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Identification
NameFluorouracil
Accession NumberDB00544  (APRD00516, EXPT03204)
TypeSmall Molecule
GroupsApproved
Description

A pyrimidine analog that is an antineoplastic antimetabolite. It interferes with DNA synthesis by blocking the thymidylate synthetase conversion of deoxyuridylic acid to thymidylic acid. [PubChem]

Structure
Thumb
Synonyms
SynonymLanguageCode
5-FluoracilNot AvailableNot Available
5-Fluoropyrimidine-2,4-dioneNot AvailableNot Available
5-FluorouracilNot AvailableNot Available
5-FluracilNot AvailableNot Available
5-FUNot AvailableNot Available
Fluoro UracilNot AvailableNot Available
FluorouracilNot AvailableNot Available
FluorouraciloNot AvailableNot Available
FluorouracilumNot AvailableNot Available
FluouracilNot AvailableNot Available
FUNot AvailableNot Available
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Caraccream5 mg/gtopicalDermik Laboratories2000-10-272015-11-30Us 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Efudexcream2 g/40gtopicalValeant Pharmaceuticals North America LLC1970-07-29Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Caraccream5 mg/gtopicalValeant Pharmaceuticals North America LLC2013-06-28Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Fluorouracilcream5 mg/gtopicalMylan Pharmaceuticals Inc.2013-07-23Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Fluoroplexcream10 mg/gtopicalAqua Pharmaceuticals, LLC1993-12-03Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Fluorouracilsolution50 mg/mLtopicalSolco Healthcare US LLC2010-06-01Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Fluorouracilsolution20 mg/mLtopicalSolco Healthcare US LLC2010-06-01Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Fluorouracilcream5 mg/gtopicalSpear Dermatology Products Inc2014-10-28Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Fluorouracilinjection, solution50 mg/mLintravenousPfizer Laboratories Div Pfizer Inc.2012-07-18Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Fluorouracilinjection, solution50 mg/mLintravenousPfizer Laboratories Div Pfizer Inc.2012-07-18Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Fluorouracilinjection, solution50 mg/mLintravenousPfizer Laboratories Div Pfizer Inc.2012-07-18Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Fluorouracilinjection, solution50 mg/mLintravenousPfizer Laboratories Div Pfizer Inc.2012-07-18Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Adrucilinjection50 mg/mLintravenousTeva Parenteral Medicines, Inc.2003-10-01Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Adrucilinjection2.5 g/50mLintravenousTeva Parenteral Medicines, Inc.2003-10-01Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Adrucilinjection5 g/100mLintravenousTeva Parenteral Medicines, Inc.2003-10-01Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Fluorouracilinjection, solution50 mg/mLintravenousAccord Healthcare, Inc.2014-02-01Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Fluorouracilinjection, solution50 mg/mLintravenousAccord Healthcare, Inc.2014-02-01Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Fluorouracilcream50 mg/gtopicalRebel Distributors Corp2008-04-11Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Fluorouracilsolution20 mg/mLtopicalTaro Pharmaceuticals U.S.A., Inc.2003-11-05Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Fluorouracilsolution50 mg/mLtopicalTaro Pharmaceuticals U.S.A., Inc.2003-11-05Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Fluorouracilcream50 mg/gtopicalTaro Pharmaceuticals U.S.A., Inc.2010-03-05Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Fluorouracilcream50 mg/gtopicalTaro Pharmaceutical Industries Ltd.2010-03-05Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Fluorouracilcream50 mg/gtopicalPhysicians Total Care, Inc.2011-09-06Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Fluorouracilinjection, solution50 mg/mLintravenousFresenius Kabi USA, LLC2000-07-12Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Fluorouracilinjection, solution50 mg/mLintravenousFresenius Kabi USA, LLC2000-07-12Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Fluorouracilinjection, solution50 mg/mLintravenousFresenius Kabi USA, LLC2000-07-12Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Fluorouracilinjection, solution50 mg/mLintravenousFresenius Kabi USA, LLC2000-07-12Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Fluorouracilinjection, solution50 mg/mLintravenousFresenius Kabi USA, LLC2000-07-12Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Fluorouracilinjection, solution50 mg/mLintravenousFresenius Kabi USA, LLC2000-07-12Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Fluorouracilcream50 mg/gtopicalSpear Dermatology Products2008-04-11Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Fluorouracilinjection, solution50 mg/mLintravenousSandoz Inc2008-09-10Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Fluorouracilinjection, solution50 mg/mLintravenousSandoz Inc2011-05-02Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Fluorouracilinjection, solution50 mg/mLintravenousBlue Point Laboratories2014-12-15Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Fluorouracilinjection, solution50 mg/mLintravenousBlue Point Laboratories2014-12-16Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Over the Counter ProductsNot Available
International Brands
NameCompany
CarzonalTobishi
EfudixMeda
EfurixValeant
FtoruracilVerofarm
Brand mixturesNot Available
SaltsNot Available
Categories
CAS number51-21-8
WeightAverage: 130.0772
Monoisotopic: 130.017855555
Chemical FormulaC4H3FN2O2
InChI KeyGHASVSINZRGABV-UHFFFAOYSA-N
InChI
InChI=1S/C4H3FN2O2/c5-2-1-6-4(9)7-3(2)8/h1H,(H2,6,7,8,9)
IUPAC Name
5-fluoro-1,2,3,4-tetrahydropyrimidine-2,4-dione
SMILES
FC1=CNC(=O)NC1=O
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as halopyrimidines. These are aromatic compounds containing a halogen atom linked to a pyrimidine ring. Pyrimidine is a 6-membered ring consisting of four carbon atoms and two nitrogen centers at the 1- and 3- ring positions.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassDiazines
Sub ClassPyrimidines and pyrimidine derivatives
Direct ParentHalopyrimidines
Alternative Parents
Substituents
  • Pyrimidone
  • Halopyrimidine
  • Hydropyrimidine
  • Aryl halide
  • Aryl fluoride
  • Heteroaromatic compound
  • Vinylogous amide
  • Urea
  • Lactam
  • Azacycle
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Organofluoride
  • Organohalogen compound
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Pharmacology
IndicationFor the topical treatment of multiple actinic or solar keratoses. In the 5% strength it is also useful in the treatment of superficial basal cell carcinomas when conventional methods are impractical, such as with multiple lesions or difficult treatment sites. Fluorouracil injection is indicated in the palliative management of some types of cancer, including colon, esophageal, gastric, rectum, breast, biliary tract, stomach, head and neck, cervical, pancreas, renal cell, and carcinoid.
PharmacodynamicsFluorouracil is an antineoplastic anti-metabolite. Anti-metabolites masquerade as purine or pyrimidine - which become the building blocks of DNA. They prevent these substances from becoming incorporated into DNA during the "S" phase (of the cell cycle), stopping normal development and division. Fluorouracil blocks an enzyme which converts the cytosine nucleotide into the deoxy derivative. In addition, DNA synthesis is further inhibited because Fluorouracil blocks the incorporation of the thymidine nucleotide into the DNA strand.
Mechanism of actionThe precise mechanism of action has not been fully determined, but the main mechanism of fluorouracil is thought to be the binding of the deoxyribonucleotide of the drug (FdUMP) and the folate cofactor, N5–10-methylenetetrahydrofolate, to thymidylate synthase (TS) to form a covalently bound ternary complex. This results in the inhibition of the formation of thymidylate from uracil, which leads to the inhibition of DNA and RNA synthesis and cell death. Fluorouracil can also be incorporated into RNA in place of uridine triphosphate (UTP), producing a fraudulent RNA and interfering with RNA processing and protein synthesis.
Absorption28-100%
Volume of distributionNot Available
Protein binding8-12%
Metabolism

Hepatic. The catabolic metabolism of fluorouracil results in degradation products ( e.g., CO2, urea and α-fluoro-ß-alanine) which are inactive.

Route of eliminationSeven percent to 20% of the parent drug is excreted unchanged in the urine in 6 hours; of this over 90% is excreted in the first hour. The remaining percentage of the administered dose is metabolized, primarily in the liver.
Half life10-20 minutes
ClearanceNot Available
ToxicityLD50=230mg/kg (orally in mice)
Affected organisms
  • Humans and other mammals
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug Reactions
Interacting Gene/EnzymeSNP RS IDAllele nameDefining changeAdverse ReactionReference(s)
Thymidylate synthase
Gene symbol: TYMS
UniProt: P04818
rs34743033 TSER*2Not AvailableNeutropenia, diarrhea16818689
Uridine 5'-monophosphate synthase
Gene symbol: UMPS
UniProt: P11172
rs1801019 Not AvailableC AlleleNeutropenia, diarrhea16818689
Dihydropyrimidine dehydrogenase [NADP(+)]
Gene symbol: DPYD
UniProt: Q12882
rs1801265 Not AvailableC alleleNausea, vomiting, reduced white cell count17848752
Dihydropyrimidine dehydrogenase [NADP(+)]
Gene symbol: DPYD
UniProt: Q12882
rs1801159 Not AvailableG alleleNausea, vomiting, reduced white cell count17848752
Glutathione S-transferase P
Gene symbol: GSTP1
UniProt: P09211
rs1695 Not AvailableA alleleHematological toxicity, gastrointestinal toxicity18540691
Dihydropyrimidine dehydrogenase [NADP(+)]
Gene symbol: DPYD
UniProt: Q12882
rs3918290 Not AvailableA alleleLeukopenia, diarrhea, mucositis18299612
Dihydropyrimidine dehydrogenase [NADP(+)]
Gene symbol: DPYD
UniProt: Q12882
rs67376798 Not AvailableT > APatients are at a higher risk of toxicity23603345
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9605
Blood Brain Barrier+0.9791
Caco-2 permeable-0.7583
P-glycoprotein substrateNon-substrate0.7752
P-glycoprotein inhibitor INon-inhibitor0.8991
P-glycoprotein inhibitor IINon-inhibitor1.0
Renal organic cation transporterNon-inhibitor0.9053
CYP450 2C9 substrateNon-substrate0.7898
CYP450 2D6 substrateNon-substrate0.9116
CYP450 3A4 substrateNon-substrate0.7558
CYP450 1A2 substrateNon-inhibitor0.9045
CYP450 2C9 substrateNon-inhibitor0.9658
CYP450 2D6 substrateNon-inhibitor0.9361
CYP450 2C19 substrateNon-inhibitor0.9688
CYP450 3A4 substrateNon-inhibitor0.9661
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9839
Ames testNon AMES toxic0.8941
CarcinogenicityNon-carcinogens0.9288
BiodegradationNot ready biodegradable0.922
Rat acute toxicity2.2529 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9685
hERG inhibition (predictor II)Non-inhibitor0.9325
Pharmacoeconomics
Manufacturers
  • Sanofi aventis us llc
  • Valeant pharmaceuticals international
  • Allergan herbert skin care div allergan inc
  • Spear pharmaceuticals inc
  • Taro pharmaceutical industries ltd
  • Pharmacia and upjohn co
  • Teva parenteral medicines inc
  • Abic ltd
  • Abraxis pharmaceutical products
  • App pharmaceuticals llc
  • Bedford laboratories div ben venue laboratories inc
  • Bioniche pharma usa llc
  • Ebewe pharma ges mbh nfg kg
  • Marchar laboratories inc ltd
  • Smith and nephew solopak div smith and nephew
  • Watson laboratories inc
  • Elorac inc
  • Taro pharmaceuticals usa inc
Packagers
Dosage forms
FormRouteStrength
Creamtopical10 mg/g
Creamtopical2 g/40g
Creamtopical5 mg/g
Creamtopical50 mg/g
Injectionintravenous2.5 g/50mL
Injectionintravenous5 g/100mL
Injectionintravenous50 mg/mL
Injection, solutionintravenous50 mg/mL
Solutiontopical20 mg/mL
Solutiontopical50 mg/mL
Prices
Unit descriptionCostUnit
Efudex 5% Cream 40 gm Tube478.39USD tube
Fluoroplex 1% Cream 30 gm Tube268.61USD tube
Fluorouracil 5% Cream 40 gm Tube249.98USD tube
Carac 0.5% Cream 30 gm Tube209.77USD tube
Efudex 5% Solution 10ml Bottle136.51USD bottle
Fluorouracil 5% Solution 10ml Bottle115.78USD bottle
Fluorouracil 2% Solution 10ml Bottle78.63USD bottle
Efudex 5% cream10.28USD g
Fluorouracil 5% cream9.62USD g
Fluorouracil powder8.45USD g
Fluoroplex 1% cream7.85USD g
Carac cream6.43USD g
Efudex 50 mg/g Cream0.9USD g
Fluorouracil 50 mg/ml Solution0.52USD ml
Adrucil 50 mg/ml vial0.4USD ml
Fluorouracil 5000 mg/100 ml0.28USD ml
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
CountryPatent NumberApprovedExpires (estimated)
United States66703352001-06-022021-06-02
Properties
StateSolid
Experimental Properties
PropertyValueSource
melting point282-283Heidelberger, C. and Duschinsky, R.; US. Patent 2,802,005; August 6, 1957. Heidelberger, C. and Duschinsky, R.; U.S.Patent 2,885,396; May 5, 1959.
water solubility1.11E+004 mg/L (at 22 °C)BURR,A & BUNDGAARD,H (1985)
logP-0.89HANSCH,C ET AL. (1995)
logS-1.07ADME Research, USCD
pKa8.02SANGSTER (1994)
Predicted Properties
PropertyValueSource
Water Solubility5.86 mg/mLALOGPS
logP-0.58ALOGPS
logP-0.66ChemAxon
logS-1.4ALOGPS
pKa (Strongest Acidic)7.76ChemAxon
pKa (Strongest Basic)-8ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area58.2 Å2ChemAxon
Rotatable Bond Count0ChemAxon
Refractivity26.17 m3·mol-1ChemAxon
Polarizability9.46 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Download (7.93 KB)
SpectraMS/MSMS1D NMR
References
Synthesis Reference

Leroy B. Townsend, Robert A. Earl, Steven J. Manning, “Method of synthesizing 1-(tetrahydro-2-furanyl)-5-fluorouracil.” U.S. Patent US3960864, issued October, 1969.

US3960864
General Reference
  1. Longley DB, Harkin DP, Johnston PG: 5-fluorouracil: mechanisms of action and clinical strategies. Nat Rev Cancer. 2003 May;3(5):330-8. Pubmed
  2. Petty RD, Cassidy J: Novel fluoropyrimidines: improving the efficacy and tolerability of cytotoxic therapy. Curr Cancer Drug Targets. 2004 Mar;4(2):191-204. Pubmed
External Links
ATC CodesL01BC02
AHFS Codes
  • 10:00.00
  • 84:92.00
PDB Entries
FDA labelDownload (378 KB)
MSDSDownload (74 KB)
Interactions
Drug InteractionsNot Available
Food InteractionsNot Available

Targets

1. Thymidylate synthase

Kind: protein

Organism: Human

Pharmacological action: yes

Actions: other/unknown

Components

Name UniProt ID Details
Thymidylate synthase P04818 Details

References:

  1. Formentini A, Sander S, Denzer S, Straeter J, Henne-Bruns D, Kornmann M: Thymidylate synthase expression in resectable and unresectable pancreatic cancer: role as predictive or prognostic marker? Int J Colorectal Dis. 2007 Jan;22(1):49-55. Epub 2006 Mar 15. Pubmed
  2. Huang CL, Yokomise H, Fukushima M, Kinoshita M: Tailor-made chemotherapy for non-small cell lung cancer patients. Future Oncol. 2006 Apr;2(2):289-99. Pubmed
  3. Fernandez-Contreras ME, Sanchez-Prudencio S, Sanchez-Hernandez JJ, Garcia de Paredes ML, Gisbert JP, Roda-Navarro P, Gamallo C: Thymidylate synthase expression pattern, expression level and single nucleotide polymorphism are predictors for disease-free survival in patients of colorectal cancer treated with 5-fluorouracil. Int J Oncol. 2006 May;28(5):1303-10. Pubmed
  4. Garcia V, Garcia JM, Pena C, Silva J, Dominguez G, Hurtado A, Alonso I, Rodriguez R, Provencio M, Bonilla F: Thymidylate synthase messenger RNA expression in plasma from patients with colon cancer: prognostic potential. Clin Cancer Res. 2006 Apr 1;12(7 Pt 1):2095-100. Pubmed
  5. Ploylearmsaeng SA, Fuhr U, Jetter A: How may anticancer chemotherapy with fluorouracil be individualised? Clin Pharmacokinet. 2006;45(6):567-92. Pubmed
  6. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. Pubmed
  7. Rustum YM: Thymidylate synthase: a critical target in cancer therapy? Front Biosci. 2004 Sep 1;9:2467-73. Pubmed

2. DNA

Kind: nucleotide

Organism: Human

Pharmacological action: yes

Actions: incorporation into and destabilization

Components

Name UniProt ID Details

References:

  1. Wyatt MD, Wilson DM 3rd: Participation of DNA repair in the response to 5-fluorouracil. Cell Mol Life Sci. 2009 Mar;66(5):788-99. Pubmed
  2. Ghoshal K, Jacob ST: An alternative molecular mechanism of action of 5-fluorouracil, a potent anticancer drug. Biochem Pharmacol. 1997 Jun 1;53(11):1569-75. Pubmed
  3. Longley DB, Harkin DP, Johnston PG: 5-fluorouracil: mechanisms of action and clinical strategies. Nat Rev Cancer. 2003 May;3(5):330-8. Pubmed
  4. Petty RD, Cassidy J: Novel fluoropyrimidines: improving the efficacy and tolerability of cytotoxic therapy. Curr Cancer Drug Targets. 2004 Mar;4(2):191-204. Pubmed

3. RNA

Kind: nucleotide

Organism: Human

Pharmacological action: yes

Actions: incorporation into and destabilization

Components

Name UniProt ID Details

References:

  1. Wyatt MD, Wilson DM 3rd: Participation of DNA repair in the response to 5-fluorouracil. Cell Mol Life Sci. 2009 Mar;66(5):788-99. Pubmed
  2. Ghoshal K, Jacob ST: An alternative molecular mechanism of action of 5-fluorouracil, a potent anticancer drug. Biochem Pharmacol. 1997 Jun 1;53(11):1569-75. Pubmed
  3. Longley DB, Harkin DP, Johnston PG: 5-fluorouracil: mechanisms of action and clinical strategies. Nat Rev Cancer. 2003 May;3(5):330-8. Pubmed
  4. Petty RD, Cassidy J: Novel fluoropyrimidines: improving the efficacy and tolerability of cytotoxic therapy. Curr Cancer Drug Targets. 2004 Mar;4(2):191-204. Pubmed

Enzymes

1. Cytochrome P450 1A2

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: substrate

Components

Name UniProt ID Details
Cytochrome P450 1A2 P05177 Details

References:

  1. 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. Thymidine phosphorylase

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: substrate

Components

Name UniProt ID Details
Thymidine phosphorylase P19971 Details

References:

  1. Scartozzi M, Maccaroni E, Giampieri R, Pistelli M, Bittoni A, Del Prete M, Berardi R, Cascinu S: 5-Fluorouracil pharmacogenomics: still rocking after all these years? Pharmacogenomics. 2011 Feb;12(2):251-65. Pubmed

3. Cytochrome P450 2C9

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: inhibitor

Components

Name UniProt ID Details
Cytochrome P450 2C9 P11712 Details

References:

  1. 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. Dihydropyrimidine dehydrogenase [NADP(+)]

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: substrate

Components

Name UniProt ID Details
Dihydropyrimidine dehydrogenase [NADP(+)] Q12882 Details

References:

  1. Ho DH, Townsend L, Luna MA, Bodey GP: Distribution and inhibition of dihydrouracil dehydrogenase activities in human tissues using 5-fluorouracil as a substrate. Anticancer Res. 1986 Jul-Aug;6(4):781-4. Pubmed
  2. Keizer HJ, De Bruijn EA, Tjaden UR, De Clercq E: Inhibition of fluorouracil catabolism in cancer patients by the antiviral agent (E)-5-(2-bromovinyl)-2’-deoxyuridine. J Cancer Res Clin Oncol. 1994;120(9):545-9. Pubmed

5. Uridine phosphorylase 1

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: substrate

Components

Name UniProt ID Details
Uridine phosphorylase 1 Q16831 Details

References:

  1. Yan R, Wan L, Pizzorno G, Cao D: Uridine phosphorylase in breast cancer: a new prognostic factor? Front Biosci. 2006 Sep 1;11:2759-66. Pubmed

6. Uridine phosphorylase 2

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: substrate

Components

Name UniProt ID Details
Uridine phosphorylase 2 O95045 Details

References:

  1. Yan R, Wan L, Pizzorno G, Cao D: Uridine phosphorylase in breast cancer: a new prognostic factor? Front Biosci. 2006 Sep 1;11:2759-66. Pubmed

7. Cytochrome P450 2A6

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: substrate

Components

Name UniProt ID Details
Cytochrome P450 2A6 P11509 Details

References:

  1. 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

8. Cytochrome P450 2C8

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: substrate

Components

Name UniProt ID Details
Cytochrome P450 2C8 P10632 Details

References:

  1. 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

9. Methylenetetrahydrofolate reductase

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: substrate

Components

Name UniProt ID Details
Methylenetetrahydrofolate reductase P42898 Details

References:

  1. Scartozzi M, Maccaroni E, Giampieri R, Pistelli M, Bittoni A, Del Prete M, Berardi R, Cascinu S: 5-Fluorouracil pharmacogenomics: still rocking after all these years? Pharmacogenomics. 2011 Feb;12(2):251-65. Pubmed

10. Thymidylate synthase

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: substrate

Components

Name UniProt ID Details
Thymidylate synthase P04818 Details

References:

  1. Scartozzi M, Maccaroni E, Giampieri R, Pistelli M, Bittoni A, Del Prete M, Berardi R, Cascinu S: 5-Fluorouracil pharmacogenomics: still rocking after all these years? Pharmacogenomics. 2011 Feb;12(2):251-65. Pubmed

11. Uridine 5'-monophosphate synthase

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: substrate

Components

Name UniProt ID Details
Uridine 5'-monophosphate synthase P11172 Details

References:

  1. https://www.pharmgkb.org/pathway/PA150653776

12. Amidophosphoribosyltransferase

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: substrate

Components

Name UniProt ID Details
Amidophosphoribosyltransferase Q06203 Details

References:

  1. https://www.pharmgkb.org/pathway/PA150653776

Carriers

1. Serum albumin

Kind: protein

Organism: Human

Pharmacological action: no

Components

Name UniProt ID Details
Serum albumin P02768 Details

References:

  1. Sulkowska A, Bojko B, Rownicka J, Sulkowski W: Competition of drugs to serum albumin in combination therapy. Biopolymers. 2004 Jun 15;74(3):256-62. Pubmed
  2. Bertucci C, Ascoli G, Uccello-Barretta G, Di Bari L, Salvadori P: The binding of 5-fluorouracil to native and modified human serum albumin: UV, CD, and 1H and 19F NMR investigation. J Pharm Biomed Anal. 1995 Aug;13(9):1087-93. Pubmed

Transporters

1. Solute carrier family 22 member 7

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: substrate

Components

Name UniProt ID Details
Solute carrier family 22 member 7 Q9Y694 Details

References:

  1. Kobayashi Y, Ohshiro N, Sakai R, Ohbayashi M, Kohyama N, Yamamoto T: Transport mechanism and substrate specificity of human organic anion transporter 2 (hOat2 [SLC22A7]). J Pharm Pharmacol. 2005 May;57(5):573-8. Pubmed

2. Equilibrative nucleoside transporter 1

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: substrate

Components

Name UniProt ID Details
Equilibrative nucleoside transporter 1 Q99808 Details

References:

  1. Tsujie M, Nakamori S, Nakahira S, Takahashi Y, Hayashi N, Okami J, Nagano H, Dono K, Umeshita K, Sakon M, Monden M: Human equilibrative nucleoside transporter 1, as a predictor of 5-fluorouracil resistance in human pancreatic cancer. Anticancer Res. 2007 Jul-Aug;27(4B):2241-9. Pubmed

3. ATP-binding cassette sub-family G member 2

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: substrate

Components

Name UniProt ID Details
ATP-binding cassette sub-family G member 2 Q9UNQ0 Details

References:

  1. Yuan J, Lv H, Peng B, Wang C, Yu Y, He Z: Role of BCRP as a biomarker for predicting resistance to 5-fluorouracil in breast cancer. Cancer Chemother Pharmacol. 2009 May;63(6):1103-10. doi: 10.1007/s00280-008-0838-z. Epub 2008 Sep 27. Pubmed

4. Canalicular multispecific organic anion transporter 2

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: substrate

Components

Name UniProt ID Details
Canalicular multispecific organic anion transporter 2 O15438 Details

References:

  1. Hagmann W, Jesnowski R, Faissner R, Guo C, Lohr JM: ATP-binding cassette C transporters in human pancreatic carcinoma cell lines. Upregulation in 5-fluorouracil-resistant cells. Pancreatology. 2009;9(1-2):136-44. doi: 10.1159/000178884. Epub 2008 Dec 13. Pubmed

5. Multidrug resistance-associated protein 4

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: substrate

Components

Name UniProt ID Details
Multidrug resistance-associated protein 4 O15439 Details

References:

  1. Hagmann W, Jesnowski R, Faissner R, Guo C, Lohr JM: ATP-binding cassette C transporters in human pancreatic carcinoma cell lines. Upregulation in 5-fluorouracil-resistant cells. Pancreatology. 2009;9(1-2):136-44. doi: 10.1159/000178884. Epub 2008 Dec 13. Pubmed

6. Multidrug resistance-associated protein 5

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: substrate

Components

Name UniProt ID Details
Multidrug resistance-associated protein 5 O15440 Details

References:

  1. Hagmann W, Jesnowski R, Faissner R, Guo C, Lohr JM: ATP-binding cassette C transporters in human pancreatic carcinoma cell lines. Upregulation in 5-fluorouracil-resistant cells. Pancreatology. 2009;9(1-2):136-44. doi: 10.1159/000178884. Epub 2008 Dec 13. Pubmed

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Drug created on June 13, 2005 07:24 / Updated on September 16, 2013 17:11