Chemical substance record

Doxifluridine

3094-09-5C₉H₁₁FN₂O₅246.194 g/mol

Organic/Inorganic Small MoleculeChEBI source record

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. — ChEBI

Safety references

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Identity & molecular properties

Source-linked values

CAS number	3094-09-5	ChEBI ↗
Molecular formula	C₉H₁₁FN₂O₅	ChEBI ↗
Molar mass	246.194 g/mol	ChEBI ↗
Monoisotopic mass	246.0652 Da	ChEBI ↗
Formal charge	0	ChEBI ↗
ChEBI identifier	CHEBI:31521	ChEBI ↗

Cross-source molecular data

PubChem

Molar mass	246.19 g/mol	PubChem ↗
Exact mass	246.06519962 Da	PubChem ↗
Computed XLogP	-1.7	PubChem ↗
Topological polar surface area (Å²)	99.1	PubChem ↗
H-bond donors	3	PubChem ↗
H-bond acceptors	6	PubChem ↗
Rotatable bonds	1	PubChem ↗

PubChem computed values are shown separately from the ChEBI record. An exact InChIKey match was used to connect the records. Molecular descriptors do not describe a supplied product’s purity, particle size or performance.

Names & structural identifiers

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Source preferred name

doxifluridine

IUPAC name

5'-deoxy-5-fluorouridine

InChIKey

ZWAOHEXOSAUJHY-ZIYNGMLESA-N

SMILES

C[C@H]1O[C@@H](n2cc(F)c(=O)nc2=O)[C@H](O)[C@@H]1O

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

Names & synonyms

5'-deoxy-5-fluorouridinedoxifluridinadoxifluridinumFurtulon

Names are supplied by ChEBI. Trade names and related synonyms may describe a broader product context.

Classification & relationships

ChEBI ontology

organofluorine compoundChEBI parent class · 37143 ↗pyrimidine 5'-deoxyribonucleosideChEBI parent class · 74494 ↗

nucleoside organofluorine compound organic heterocyclic compound organic molecular entity

Roles recorded in ChEBI

antimetaboliteantineoplastic agentprodrug

Database role annotations describe reported biological or chemical roles; they are not product approvals or recommendations for use.

Mass ↔ amount of substance

Calculated from sourced mass

Amount

Input unit

Equivalent amount

0.00406184 mol

Uses 246.194 g/mol from ChEBI. Assumes the substance described by this record; no purity or concentration correction is applied.

Elemental composition

Theoretical mass fractions

C

Carbon · 9 atoms

43.91%

O

Oxygen · 5 atoms

32.49%

N

Nitrogen · 2 atoms

11.38%

F

Fluorine · 1 atom

7.72%

H

Hydrogen · 11 atoms

4.50%

Calculated theoretical mass fractions from the reported formula and PubChem periodic-table atomic masses. These are not assay or purity results.

Research & patent references

Selected source associations

Ring-opening polymerization of epsilon-caprolactone initiated by the antitumor agent doxifluridine. ↗Acta biomaterialia · 2009 May · PMID 19101214

Significance of microsatellite instability (MSI) for colorectal cancer following adjuvant therapy with doxifluridine. ↗Medical oncology (Northwood, London, England) · 2012 Mar · PMID 21234714

US4071680 · Patent reference ↗Patent cross-reference supplied by ChEBI. Association alone does not establish claim scope.

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Sources & record history

Checked 27 Sep 2026

Identity, formula, mass, synonyms & ontologyEMBL-EBI ChEBI · CHEBI:31521

Release 255, 9 September 2026. ChEBI three-star (manually annotated) source entry. View original record ↗ · CC BY 4.0

Additional molecular descriptorsNCBI PubChem · CID 18343 · retrieved 2026-09-27

PubCAS formats source data, connects references and computes explicitly labelled conversions. CAS cross-references are supplied by ChEBI; they do not constitute CAS verification or endorsement.

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