet US
Warfarin Sodium tablet US
Warfarin Sodium tablet US
Warfarin Sodium tablet US
Warfarin Sodium tablet US
Warfarin Sodium tablet US
Warfarin Sodium tablet US
Warfarin Sodium tablet US
Warfarin Sodium tablet US
Warfarin Sodium tablet US
Warfarin Sodium tablet US
Warfarin Sodium tablet US
Warfarin Sodium tablet US
Warfarin Sodium tablet US
Warfarin Sodium tablet US
Warfarin Sodium tablet US
Warfarin Sodium tablet US
Warfarin Sodium tablet US
Warfarin Sodium tablet US
Warfarin Sodium tablet US
Warfarin Sodium tablet US
Warfarin Sodium tablet US
Warfarin Sodium tablet US
Warfarin Sodium tablet US
Warfarin Sodium tablet US
Warfarin Sodium tablet US
Warfarin Sodium tablet US
Warfarin Sodium tablet US
Warfarin Sodium tablet US
Warfarin Sodium tablet US
Warfarin Sodium tablet US
Warfarin Sodium tablet US
Warfarin Sodium tablet US
Warfarin Sodium tablet US
Warfarin Sodium tablet US
Warfarin Sodium tablet US
Warfarin Sodium tablet US
Warfarin Sodium tablet US
Warfarin Sodium tablet US
Warfarin Sodium tablet US
Warfarin Sodium tablet US
Warfarin Sodium tablet US
Warfarin Sodium tablet US
Warfarin Sodium tablet US
Warfarin Sodium tablet US
Warfarin Sodium tablet US
Warfarin Sodium tablet US
Warfarin Sodium tablet US
Warfarin Sodium tablet US
Warfarin Sodium tablet US
Warfarin Sodium tablet US
Warfarin Sodium tablet US
Warfarin Sodium tablet US
Warfarin Sodium tablet US
Warfarin Sodium tablet US
Warfarin Sodium tablet US
Warfarin Sodium tablet US
Warfarin Sodium tablet US
Warfarin Sodium tablet US
Warfarin Sodium tablet US
Warfarin Sodium tablet US
Warfarin Sodium tablet US
Warfarin Sodium tablet US
Warfarin Sodium tablet US
Warfarin Sodium tablet US
Warfarin Sodium tablet US
Warfarin Sodium tablet US
Warfarin Sodium tablet US
Warfarin Sodium tablet US
Warfarin Sodium tablet US
Warfarin Sodium tablet US
Warfarin Sodium tablet US
Warfarin Sodium tablet US
Warfarin Sodium tablet US
Warfarin Sodium tablet US
Warfarin Sodium tablet US
Warfarin Sodium tablet US
Warfarin Sodium tablet US
Warfarin Sodium tablet US
Warfarin Sodium tablet US
Warfarin Sodium tablet US
Warfarin Sodium tablet US
Warfarin Sodium tablet US
Warfarin Sodium tablet US
Warfarin Sodium tablet US
Warfarin Sodium tablet US
Warfarin Sodium tablet US
Warfarin Sodium tablet US
Warfarin Sodium tablet US
Warfarin Sodium tablet US
Warfarin Sodium tablet US
Warfarin Sodium tablet US
Warfarin Sodium tablet US
Warfarin Sodium tablet US
Warfarin Sodium tablet US
Warfarin Sodium tablet US
Warfarin Sodium tablet US
Warfarin Sodium tablet US
Warfarin Sodium tablet US
Warfarin Sodium tablet US
Warfarin Sodium tablet US
Warfarin Sodium tablet US
Warfarin Sodium tablet US
Warfarin Sodium tablet US
Warfarin Sodium tablet US
Warfarin Sodium tablet US
Warfarin Sodium tablet US
Warfarin Sodium tablet US
Warfarin Sodium tablet US
Warfarin Sodium tablet US
Warfarin Sodium tablet US
Warfarin Sodium tablet US
Warfarin Sodium tablet US
Warfarin Sodium tablet US
Warfarin Sodium tablet US
Warfarin Sodium tablet US
Warfarin Sodium tablet US
Warfarin Sodium tablet US
Warfarin Sodium tablet US
Warfarin Sodium tablet US
Warfarin Sodium tablet US
Warfarin Sodium tablet US
Warfarin Sodium tablet US
Warfarin Sodium tablet US
Warfarin Sodium tablet US
Warfarin Sodium tablet US
Warfarin Sodium tablet US
Warfarin Sodium tablet US
Warfarin Sodium tablet US
Warfarin Sodium tablet US
Warfarin Sodium tablet US
Warfarin Sodium tablet US
Warfarin Sodium tablet US
Warfarin Sodium tablet US
Warfarin Sodium tablet US
Warfarin Sodium tablet US
Warfarin Sodium tablet US
Warfarin Sodium tablet US
Warfarin Sodium tablet US
Warfarin Sodium tablet US
Warfarin Sodium tablet US
Warfarin Sodium tablet US
Warfarin Sodium tablet US
Warfarin Sodium tablet US
Warfarin Sodium tablet US
Warfarin Sodium tablet US
Warfarin Sodium tablet US
Warfarin Sodium tablet US
Warfarin Sodium tablet US
Warfarin Sodium tablet US
Warfarin Sodium tablet US
Warfarin Sodium tablet US
Warfarin Sodium tablet US
Warfarin Sodium tablet US
Warfarin Sodium tablet US
Warfarin Sodium tablet US
Warfarin Sodium tablet US
Warfarin Sodium tablet US
Warfarin Sodium tablet US
Warfarin Sodium tablet US
Warfarin Sodium tablet US
Warfarin Sodium tablet US
Warfarin Sodium tablet US
Warfarin Sodium tablet US
Warfarin Sodium tablet US
Warfarin Sodium tablet US
Warfarin Sodium tablet US
Warfarin Sodium tablet US
Warfarin Sodium tablet US
Warfilone Tab 5mg tablet Canada

Drug Drug Interactions

  •  Abciximab  : Agents with Antiplatelet Properties may enhance the anticoagulant effect of Anticoagulants.
  •  Acenocoumarol  : May enhance the anticoagulant effect of other Anticoagulants.
  •  Acetaminophen  : May enhance the anticoagulant effect of Vitamin K Antagonists. This appears most likely with daily Acetaminophen doses exceeding 1.3 or 2 g/day for multiple consecutive days.
  •  Acetylsalicylic acid  : May enhance the anticoagulant effect of Vitamin K Antagonists.
  •  Adalimumab  : May decrease the serum concentration of Warfarin.
  •  Allopurinol  : May enhance the anticoagulant effect of Vitamin K Antagonists.
  •  Alteplase  : Thrombolytic Agents may enhance the anticoagulant effect of Anticoagulants.
  •  Amdinocillin  : May enhance the anticoagulant effect of Vitamin K Antagonists.
  •  Aminosalicylic Acid  : Salicylates may enhance the anticoagulant effect of Anticoagulants.
  •  Amiodarone  : May enhance the anticoagulant effect of Vitamin K Antagonists. Amiodarone may increase the serum concentration of Vitamin K Antagonists.
  •  Amoxicillin  : May enhance the anticoagulant effect of Vitamin K Antagonists.
  •  Ampicillin  : May enhance the anticoagulant effect of Vitamin K Antagonists.
  •  Anagrelide  : Agents with Antiplatelet Properties may enhance the anticoagulant effect of Anticoagulants.
  •  Anistreplase  : May enhance the anticoagulant effect of Anticoagulants.
  •  Apixaban  : May enhance the anticoagulant effect of Anticoagulants.
  •  Aprepitant  : May decrease the serum concentration of Warfarin.
  •  Argatroban  : May enhance the anticoagulant effect of other Anticoagulants.
  •  Atazanavir  : May increase the serum concentration of Warfarin.
  •  Azathioprine  : May diminish the anticoagulant effect of Vitamin K Antagonists.
  •  Azidocillin  : May enhance the anticoagulant effect of Vitamin K Antagonists.
  •  Azlocillin  : May enhance the anticoagulant effect of Vitamin K Antagonists.
  •  Bacampicillin  : May enhance the anticoagulant effect of Vitamin K Antagonists.
  •  Benzylpenicillin  : May enhance the anticoagulant effect of Vitamin K Antagonists.
  •  Betamethasone  : Corticosteroids (Systemic) may enhance the anticoagulant effect of Warfarin.
  •  Bicalutamide  : May increase the serum concentration of Vitamin K Antagonists. Specifically, free concentrations of the vitamin K antagonists may be increased.
  •  Bismuth Subsalicylate  : Salicylates may enhance the anticoagulant effect of Anticoagulants.
  •  Bivalirudin  : May enhance the anticoagulant effect of other Anticoagulants.
  •  Boceprevir  : May decrease the serum concentration of Warfarin. Boceprevir may increase the serum concentration of Warfarin.
  •  Bosentan  : May increase the metabolism of Vitamin K Antagonists.
  •  Butabarbital  : May increase the metabolism of Vitamin K Antagonists.
  •  Butethal  : May increase the metabolism of Vitamin K Antagonists.
  •  Calcidiol  : May diminish the anticoagulant effect of Vitamin K Antagonists.
  •  Calcitriol  : May diminish the anticoagulant effect of Vitamin K Antagonists.
  •  Cangrelor  : Agents with Antiplatelet Properties may enhance the anticoagulant effect of Anticoagulants.
  •  Capecitabine  : May increase the serum concentration of Vitamin K Antagonists.
  •  Carbamazepine  : May decrease the serum concentration of Vitamin K Antagonists.
  •  Carbenicillin  : May enhance the anticoagulant effect of Vitamin K Antagonists.
  •  Carbimazole  : May diminish the anticoagulant effect of Vitamin K Antagonists.
  •  Cefacetrile  : May enhance the anticoagulant effect of Vitamin K Antagonists.
  •  Cefaclor  : May enhance the anticoagulant effect of Vitamin K Antagonists.
  •  Cefadroxil  : May enhance the anticoagulant effect of Vitamin K Antagonists.
  •  Cefalotin  : May enhance the anticoagulant effect of Vitamin K Antagonists.
  •  Cefamandole  : May enhance the anticoagulant effect of Vitamin K Antagonists.
  •  Cefapirin  : May enhance the anticoagulant effect of Vitamin K Antagonists.
  •  Cefazolin  : May enhance the anticoagulant effect of Vitamin K Antagonists.
  •  Cefdinir  : May enhance the anticoagulant effect of Vitamin K Antagonists.
  •  Cefditoren  : May enhance the anticoagulant effect of Vitamin K Antagonists.
  •  Cefepime  : May enhance the anticoagulant effect of Vitamin K Antagonists.
  •  Cefixime  : May enhance the anticoagulant effect of Vitamin K Antagonists.
  •  Cefmenoxime  : May enhance the anticoagulant effect of Vitamin K Antagonists.
  •  Cefmetazole  : May enhance the anticoagulant effect of Vitamin K Antagonists.
  •  Cefonicid  : May enhance the anticoagulant effect of Vitamin K Antagonists.
  •  Cefoperazone  : May enhance the anticoagulant effect of Vitamin K Antagonists.
  •  Ceforanide  : May enhance the anticoagulant effect of Vitamin K Antagonists.
  •  Cefotaxime  : May enhance the anticoagulant effect of Vitamin K Antagonists.
  •  Cefotetan  : May enhance the anticoagulant effect of Vitamin K Antagonists.
  •  Cefotiam  : May enhance the anticoagulant effect of Vitamin K Antagonists.
  •  Cefoxitin  : May enhance the anticoagulant effect of Vitamin K Antagonists.
  •  Cefpiramide  : May enhance the anticoagulant effect of Vitamin K Antagonists.
  •  Cefpodoxime  : May enhance the anticoagulant effect of Vitamin K Antagonists.
  •  Cefprozil  : May enhance the anticoagulant effect of Vitamin K Antagonists.
  •  Cefradine  : May enhance the anticoagulant effect of Vitamin K Antagonists.
  •  Ceftaroline fosamil  : May enhance the anticoagulant effect of Vitamin K Antagonists.
  •  Ceftazidime  : May enhance the anticoagulant effect of Vitamin K Antagonists.
  •  Ceftibuten  : May enhance the anticoagulant effect of Vitamin K Antagonists.
  •  Ceftizoxime  : May enhance the anticoagulant effect of Vitamin K Antagonists.
  •  Ceftobiprole  : May enhance the anticoagulant effect of Vitamin K Antagonists.
  •  Ceftriaxone  : May enhance the anticoagulant effect of Vitamin K Antagonists.
  •  Cefuroxime  : May enhance the anticoagulant effect of Vitamin K Antagonists.
  •  Celecoxib  : Nonsteroidal Anti-Inflammatory Agents may enhance the anticoagulant effect of Anticoagulants.
  •  Cephalexin  : May enhance the anticoagulant effect of Vitamin K Antagonists.
  •  Cephaloglycin  : May enhance the anticoagulant effect of Vitamin K Antagonists.
  •  Ceritinib  : May increase the serum concentration of CYP2C9 Substrates.
  •  Chloral hydrate  : May increase the serum concentration of Vitamin K Antagonists.
  •  Chloramphenicol  : May enhance the anticoagulant effect of Vitamin K Antagonists. Chloramphenicol may increase the serum concentration of Vitamin K Antagonists.
  •  Cholecalciferol  : May diminish the anticoagulant effect of Vitamin K Antagonists.
  •  Cilostazol  : Agents with Antiplatelet Properties may enhance the anticoagulant effect of Anticoagulants.
  •  Cimetidine  : May enhance the anticoagulant effect of Vitamin K Antagonists.
  •  Citalopram  : Agents with Antiplatelet Properties may enhance the anticoagulant effect of Anticoagulants.
  •  Citric Acid  : May enhance the anticoagulant effect of other Anticoagulants.
  •  Clopidogrel  : May enhance the anticoagulant effect of Warfarin.
  •  Cloxacillin  : May diminish the anticoagulant effect of Vitamin K Antagonists. Cloxacillin may enhance the anticoagulant effect of Vitamin K Antagonists.
  •  Cobicistat  : May increase the serum concentration of Warfarin.
  •  Colesevelam  : May decrease the absorption of Vitamin K Antagonists.
  •  Collagenase clostridium histolyticum  : May enhance the adverse/toxic effect of Collagenase (Systemic). Specifically, the risk of injection site bruising and/or bleeding may be increased.
  •  Corticotropin  : Corticosteroids (Systemic) may enhance the anticoagulant effect of Warfarin.
  •  Cortisone acetate  : Corticosteroids (Systemic) may enhance the anticoagulant effect of Warfarin.
  •  Cyclacillin  : May enhance the anticoagulant effect of Vitamin K Antagonists.
  •  Cyproterone acetate  : Progestins may diminish the therapeutic effect of Anticoagulants. More specifically, the potential prothrombotic effects of some progestins and progestin-estrogen combinations may counteract anticoagulant effects.
  •  Dabigatran etexilate  : May enhance the anticoagulant effect of Anticoagulants.
  •  Dabrafenib  : May decrease the serum concentration of CYP2C9 Substrates.
  •  Dalteparin  : May enhance the anticoagulant effect of other Anticoagulants.
  •  Danaparoid  : May enhance the anticoagulant effect of other Anticoagulants.
  •  Darunavir  : May decrease the serum concentration of Warfarin.
  •  Dasatinib  : May enhance the anticoagulant effect of Anticoagulants.
  •  Deferasirox  : Anticoagulants may enhance the adverse/toxic effect of Deferasirox. Specifically, the risk for GI ulceration/irritation or GI bleeding may be increased.
  •  Deoxycholic Acid  : Anticoagulants may enhance the adverse/toxic effect of Deoxycholic Acid. Specifically, the risk for bleeding or bruising in the treatment area may be increased.
  •  Desogestrel  : Estrogen Derivatives may diminish the anticoagulant effect of Anticoagulants. More specifically, the potential prothrombotic effects of some estrogens and progestin-estrogen combinations may counteract anticoagulant effects.
  •  Desvenlafaxine  : May enhance the adverse/toxic effect of Vitamin K Antagonists. Specifically, the risk for bleeding may be increased.
  •  Dexamethasone  : Corticosteroids (Systemic) may enhance the anticoagulant effect of Warfarin.
  •  Dexmethylphenidate  : May increase the serum concentration of Vitamin K Antagonists.
  •  Diclofenac  : Agents with Antiplatelet Properties may enhance the anticoagulant effect of Anticoagulants.
  •  Dicloxacillin  : May diminish the anticoagulant effect of Vitamin K Antagonists.
  •  Dicoumarol  : May enhance the anticoagulant effect of other Anticoagulants.
  •  Dienogest  : Progestins may diminish the therapeutic effect of Anticoagulants. More specifically, the potential prothrombotic effects of some progestins and progestin-estrogen combinations may counteract anticoagulant effects.
  •  Diflunisal  : Agents with Antiplatelet Properties may enhance the anticoagulant effect of Anticoagulants.
  •  Dihydrocodeine  : Agents with Antiplatelet Properties may enhance the anticoagulant effect of Anticoagulants.
  •  Dihydrotachysterol  : May diminish the anticoagulant effect of Vitamin K Antagonists.
  •  Dihydrotestosterone  : May enhance the anticoagulant effect of Vitamin K Antagonists.
  •  Dipyridamole  : Agents with Antiplatelet Properties may enhance the anticoagulant effect of Anticoagulants.
  •  Disulfiram  : May increase the serum concentration of Vitamin K Antagonists.
  •  Dronedarone  : May increase the serum concentration of Vitamin K Antagonists.
  •  Drospirenone  : Estrogen Derivatives may diminish the anticoagulant effect of Anticoagulants. More specifically, the potential prothrombotic effects of some estrogens and progestin-estrogen combinations may counteract anticoagulant effects.
  •  Duloxetine  : Agents with Antiplatelet Properties may enhance the anticoagulant effect of Anticoagulants.
  •  Dydrogesterone  : May diminish the therapeutic effect of Anticoagulants. More specifically, the potential prothrombotic effects of some progestins and progestin-estrogen combinations may counteract anticoagulant effects.
  •  Econazole  : May increase the serum concentration of Vitamin K Antagonists.
  •  Edetic Acid  : May enhance the anticoagulant effect of other Anticoagulants.
  •  Edoxaban  : May enhance the anticoagulant effect of Anticoagulants.
  •  Efavirenz  : May decrease the serum concentration of Vitamin K Antagonists. Efavirenz may increase the serum concentration of Vitamin K Antagonists.
  •  Elvitegravir  : May decrease the serum concentration of Warfarin.
  •  Enoxaparin  : May enhance the anticoagulant effect of other Anticoagulants.
  •  Enzalutamide  : May decrease the serum concentration of Warfarin. More specifically, Enzalutamide may decrease concentrations of the S-warfarin enantiomer.
  •  Epoprostenol  : Prostacyclin Analogues may enhance the adverse/toxic effect of Anticoagulants. Specifically, the antiplatelet effects of these agents may lead to an increased risk of bleeding with the combination.
  •  Eptifibatide  : Agents with Antiplatelet Properties may enhance the anticoagulant effect of Anticoagulants.
  •  Ergocalciferol  : May diminish the anticoagulant effect of Vitamin K Antagonists.
  •  Erlotinib  : May increase the serum concentration of Warfarin.
  •  Escitalopram  : Agents with Antiplatelet Properties may enhance the anticoagulant effect of Anticoagulants.
  •  Eslicarbazepine acetate  : Eslicarbazepine may decrease the serum concentration of Warfarin. Specifically, S-warfarin serum concentrations may be decreased.
  •  Esomeprazole  : May increase the serum concentration of Vitamin K Antagonists.
  •  Estradiol  : Estrogen Derivatives may diminish the anticoagulant effect of Anticoagulants. More specifically, the potential prothrombotic effects of some estrogens and progestin-estrogen combinations may counteract anticoagulant effects.
  •  Estropipate  : Estrogen Derivatives may diminish the anticoagulant effect of Anticoagulants. More specifically, the potential prothrombotic effects of some estrogens and progestin-estrogen combinations may counteract anticoagulant effects.
  •  Ethacrynic acid  : May increase the serum concentration of Vitamin K Antagonists.
  •  Ethinyl Estradiol  : Estrogen Derivatives may diminish the anticoagulant effect of Anticoagulants. More specifically, the potential prothrombotic effects of some estrogens and progestin-estrogen combinations may counteract anticoagulant effects.
  •  Ethotoin  : May enhance the anticoagulant effect of Vitamin K Antagonists. Vitamin K Antagonists may increase the serum concentration of Ethotoin.
  •  Ethyl biscoumacetate  : May enhance the anticoagulant effect of other Anticoagulants.
  •  Ethynodiol  : Estrogen Derivatives may diminish the anticoagulant effect of Anticoagulants. More specifically, the potential prothrombotic effects of some estrogens and progestin-estrogen combinations may counteract anticoagulant effects.
  •  Etodolac  : Agents with Antiplatelet Properties may enhance the anticoagulant effect of Anticoagulants.
  •  Etonogestrel  : Progestins may diminish the therapeutic effect of Anticoagulants. More specifically, the potential prothrombotic effects of some progestins and progestin-estrogen combinations may counteract anticoagulant effects.
  •  Etoposide  : May enhance the anticoagulant effect of Vitamin K Antagonists.
  •  Etoposide  : May enhance the anticoagulant effect of Vitamin K Antagonists.
  •  Exenatide  : May enhance the anticoagulant effect of Vitamin K Antagonists.
  •  Fenofibrate  : Fenofibrate and Derivatives may enhance the anticoagulant effect of Warfarin. Fenofibrate and Derivatives may increase the serum concentration of Warfarin.
  •  Fenoprofen  : Agents with Antiplatelet Properties may enhance the anticoagulant effect of Anticoagulants.
  •  Floctafenine  : Agents with Antiplatelet Properties may enhance the anticoagulant effect of Anticoagulants.
  •  Flucloxacillin  : May enhance the anticoagulant effect of Vitamin K Antagonists.
  •  Fluconazole  : May increase the serum concentration of Vitamin K Antagonists.
  •  Fludrocortisone  : Corticosteroids (Systemic) may enhance the anticoagulant effect of Warfarin.
  •  Fluoxetine  : Agents with Antiplatelet Properties may enhance the anticoagulant effect of Anticoagulants.
  •  Flurbiprofen  : Agents with Antiplatelet Properties may enhance the anticoagulant effect of Anticoagulants.
  •  Fluvoxamine  : Agents with Antiplatelet Properties may enhance the anticoagulant effect of Anticoagulants.
  •  Fondaparinux sodium  : May enhance the anticoagulant effect of other Anticoagulants.
  •  Fosamprenavir  : May increase the serum concentration of Warfarin.
  •  Fosaprepitant  : May decrease the serum concentration of Warfarin. The active metabolite aprepitant is likely responsible for this effect.
  •  Fosphenytoin  : May enhance the anticoagulant effect of Vitamin K Antagonists. Vitamin K Antagonists may increase the serum concentration of Fosphenytoin.
  •  Gefitinib  : May enhance the anticoagulant effect of Vitamin K Antagonists.
  •  Gemcitabine  : May enhance the anticoagulant effect of Warfarin.
  •  Gestodene  : May diminish the therapeutic effect of Anticoagulants. More specifically, the potential prothrombotic effects of some progestins and progestin-estrogen combinations may counteract anticoagulant effects.
  •  Ginkgo biloba  : May enhance the adverse/toxic effect of Vitamin K Antagonists.
  •  Glucagon recombinant  : May enhance the anticoagulant effect of Vitamin K Antagonists.
  •  Glucosamine  : May enhance the anticoagulant effect of Warfarin.
  •  Glutethimide  : May increase the metabolism of Vitamin K Antagonists.
  •  Griseofulvin  : May decrease the serum concentration of Vitamin K Antagonists.
  •  Heparin  : May enhance the anticoagulant effect of other Anticoagulants.
  •  Heptabarbital  : May increase the metabolism of Vitamin K Antagonists.
  •  Hetacillin  : May enhance the anticoagulant effect of Vitamin K Antagonists.
  •  Hexobarbital  : May increase the metabolism of Vitamin K Antagonists.
  •  Hydrocortisone  : Corticosteroids (Systemic) may enhance the anticoagulant effect of Warfarin.
  •  Hydroxyprogesterone caproate  : Progestins may diminish the therapeutic effect of Anticoagulants. More specifically, the potential prothrombotic effects of some progestins and progestin-estrogen combinations may counteract anticoagulant effects.
  •  Ibritumomab  : Anticoagulants may enhance the adverse/toxic effect of Ibritumomab. Both agents may contribute to an increased risk of bleeding.
  •  Ibrutinib  : May enhance the adverse/toxic effect of Anticoagulants.
  •  Ibuprofen  : Agents with Antiplatelet Properties may enhance the anticoagulant effect of Anticoagulants.
  •  Icosapent  : Omega-3 Fatty Acids may enhance the anticoagulant effect of Anticoagulants.
  •  Icosapent ethyl  : Omega-3 Fatty Acids may enhance the anticoagulant effect of Anticoagulants.
  •  Ifosfamide  : May enhance the anticoagulant effect of Vitamin K Antagonists.
  •  Iloprost  : Prostacyclin Analogues may enhance the adverse/toxic effect of Anticoagulants. Specifically, the antiplatelet effects of these agents may lead to an increased risk of bleeding with the combination.
  •  Imatinib  : May enhance the anticoagulant effect of Warfarin. Imatinib may decrease the metabolism of Warfarin.
  •  Indomethacin  : Agents with Antiplatelet Properties may enhance the anticoagulant effect of Anticoagulants.
  •  Itraconazole  : May increase the serum concentration of Vitamin K Antagonists.
  •  Ketoprofen  : Agents with Antiplatelet Properties may enhance the anticoagulant effect of Anticoagulants.
  •  Ketorolac  : Agents with Antiplatelet Properties may enhance the anticoagulant effect of Anticoagulants.
  •  L-Carnitine  : May enhance the anticoagulant effect of Vitamin K Antagonists.
  •  Lansoprazole  : May increase the serum concentration of Vitamin K Antagonists.
  •  Latamoxef  : May enhance the anticoagulant effect of Vitamin K Antagonists.
  •  Leflunomide  : May enhance the anticoagulant effect of Vitamin K Antagonists.
  •  Levomilnacipran  : May enhance the adverse/toxic effect of Vitamin K Antagonists. Specifically, the risk for bleeding may be increased.
  •  Levonorgestrel  : Progestins may diminish the therapeutic effect of Anticoagulants. More specifically, the potential prothrombotic effects of some progestins and progestin-estrogen combinations may counteract anticoagulant effects.
  •  Lomitapide  : May increase the serum concentration of Warfarin.
  •  Lopinavir  : May decrease the serum concentration of Warfarin.
  •  Magnesium salicylate  : Salicylates may enhance the anticoagulant effect of Anticoagulants.
  •  Medroxyprogesterone Acetate  : Progestins may diminish the therapeutic effect of Anticoagulants. More specifically, the potential prothrombotic effects of some progestins and progestin-estrogen combinations may counteract anticoagulant effects.
  •  Mefenamic acid  : Agents with Antiplatelet Properties may enhance the anticoagulant effect of Anticoagulants.
  •  Megestrol acetate  : Progestins may diminish the therapeutic effect of Anticoagulants. More specifically, the potential prothrombotic effects of some progestins and progestin-estrogen combinations may counteract anticoagulant effects.
  •  Meloxicam  : Agents with Antiplatelet Properties may enhance the anticoagulant effect of Anticoagulants.
  •  Mercaptopurine  : May diminish the anticoagulant effect of Vitamin K Antagonists.
  •  Mestranol  : Estrogen Derivatives may diminish the anticoagulant effect of Anticoagulants. More specifically, the potential prothrombotic effects of some estrogens and progestin-estrogen combinations may counteract anticoagulant effects.
  •  Methimazole  : May diminish the anticoagulant effect of Vitamin K Antagonists.
  •  Methohexital  : May increase the metabolism of Vitamin K Antagonists.
  •  Methylphenidate  : May increase the serum concentration of Vitamin K Antagonists.
  •  Methylprednisolone  : Corticosteroids (Systemic) may enhance the anticoagulant effect of Warfarin.
  •  Meticillin  : May enhance the anticoagulant effect of Vitamin K Antagonists.
  •  Metreleptin  : May decrease the serum concentration of Warfarin. Metreleptin may increase the serum concentration of Warfarin.
  •  Mezlocillin  : May enhance the anticoagulant effect of Vitamin K Antagonists.
  •  Miconazole  : Miconazole (Oral) may increase the serum concentration of Warfarin.
  •  Mifepristone  : May increase the serum concentration of CYP2C9 Substrates.
  •  Milnacipran  : May enhance the adverse/toxic effect of Vitamin K Antagonists. Specifically, the risk for bleeding may be increased.
  •  Mirtazapine  : May enhance the anticoagulant effect of Warfarin.
  •  Nabumetone  : Agents with Antiplatelet Properties may enhance the anticoagulant effect of Anticoagulants.
  •  Nadroparin  : May enhance the anticoagulant effect of other Anticoagulants.
  •  Nafcillin  : May diminish the anticoagulant effect of Vitamin K Antagonists.
  •  Naproxen  : Agents with Antiplatelet Properties may enhance the anticoagulant effect of Anticoagulants.
  •  Nelfinavir  : May decrease the serum concentration of Warfarin. Nelfinavir may increase the serum concentration of Warfarin.
  •  Neomycin  : May enhance the anticoagulant effect of Vitamin K Antagonists.
  •  Nintedanib  : Anticoagulants may enhance the adverse/toxic effect of Nintedanib. Specifically, the risk for bleeding may be increased.
  •  Norethindrone  : Progestins may diminish the therapeutic effect of Anticoagulants. More specifically, the potential prothrombotic effects of some progestins and progestin-estrogen combinations may counteract anticoagulant effects.
  •  Norgestimate  : Estrogen Derivatives may diminish the anticoagulant effect of Anticoagulants. More specifically, the potential prothrombotic effects of some estrogens and progestin-estrogen combinations may counteract anticoagulant effects.
  •  Obinutuzumab  : Anticoagulants may enhance the adverse/toxic effect of Obinutuzumab. Specifically, the risk of serious bleeding-related events may be increased.
  •  Omeprazole  : May increase the serum concentration of Vitamin K Antagonists.
  •  Oritavancin  : May increase the serum concentration of Vitamin K Antagonists.
  •  Orlistat  : May enhance the anticoagulant effect of Warfarin.
  •  Oxacillin  : May enhance the anticoagulant effect of Vitamin K Antagonists.
  •  Oxandrolone  : May enhance the anticoagulant effect of Vitamin K Antagonists.
  •  Oxaprozin  : Agents with Antiplatelet Properties may enhance the anticoagulant effect of Anticoagulants.
  •  Paroxetine  : Agents with Antiplatelet Properties may enhance the anticoagulant effect of Anticoagulants.
  •  Pentobarbital  : May increase the metabolism of Vitamin K Antagonists.
  •  Pentosan Polysulfate  : May enhance the anticoagulant effect of Anticoagulants.
  •  Pentoxifylline  : May enhance the anticoagulant effect of Vitamin K Antagonists.
  •  Phenindione  : May enhance the anticoagulant effect of other Anticoagulants.
  •  Phenoxymethylpenicillin  : May enhance the anticoagulant effect of Vitamin K Antagonists.
  •  Phenprocoumon  : May enhance the anticoagulant effect of other Anticoagulants.
  •  Phenytoin  : May enhance the anticoagulant effect of Vitamin K Antagonists. Vitamin K Antagonists may increase the serum concentration of Phenytoin.
  •  Phylloquinone  : May diminish the anticoagulant effect of Vitamin K Antagonists.
  •  Piperacillin  : May enhance the anticoagulant effect of Vitamin K Antagonists.
  •  Piperazine  : Estrogen Derivatives may diminish the anticoagulant effect of Anticoagulants. More specifically, the potential prothrombotic effects of some estrogens and progestin-estrogen combinations may counteract anticoagulant effects.
  •  Piroxicam  : Agents with Antiplatelet Properties may enhance the anticoagulant effect of Anticoagulants.
  •  Pivampicillin  : May enhance the anticoagulant effect of Vitamin K Antagonists.
  •  Pivmecillinam  : May enhance the anticoagulant effect of Vitamin K Antagonists.
  •  Posaconazole  : May increase the serum concentration of Vitamin K Antagonists.
  •  Prasugrel  : Agents with Antiplatelet Properties may enhance the anticoagulant effect of Anticoagulants.
  •  Prednisolone  : Corticosteroids (Systemic) may enhance the anticoagulant effect of Warfarin.
  •  Prednisone  : Corticosteroids (Systemic) may enhance the anticoagulant effect of Warfarin.
  •  Primidone  : May increase the metabolism of Vitamin K Antagonists.
  •  Progesterone  : Progestins may diminish the therapeutic effect of Anticoagulants. More specifically, the potential prothrombotic effects of some progestins and progestin-estrogen combinations may counteract anticoagulant effects.
  •  Proguanil  : May enhance the anticoagulant effect of Warfarin.
  •  Propafenone  : May increase the serum concentration of Vitamin K Antagonists.
  •  Propylthiouracil  : May diminish the anticoagulant effect of Vitamin K Antagonists.
  •  Quinidine  : May enhance the anticoagulant effect of Vitamin K Antagonists. Note that the INR/PT might be unchanged in the face of increased bleeding.
  •  Quinine  : May enhance the anticoagulant effect of Vitamin K Antagonists.
  •  Ranitidine  : May increase the serum concentration of Warfarin.
  •  Regorafenib  : Warfarin may enhance the adverse/toxic effect of Regorafenib. Specifically, the risk for bleeding may be increased.
  •  Reteplase  : Thrombolytic Agents may enhance the anticoagulant effect of Anticoagulants.
  •  Ridogrel  : May enhance the anticoagulant effect of Anticoagulants.
  •  Ritonavir  : May decrease the serum concentration of Warfarin.
  •  Rivaroxaban  : Anticoagulants may enhance the anticoagulant effect of Rivaroxaban.
  •  Romidepsin  : May enhance the anticoagulant effect of Warfarin.
  •  Salicylate-sodium  : May enhance the anticoagulant effect of Vitamin K Antagonists.
  •  Salsalate  : Salicylates may enhance the anticoagulant effect of Anticoagulants.
  •  Saquinavir  : May increase the serum concentration of Warfarin.
  •  Secobarbital  : May increase the metabolism of Vitamin K Antagonists.
  •  Sertraline  : Agents with Antiplatelet Properties may enhance the anticoagulant effect of Anticoagulants.
  •  Sitaxentan  : May increase the serum concentration of Warfarin.
  •  Sorafenib  : May enhance the anticoagulant effect of Warfarin. Sorafenib may increase the serum concentration of Warfarin.
  •  Streptokinase  : May enhance the anticoagulant effect of Vitamin K Antagonists.
  •  Sucralfate  : May diminish the anticoagulant effect of Vitamin K Antagonists. Sucralfate may decrease the serum concentration of Vitamin K Antagonists. Specifically, sucralfate may decrease the absorption of Vitamin K Antagonists.
  •  Sugammadex  : May enhance the anticoagulant effect of Anticoagulants.
  •  Sulfinpyrazone  : May decrease the metabolism of Vitamin K Antagonists. Sulfinpyrazone may decrease the protein binding of Vitamin K Antagonists.
  •  Sulindac  : Agents with Antiplatelet Properties may enhance the anticoagulant effect of Anticoagulants.
  •  Sulodexide  : May enhance the anticoagulant effect of other Anticoagulants.
  •  Tamoxifen  : May increase the serum concentration of Vitamin K Antagonists.
  •  Telaprevir  : May decrease the serum concentration of Warfarin. Telaprevir may increase the serum concentration of Warfarin.
  •  Tenecteplase  : Thrombolytic Agents may enhance the anticoagulant effect of Anticoagulants.
  •  Teriflunomide  : May decrease the serum concentration of Warfarin.
  •  Testosterone  : May enhance the anticoagulant effect of Vitamin K Antagonists.
  •  Tiaprofenic acid  : Agents with Antiplatelet Properties may enhance the anticoagulant effect of Anticoagulants.
  •  Tibolone  : May enhance the anticoagulant effect of Anticoagulants.
  •  Ticagrelor  : Agents with Antiplatelet Properties may enhance the anticoagulant effect of Anticoagulants.
  •  Ticarcillin  : May enhance the anticoagulant effect of Vitamin K Antagonists.
  •  Ticlopidine  : Agents with Antiplatelet Properties may enhance the anticoagulant effect of Anticoagulants.
  •  Tigecycline  : May increase the serum concentration of Warfarin.
  •  Tinzaparin  : May enhance the anticoagulant effect of other Anticoagulants.
  •  Tipranavir  : May enhance the anticoagulant effect of Anticoagulants.
  •  Tirofiban  : Agents with Antiplatelet Properties may enhance the anticoagulant effect of Anticoagulants.
  •  Tolmetin  : Agents with Antiplatelet Properties may enhance the anticoagulant effect of Anticoagulants.
  •  Tolterodine  : May enhance the anticoagulant effect of Warfarin.
  •  Torasemide  : May increase the serum concentration of Warfarin.
  •  Toremifene  : May enhance the anticoagulant effect of Vitamin K Antagonists.
  •  Tositumomab  : May enhance the adverse/toxic effect of Tositumomab and Iodine I 131 Tositumomab. Specifically, the risk of bleeding-related adverse effects may be increased.
  •  Tramadol  : May enhance the anticoagulant effect of Vitamin K Antagonists.
  •  Trazodone  : May diminish the anticoagulant effect of Warfarin.
  •  Treprostinil  : Prostacyclin Analogues may enhance the adverse/toxic effect of Anticoagulants. Specifically, the antiplatelet effects of these agents may lead to an increased risk of bleeding with the combination.
  •  Triamcinolone  : Corticosteroids (Systemic) may enhance the anticoagulant effect of Warfarin.
  •  Urokinase  : May enhance the anticoagulant effect of Anticoagulants.
  •  Vemurafenib  : May increase the serum concentration of Warfarin.
  •  Venlafaxine  : May enhance the adverse/toxic effect of Vitamin K Antagonists. Specifically, the risk for bleeding may be increased.
  •  Vilazodone  : Agents with Antiplatelet Properties may enhance the anticoagulant effect of Anticoagulants.
  •  Vitamin E  : May enhance the anticoagulant effect of Anticoagulants. Vitamin E may also increase the overall risk for bleeding.
  •  Vorapaxar  : May enhance the adverse/toxic effect of Anticoagulants. More specifically, this combination is expected to increase the risk of bleeding.
  •  Voriconazole  : May increase the serum concentration of Vitamin K Antagonists.
  •  Vorinostat  : May enhance the anticoagulant effect of Vitamin K Antagonists.
  •  Vortioxetine  : Agents with Antiplatelet Properties may enhance the anticoagulant effect of Anticoagulants.
  •  Zafirlukast  : May increase the serum concentration of Vitamin K Antagonists.
  •  Zileuton  : May increase the serum concentration of Warfarin.

Food Interactions

  • Avoid alcohol., Avoid drastic changes in dietary habit., Avoid St. John’s Wort., Consult your doctor before ingesting large amounts of dietary Vitamin K (e.g. from green leafy vegetables)., Limit garlic, ginger, gingko, and horse chestnut.

Calculated Property

kind Value Source
logP 2.41 ALOGPS
logS -3.8 ALOGPS
Water Solubility 4.72e-02 g/l ALOGPS
logP 2.74 ChemAxon
IUPAC Name 4-hydroxy-3-(3-oxo-1-phenylbutyl)-2H-chromen-2-one ChemAxon
Traditional IUPAC Name warfarin ChemAxon
Molecular Weight 308.3279 ChemAxon
Monoisotopic Weight 308.104859 ChemAxon
SMILES CC(=O)CC(C1=CC=CC=C1)C1=C(O)C2=C(OC1=O)C=CC=C2 ChemAxon
Molecular Formula C19H16O4 ChemAxon
InChI InChI=1/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,11H2,1H3 ChemAxon
InChIKey InChIKey=PJVWKTKQMONHTI-UHFFFAOYNA-N ChemAxon
Polar Surface Area (PSA) 63.6 ChemAxon
Refractivity 86.86 ChemAxon
Polarizability 31.93 ChemAxon
Rotatable Bond Count 4 ChemAxon
H Bond Acceptor Count 3 ChemAxon
H Bond Donor Count 1 ChemAxon
pKa (strongest acidic) 6.33 ChemAxon
pKa (strongest basic) -6.6 ChemAxon
Physiological Charge -1 ChemAxon
Number of Rings 3 ChemAxon
Bioavailability 1 ChemAxon
Rule of Five 1 ChemAxon
Ghose Filter 1 ChemAxon
MDDR-Like Rule 0 ChemAxon

Affected organism

Humans and other mammals

Target within organism

  • Vitamin K epoxide reductase complex subunit 1 : in Human