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Showing metabocard for Floxuridine (HMDB0014467)

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IdentificationTaxonomyOntologyPhysical propertiesSpectraBiological propertiesConcentrationsLinksReferencesenzymes (6) Show 6 proteinsXML
enzymes (6) Show 6 proteins
Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:49 UTC
Update Date2020-02-26 21:39:43 UTC
HMDB IDHMDB0014467
Secondary Accession Numbers
  • HMDB14467
Metabolite Identification
Common NameFloxuridine
DescriptionFloxuridine, also known as 5FDU or FUDR, belongs to the class of organic compounds known as pyrimidine 2'-deoxyribonucleosides. Pyrimidine 2'-deoxyribonucleosides are compounds consisting of a pyrimidine linked to a ribose which lacks a hydroxyl group at position 2. Floxuridine is a drug which is used for palliative management of gastrointestinal adenocarcinoma metastatic to the liver, when given by continuous regional intra-arterial infusion in carefully selected patients who are considered incurable by surgery or other means. also for the palliative management of liver cancer (usually administered by hepatic intra-arterial infusion). Floxuridine is available as a sterile, nonpyrogenic, lyophilized powder for reconstitution. An antineoplastic antimetabolite that is metabolized to fluorouracil when administered by rapid injection. Floxuridine is an anti-metabolite or a pyrimidine analog that works by disrupting the process S-phase of cell division, selectively targeting rapidly dividing cells. Floxuridine is an extremely weak basic (essentially neutral) compound (based on its pKa). Floxuridine exists in all living organisms, ranging from bacteria to humans. 5-Fluorouracil primarily works by interfering with DNA synthesis; however, it may also inhibit the formation of fraudulent RNA via physical incorporation into the RNA. After successful biotransformation, floxuridine is converted into an active component, flurouracil, which blocks the enzyme which converts cytosine nucleosides into the deoxy derivative. Oral, rat LD50: 215 mg/kg.
Structure
Data?1582753183
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
1-(2-Deoxy-beta-D-ribofuranosyl)-5-fluorouracilChEBI
1-beta-D-2'-Deoxyribofuranosyl-5-flurouracilChEBI
1beta-D-2'-Deoxyribofuranosyl-5-flurouracilChEBI
2'-Deoxy-5-fluorouridineChEBI
5-Fluoro-2'-deoxyuridineChEBI
5-Fluoro-2-desoxyuridineChEBI
5-FluorodeoxyuridineChEBI
5-Fluorouracil 2'-deoxyribosideChEBI
5-Fluorouracil deoxyribosideChEBI
5FDUChEBI
beta-5-Fluoro-2'-deoxyuridineChEBI
DeoxyfluorouridineChEBI
FdUChEBI
FloxiridinaChEBI
FloxuridinChEBI
FloxuridinumChEBI
FluorodeoxyuridineChEBI
Fluoruridine deoxyriboseChEBI
FUDRKegg
1-(2-Deoxy-b-D-ribofuranosyl)-5-fluorouracilGenerator
1-(2-Deoxy-β-D-ribofuranosyl)-5-fluorouracilGenerator
1-b-D-2'-Deoxyribofuranosyl-5-flurouracilGenerator
1-Β-D-2'-deoxyribofuranosyl-5-flurouracilGenerator
1b-D-2'-Deoxyribofuranosyl-5-flurouracilGenerator
1Β-D-2'-deoxyribofuranosyl-5-flurouracilGenerator
b-5-Fluoro-2'-deoxyuridineGenerator
Β-5-fluoro-2'-deoxyuridineGenerator
5 FluorodeoxyuridineHMDB
FDURHMDB
FDURDHMDB
5-FUdRHMDB
Chemical FormulaC9H11FN2O5
Average Molecular Weight246.1924
Monoisotopic Molecular Weight246.065199677
IUPAC Name5-fluoro-1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-1,2,3,4-tetrahydropyrimidine-2,4-dione
Traditional Namefloxuridine
CAS Registry Number50-91-9
SMILES
OC[C@H]1O[C@H](C[C@@H]1O)N1C=C(F)C(=O)NC1=O
InChI Identifier
InChI=1S/C9H11FN2O5/c10-4-2-12(9(16)11-8(4)15)7-1-5(14)6(3-13)17-7/h2,5-7,13-14H,1,3H2,(H,11,15,16)/t5-,6+,7+/m0/s1
InChI KeyODKNJVUHOIMIIZ-RRKCRQDMSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as pyrimidine 2'-deoxyribonucleosides. Pyrimidine 2'-deoxyribonucleosides are compounds consisting of a pyrimidine linked to a ribose which lacks a hydroxyl group at position 2.
KingdomOrganic compounds
Super ClassNucleosides, nucleotides, and analogues
ClassPyrimidine nucleosides
Sub ClassPyrimidine 2'-deoxyribonucleosides
Direct ParentPyrimidine 2'-deoxyribonucleosides
Alternative Parents
Substituents
  • Pyrimidine 2'-deoxyribonucleoside
  • Halopyrimidine
  • Hydroxypyrimidine
  • Pyrimidone
  • Aryl fluoride
  • Aryl halide
  • Hydropyrimidine
  • Pyrimidine
  • Heteroaromatic compound
  • Tetrahydrofuran
  • Secondary alcohol
  • Oxacycle
  • Organoheterocyclic compound
  • Azacycle
  • Alcohol
  • Hydrocarbon derivative
  • Primary alcohol
  • Organooxygen compound
  • Organonitrogen compound
  • Organofluoride
  • Organohalogen compound
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Organic nitrogen compound
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Ontology
Disposition

Biological location:

Role

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point150.5 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility40.8 g/LNot Available
LogP-1.4Not Available
Predicted Properties
PropertyValueSource
Water Solubility40.8 g/LALOGPS
logP-1.2ALOGPS
logP-1.3ChemAxon
logS-0.78ALOGPS
pKa (Strongest Acidic)7.68ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area99.1 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity51.26 m³·mol⁻¹ChemAxon
Polarizability20.78 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-00lr-9600000000-155a97133c7827d2a1ceSpectrum
GC-MSGC-MS Spectrum - CI-B (Non-derivatized)splash10-001i-3900000000-44f00976f508bab47f36Spectrum
GC-MSGC-MS Spectrum - CI-B (Non-derivatized)splash10-00kb-2910000000-2efae68e874a5fdba01cSpectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-00lr-9600000000-155a97133c7827d2a1ceSpectrum
GC-MSGC-MS Spectrum - CI-B (Non-derivatized)splash10-001i-3900000000-44f00976f508bab47f36Spectrum
GC-MSGC-MS Spectrum - CI-B (Non-derivatized)splash10-00kb-2910000000-2efae68e874a5fdba01cSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0036-9340000000-625fd93cccce9bbf8234Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-0gk9-8926000000-e5bea4ee2a8fa95520d5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-0900000000-e75f17c5e6c58cb63cc4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001i-1900000000-ab9d2ecf3f514e6cd7fdSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-01q9-7900000000-5b44e036090ffa5616c4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0ikd-5890000000-537ea470ce67d29de875Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-056r-2930000000-9edc79b79e109479fd9bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9200000000-8d9d5de0ec79de7d99fdSpectrum
Biological Properties
Cellular Locations
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue Locations
  • Kidney
  • Liver
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00322 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00322 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00322
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID5586
KEGG Compound IDC11736
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkFloxuridine
METLIN IDNot Available
PubChem Compound5790
PDB IDNot Available
ChEBI ID60761
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB ID
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

Enzyme Details
1. Cytochrome P450 2C9
General function:
Involved in monooxygenase activity
Specific function:
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.
Gene Name:
CYP2C9
Uniprot ID:
P11712
Molecular weight:
55627.365
References
  1. Konishi H, Morita K, Minouchi T, Nakajima M, Matsuda M, Yamaji A: Probable metabolic interaction of doxifluridine with phenytoin. Ann Pharmacother. 2002 May;36(5):831-4. [PubMed:11978162 ]
  2. Konishi H, Yoshimoto T, Morita K, Minouchi T, Sato T, Yamaji A: Depression of phenytoin metabolic capacity by 5-fluorouracil and doxifluridine in rats. J Pharm Pharmacol. 2003 Jan;55(1):143-9. [PubMed:12625878 ]
Enzyme Details
2. Cytochrome P450 2A6
General function:
Involved in monooxygenase activity
Specific function:
Exhibits a high coumarin 7-hydroxylase activity. Can act in the hydroxylation of the anti-cancer drugs cyclophosphamide and ifosphamide. Competent in the metabolic activation of aflatoxin B1. Constitutes the major nicotine C-oxidase. Acts as a 1,4-cineole 2-exo-monooxygenase. Possesses low phenacetin O-deethylation activity.
Gene Name:
CYP2A6
Uniprot ID:
P11509
Molecular weight:
56517.005
References
  1. Ozawa S, Hamada M, Murayama N, Nakajima Y, Kaniwa N, Matsumoto Y, Fukuoka M, Sawada J, Ohno Y: Cytosolic and microsomal activation of doxifluridine and tegafur to produce 5-fluorouracil in human liver. Cancer Chemother Pharmacol. 2002 Dec;50(6):454-8. Epub 2002 Oct 26. [PubMed:12451471 ]
Enzyme Details
3. Thymidine kinase, cytosolic
General function:
Nucleotide transport and metabolism
Specific function:
Not Available
Gene Name:
TK1
Uniprot ID:
P04183
Molecular weight:
25468.455
Reactions
Floxuridine + Adenosine triphosphate → 5-Fluorodeoxyuridine monophosphate + ADPdetails
Enzyme Details
4. Thymidine kinase 2, mitochondrial
General function:
Involved in ATP binding
Specific function:
Deoxyribonucleoside kinase that phosphorylates thymidine, deoxycytidine, and deoxyuridine. Also phosphorylates anti-viral and anti-cancer nucleoside analogs.
Gene Name:
TK2
Uniprot ID:
O00142
Molecular weight:
27561.495
Reactions
Floxuridine + Adenosine triphosphate → 5-Fluorodeoxyuridine monophosphate + ADPdetails
Enzyme Details
5. Thymidine phosphorylase
General function:
Involved in transferase activity, transferring glycosyl groups
Specific function:
May have a role in maintaining the integrity of the blood vessels. Has growth promoting activity on endothelial cells, angiogenic activity in vivo and chemotactic activity on endothelial cells in vitro. Catalyzes the reversible phosphorolysis of thymidine. The produced molecules are then utilized as carbon and energy sources or in the rescue of pyrimidine bases for nucleotide synthesis.
Gene Name:
TYMP
Uniprot ID:
P19971
Molecular weight:
49954.965
Reactions
Fluorouracil + Deoxyribose 1-phosphate → Floxuridine + Phosphatedetails
References
  1. Hara Y: [5'-Deoxy-5-fluorouridine enzymatic activation from the masked compound to 5-fluorouracil in human malignant tissues]. Gan To Kagaku Ryoho. 1984 Oct;11(10):2133-43. [PubMed:6237613 ]
  2. Ozawa S, Hamada M, Murayama N, Nakajima Y, Kaniwa N, Matsumoto Y, Fukuoka M, Sawada J, Ohno Y: Cytosolic and microsomal activation of doxifluridine and tegafur to produce 5-fluorouracil in human liver. Cancer Chemother Pharmacol. 2002 Dec;50(6):454-8. Epub 2002 Oct 26. [PubMed:12451471 ]
  3. Sadahiro S, Otani Y, Oya K, Ike H, Shimada H, Yamaguchi S, Hiki Y, Fujita H, Mitomi T: Thymidine phosphorylase expression and effect of doxifluridine: a phase II study. Oncol Rep. 2001 Jul-Aug;8(4):753-8. [PubMed:11410777 ]
Enzyme Details
6. Thymidylate synthase
General function:
Involved in thymidylate synthase activity
Specific function:
Contributes to the de novo mitochondrial thymidylate biosynthesis pathway.
Gene Name:
TYMS
Uniprot ID:
P04818
Molecular weight:
35715.65
References
  1. Ferguson PJ, Collins O, Dean NM, DeMoor J, Li CS, Vincent MD, Koropatnick J: Antisense down-regulation of thymidylate synthase to suppress growth and enhance cytotoxicity of 5-FUdR, 5-FU and Tomudex in HeLa cells. Br J Pharmacol. 1999 Aug;127(8):1777-86. [PubMed:10482907 ]
  2. Kubota T: [Theoretical basis for low-dose CDDP/5-FU therapy]. Gan To Kagaku Ryoho. 1999 Oct;26(11):1536-41. [PubMed:10553409 ]
  3. Kuwa K, Sakamoto S, Sassa S, Yoshimura S, Maemura M, Nakayama T: Effects of long-term administration of UFT plus leucovorin on colorectal tumors induced with 1,2-dimethylhydrazine in rats. Anticancer Res. 1999 Nov-Dec;19(6B):5139-42. [PubMed:10697523 ]
  4. Kuwa K, Sakamoto S, Mitamura T, Kudo H, Suzuki S, Fukushima M: Effects of a low dose leucovorin with 5-fluorouracil derivative on colorectal tumors induced with 1,2-dimethylhydrazine in rats. Anticancer Res. 1999 Nov-Dec;19(6B):5143-8. [PubMed:10697524 ]
  5. Murakami Y, Kazuno H, Emura T, Tsujimoto H, Suzuki N, Fukushima M: Different mechanisms of acquired resistance to fluorinated pyrimidines in human colorectal cancer cells. Int J Oncol. 2000 Aug;17(2):277-83. [PubMed:10891536 ]
  6. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]