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Identification
Name Warfarin
Accession Number DB00682 (APRD00341)
Type small molecule
Groups approved
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. [PubChem]
Structure Thumb
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  • Warfarin sodium
Brand names
  • Athrombin
  • Athrombin-K
  • Athrombine-K
  • Brumolin
  • Co-Rax
  • Coumadin
  • Coumadin Tabs
  • Coumafen
  • Coumafene
  • Coumaphen
  • Coumaphene
  • Coumarins
  • Coumefene
  • D-Con
  • Dethmor
  • Dethnel
  • Dicusat E
  • Frass-Ratron
  • Jantoven
  • Kumader
  • Kumadu
  • Kumatox
  • Kypfarin
  • Latka 42
  • Mar-Frin
  • Marevan
  • Maveran
  • Panwarfin
  • Place-Pax
  • Prothromadin
  • RAX
  • Rosex
  • Sofarin
  • Solfarin
  • Sorexa Plus
  • Temus W
  • Tintorane
  • Tox-Hid
  • Vampirinip II
  • Vampirinip III
  • Warf 42
  • Warfarat
  • Warfarin Plus
  • Warfarin Q
  • Warfarine
  • Warficide
  • Warfilone
  • Zoocoumarin
Brand name mixtures Not Available
Categories
  • Anticoagulants
  • Rodenticides
  • Coumarin and Indandione Derivatives
CAS number 81-81-2
Weight Average: 308.3279
Monoisotopic: 308.104859000
Chemical Formula C19H16O4
InChI Key InChIKey=QTXVAVXCBMYBJW-UHFFFAOYSA-N
InChI
InChI=1S/C19H16O4/c1-12(20)11-15(13-7-3-2-4-8-13)17-18(21)14-9-5-6-10-16(14)23-19(17)22/h2-10,15,22H,11H2,1H3
Plain Text
IUPAC Name
2-hydroxy-3-(3-oxo-1-phenylbutyl)-4H-chromen-4-one
SMILES
CC(=O)CC(C1=CC=CC=C1)C1=C(O)OC2=C(C=CC=C2)C1=O
Plain Text
Mass Spec show (8.7 KB)
Taxonomy
Kingdom Organic
Classes
  • Chromones
Substructures
  • Hydroxy Compounds
  • Benzene and Derivatives
  • Chromones
  • Heterocyclic compounds
  • Aromatic compounds
  • Phenols and Derivatives
  • Ketones
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.
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).
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.
Absorption Rapidly absorbed following oral administration with considerable interindividual variations. Also absorbed percutaneously.
Volume of distribution
  • 0.14 L/kg
Protein binding 99% 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.

Enzyme Metabolite Reaction Km Vmax
Cytochrome P450 1A2 R-6-Hydroxywarfarin
Cytochrome P450 1A2 R-8-Hydroxywarfarin
Cytochrome P450 1A2 R-7-Hydroxywarfarin
Cytochrome P450 3A4 R-10-Hydroxywarfarin
Cytochrome P450 2C9 S-6-Hydroxywarfarin
Cytochrome P450 2C9 R-4'-Hydroxywarfarin
Cytochrome P450 2C8 S-4'-Hydroxywarfarin
Cytochrome P450 2C8 R-7-Hydroxywarfarin
Cytochrome P450 2C19 S-4'-Hydroxywarfarin
Cytochrome P450 2C19 R-6-Hydroxywarfarin
Cytochrome P450 2C19 R-8-Hydroxywarfarin
Cytochrome P450 1A1 R-6-Hydroxywarfarin
Cytochrome P450 1A1 R-8-Hydroxywarfarin
Cytochrome P450 1A1 R-7-Hydroxywarfarin
Cytochrome P450 2C18 S-4'-Hydroxywarfarin
Cytochrome P450 2C18 R-4'-Hydroxywarfarin
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
Pathways
Pathway Name SMPDB ID
Smp00268 Warfarin Pathway SMP00268
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
Form Route Strength
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
Prices
Unit description Cost Unit
Warfarin sodium powder 54.53 USD g
Coumadin 5 mg vial 34.07 USD vial
Coumadin 10 mg tablet 2.01 USD tablet
Coumadin 7.5 mg tablet 1.97 USD tablet
Coumadin 6 mg tablet 1.94 USD tablet
Coumadin 3 mg tablet 1.51 USD tablet
Coumadin 5 mg tablet 1.51 USD tablet
Coumadin 4 mg tablet 1.49 USD tablet
Coumadin 2.5 mg tablet 1.46 USD tablet
Coumadin 2 mg tablet 1.4 USD tablet
Coumadin 1 mg tablet 1.37 USD tablet
Warfarin sodium 10 mg tablet 1.0 USD tablet
Warfarin sodium 7.5 mg tablet 0.96 USD tablet
Jantoven 10 mg tablet 0.76 USD tablet
Jantoven 7.5 mg tablet 0.74 USD tablet
Jantoven 6 mg tablet 0.72 USD tablet
Warfarin sodium 6 mg tablet 0.68 USD tablet
Warfarin sodium 3 mg tablet 0.66 USD tablet
Warfarin sodium 4 mg tablet 0.66 USD tablet
Warfarin sodium 2.5 mg tablet 0.65 USD tablet
Warfarin sodium 5 mg tablet 0.65 USD tablet
Warfarin sodium 2 mg tablet 0.63 USD tablet
Warfarin sodium 1 mg tablet 0.61 USD tablet
Jantoven 5 mg tablet 0.59 USD tablet
Jantoven 2 mg tablet 0.56 USD tablet
Jantoven 4 mg tablet 0.56 USD tablet
Jantoven 2.5 mg tablet 0.53 USD tablet
Jantoven 3 mg tablet 0.53 USD tablet
Coumadin 10 mg Tablet 0.5 USD tablet
Jantoven 1 mg tablet 0.49 USD tablet
Coumadin 3 mg Tablet 0.43 USD tablet
Coumadin 4 mg Tablet 0.43 USD tablet
Coumadin 2 mg Tablet 0.35 USD tablet
Coumadin 1 mg Tablet 0.33 USD tablet
Taro-Warfarin 7.5 mg Tablet 0.33 USD tablet
Taro-Warfarin 6 mg Tablet 0.31 USD tablet
Apo-Warfarin 10 mg Tablet 0.28 USD tablet
Coumadin 2.5 mg Tablet 0.28 USD tablet
Coumadin 5 mg Tablet 0.28 USD tablet
Mylan-Warfarin 10 mg Tablet 0.28 USD tablet
Taro-Warfarin 10 mg Tablet 0.28 USD tablet
Warfarin 10 mg Tablet 0.28 USD tablet
Apo-Warfarin 3 mg Tablet 0.24 USD tablet
Apo-Warfarin 4 mg Tablet 0.24 USD tablet
Mylan-Warfarin 3 mg Tablet 0.24 USD tablet
Mylan-Warfarin 4 mg Tablet 0.24 USD tablet
Novo-Warfarin 3 mg Tablet 0.24 USD tablet
Novo-Warfarin 4 mg Tablet 0.24 USD tablet
Taro-Warfarin 3 mg Tablet 0.24 USD tablet
Taro-Warfarin 4 mg Tablet 0.24 USD tablet
Warfarin 3 mg Tablet 0.24 USD tablet
Warfarin 4 mg Tablet 0.24 USD tablet
Apo-Warfarin 2 mg Tablet 0.19 USD tablet
Mylan-Warfarin 2 mg Tablet 0.19 USD tablet
Novo-Warfarin 2 mg Tablet 0.19 USD tablet
Taro-Warfarin 2 mg Tablet 0.19 USD tablet
Warfarin 2 mg Tablet 0.19 USD tablet
Apo-Warfarin 1 mg Tablet 0.18 USD tablet
Mylan-Warfarin 1 mg Tablet 0.18 USD tablet
Novo-Warfarin 1 mg Tablet 0.18 USD tablet
Taro-Warfarin 1 mg Tablet 0.18 USD tablet
Warfarin 1 mg Tablet 0.18 USD tablet
Apo-Warfarin 5 mg Tablet 0.16 USD tablet
Mylan-Warfarin 5 mg Tablet 0.16 USD tablet
Novo-Warfarin 5 mg Tablet 0.16 USD tablet
Taro-Warfarin 5 mg Tablet 0.16 USD tablet
Warfarin 5 mg Tablet 0.16 USD tablet
Apo-Warfarin 2.5 mg Tablet 0.15 USD tablet
Mylan-Warfarin 2.5 mg Tablet 0.15 USD tablet
Novo-Warfarin 2.5 mg Tablet 0.15 USD tablet
Taro-Warfarin 2.5 mg Tablet 0.15 USD tablet
Warfarin 2.5 mg Tablet 0.15 USD tablet
Patents Not Available
Properties
State solid
Melting point 161 oC
Experimental Properties
Property Value Source
water solubility 17 mg/L PhysProp
logP 3 PhysProp
logS -3.89 [ADME Research, USCD] PhysProp
Caco2 permeability -4.68 [ADME Research, USCD] BiGG
pKa 5.08 Various sources
Predicted Properties
Property Value Source
water solubility 4.77e-02 g/l ALOGPS
logP 2.55 ALOGPS
logP 3.52 ChemAxon Molconvert
logS -3.81 ALOGPS
pKa 19.48 ChemAxon Molconvert
hydrogen acceptor count 4 ChemAxon Molconvert
hydrogen donor count 1 ChemAxon Molconvert
polar surface area 63.60 ChemAxon Molconvert
rotatable bond count 4 ChemAxon Molconvert
refractivity 95.99 ChemAxon Molconvert
polarizability 32.03 ChemAxon Molconvert
References
Synthesis Reference Not Available
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
External Links
Resource Link
KEGG Compound C01541 Link_out
PubChem Compound 6691 Link_out
PubChem Substance 46504711 Link_out
ChemSpider 6436 Link_out
BindingDB 50088240 Link_out
ChEBI 10033 Link_out
ChEMBL 10033 Link_out
Therapeutic Targets Database DAP000770 Link_out
PharmGKB PA451906 Link_out
Drug Product Database 2244463 Link_out
RxList http://www.rxlist.com/cgi/generic/warfarin.htm Link_out
Drugs.com http://www.drugs.com/warfarin.html Link_out
Wikipedia http://en.wikipedia.org/wiki/Warfarin Link_out
ATC Codes
  • B01AA03
AHFS Codes
  • 20:12.04.08
PDB Entries Not Available
FDA label show (641.2 KB)
MSDS show (59.5 KB)
Interactions
Drug Interactions Not Available
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.
Targets

1. Vitamin K epoxide reductase complex subunit 1

Pharmacological action: yes
Actions: inhibitor

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

Organism class: human
UniProt ID: Q9BQB6 Link_out
Gene: VKORC1 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

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
Enzymes

1. Cytochrome P450 2C9

Actions: substrate, inhibitor

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 Link_out
Gene: CYP2C9
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

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

Actions: substrate

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 Link_out
Gene: CYP1A2
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

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

Actions: substrate, inhibitor

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 Link_out
Gene: CYP2C19 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

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

Actions: substrate

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 Link_out
Gene: CYP3A4
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

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

Actions: substrate, inhibitor

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 Link_out
Gene: CYP2C8
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

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

Actions: substrate

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 Link_out
Gene: CYP2C18 Link_out
Protein Sequence: FASTA
SNPs: SNPJam Report Link_out

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

Actions: substrate

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 Link_out
Gene: CYP1A1 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

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
Carriers

1. Serum albumin

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 Link_out
Gene: ALB Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

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

Appears to function in modulating the activity of the immune system during the acute-phase reaction

UniProt ID: P02763 Link_out
Gene: ORM1 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

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 June 23, 2011 23:33

This project is supported by Genome Alberta & Genome Canada, a not-for-profit organization that is leading Canada's national genomics strategy with $600 million in funding from the federal government. This project is also supported in part by GenomeQuest, Inc., an enterprise genomic information company serving the life science community.