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Warfarin, sold under the brand name Coumadin among others,
The common side effect is bleeding.
Warfarin decreases blood clotting by blocking an enzyme called vitamin K epoxide reductase that reactivates vitamin K 1.
Warfarin first came into commercial use in 1948 as a rat poison.
1 Medical uses
1.1 Dosing
1.1.1 Maintenance dose
1.1.2 Self-testing
1.2 Alternative anticoagulants
2 Contraindications
2.1 Pregnancy
2.1.1 First trimester of pregnancy
2.1.2 Second trimester and later
3 Adverse effects
3.1 Bleeding
3.2 Warfarin necrosis
3.3 Osteoporosis
3.4 Purple toe syndrome
3.5 Calcification
4 Overdose
5 Interactions
6 Chemistry
6.1 Stereochemistry
7 Pharmacology
7.1 Pharmacokinetics
7.2 Mechanism of action
7.3 Pharmacogenomics
8 History
9 Pest control
9.1 Rodents
9.2 Vampire bats
10 Occupational safety
11 Names
12 References
13 External links
Medical uses
Warfarin is used to decrease the tendency for thrombosis or as secondary prophylaxis (prevention of further episodes) in those individuals who have already formed a blood clot ( thrombus ). Warfarin treatment can help prevent formation of future blood clots and help reduce the risk of embolism (migration of a thrombus to a spot where it blocks blood supply to a vital organ).
Warfarin is best suited for anticoagulation (clot formation inhibition) in areas of slowly running blood (such as in veins and the pooled blood behind artificial and natural valves) and in blood pooled in dysfunctional cardiac atria. Thus, common clinical indications for warfarin use are atrial fibrillation, the presence of artificial heart valves, deep venous thrombosis, and pulmonary embolism (where the embolized clots first form in veins). Warfarin is also used in antiphospholipid syndrome. It has been used occasionally after heart attacks ( myocardial infarctions ), but is far less effective at preventing new thromboses in coronary arteries. Prevention of clotting in arteries is usually undertaken with antiplatelet drugs, which act by a different mechanism from warfarin (which normally has no effect on platelet function).
Dosing of warfarin is complicated because it is known to interact with many commonly used medications and certain foods.
When initiating warfarin therapy (“warfarinization”), the doctor will decide how strong the anticoagulant therapy needs to be. The target INR level varies from case to case depending on the clinical indicators, but tends to be 2–3 in most conditions. In particular, target INR may be 2.5–3.5 (or even 3.0–4.5) in patients with one or more mechanical heart valves.
In addition, for the first three days of “warfarinization”, the levels of protein C and protein S (anticoagulation factors) drop faster than procoagulation proteins such as factor II, VII, IX, and X. Therefore, bridging anticoagulant therapies (usually heparin) are often used to reverse this temporary hypercoagulable state.
Maintenance dose
Vitamin K1-warfarin interaction effect. When warfarin levels are high, people have more risk of bleeding. Conversely, lower levels of warfarin lead to increased risk of blood clots. There is a narrow range where the benefits of warfarin are greater than the risks, its therapeutic window. Certain drugs, herbal medicines and foods can interact with warfarin, increasing or decreasing a previously stable warfarin level.
Recommendations by many national bodies, including the American College of Chest Physicians,
The maintenance dose of warfarin can fluctuate significantly depending on the amount of vitamin K 1 in the diet. Keeping vitamin K 1 intake at a stable level can prevent these fluctuations. Leafy green vegetables tend to contain higher amounts of vitamin K 1. Green parts of members of the family Apiaceae, such as parsley, cilantro, and dill, are extremely rich sources of vitamin K; cruciferous vegetables such as cabbage and broccoli, as well as the darker varieties of lettuces and other leafy greens, are also relatively high in vitamin K 1. Green vegetables such a peas and green beans do not have such high amounts of vitamin K 1 as leafy greens. Certain vegetable oils have high amounts of vitamin K 1. Foods low in vitamin K 1 include roots, bulbs, tubers, and most fruits and fruit juices. Cereals, grains and other milled products are also low in vitamin K 1.
Main article: INR self-monitoring
Patients are making increasing use of self-testing and home monitoring of oral anticoagulation. International guidelines on home testing were published in 2005.
Alternative anticoagulants
In some countries, other coumarins are used instead of warfarin, such as acenocoumarol and phenprocoumon. These have a shorter (acenocoumarol) or longer (phenprocoumon) half-life, and are not completely interchangeable with warfarin. Several types of anticoagulant drugs offering the efficacy of warfarin without a need for monitoring, such as dabigatran, apixaban, edoxaban and rivaroxaban, have been approved in a number of countries for classical warfarin uses. There is a reversal agent available for dabigatran ( idarucizumab )
All anticoagulants are generally contraindicated in situations where the reduction in clotting that they cause might lead to serious and potentially life-threatening bleeds. This includes people with active bleeding conditions (such as gastrointestinal ulcers), or disease states with increased risk of bleeding e.g. low platelets, severe liver disease, uncontrolled hypertension. For patients undergoing surgery, treatment with anticoagulants is generally suspended. Similarly, spinal or lumbar puncture (e.g. spinal injections, epidurals, etc.) carry increased risk so treatment is suspended prior to these procedures.
Warfarin should not be given to people with heparin-induced thrombocytopenia until platelet count has improved or normalised.
Further information: Anticoagulation in pregnancy
Warfarin is contraindicated in pregnancy, as it passes through the placental barrier and may cause bleeding in the fetus; warfarin use during pregnancy is commonly associated with spontaneous abortion, stillbirth, neonatal death, and preterm birth.
First trimester of pregnancy
Usually, warfarin is avoided in the first trimester, and a low molecular weight heparin such as enoxaparin is substituted. With heparin, risk of maternal haemorrhage and other complications are still increased, but heparins do not cross the placental barrier, so do not cause birth defects. Various solutions exist for the time around delivery.
When warfarin (or another 4-hydroxycoumarin derivative) is given during the first trimester—particularly between the sixth and ninth weeks of pregnancy—a constellation of birth defects known variously as fetal warfarin syndrome (FWS), warfarin embryopathy, or coumarin embryopathy can occur. FWS is characterized mainly by skeletal abnormalities, which include nasal hypoplasia, a depressed or narrowed nasal bridge, scoliosis, and calcifications in the vertebral column, femur, and heel bone, which show a peculiar stippled appearance on X-rays. Limb abnormalities, such as brachydactyly (unusually short fingers and toes) or underdeveloped extremities, can also occur.
Second trimester and later
Warfarin administration in the second and third trimesters is much less commonly associated with birth defects, and when they do occur, are considerably different from fetal warfarin syndrome. The most common congenital abnormalities associated with warfarin use in late pregnancy are central nervous system disorders, including spasticity and seizures, and eye defects. Because of such later pregnancy birth defects, anticoagulation with warfarin poses a problem in pregnant women requiring warfarin for vital indications, such as stroke prevention in those with artificial heart valves.
According to the American College of Chest Physicians (ACCP), warfarin may be used in lactating women who wish to breast-feed their infants.
Adverse effects
The only common side effect of warfarin is bleeding. The risk of severe bleeding is small but definite (a typically yearly rate of 1-3% has been reported)
A number of risk scores exist to predict bleeding in people using warfarin and similar anticoagulants. A commonly used score ( HAS-BLED ) includes known predictors of warfarin-related bleeding: uncontrolled high blood pressure (H), abnormal kidney function (A), previous stroke (S), known previous bleeding condition (B), previous labile INR when on anticoagulation (L), elderly as defined by age over 65 (E), and drugs associated with bleeding (e.g. aspirin) or alcohol misuse (D). While their use is recommended in clinical practice guidelines,
Warfarin necrosis
Main article: Warfarin necrosis
A rare but serious complication resulting from treatment with warfarin is warfarin necrosis, which occurs more frequently shortly after commencing treatment in patients with a deficiency of protein C. Protein C is an innate anticoagulant that, like the procoagulant factors that warfarin inhibits, requires vitamin K-dependent carboxylation for its activity. Since warfarin initially decreases protein C levels faster than the coagulation factors, it can paradoxically increase the blood’s tendency to coagulate when treatment is first begun (many patients when starting on warfarin are given heparin in parallel to combat this), leading to massive thrombosis with skin necrosis and gangrene of limbs. Its natural counterpart, purpura fulminans, occurs in children who are homozygous for certain protein C mutations.
After initial reports that warfarin could reduce bone mineral density, several studies have demonstrated a link between warfarin use and osteoporosis -related fracture. A 1999 study in 572 women taking warfarin for deep venous thrombosis, risk of vertebral fracture and rib fracture was increased; other fracture types did not occur more commonly.
A 2006 retrospective study of 14,564 Medicare recipients showed that warfarin use for more than one year was linked with a 60% increased risk of osteoporosis-related fracture in men; there was no association in women. The mechanism was thought to be a combination of reduced intake of vitamin K (a vitamin necessary for bone health) and inhibition by warfarin of vitamin K-mediated carboxylation of certain bone proteins, rendering them nonfunctional.
Purple toe syndrome
See also: Blue toe syndrome
Another rare complication that may occur early during warfarin treatment (usually within 3 to 8 weeks of commencement) is purple toe syndrome. This condition is thought to result from small deposits of cholesterol breaking loose and causing embolisms in blood vessels in the skin of the feet, which causes a blueish purple colour and may be painful.
It is typically thought to affect the big toe, but it affects other parts of the feet as well, including the bottom of the foot (plantar surface). The occurrence of purple toe syndrome may require discontinuation of warfarin.
Several studies have also implicated warfarin use in valvular and vascular calcification. No specific treatment is available, but some modalities are under investigation.
The major side effect of warfarin use is bleeding. Risk of bleeding is increased if the INR is out of range (due to accidental or deliberate overdose or due to interactions).
For people who need rapid reversal of warfarin such as due to serious bleeding or need emergency surgery, the effects of warfarin can be reversed with vitamin K, prothrombin complex concentrate (PCC), or fresh frozen plasma (FFP).
Details on reversing warfarin are provided in clinical practice guidelines from the American College of Chest Physicians.
Warfarin interacts with many commonly used drugs, and the metabolism of warfarin varies greatly between patients. This makes finding the correct dosage difficult, and accentuates the need of monitoring; when initiating a medication that is known to interact with warfarin (e.g. simvastatin ), INR checks are increased or dosages adjusted until a new ideal dosage is found.
When taken with nonsteroidal anti-inflammatory drugs (NSAIDs), warfarin increases the risk for gastrointestinal bleeding. This increased risk is due to the anti-platelet effect of NSAIDs as well as the possible damage to the gastrointestinal mucosa.
Many commonly used antibiotics, such as metronidazole or the macrolides, will greatly increase the effect of warfarin by reducing the metabolism of warfarin in the body. Other broad-spectrum antibiotics can reduce the amount of the normal bacterial flora in the bowel, which make significant quantities of vitamin K 1, thus potentiating the effect of warfarin.
Excessive use of alcohol is also known to affect the metabolism of warfarin and can elevate the INR and thus increase the risk of bleeding.
Warfarin also interacts with many herbs and spices,
Between 2003 and 2004, the UK Committee on Safety of Medicines received several reports of increased INR and risk of haemorrhage in people taking warfarin and cranberry juice.
Acyclic tautomer (left) and cyclic hemiketal tautomer (right)
X-ray crystallographic studies of warfarin show that it exists in tautomeric form, as the cyclic hemiketal, which is formed from the 4-hydroxycoumarin and the ketone in the 3-position substituent.
Warfarin contains a stereocenter and consists of two enantiomers. This is a racemate, i.e. a 1: 1 mixture of ( R ) – and the ( S ) – form:
Enantiomers of warfarin
CAS Number: 5543-58-8
CAS Number: 5543-57-7
3 mg (blue), 5 mg (pink) and 1 mg (brown) warfarin tablets (UK colours)
Warfarin consists of a racemic mixture of two active enantiomers — R – and S – forms—each of which is cleared by different pathways. S-warfarin is 2-5 times more potent than the R-isomer in producing an anticoagulant response.
Warfarin is slower acting than the common anticoagulant heparin, though it has a number of advantages. Heparin must be given by injection, whereas warfarin is available orally. Warfarin has a long half-life and need only be given once a day. Heparin can also cause a prothrombotic condition, heparin-induced thrombocytopenia (an antibody-mediated decrease in platelet levels), which increases the risk for thrombosis. It takes several days for warfarin to reach the therapeutic effect since the circulating coagulation factors are not affected by the drug (thrombin has a half-life time of days). Warfarin’s long half-life means that it remains effective for several days after it was stopped. Furthermore, if given initially without additional anticoagulant cover, it can increase thrombosis risk (see below). For these main reasons, hospitalised patients are usually given heparin with warfarin initially, the heparin covering the 3–5 day lag period and being withdrawn after a few days.
Mechanism of action
While warfarin is one of several drugs popularly referred to as a “blood thinner”; this is a misnomer since it does not affect the viscosity of blood.
Warfarin inhibits the vitamin K -dependent synthesis of biologically active forms of the calcium -dependent clotting factors II, VII, IX and X, as well as the regulatory factors protein C, protein S, and protein Z. Other proteins not involved in blood clotting, such as osteocalcin, or matrix Gla protein, may also be affected.
The precursors of these factors require gamma carboxylation of their glutamic acid residues to allow the coagulation factors to bind to phospholipid surfaces inside blood vessels, on the vascular endothelium. The enzyme that carries out the carboxylation of glutamic acid is gamma-glutamyl carboxylase. The carboxylation reaction will proceed only if the carboxylase enzyme is able to convert a reduced form of vitamin K (vitamin K hydroquinone) to vitamin K epoxide at the same time. The vitamin K epoxide is in turn recycled back to vitamin K and vitamin K hydroquinone by another enzyme, the vitamin K epoxide reductase (VKOR). Warfarin inhibits epoxide reductase vitamin K absence/antagonism), and individual coagulation factors as PIVKA- number (e.g. PIVKA-II ). The end result of warfarin use, therefore, is to diminish blood clotting in the patient.
When warfarin is newly started, it may promote clot formation temporarily. This is because the level of protein C and protein S are also dependent on vitamin K activity. Warfarin causes decline in protein C levels in first 36 hours. In addition, reduced levels of protein S lead to a reduction in activity of protein C (for which it is the co-factor) and therefore reduced degradation of factor Va and factor VIIIa. Although loading doses of warfarin over 5 mg also produce a precipitous decline in factor VII, resulting in an initial prolongation of the INR, full antithrombotic effect does not take place until significant reduction in factor II occurs days later. The haemostasis system becomes temporarily biased towards thrombus formation, leading to a prothrombotic state. Thus, when warfarin is loaded rapidly at greater than 5 mg per day, it is beneficial to co-administer heparin, an anticoagulant that acts upon antithrombin and helps reduce the risk of thrombosis, with warfarin therapy for four to five days, in order to have the benefit of anticoagulation from heparin until the full effect of warfarin has been achieved.
Warfarin activity is determined partially by genetic factors. Polymorphisms in two genes ( VKORC1 and CYP2C9 ) play a particularly large role in response to warfarin.
VKORC1 polymorphisms explain 30% of the dose variation between patients:
CYP2C9 polymorphisms explain 10% of the dose variation between patients,
Despite the promise of pharmacogenomic testing in warfarin dosing, its use in clinical practice is controversial. In August 2009 the Centers for Medicare and Medicaid Services concluded that “the available evidence does not demonstrate that pharmacogenomic testing of CYP2C9 or VKORC1 alleles to predict warfarin responsiveness improves health outcomes in Medicare beneficiaries.”
In the early 1920s, there was an outbreak of a previously unrecognized cattle disease in the northern United States and Canada. Cattle were haemorrhaging after minor procedures and on some occasions, spontaneously.
In 1921, Frank Schofield, a Canadian veterinary pathologist, determined that the cattle were ingesting moldy silage made from sweet clover, and that this was functioning as a potent anticoagulant.
The identity of the anticoagulant substance in spoiled sweet clover remained a mystery until 1940. In 1933 Karl Paul Link and his lab of chemists working at the University of Wisconsin set out to isolate and characterize the haemorrhagic agent from the spoiled hay.
Dicoumarol was a product of the plant molecule coumarin (not to be confused with Couma d in, a later tradename for warfarin). Coumarin is now known to be present in many plants, and produces the notably sweet smell of freshly cut grass or hay and plants like sweet grass ; in fact, the plant’s high content of coumarin is responsible for the original common name of “sweet clover”, which is named for its sweet smell, not its bitter taste.
Over the next few years, numerous similar chemicals (specifically 4-hydroxycoumarins with a large aromatic substituent at the 3 position) were found to have the same anticoagulant properties. The first drug in the class to be widely commercialized was dicoumarol itself, patented in 1941 and later used as a pharmaceutical. Karl Link continued working on developing more potent coumarin-based anticoagulants for use as rodent poisons, resulting in warfarin in 1948. The name “warfarin” stems from the acronym WARF, for Wisconsin Alumni Research Foundation + the ending -arin indicating its link with coumarin. Warfarin was first registered for use as a rodenticide in the US in 1948, and was immediately popular. Although warfarin was developed by Link, the Wisconsin Alumni Research Foundation financially supported the research and was assigned the patent.
After an incident in 1951, where a US Navy officer attempted suicide with multiple doses of warfarin in rodenticide but recovered fully after presenting to a hospital and being treated with vitamin K (by then known as a specific antidote),
The exact mechanism of action remained unknown until it was demonstrated, in 1978, that warfarin inhibits the enzyme epoxide reductase and hence interferes with vitamin K metabolism.
It has been posited that Lavrenty Beria, Nikita Khrushchev and others conspired to use warfarin to poison Soviet leader Joseph Stalin. Warfarin is tasteless and colourless, and produces symptoms similar to those that Stalin exhibited.
Pest control
Main article: 4-hydroxycoumarins
Warning label on a tube of rat poison laid on a dike of the Scheldt river in Steendorp, Belgium. The tube contains bromadiolone, a second-generation (“super-warfarin”) anticoagulant.
Coumarins (4-hydroxycoumarin derivatives) are used as rodenticides for controlling rats and mice in residential, industrial, and agricultural areas. Warfarin is both odorless and tasteless, and is effective when mixed with food bait, because the rodents will return to the bait and continue to feed over a period of days until a lethal dose is accumulated (considered to be 1 mg/kg/day over about six days). It may also be mixed with talc and used as a tracking powder, which accumulates on the animal’s skin and fur, and is subsequently consumed during grooming. The LD 50 is 50–500 mg/kg. The IDLH value is 100 mg/m 3 (warfarin; various species).
The use of warfarin itself as a rat poison is now declining, because many rat populations have developed resistance to it, and poisons of considerably greater potency are now available. Other 4-hydroxycoumarins used as rodenticides include coumatetralyl and brodifacoum, which is sometimes referred to as “super-warfarin”, because it is more potent, longer-acting, and effective even in rat and mouse populations that are resistant to warfarin. Unlike warfarin, which is readily excreted, newer anticoagulant poisons also accumulate in the liver and kidneys after ingestion.
Vampire bats
Warfarin is used to cull vampire bat populations in areas where human–wildlife conflict is a concern.
Occupational safety
People can be exposed to warfarin in the workplace by breathing it in, swallowing it, skin absorption, and eye contact. The Occupational Safety and Health Administration (OSHA) has set the legal limit ( permissible exposure limit ) for warfarin exposure in the workplace as 0.1 mg/m 3 over an 8-hour workday. The National Institute for Occupational Safety and Health (NIOSH) has set a recommended exposure limit (REL) of 0.1 mg/m 3 over an 8-hour workday. At levels of 100 mg/m 3, warfarin is immediately dangerous to life and health.
It is classified as an extremely hazardous substance in the United States as defined in Section 302 of the U.S. Emergency Planning and Community Right-to-Know Act (42 U.S.C. 11002), and is subject to strict reporting requirements by facilities which produce, store, or use it in significant quantities.
Warfarin is a derivative of dicoumarol, an anticoagulant originally discovered in spoiled sweet clover. Dicoumarol, in turn, is from coumarin, a sweet-smelling but coagulation-inactive chemical found in “sweet” clover and tonka beans (also known as cumaru from which coumarin’s name derives). The name warfarin stems from its discovery at the University of Wisconsin, incorporating the acronym for the organization that funded the key research, WARF for the Wisconsin Alumni Research Foundation and the ending -arin, indicating its link with coumarin.
The drug is marketed under many brand and generic names including Aldocumar, Anasmol, Anticoag, Befarin, Cavamed, Cicoxil, Circuvit, Cofarin, Coumadin, Coumadine, Cumar, Farin, Foley, Haemofarin, Jantoven, Kovar, Lawarin, Maforan, Marevan, Marfarin, Marivanil, Martefarin, Morfarin, Orfarin, Panwarfin, Scheme, Simarc, Varfarin, Varfarins, Varfine, Waran, Warcok, Warf, Warfareks, Warfarin, Warfarina, Warfarine, Warfarinum, Warfen, Warfin, Warik, Warin, Warlin, and Zyfarin.

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