CHEBI:31521 - doxifluridine

Main ChEBI Ontology Automatic Xrefs Reactions Pathways Models
ChEBI Name doxifluridine
ChEBI ID CHEBI:31521
Definition A pyrimidine 5'-deoxyribonucleoside that is 5-fluorouridine in which the hydroxy group at the 5' position is replaced by a hydrogen. It is an oral prodrug of the antineoplastic agent 5-fluorouracil. Designed to circumvent the rapid degradation of 5-fluorouracil by dihydropyrimidine dehydrogenase in the gut wall, it is converted into 5-fluorouracil in the presence of pyrimidine nucleoside phosphorylase.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:74488
Supplier Information
Download Molfile XML SDF
Formula C9H11FN2O5
Net Charge 0
Average Mass 246.19240
Monoisotopic Mass 246.06520
InChI InChI=1S/C9H11FN2O5/c1-3-5(13)6(14)8(17-3)12-2-4(10)7(15)11-9(12)16/h2-3,5-6,8,13-14H,1H3,(H,11,15,16)/t3-,5-,6-,8-/m1/s1
InChIKey ZWAOHEXOSAUJHY-ZIYNGMLESA-N
SMILES C[C@H]1O[C@H]([C@H](O)[C@@H]1O)n1cc(F)c(=O)[nH]c1=O
Roles Classification
Biological Role(s): antimetabolite
A substance which is structurally similar to a metabolite but which competes with it or replaces it, and so prevents or reduces its normal utilization.
Application(s): antineoplastic agent
A substance that inhibits or prevents the proliferation of neoplasms.
prodrug
A compound that, on administration, must undergo chemical conversion by metabolic processes before becoming the pharmacologically active drug for which it is a prodrug.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing doxifluridine (CHEBI:31521) has role antimetabolite (CHEBI:35221)
doxifluridine (CHEBI:31521) has role antineoplastic agent (CHEBI:35610)
doxifluridine (CHEBI:31521) has role prodrug (CHEBI:50266)
doxifluridine (CHEBI:31521) is a organofluorine compound (CHEBI:37143)
doxifluridine (CHEBI:31521) is a pyrimidine 5'-deoxyribonucleoside (CHEBI:74494)
IUPAC Name
5'-deoxy-5-fluorouridine
INNs Sources
doxifluridina ChemIDplus
doxifluridine WHO MedNet
doxifluridine ChemIDplus
doxifluridinum ChemIDplus
Synonyms Sources
1-(β-D-5-desoxyribofuranoxyl)-5-fluoruracil ChemIDplus
5'-DFUR ChEBI
5'-Dfur ChemIDplus
5'-dFUrd ChEBI
5-fluoro-5'-deoxyuridine ChEBI
Doxifluridine KEGG COMPOUND
Ro 21-9738 ChemIDplus
Ro 219738 ChemIDplus
Brand Name Source
Furtulon KEGG DRUG
Manual Xrefs Databases
958 DrugCentral
C12739 KEGG COMPOUND
D01309 KEGG DRUG
HMDB0060406 HMDB
LSM-6359 LINCS
US4071680 Patent
View more database links
Registry Numbers Types Sources
3094-09-5 CAS Registry Number ChemIDplus
890191 Reaxys Registry Number Reaxys
Citations Waiting for Citations Types Sources
19101214 PubMed citation Europe PMC
21234714 PubMed citation Europe PMC
23564503 PubMed citation Europe PMC
2947416 PubMed citation Europe PMC
3020904 PubMed citation Europe PMC
Last Modified
22 February 2017