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PubChem
| Name: | Warfarin |
|---|---|
| PubChem Compound ID: | 447632 |
| Description: | An anticoagulant that acts by inhibiting the synthesis of vitamin K-dependent coagulation factors. Warfarin is indicated for the prophylaxis and/or treatment of venous thrombosis and its extension, pulmonary embolism, and atrial fibrillation with embolization. It is also used as an adjunct in the prophylaxis of systemic embolism after myocardial infarction. Warfarin is also used as a rodenticide. |
| Molecular formula: | C19H16O4 |
| Molecular weight: | 308.328 g/mol |
| Synonyms: |
4-HYDROXY-3-[(1S)-3-OXO-1-PHENYLBUTYL]-2H-CHROMEN-2-ONE; SWF; S-WARFARIN; ZINC00044634
|
DrugBank
Identification
| Name: | Warfarin |
|---|---|
| Name (isomeric): | DB00682 |
| Drug Type: | small molecule |
| Description: | An anticoagulant that acts by inhibiting the synthesis of vitamin K-dependent coagulation factors. Warfarin is indicated for the prophylaxis and/or treatment of venous thrombosis and its extension, pulmonary embolism, and atrial fibrillation with embolization. It is also used as an adjunct in the prophylaxis of systemic embolism after myocardial infarction. Warfarin is also used as a rodenticide. |
| Synonyms: |
Warfarin sodium
|
| Brand: | Dicusat E, Rosex, Tintorane, Kumadu, Kypfarin, D-Con, Warfarin Q, Dethmor, Frass-Ratron, Brumolin, Vampirinip III, Co-Rax, Temus W, Warf 42, Sofarin, Athrombin, Coumarins, Prothromadin, Place-Pax, Dethnel, Athrombin-K, Kumatox, Warficide, Coumaphene, RAX, Marevan, Solfarin, Coumadin Tabs, Coumadin, Athrombine-K, Warfilone, Coumefene, Coumafene, Jantoven, Kumader, Coumaphen, Tox-Hid, Panwarfin, Warfarat, Maveran, Latka 42, Warfarin Plus, Sorexa Plus, Vampirinip II, Warfarine, Zoocoumarin, Mar-Frin, Coumafen |
| Category: | Rodenticides, Anticoagulants, Coumarin and Indandione Derivatives |
| CAS number: | 81-81-2 |
Pharmacology
| Indication: | For the treatment of retinal vascular occlusion, pulmonary embolism, cardiomyopathy, atrial fibrillation and flutter, cerebral embolism, transient cerebral ischaemia, arterial embolism and thrombosis. |
|---|---|
| Pharmacology: | 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). |
| 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. T...
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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.
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| Absorption: | Rapidly absorbed following oral administration with considerable interindividual variations. Also absorbed percutaneously. |
| Protein binding: | 99% bound primarily to albumin |
| Biotransformation: | 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. |
| Route of elimination: | 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. |
| Half Life: | R-warfarin t1/2=37-89 hours; S-warfarin t1/2=21-43 hours. |
| 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] |
| Toxicity: | LD50=374 (orally in mice) |
| Affected organisms: | Humans and other mammals |
Interactions
| Food interaction: |
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| Drug interaction: |
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Targets
Involved in vitamin K metabolism. Catalytic subunit of the vitamin K epoxide reductase (VKOR) complex which reduces inactive vitamin K 2,3-epoxide to active vitamin K
| UniProt ID: | Q9BQB6 | ||||||
|---|---|---|---|---|---|---|---|
| Gene: | VKORC1 | ||||||
| Actions: | inhibitor | ||||||
| References: |
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Enzymes
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
| UniProt ID: | P11712 | |||
|---|---|---|---|---|
| Gene: | CYP2C9 | |||
| Actions: | substrate, inhibitor | |||
| References: |
|
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
| UniProt ID: | P05177 | |||
|---|---|---|---|---|
| Gene: | CYP1A2 | |||
| Actions: | substrate | |||
| References: |
|
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
| UniProt ID: | P33261 | |||
|---|---|---|---|---|
| Gene: | CYP2C19 | |||
| Actions: | substrate, inhibitor | |||
| References: |
|
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. The enzyme also hydroxylates etoposide
| UniProt ID: | P08684 | ||
|---|---|---|---|
| Gene: | CYP3A4 | ||
| Actions: | substrate | ||
| References: |
|
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)
| UniProt ID: | P10632 | ||
|---|---|---|---|
| Gene: | CYP2C8 | ||
| Actions: | substrate, inhibitor | ||
| References: |
|
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
| UniProt ID: | P33260 | ||
|---|---|---|---|
| Gene: | CYP2C18 | ||
| Actions: | substrate | ||
| References: |
|
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
| UniProt ID: | P04798 | |
|---|---|---|
| Gene: | CYP1A1 | |
| Actions: | substrate | |
| References: |
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Carriers
Serum albumin, the main protein of plasma, has a good binding capacity for water, Ca(2+), Na(+), K(+), fatty acids, hormones, bilirubin and drugs. Its main function is the regulation of the colloidal osmotic pressure of blood
| UniProt ID: | P02768 | ||||
|---|---|---|---|---|---|
| Gene: | ALB | ||||
| References: |
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Appears to function in modulating the activity of the immune system during the acute-phase reaction
| UniProt ID: | P02763 | ||
|---|---|---|---|
| Gene: | ORM1 | ||
| References: |
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