Welcome to DrugBank 4.0! If you prefer, you can still go back to version 3.0.
Identification
NameWarfarin
Accession NumberDB00682  (APRD00341)
Typesmall molecule
Groupsapproved
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.

Structure
Thumb
Synonyms
SynonymLanguageCode
4-Hydroxy-3-(3-oxo-1-phenylbutyl)coumarinNot AvailableNot Available
CoumafeneFrenchNot Available
ZoocoumarinNot AvailableNot Available
Salts
Name/CAS Structure Properties
Warfarin sodium
129-06-6
Thumb
  • InChI Key: KYITYFHKDODNCQ-UHFFFAOYNA-M
  • Monoisotopic Mass: 330.086803643
  • Average Mass: 330.3098
DBSALT000278
Brand names
NameCompany
CoumadinNot Available
JantovenNot Available
LawarinNot Available
MarevanNot Available
WaranNot Available
WarfantNot Available
Brand mixturesNot Available
Categories
CAS number81-81-2
WeightAverage: 308.3279
Monoisotopic: 308.104859
Chemical FormulaC19H16O4
InChI KeyInChIKey=PJVWKTKQMONHTI-UHFFFAOYNA-N
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
IUPAC Name
4-hydroxy-3-(3-oxo-1-phenylbutyl)-2H-chromen-2-one
SMILES
CC(=O)CC(C1=CC=CC=C1)C1=C(O)C2=C(OC1=O)C=CC=C2
Mass Specshow(8.72 KB)
Taxonomy
KingdomOrganic Compounds
SuperclassPhenylpropanoids and Polyketides
ClassCoumarins and Derivatives
SubclassNot Available
Direct parentCoumarins and Derivatives
Alternative parentsBenzopyrans; Pyranones and Derivatives; Benzene and Substituted Derivatives; Ketones; Polyamines; Enolates
Substituentspyranone; benzene; pyran; ketone; enolate; polyamine; carbonyl group
Classification descriptionThis compound belongs to the coumarins and derivatives. These are polycyclic aromatic compounds containing a 1-benzopyran moiety with a ketone group at the C2 carbon atom (1-benzopyran-2-one).
Pharmacology
IndicationFor the treatment of retinal vascular occlusion, pulmonary embolism, cardiomyopathy, atrial fibrillation and flutter, cerebral embolism, transient cerebral ischaemia, arterial embolism and thrombosis.
PharmacodynamicsWarfarin, 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 actionWarfarin 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.
AbsorptionRapidly absorbed following oral administration with considerable interindividual variations. Also absorbed percutaneously.
Volume of distribution
  • 0.14 L/kg
Protein binding99% bound primarily to albumin
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.

SubstrateEnzymesProduct
Warfarin
S-6-HydroxywarfarinDetails
Warfarin
S-4'-HydroxywarfarinDetails
Warfarin
R-4'-HydroxywarfarinDetails
Warfarin
R-6-HydroxywarfarinDetails
Warfarin
R-10-HydroxywarfarinDetails
Warfarin
R-8-HydroxywarfarinDetails
Warfarin
R-7-HydroxywarfarinDetails
Warfarin
S-7-HydroxywarfarinDetails
Route of eliminationThe 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 lifeR-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]
ToxicityLD50=374 (orally in mice)
Affected organisms
  • Humans and other mammals
Pathways
PathwayCategorySMPDB ID
Warfarin Action PathwayDrug actionSMP00268
SNP Mediated Effects
Interacting Gene/EnzymeSNP RS IDAllele nameDefining changeEffectReference(s)
Cytochrome P450 2C9
Gene symbol: CYP2C9
UniProt: P11712
rs1799853 CYP2C9*2T AllelePoor drug metabolizer, lower dose requirements15608560
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
Property Value Probability
Human Intestinal Absorption + 0.9109
Blood Brain Barrier + 0.9124
Caco-2 permeable + 0.8867
P-glycoprotein substrate Substrate 0.5502
P-glycoprotein inhibitor I Non-inhibitor 0.8782
P-glycoprotein inhibitor II Non-inhibitor 0.8382
Renal organic cation transporter Non-inhibitor 0.8863
CYP450 2C9 substrate Non-substrate 0.678
CYP450 2D6 substrate Substrate 0.5658
CYP450 3A4 substrate Non-substrate 0.6007
CYP450 1A2 substrate Non-inhibitor 0.714
CYP450 2C9 substrate Inhibitor 0.7657
CYP450 2D6 substrate Non-inhibitor 0.9286
CYP450 2C19 substrate Non-inhibitor 0.9161
CYP450 3A4 substrate Non-inhibitor 0.8309
CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.8785
Ames test Non AMES toxic 0.6844
Carcinogenicity Non-carcinogens 0.9352
Biodegradation Not ready biodegradable 0.7474
Rat acute toxicity 4.1700 LD50, mol/kg Not applicable
hERG inhibition (predictor I) Weak inhibitor 0.8768
hERG inhibition (predictor II) Non-inhibitor 0.9615
Pharmacoeconomics
Manufacturers
  • Pharmaceutical research assoc inc
  • Bristol myers squibb pharma co
  • Usl pharma inc
  • Abbott laboratories pharmaceutical products div
  • Barr laboratories inc
  • Mylan pharmaceuticals inc
  • Pliva inc
  • Sandoz inc
  • Taro pharmaceuticals inc
  • Watson laboratories inc
  • Zydus pharmaceuticals usa inc
Packagers
Dosage forms
FormRouteStrength
TabletOral1 mg
TabletOral10 mg
TabletOral2 mg
TabletOral2.5 mg
TabletOral3 mg
TabletOral4 mg
TabletOral5 mg
TabletOral6 mg
TabletOral7.5 mg
Prices
Unit descriptionCostUnit
Warfarin sodium powder54.53USDg
Coumadin 5 mg vial34.07USDvial
Coumadin 10 mg tablet2.01USDtablet
Coumadin 7.5 mg tablet1.97USDtablet
Coumadin 6 mg tablet1.94USDtablet
Coumadin 3 mg tablet1.51USDtablet
Coumadin 5 mg tablet1.51USDtablet
Coumadin 4 mg tablet1.49USDtablet
Coumadin 2.5 mg tablet1.46USDtablet
Coumadin 2 mg tablet1.4USDtablet
Coumadin 1 mg tablet1.37USDtablet
Warfarin sodium 10 mg tablet1.0USDtablet
Warfarin sodium 7.5 mg tablet0.96USDtablet
Jantoven 10 mg tablet0.76USDtablet
Jantoven 7.5 mg tablet0.74USDtablet
Jantoven 6 mg tablet0.72USDtablet
Warfarin sodium 6 mg tablet0.68USDtablet
Warfarin sodium 3 mg tablet0.66USDtablet
Warfarin sodium 4 mg tablet0.66USDtablet
Warfarin sodium 2.5 mg tablet0.65USDtablet
Warfarin sodium 5 mg tablet0.65USDtablet
Warfarin sodium 2 mg tablet0.63USDtablet
Warfarin sodium 1 mg tablet0.61USDtablet
Jantoven 5 mg tablet0.59USDtablet
Jantoven 2 mg tablet0.56USDtablet
Jantoven 4 mg tablet0.56USDtablet
Jantoven 2.5 mg tablet0.53USDtablet
Jantoven 3 mg tablet0.53USDtablet
Coumadin 10 mg Tablet0.5USDtablet
Jantoven 1 mg tablet0.49USDtablet
Coumadin 3 mg Tablet0.43USDtablet
Coumadin 4 mg Tablet0.43USDtablet
Coumadin 2 mg Tablet0.35USDtablet
Coumadin 1 mg Tablet0.33USDtablet
Taro-Warfarin 7.5 mg Tablet0.33USDtablet
Taro-Warfarin 6 mg Tablet0.31USDtablet
Apo-Warfarin 10 mg Tablet0.28USDtablet
Coumadin 2.5 mg Tablet0.28USDtablet
Coumadin 5 mg Tablet0.28USDtablet
Mylan-Warfarin 10 mg Tablet0.28USDtablet
Taro-Warfarin 10 mg Tablet0.28USDtablet
Warfarin 10 mg Tablet0.28USDtablet
Apo-Warfarin 3 mg Tablet0.24USDtablet
Apo-Warfarin 4 mg Tablet0.24USDtablet
Mylan-Warfarin 3 mg Tablet0.24USDtablet
Mylan-Warfarin 4 mg Tablet0.24USDtablet
Novo-Warfarin 3 mg Tablet0.24USDtablet
Novo-Warfarin 4 mg Tablet0.24USDtablet
Taro-Warfarin 3 mg Tablet0.24USDtablet
Taro-Warfarin 4 mg Tablet0.24USDtablet
Warfarin 3 mg Tablet0.24USDtablet
Warfarin 4 mg Tablet0.24USDtablet
Apo-Warfarin 2 mg Tablet0.19USDtablet
Mylan-Warfarin 2 mg Tablet0.19USDtablet
Novo-Warfarin 2 mg Tablet0.19USDtablet
Taro-Warfarin 2 mg Tablet0.19USDtablet
Warfarin 2 mg Tablet0.19USDtablet
Apo-Warfarin 1 mg Tablet0.18USDtablet
Mylan-Warfarin 1 mg Tablet0.18USDtablet
Novo-Warfarin 1 mg Tablet0.18USDtablet
Taro-Warfarin 1 mg Tablet0.18USDtablet
Warfarin 1 mg Tablet0.18USDtablet
Apo-Warfarin 5 mg Tablet0.16USDtablet
Mylan-Warfarin 5 mg Tablet0.16USDtablet
Novo-Warfarin 5 mg Tablet0.16USDtablet
Taro-Warfarin 5 mg Tablet0.16USDtablet
Warfarin 5 mg Tablet0.16USDtablet
Apo-Warfarin 2.5 mg Tablet0.15USDtablet
Mylan-Warfarin 2.5 mg Tablet0.15USDtablet
Novo-Warfarin 2.5 mg Tablet0.15USDtablet
Taro-Warfarin 2.5 mg Tablet0.15USDtablet
Warfarin 2.5 mg Tablet0.15USDtablet
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
PatentsNot Available
Properties
Statesolid
Experimental Properties
PropertyValueSource
melting point161 °CPhysProp
water solubility17 mg/L (at 20 °C)TOMLIN,C (1997)
logP2.70HANSCH,C ET AL. (1995)
logS-3.89ADME Research, USCD
Caco2 permeability-4.68ADME Research, USCD
pKa5.08Not Available
Predicted Properties
PropertyValueSource
water solubility4.72e-02 g/lALOGPS
logP2.41ALOGPS
logP2.74ChemAxon
logS-3.8ALOGPS
pKa (strongest acidic)6.33ChemAxon
pKa (strongest basic)-6.6ChemAxon
physiological charge-1ChemAxon
hydrogen acceptor count3ChemAxon
hydrogen donor count1ChemAxon
polar surface area63.6ChemAxon
rotatable bond count4ChemAxon
refractivity86.86ChemAxon
polarizability31.93ChemAxon
number of rings3ChemAxon
bioavailability1ChemAxon
rule of fiveYesChemAxon
Ghose filterYesChemAxon
Veber's ruleNoChemAxon
MDDR-like ruleNoChemAxon
Spectra
SpectraNot Available
References
Synthesis Reference

Nasri W. Badran, “Microcrystalline 3-(alpha-acetonylbenzyl)-4-hydroxycoumarin (warfarin) and methods of making.” U.S. Patent US4113744, issued April, 1960.

US4113744
General Reference
  1. Ansell J, Hirsh J, Poller L, Bussey H, Jacobson A, Hylek E: The pharmacology and management of the vitamin K antagonists: the Seventh ACCP Conference on Antithrombotic and Thrombolytic Therapy. Chest. 2004 Sep;126(3 Suppl):204S-233S. Pubmed
  2. Whitlon DS, Sadowski JA, Suttie JW: Mechanism of coumarin action: significance of vitamin K epoxide reductase inhibition. Biochemistry. 1978 Apr 18;17(8):1371-7. Pubmed
  3. Li T, Chang CY, Jin DY, Lin PJ, Khvorova A, Stafford DW: Identification of the gene for vitamin K epoxide reductase. Nature. 2004 Feb 5;427(6974):541-4. Pubmed
  4. Rost S, Fregin A, Ivaskevicius V, Conzelmann E, Hortnagel K, Pelz HJ, Lappegard K, Seifried E, Scharrer I, Tuddenham EG, Muller CR, Strom TM, Oldenburg J: Mutations in VKORC1 cause warfarin resistance and multiple coagulation factor deficiency type 2. Nature. 2004 Feb 5;427(6974):537-41. Pubmed
  5. Hirsh J, Fuster V, Ansell J, Halperin JL: American Heart Association/American College of Cardiology Foundation guide to warfarin therapy. J Am Coll Cardiol. 2003 May 7;41(9):1633-52. Pubmed
  6. Holbrook AM, Pereira JA, Labiris R, McDonald H, Douketis JD, Crowther M, Wells PS: Systematic overview of warfarin and its drug and food interactions. Arch Intern Med. 2005 May 23;165(10):1095-106. Pubmed
  7. Macina, Orest T.; Schardein, James L. (2007). “Warfarin”. Human Developmental Toxicants. Boca Raton: CRC Taylor & Francis. pp. 193–4
  8. Ansell J, Hirsh J, Hylek E, Jacobson A, Crowther M, Palareti G: Pharmacology and management of the vitamin K antagonists: American College of Chest Physicians Evidence-Based Clinical Practice Guidelines (8th Edition). Chest. 2008 Jun;133(6 Suppl):160S-198S. doi: 10.1378/chest.08-0670. Pubmed
  9. Freedman MD: Oral anticoagulants: pharmacodynamics, clinical indications and adverse effects. J Clin Pharmacol. 1992 Mar;32(3):196-209. Pubmed
  10. Loftus, Christopher M. (1995). “Fetal toxicity of common neurosurgical drugs”. Neurosurgical Aspects of Pregnancy. Park Ridge, Ill: American Association of Neurological Surgeons. pp. 11–3.
External Links
ResourceLink
KEGG CompoundC01541
BindingDB50088240
ChEBI10033
ChEMBLCHEMBL1464
Therapeutic Targets DatabaseDAP000770
PharmGKBPA451906
Drug Product Database2244463
RxListhttp://www.rxlist.com/cgi/generic/warfarin.htm
Drugs.comhttp://www.drugs.com/warfarin.html
WikipediaWarfarin
ATC CodesB01AA03
AHFS Codes
  • 20:12.04.08
PDB EntriesNot Available
FDA labelshow(641 KB)
MSDSshow(59.5 KB)
Interactions
Drug Interactions
Drug
AcetaminophenAcetaminophen increases the anticoagulant effect of warfarin. Monitor for changes in the therapeutic and adverse effects of warfarin if acetaminophen is initiated, discontinued or dose changed.
Acetylsalicylic acidThe antiplatelet effects of acetylsalicylic acid may increase the bleed risk associated with warfarin.
AllopurinolAllopurinol may increase the anticoagulant effect of warfarin. Monitor for changes in prothrombin times and therapeutic effects of warfarin if allopurinol is initiated, discontinued or dose changed.
AminoglutethimideAminoglutethimide may decrease the anticoagulant effect of warfarin by increasing its metabolism. Monitor for changes in prothrombin time and therapeutic effects of warfarin if aminoglutethimide is initiated, discontinued or dose changed.
Aminosalicylic AcidThe antiplatelet effects of aminosalicylic acid may increase the bleed risk associated with warfarin.
AmiodaroneAmiodarone may increase the anticoagulant effect of warfarin. Monitor for changes in prothrombin time and therapeutic effects of warfarin if amiodarone is initiated, discontinued or dose changed.
AmobarbitalAmobarbital may decrease the serum concentration of warfarin by increasing its metabolism. Monitor for changes in the therapeutic and adverse effects of warfarin if amobarbital is initiated, discontinued or dose changed.
AmprenavirAmprenavir may increase the anticoagulant effect of warfarin by increasing its serum concentration.
AprepitantAprepitant may decrease the anticoagulant effect of warfarin by decreasing its serum concentration.
AtazanavirThe protease inhibitor, atazanavir, may increase the anticoagulant effect of warfarin.
AvanafilCo-administration with avanafil resulted in an approximate 1.6% increase in AUC(0-inf) and 5.2% decrease in Cmax of S-warfarin.
AzathioprineAzathioprine may decrease the anticoagulant effect of warfarin.
AzithromycinAzithromycin may increase the anticoagulant effect of warfarin by increasing its serum concentration.
BetamethasoneThe corticosteroid, betamethasone, alters the anticoagulant effect of warfarin.
BezafibrateBezafibrate may increase the anticoagulant effect of warfarin. Monitor prothrombin time and therapeutic and adverse effects of warfarin if bezafibrate is initiated, discontinued or dose changed.
BosentanBosentan may decrease the anticoagulant effect of warfarin by increasing its metabolism.
ButabarbitalButabarbital may decrease the serum concentration of warfarin by increasing its metabolism. Monitor for changes in the therapeutic and adverse effects of warfarin if butabarbital is initiated, discontinued or dose changed.
ButalbitalButalbital may decrease the serum concentration of warfarin by increasing its metabolism. Monitor for changes in the therapeutic and adverse effects of warfarin if butalbital is initiated, discontinued or dose changed.
CapecitabineCapecitabine may increase the serum concentration of warfarin by decreasing its metabolism. Monitor for changes in prothrombin time and therapeutic effects of warfarin if capecitabine is initiated or discontinued. Subsequent cycles of capecitabine may increase this effect.
CarbamazepineCarbamazepine may decrease the anticoagulant effect of warfarin. Monitor for changes in prothrombin time and therapeutic and adverse effects of warfarin if carbamazepine is initiated, discontinued or dose changed.
CefotetanThe cephalosporin, cefotetan, may increase the anticoagulant effect of warfarin.
CefoxitinThe cephalosporin, cefoxitin, may increase the anticoagulant effect of warfarin.
CeftriaxoneThe cephalosporin, ceftriaxone, may increase the anticoagulant effect of warfarin.
CelecoxibCelecoxib may increase the anticoagulant effect of warfarin.
CholestyramineThe bile acid sequestrant, cholestyramine, may decrease the anticoagulant effect of warfarin by decreasing its absorption.
CimetidineCimetidine may increase the serum concentration of warfarin. Monitor for changes in prothrombin time and therapeutic and adverse effects of warfarin if cimetidine is initiated, discontinued or dose changed.
CiprofloxacinThe quinolone antibiotic, ciprofloxacin, may increase the anticoagulant effect of warfarin.
CisaprideCisapride may increase the anticoagulant effect of warfarin.
CitalopramThe SSRI, citalopram, increases the effect of anticoagulant, warfarin.
ClarithromycinThe macrolide, clarithromycin, may increase the anticoagulant effect of warfarin.
ClofibrateThe fibrate increases the anticoagulant effect
ClopidogrelIncreased bleed risk may occur as a result of additive anticoagulant effects. Increase monitoring for signs and symptoms of bleeding during concomitant therapy.
ColestipolThe bile acid sequestrant, colestipol, may decrease the anticoagulant effect of warfarin by decreasing its absorption.
CyclophosphamideThe antineoplastic agent, cyclophosphamide may alter the anticoagulant effect of warfarin.
DanazolDanazol may increase the serum concentration and anticoagulant effect of warfarin. Monitor for changes in prothrombin time and therapeutic effects of warfarin if danazol is initiated, discontinued or dose changed.
DelavirdineDelavirdine, a strong CYP2C9 inhibitor, may decrease the metabolism of warfarin. Consider alternate therapy or monitor for changes in the therapeutic and adverse effects of warfarin if delavirdine is initiated, discontinued or dose changed.
DemeclocyclineThe tetracycline, demeclocycline, may increase the anticoagulant effect of warfarin.
DesogestrelDesogestrol may alter the anticoagulant effect of warfarin. Concomitant therapy should be avoided. Monitor for changes in coagulation status if desogestrol is initiated, discontinued or dose changed.
DexamethasoneThe corticosteroid, dexamethasone, alters the anticoagulant effect of warfarin.
DextropropoxyphenePropoxyphene may increase the anticoagulant effect of warfarin.
DextrothyroxineThe thyroid hormone, dextrothyroxine, increase the anticoagulant effect of warfarin.
DiclofenacThe antiplatelet effects of oral diclofenac may increase the bleed risk associated with warfarin. Consider alternate therapy or monitor for signs and symptoms of bleeding during concomitant therapy.
DicloxacillinDicloxacillin may decrease the anticoagulant effect of warfarin.
DiflunisalThe antiplatelet effects of diflunisal may increase the bleed risk associated with warfarin. Consider alternate therapy or monitor for signs and symptoms of bleeding during concomitant therapy.
DisulfiramDisulfiram may increase the anticoagulant effect of warfarin.
DoxycyclineThe tetracycline, doxycycline, may increase the anticoagulant effect of warfarin.
DronedaroneDronedarone is a moderate inhibitor of CYP3A4 which is responsible for warfarin metabolism. Increases serum concentration of S-isomer warfarin by 1.2 fold
DrospirenoneDrospirenone may alter the anticoagulant effect of warfarin. Concomitant therapy should be avoided. Monitor for changes in coagulation status if drospirenone is initiated, discontinued or dose changed.
Drotrecogin alfaIncreased risk of bleeding.
ErythromycinThe macrolide, erythromycin, may increase the anticoagulant effect of warfarin.
EthchlorvynolEthchlorvynol may decrease the anticoagulant effect of warfarin.
Ethinyl EstradiolEthinyl estradiol may alter the anticoagulant effect of warfarin. Concomitant therapy should be avoided. Monitor for changes in coagulation status if ethinyl estradiol is initiated, discontinued or dose changed.
EthynodiolEthynodiol diacetate may alter the anticoagulant effect of warfarin. Concomitant therapy should be avoided. Monitor for changes in coagulation status if ethynodiol diacetate is initiated, discontinued or dose
EtodolacThe antiplatelet effects of etodolac may increase the bleed risk associated with warfarin. Consider alternate therapy or monitor for signs and symptoms of bleeding during concomitant therapy.
EtonogestrelEtonogestrel may alter the anticoagulant effect of warfarin. Concomitant therapy should be avoided. Monitor for changes in coagulation status if etonogestrel is initiated, discontinued or dose changed.
EtoricoxibEtoricoxib may increase the anticoagulant effect of warfarin.
EzetimibeIf ezetimibe is added to warfarin, a coumarin anticoagulant, the International Normalized Ratio (INR) should be appropriately monitored.
Fdecreases the effect of cortisone by metabolism alteration.
FenofibrateFenofibrate may increase the anticoagulant effect of warfarin. Monitor prothrombin time and therapeutic and adverse effects of warfarin if fenofibrate is initiated, discontinued or dose changed.
FenoprofenThe antiplatelet effects of fenoprofen may increase the bleed risk associated with warfarin. Consider alternate therapy or monitor for signs and symptoms of bleeding during concomitant therapy.
FloxuridineFloxuridine, a strong CYP2C9 inhibitor, may decrease the metabolism of warfarin. Consider alternate therapy or monitor for changes in the therapeutic and adverse effects of warfarin if floxuridine is initiated, discontinued or dose changed.
FluconazoleFluconazole, a strong CYP2C9 inhibitor, may decrease the metabolism of warfarin. Consider alternate therapy or monitor for changes in the therapeutic and adverse effects of warfarin if fluconazole is initiated, discontinued or dose changed.
FludrocortisoneThe corticosteroid, fludrocortisone, alters the anticoagulant effect of warfarin.
FluorouracilFluorouracil, a strong CYP2C9 inhibitor, may decrease the metabolism of warfarin. Consider alternate therapy or monitor for changes in the therapeutic and adverse effects of warfarin if fluorouracil is initiated, discontinued or dose changed.
FluoxetineThe SSRI, fluoxetine, increases the effect of anticoagulant, warfarin.
FluoxymesteroneFluoxymesterone may increase the serum concentration and anticoagulant effect of warfarin. Monitor for changes in prothrombin time and therapeutic effects of warfarin if fluoxymesterone is initiated, discontinued or dose changed.
FlurbiprofenFlurbiprofen, a strong CYP2C9 inhibitor, may decrease the metabolism of warfarin. The antiplatelet effect of flurbiprofen may also increase the bleed risk associated with warfarin. Consider alternate therapy or monitor for changes in the therapeutic and adverse effects of warfarin if flurbiprofen is initiated, discontinued or dose changed.
FluvastatinFluvastatin may increase the anticoagulant effect of warfarin. Monitor for changes in the therapeutic and adverse effects of warfarin if fluvastatin is initiated, discontinued or dose changed.
FluvoxamineFluvoxamine may increase the anticoagulant effect of warfarin by increasing its serum concentration.
FosamprenavirThe protease inhibitor, fosamprenavir, may increase the anticoagulant effect of warfarin.
FosphenytoinIncreased hydantoin levels and risk of bleeding
Gadofosveset trisodiumIn a clinical trial of 10 patients receiving a stable dose of warfarin, a single dose of ABLAVAR (0.05 mmol/kg) did not alter the anticoagulant activity of warfarin as measured by the International Normalized Ratio (INR).
GefitinibGefitinib may increase the anticoagulant effect of warfarin.
GemcitabineGemcitabine may increase the anticoagulant effect of warfarin.
GemfibrozilGemfibrozil, a strong CYP2C9 inhibitor, may decrease the metabolism of warfarin. Consider alternate therapy or monitor for changes in the therapeutic and adverse effects of warfarin if gemfibrozil is initiated, discontinued or dose changed.
Ginkgo bilobaAdditive anticoagulant/antiplatelet effects may increase bleed risk. Concomitant therapy should be avoided.
GinsengAdditive anticoagulant effects increase the risk of bleeding. Concomitant therapy should be avoided.
GlutethimideGlutethimide may decrease the serum concentration of warfarin by increasing its metabolism. Consider alternate therapy or monitor for changes in the therapeutic and adverse effects of warfarin if glutethimide is initiated, discontinued or dose changed.
GriseofulvinGriseofulvin may decrease the anticoagulant effect of warfarin.
HomoharringtonineAvoid combination with warfarin and other anticoagulants due to the potential enhancement of homoharringtonine associated bleeding-related adverse effects. Specifically it is suggested to avoid this combination in patients with a platelet count of less than 50,000/uL.
HydrocortisoneThe corticosteroid, hydrocortisone, alters the anticoagulant effect of warfarin.
IbuprofenIbuprofen, a strong CYP2C9 inhibitor, may decrease the metabolism of warfarin. The antiplatelet effect of ibuprofen may also increase the bleed risk associated with warfarin. Consider alternate therapy or monitor for changes in the therapeutic and adverse effects of warfarin if ibuprofen is initiated, discontinued or dose changed.
ImatinibImatinib may increase the anticoagulant effect of warfarin increasing the risk of bleeding. Monitor for changes in prothrombin time and therapeutic and adverse effects of warfarin if imatinib is initiated, discontinued or dose changed.
IndinavirThe protease inhibitor, indinavir, may increase the anticoagulant effect of warfarin.
IndomethacinIndomethacin, a strong CYP2C9 inhibitor, may decrease the metabolism of warfarin. The antiplatelet effect of indomethacin may also increase the bleed risk associated with warfarin. Consider alternate therapy or monitor for changes in the therapeutic and adverse effects of warfarin if indomethacin is initiated, discontinued or dose changed.
IsoniazidIsoniazid may increase the anticoagulant effect of warfarin.
ItraconazoleItraconazole may increase the anticoagulant effect of warfarin by decreasing its metabolism.
KetoconazoleKetoconazole, a strong CYP2C9 inhibitor, may decrease the metabolism of warfarin. Consider alternate therapy or monitor for changes in the therapeutic and adverse effects of warfarin if ketoconazole is initiated, discontinued or dose changed.
KetoprofenThe antiplatelet effects of ketoprofen may increase the bleed risk associated with warfarin. Consider alternate therapy or monitor for signs and symptoms of bleeding during concomitant therapy.
KetorolacThe antiplatelet effects of ketorolac may increase the bleed risk associated with warfarin. Consider alternate therapy or monitor for signs and symptoms of bleeding during concomitant therapy.
LeflunomideLeflunomide may increase the anticoagulant effect of warfarin.
LevamisoleLevamisole may increase the anticoagulant effect of warfarin.
LevofloxacinThe quinolone antibiotic, levofloxacin, may increase the anticoagulant effect of warfarin.
LevonorgestrelLevonorgestrel may alter the anticoagulant effect of warfarin. Concomitant therapy should be avoided. Monitor for changes in coagulation status if levonorgestrel is initiated, discontinued or dose changed.
LevothyroxineLevothyroxine may contribute to the anticoagulant effect of warfarin by increasing the metabolism of vitamin K-dependent clotting factors. Monitor for changes in prothrombin time and anticoagulant effects if levothyroxine is initiated, discontinued or dose changed.
LiothyronineLiothyronine may contribute to the anticoagulant effect of warfarin by increasing the metabolism of vitamin K-dependent clotting factors. Monitor for changes in prothrombin time and anticoagulant effects if liothyronine is initiated, discontinued or dose changed.
LiotrixLiotrix may contribute to the anticoagulant effect of warfarin by increasing the metabolism of vitamin K-dependent clotting factors. Monitor for changes in prothrombin time and anticoagulant effects if liotrix is initiated, discontinued or dose changed.
LomitapideWarfarin plasma concentrations may increase by lomitapide by 30%.. INR levels may increase by 22%. Regular INR monitoring is required.
LovastatinLovastatin may increase the anticoagulant effect warfarin. Monitor for changes in the therapeutic and adverse effects of warfarin if lovastatin is initiated, discontinued or dose changed .
LumiracoxibLumiracoxib may increase the anticoagulant effect of warfarin.
Meclofenamic acidThe antiplatelet effects of meclofenamic acid may increase the bleed risk associated with warfarin. Consider alternate therapy or monitor for signs and symptoms of bleeding during concomitant therapy.
Medroxyprogesterone AcetateMedroxyprogesterone may alter the anticoagulant effect of warfarin. Concomitant therapy should be avoided. Monitor for changes in coagulation status if medroxyprogesterone is initiated, discontinued or dose changed.
Mefenamic acidMefenamic acid, a strong CYP2C9 inhibitor, may decrease the metabolism of warfarin. The antiplatelet effect of mefenamic acid may also increase the bleed risk associated with warfarin. Consider alternate therapy or monitor for changes in the therapeutic and adverse effects of warfarin if mefenamic acid is initiated, discontinued or dose changed.
MefloquineMefloquine may increase the anticoagulant effect of warfarin.
MeloxicamThe antiplatelet effects of meloxicam may increase the bleed risk associated with warfarin. Consider alternate therapy or monitor for signs and symptoms of bleeding during concomitant therapy.
MercaptopurineMercaptopurine may decrease the anticoagulant effect of warfarin.
MestranolMestranol may alter the anticoagulant effect of warfarin. Concomitant therapy should be avoided. Monitor for changes in coagulation status if mestranol is initiated, discontinued or dose changed.
MethimazoleMethimazole may decrease the anticoagulant effect of warfarin. Monitor for changes in the therapeutic and adverse effects of warfarin if methimazole is initiated, discontinued or dose changed.
MethohexitalMethohexital may decrease the serum concentration of warfarin by increasing its metabolism. Monitor for changes in the therapeutic and adverse effects of warfarin if methohexital is initiated, discontinued or dose changed.
MetronidazoleMetronidazole may increase the serum concentration of warfarin by decreasing its metabolism. Consider alternate therapy or a dose reduction in warfarin. Monitor for changes in prothrombin time and therapeutic and adverse effects of warfarin if metronidazole is initiated, discontinued or dose changed.
MiconazoleMiconazole, a strong CYP2C9 inhibitor, may decrease the metabolism of warfarin. Consider alternate therapy or monitor for changes in the therapeutic and adverse effects of warfarin if miconazole is initiated, discontinued or dose changed.
MinocyclineThe tetracycline, minocycline, may increase the anticoagulant effect of warfarin.
Mirabegron Mirabegron increased Cmax and AUC of S- and R-warfarin. Monitor concomitant therapy closely.
MitotaneMitotane may decrease the anticoagulant effect of warfarin.
MoxifloxacinThe quinolone antibiotic, moxifloxacin, may increase the anticoagulant effect of warfarin.
NabumetoneThe antiplatelet effects of nabumetone may increase the bleed risk associated with warfarin. Consider alternate therapy or monitor for signs and symptoms of bleeding during concomitant therapy.
NafcillinNafcillin may increase the anticoagulant effect of warfarin increasing the risk of bleeding. Consider alternate therapy or monitor for changes in the therapeutic and adverse effects of warfarin if nafcillin is initiated, discontinued or dose changed.
Nalidixic AcidThe quinolone antibiotic, nalidixic acid, may increase the anticoagulant effect of warfarin.
Nandrolone decanoateNandrolone may increase the serum concentration and anticoagulant effect of warfarin. Monitor for changes in prothrombin time and therapeutic effects of warfarin if nandrolone is initiated, discontinued or dose changed.
Nandrolone phenpropionateNandrolone may increase the serum concentration and anticoagulant effect of warfarin. Monitor for changes in prothrombin time and therapeutic effects of warfarin if nandrolone is initiated, discontinued or dose changed.
NaproxenThe antiplatelet effects of naproxen may increase the bleed risk associated with warfarin. Consider alternate therapy or monitor for signs and symptoms of bleeding during concomitant therapy.
NelfinavirThe protease inhibitor, nelfinavir, may increase the anticoagulant effect of warfarin.
NevirapineNevirapine may decrease the anticoagulant effect of warfarin by increasing metabolism of R-warfarin via CYP3A4.
NicardipineNicardipine, a strong CYP2C9 inhibitor, may decrease the metabolism of warfarin. Consider alternate therapy or monitor for changes in the therapeutic and adverse effects of warfarin if nicardipine is initiated, discontinued or dose changed.
NorethindroneNorethindrone may alter the anticoagulant effect of warfarin. Concomitant therapy should be avoided. Monitor for changes in coagulation status if norethindrone is initiated, discontinued or dose changed.
NorfloxacinThe quinolone antibiotic, norfloxacin, may increase the anticoagulant effect of warfarin.
NorgestimateNorgestimate may alter the anticoagulant effect of warfarin. Concomitant therapy should be avoided. Monitor for changes in coagulation status if norgestimate is initiated, discontinued or dose changed.
OfloxacinThe quinolone antibiotic, ofloxacin, may increase the anticoagulant effect of warfarin.
OrlistatOrlistat may increase the anticoagulant effect of warfarin.
OxandroloneOxandrolone may increase the serum concentration and anticoagulant effect of warfarin. Monitor for changes in prothrombin time and therapeutic effects of warfarin if oxandrolone is initiated, discontinued or dose changed.
OxaprozinThe antiplatelet effects of oxaprozin may increase the bleed risk associated with warfarin. Consider alternate therapy or monitor for signs and symptoms of bleeding during concomitant therapy.
oxymetholoneOxymetholone may increase the serum concentration and anticoagulant effect of warfarin. Monitor for changes in prothrombin time and therapeutic effects of warfarin if oxymetholone is initiated, discontinued or dose changed.
OxyphenbutazoneThe NSAID, oxyphenbutazone, may increase the anticoagulant effect of warfarin.
ParoxetineThe SSRI, paroxetine, increases the effect of the anticoagulant, warfarin.
PentobarbitalPentobarbital may decrease the serum concentration of warfarin by increasing its metabolism. Monitor for changes in the therapeutic and adverse effects of warfarin if pentobarbital is initiated, discontinued or dose changed.
PentoxifyllinePentoxifylline may increase the anticoagulant effect of warfarin.
PhenobarbitalPhenobarbital may decrease the serum concentration of warfarin by increasing its metabolism. Monitor for changes in the therapeutic and adverse effects of warfarin if phenobarbital is initiated, discontinued or dose changed.
PhenylbutazoneThe NSAID, phenylbutazone, may increase the anticoagulant effect of warfarin.
PhenytoinWarfarin may increase the serum concentration of phenytoin possibly by competing for CYP2C9 metabolism. Phenytoin may increase the anticoagulant effect of warfarin. Monitor phenytoin levels, prothrombin time, and therapeutic and adverse effects of both agents during concomitant therapy.
PhylloquinonePhytonadione (vitamin K) may antagonize the anticoagulant effects of warfarin. Monitor for changes in prothrombin time if phytonadione intake (either via supplements or vitamin K-rich foods) is increased or decreased.
PiroxicamPiroxicam, a strong CYP2C9 inhibitor, may decrease the metabolism of warfarin. The antiplatelet effect of piroxicam may also increase the bleed risk associated with warfarin. Consider alternate therapy or monitor for changes in the therapeutic and adverse effects of warfarin if piroxicam is initiated, discontinued or dose changed.
PrasugrelCoadministration with warfarin may increase the risk of bleeding.
PrednisoloneThe corticosteroid, prednisolone, alters the anticoagulant effect of warfarin.
PrednisoneThe corticosteroid, prednisone, alters the anticoagulant effect of warfarin.
PrimidoneThe barbiturate, primidone, decreases the anticoagulant effect of warfarin.
PropafenonePropafenone may increase the anticoagulant effect of warfarin.
PropylthiouracilPropylthiouracil may decrease the anticoagulant effect of warfarin. Monitor for changes in the therapeutic and adverse effects of warfarin if propylthiouracil is initiated, discontinued or dose changed.
QuinidineQuinidine may increase the anticoagulant effect of warfarin.
QuinineQuinine, a moderate CYP2C9 inhibitor, may increase the serum concentration of S-warfarin by decreasing its metabolism via CYP2C9.
RanitidineRanitidine may increase the anticoagulant effect of warfarin. (Conflicting evidence)
RifabutinRifabutin may decrease the anticoagulant effect of warfarin by increasing its metabolism.
RifampicinRifampin may decrease the anticoagulant effect of warfarin by increasing its metabolism.
S-AdenosylmethionineAdditive anticoagulant effects increase the risk of bleeding. Concomitant therapy should be avoided.
Salicylate-sodiumThe antiplatelet effects of sodium salicylate may increase the bleed risk associated with warfarin.
SecobarbitalSecobarbital may decrease the serum concentration of warfarin by increasing its metabolism. Monitor for changes in the therapeutic and adverse effects of warfarin if secobarbital is initiated, discontinued or dose changed.
SitaxentanSitaxentan, a strong CYP2C9 inhibitor, may decrease the metabolism of warfarin. Warfarin doses should be decreased by 80% upon initiated of concomitant therapy. Monitor for changes in the therapeutic and adverse effects of warfarin if sitaxentan is initiated, discontinued or dose changed.
St. John's WortSt. John's Wort may decrease the serum concentration of warfarin by increasing its metabolism. Concomitant therapy should be avoided. Monitor for changes in the therapeutic and adverse effects of warfarin if St. John's Wort is initiated, discontinued or dose changed.
SucralfateSucralfate may reduce the absorption of warfarin. Warfarin should be administered at least 2 hours before or 6 hours after sucralfate administration. Monitor for changes in prothrombin time if sucralfate is initiated, discontinued or dose changed.
SulfadiazineSulfadiazine, a strong CYP2C9 inhibitor, may decrease the metabolism of warfarin. Consider alternate therapy or monitor for changes in the therapeutic and adverse effects of warfarin if sulfadiazine is initiated, discontinued or dose changed.
SulfamethoxazoleSulfamethoxazole may increase the anticoagulant effect of warfarin by decreasing its metabolism. Consider alternate therapy or monitor for changes in prothrombin time if sulfamethoxazole is initiated, discontinued or dose changed.
SulfinpyrazoneSulfinpyrazone may increase the anticoagulant effect of warfarin by decreasing its metabolism and protein binding.
SulfisoxazoleSulfisoxazole, a strong CYP2C9 inhibitor, may decrease the metabolism of warfarin. Consider alternate therapy or monitor for changes in the therapeutic and adverse effects of warfarin if sulfisoxazole is initiated, discontinued or dose changed.
SulindacThe antiplatelet effects of sulindac may increase the bleed risk associated with warfarin. Consider alternate therapy or monitor for signs and symptoms of bleeding during concomitant therapy.
TamoxifenTamoxifen, a CYP2C9 inhibitor, may increase the serum concentration of warfarin by decreasing its metabolism. Concomitant therapy is contraindicated due to significant increase in bleed risk.
TelithromycinTelithromycin may increase the anticoagulant effect of Warfarin. INR should be monitored and Warfarin dose adjusted accordingly during concomitant therapy.
TenoxicamThe NSAID, tenoxicam, may increase the anticoagulant effect of warfarin.
TestolactoneTestolactone may increase the serum concentration and anticoagulant effect of warfarin. Monitor for changes in prothrombin time and therapeutic effects of warfarin if testolactone is initiated, discontinued or dose changed.
TestosteroneTestosterone may increase the serum concentration and anticoagulant effect of warfarin. Monitor for changes in prothrombin time and therapeutic effects of warfarin if testosterone is initiated, discontinued or dose changed.
Testosterone PropionateThe androgen, Testosterone, may incrase the anticoagulant effect of the Vitamin K antagonist, Warfarin. Monitor for changes in the therapeutic effect of Warfarin if Testosterone is initiated, discontinued or dose changed.
TetracyclineTetracycline may increase the anticoagulant effect of warfarin.
ThiopentalThiopental may decrease the serum concentration of warfarin by increasing its metabolism. Monitor for changes in the therapeutic and adverse effects of warfarin if thiopental is initiated, discontinued or dose changed.
Tiaprofenic acidThe antiplatelet effects of tiaprofenic acid may increase the bleed risk associated with warfarin. Consider alternate therapy or monitor for signs and symptoms of bleeding during concomitant therapy.
TiclopidineIncreased bleeding risk. Monitor INR.
TigecyclineTigecycline may increase the serum concentration of warfarin.
TolbutamideTolbutamide, a strong CYP2C9 inhibitor, may decrease the metabolism of warfarin. Consider alternate therapy or monitor for changes in the therapeutic and adverse effects of warfarin if tolbutamide is initiated, discontinued or dose changed.
TolmetinThe antiplatelet effects of tolmetin may increase the bleed risk associated with warfarin. Consider alternate therapy or monitor for signs and symptoms of bleeding during concomitant therapy.
transdermal testosterone gelThe androgen, Testosterone, may incrase the anticoagulant effect of the Vitamin K antagonist, Warfarin. Monitor for changes in the therapeutic effect of Warfarin if Testosterone is initiated, discontinued or dose changed.
TreprostinilThe prostacyclin analogue, Treprostinil, increases the risk of bleeding when combined with the anticoagulant, Warfarin. Monitor for increased bleeding during concomitant thearpy.
TriamcinoloneThe corticosteroid, triamcinolone, alters the anticoagulant effect of warfarin.
TriflusalThe metabolite of triflusal, 2-hydroxy-4-trifluoro-methyl-benzoic acid (HTB), impairs the serum protein binding of warfarin to the same extent as acetylsalisylic acid. Thus, the free fraction of glisentide may be increased. A dosage reduction may be required if used in combination.
TrimetrexateThe anticoagulant effect of Warfarin, a Vitamin K antagonist, may be altered by antineoplastics such as Trimetrexate. Monitor for changes in the anticoagulant effects of warfarin and other coumarin derivatives during concomitant use.
Trisalicylate-cholineThe antiplatelet effects of trisalicylate-choline may increase the bleed risk associated with warfarin.
VemurafenibVemurafenib increases the AUC of S-warfarin (CYP2C9 substrate). Monitor concomitant therapy closely.
VilazodoneIncreased risk of bleeding with concomitant use of warfarin and vilazodone.
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.

1. Vitamin K epoxide reductase complex subunit 1

Kind: protein

Organism: Human

Pharmacological action: yes

Actions: inhibitor

Components

Name UniProt ID Details
Vitamin K epoxide reductase complex subunit 1 Q9BQB6 Details

References:

  1. Gebauer M: Synthesis and structure-activity relationships of novel warfarin derivatives. Bioorg Med Chem. 2007 Mar 15;15(6):2414-20. Epub 2007 Jan 17. Pubmed
  2. Zhu Y, Shennan M, Reynolds KK, Johnson NA, Herrnberger MR, Valdes R Jr, Linder MW: Estimation of warfarin maintenance dose based on VKORC1 (-1639 G>A) and CYP2C9 genotypes. Clin Chem. 2007 Jul;53(7):1199-205. Epub 2007 May 17. Pubmed
  3. Yin T, Miyata T: Warfarin dose and the pharmacogenomics of CYP2C9 and VKORC1 – rationale and perspectives. Thromb Res. 2007;120(1):1-10. Epub 2006 Dec 11. Pubmed
  4. Osman A, Enstrom C, Lindahl TL: Plasma S/R ratio of warfarin co-varies with VKORC1 haplotype. Blood Coagul Fibrinolysis. 2007 Apr;18(3):293-6. Pubmed
  5. Limdi NA, McGwin G, Goldstein JA, Beasley TM, Arnett DK, Adler BK, Baird MF, Acton RT: Influence of CYP2C9 and VKORC1 1173C/T Genotype on the Risk of Hemorrhagic Complications in African-American and European-American Patients on Warfarin. Clin Pharmacol Ther. 2007 Jul 25;. Pubmed
  6. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. Pubmed

1. Cytochrome P450 2C9

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: substrate inhibitor

Components

Name UniProt ID Details
Cytochrome P450 2C9 P11712 Details

References:

  1. Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. Pubmed
  2. Flockhart DA. Drug Interactions: Cytochrome P450 Drug Interaction Table. Indiana University School of Medicine (2007). Accessed May 28, 2010.
  3. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. Epub 2009 Nov 24. Pubmed

2. Cytochrome P450 1A2

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: substrate

Components

Name UniProt ID Details
Cytochrome P450 1A2 P05177 Details

References:

  1. Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. Pubmed
  2. Flockhart DA. Drug Interactions: Cytochrome P450 Drug Interaction Table. Indiana University School of Medicine (2007). Accessed May 28, 2010.
  3. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. Epub 2009 Nov 24. Pubmed

3. Cytochrome P450 2C19

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: substrate inhibitor

Components

Name UniProt ID Details
Cytochrome P450 2C19 P33261 Details

References:

  1. Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. Pubmed
  2. Flockhart DA. Drug Interactions: Cytochrome P450 Drug Interaction Table. Indiana University School of Medicine (2007). Accessed May 28, 2010.
  3. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. Epub 2009 Nov 24. Pubmed

4. Cytochrome P450 3A4

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: substrate

Components

Name UniProt ID Details
Cytochrome P450 3A4 P08684 Details

References:

  1. Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. Pubmed
  2. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. Epub 2009 Nov 24. Pubmed

5. Cytochrome P450 2C8

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: substrate inhibitor

Components

Name UniProt ID Details
Cytochrome P450 2C8 P10632 Details

References:

  1. Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. Pubmed
  2. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. Epub 2009 Nov 24. Pubmed

6. Cytochrome P450 2C18

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: substrate

Components

Name UniProt ID Details
Cytochrome P450 2C18 P33260 Details

References:

  1. Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. Pubmed
  2. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. Epub 2009 Nov 24. Pubmed

7. Cytochrome P450 1A1

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: substrate

Components

Name UniProt ID Details
Cytochrome P450 1A1 P04798 Details

References:

  1. Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. Pubmed

1. Serum albumin

Kind: protein

Organism: Human

Pharmacological action: no

Components

Name UniProt ID Details
Serum albumin P02768 Details

References:

  1. Yamasaki K, Maruyama T, Kragh-Hansen U, Otagiri M: Characterization of site I on human serum albumin: concept about the structure of a drug binding site. Biochim Biophys Acta. 1996 Jul 18;1295(2):147-57. Pubmed
  2. Joseph KS, Hage DS: The effects of glycation on the binding of human serum albumin to warfarin and L-tryptophan. J Pharm Biomed Anal. 2010 Nov 2;53(3):811-8. Epub 2010 May 6. Pubmed
  3. Wybranowski T, Cyrankiewicz M, Ziomkowska B, Kruszewski S: The HSA affinity of warfarin and flurbiprofen determined by fluorescence anisotropy measurements of camptothecin. Biosystems. 2008 Dec;94(3):258-62. Epub 2008 Jul 31. Pubmed
  4. Bertucci C, Wainer IW: Improved chromatographic performance of a modified human albumin based stationary phase. Chirality. 1997;9(4):335-40. Pubmed

2. Alpha-1-acid glycoprotein 1

Kind: protein

Organism: Human

Pharmacological action: no

Components

Name UniProt ID Details
Alpha-1-acid glycoprotein 1 P02763 Details

References:

  1. Hazai E, Visy J, Fitos I, Bikadi Z, Simonyi M: Selective binding of coumarin enantiomers to human alpha1-acid glycoprotein genetic variants. Bioorg Med Chem. 2006 Mar 15;14(6):1959-65. Epub 2005 Nov 15. Pubmed
  2. Nakagawa T, Kishino S, Itoh S, Sugawara M, Miyazaki K: Differential binding of disopyramide and warfarin enantiomers to human alpha(1)-acid glycoprotein variants. Br J Clin Pharmacol. 2003 Dec;56(6):664-9. Pubmed

Comments
Drug created on June 13, 2005 07:24 / Updated on March 03, 2014 08:58