ContaminantDB: Fluorouracil

You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Database of hazardous chemicals.

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References Targets (5)XML

Record Information

Version

1.0

Creation Date

2014-09-11 05:16:06 UTC

Update Date

2016-11-09 01:09:12 UTC

Accession Number

CHEM003733

Identification

Common Name

Fluorouracil

Class

Small Molecule

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.

Contaminant Sources

Clean Air Act Chemicals
HMDB Contaminants - Urine
HPV EPA Chemicals
IARC Carcinogens Group 3
STOFF IDENT Compounds
T3DB toxins
ToxCast & Tox21 Chemicals

Contaminant Type

Amide
Antimetabolite
Antimetabolite, Antineoplastic
Drug
Immunosuppressive Agent
Metabolite
Organic Compound
Organofluoride
Synthetic Compound

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
5-Fluoracil	ChEBI
5-Fluoropyrimidine-2,4-dione	ChEBI
5-FU	ChEBI
Fluorouracilo	ChEBI
Fluorouracilum	ChEBI
5-Fluorouracil	Kegg
Adrucil	Kegg
Carac	Kegg
Fluoroplex	Kegg
5-FU medac	HMDB
5-Fluorouracil-biosyn	HMDB
5FU	HMDB
Dermatech brand OF fluorouracil	HMDB
Efudex	HMDB
Fluoro uracile icn	HMDB
Fluorouracil gry	HMDB
Fluorouracil monopotassium salt	HMDB
Neocorp brand OF fluorouracil	HMDB
Roche brand OF fluorouracil	HMDB
Teva brand OF fluorouracil	HMDB
5 FU medac	HMDB
5 HU hexal	HMDB
5-HU hexal	HMDB
Dakota, fluorouracile	HMDB
Efudix	HMDB
Fluorouracil-gry	HMDB
Fluorouracile dakota	HMDB
Haemato brand OF fluorouracil	HMDB
Haemato fu	HMDB
ICN brand OF fluorouracil	HMDB
Neofluor	HMDB
5 Fluorouracil biosyn	HMDB
5-FU lederle	HMDB
CSP Brand OF fluorouracil	HMDB
Dakota brand OF fluorouracil	HMDB
Ferrer brand OF fluorouracil	HMDB
Fluoro-uracile icn	HMDB
Fluorouracil mononitrate	HMDB
Fluorouracil monosodium salt	HMDB
Fluorouracil teva brand	HMDB
Fluorouracilo ferrer far	HMDB
Fluracedyl	HMDB
Onkofluor	HMDB
Pharmachemie brand OF fluorouracil monosodium salt	HMDB
Biosyn brand OF fluorouracil	HMDB
5 FU lederle	HMDB
5 Fluorouracil	HMDB
Allergan brand OF fluorouracil	HMDB
Dermik brand OF fluorouracil	HMDB
Fluorouracil potassium salt	HMDB
Fluoruracil	HMDB
Flurodex	HMDB
Gry brand OF fluorouracil	HMDB
Haemato-fu	HMDB
Hexal brand OF fluorouracil	HMDB
Onkoworks brand OF fluorouracil	HMDB
Ribofluor	HMDB
Riemser brand OF fluorouracil	HMDB
Medac brand OF fluorouracil	HMDB
Ribosepharm brand OF fluorouracil	HMDB

Chemical Formula

C₄H₃FN₂O₂

Average Molecular Mass

130.077 g/mol

Monoisotopic Mass

130.018 g/mol

CAS Registry Number

51-21-8

IUPAC Name

5-fluoro-1,2,3,4-tetrahydropyrimidine-2,4-dione

Traditional Name

fluorouracil

SMILES

FC1=CNC(=O)NC1=O

InChI Identifier

InChI=1S/C4H3FN2O2/c5-2-1-6-4(9)7-3(2)8/h1H,(H2,6,7,8,9)

InChI Key

GHASVSINZRGABV-UHFFFAOYSA-N

Chemical Taxonomy

Description

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.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Diazines

Sub Class

Pyrimidines and pyrimidine derivatives

Direct Parent

Halopyrimidines

Alternative Parents

Substituents

Hydroxypyrimidine
Halopyrimidine
Aryl halide
Aryl fluoride
Heteroaromatic compound
Azacycle
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Organofluoride
Organohalogen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

organofluorine compound (CHEBI:46345 )
nucleobase analogue (CHEBI:46345 )
a uracil analogue (CPD0-1327 )

Biological Properties

Status

Detected and Not Quantified

Origin

Exogenous

Cellular Locations

Cytoplasm
Extracellular
Membrane

Biofluid Locations

Not Available

Tissue Locations

Kidney
Liver

Pathways

Name	SMPDB Link	KEGG Link
Capecitabine Pathway	Not Available	Not Available
Fluorouracil Pathway	Not Available	Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Physical Properties

State

Solid

Appearance

White powder.

Experimental Properties

Property	Value
Melting Point	282-283°C
Boiling Point	Not Available
Solubility	1.11E+004 mg/L (at 22°C)

Predicted Properties

Property	Value	Source
Water Solubility	5.86 g/L	ALOGPS
logP	-0.58	ALOGPS
logP	-0.66	ChemAxon
logS	-1.4	ALOGPS
pKa (Strongest Acidic)	7.18	ChemAxon
pKa (Strongest Basic)	-8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	58.2 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	26.17 m³·mol⁻¹	ChemAxon
Polarizability	9.46 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Spectrum Type	Description	Splash Key
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS	splash10-001i-9600000000-8c2b278c2716f3e6b27c	View in MoNA
GC-MS	GC-MS Spectrum - EI-B	splash10-001i-9800000000-a3301f9fea9145d07480	View in MoNA
GC-MS	GC-MS Spectrum - CI-B	splash10-001i-0900000000-76691bd3cba2765d3687	View in MoNA
GC-MS	GC-MS Spectrum - CI-B	splash10-001i-0900000000-d801d8209e9a5aa4830b	View in MoNA
GC-MS	GC-MS Spectrum - CI-B	splash10-0002-0900000000-7521695ae4a96b4a5a98	View in MoNA
GC-MS	GC-MS Spectrum - EI-B	splash10-001i-9800000000-a3301f9fea9145d07480	View in MoNA
GC-MS	GC-MS Spectrum - CI-B	splash10-001i-0900000000-76691bd3cba2765d3687	View in MoNA
GC-MS	GC-MS Spectrum - CI-B	splash10-001i-0900000000-d801d8209e9a5aa4830b	View in MoNA
GC-MS	GC-MS Spectrum - CI-B	splash10-0002-0900000000-7521695ae4a96b4a5a98	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , negative	splash10-004i-0900000000-c639ed1b5365f368b59c	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , negative	splash10-004i-0900000000-1a7a70df49a360e1458c	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , negative	splash10-004i-0900000000-d89f2d944fe1cac39f55	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , negative	splash10-004i-0900000000-50b33770c08680863cf6	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , negative	splash10-004i-0900000000-cd5bef421a05073cb1f3	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , negative	splash10-004i-3900000000-ec9c9e1dfc9a16f625a2	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , negative	splash10-004i-0900000000-df98a4532ca49a0a0436	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , negative	splash10-004i-0900000000-50b33770c08680863cf6	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , negative	splash10-004i-0900000000-50b33770c08680863cf6	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , negative	splash10-004i-0900000000-df98a4532ca49a0a0436	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , negative	splash10-004i-0900000000-b117f5fa58c8f98b5c15	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , negative	splash10-0a4i-9000000000-f3e71a41b6d4417d33fd	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-001i-9200000000-29362607b7c48b82973c	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-001i-0900000000-693d492f316b0c7d5ed5	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-001i-1900000000-0c0ee9469bf49688c5d2	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-001i-1900000000-0cecca0d265e958e19d7	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-03e9-1900000000-46f20f71dbc96630cee7	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-03di-1900000000-4330f38956afe6c47636	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-03di-2900000000-f935071622b89177697b	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-001i-1900000000-3fa9b91447db7dc7ba77	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-01q9-9800000000-32bf878787078ce9d817	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-03di-9000000000-3ef559051a5b99c94b29	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-004i-4900000000-82764fbca3290816328d	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-000f-9100000000-2da5eb3c925c027b5022	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9000000000-1cf432837297c55833a5	View in MoNA
MS	Mass Spectrum (Electron Ionization)	splash10-001i-9400000000-b8247c8f5c45b12efaa6	View in MoNA
1D NMR	1H NMR Spectrum	Not Available

Toxicity Profile

Route of Exposure

28-100%

Mechanism of Toxicity

The 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, N5дус10-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.

Metabolism

Hepatic. The catabolic metabolism of fluorouracil results in degradation products ( e.g., CO2, urea and alpha-fluoro-beta-alanine) which are inactive. Route of Elimination: Seven 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 Life: 10-20 minutes

Toxicity Values

LD₅₀=230mg/kg (orally in mice)

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

3, not classifiable as to its carcinogenicity to humans. (3)

Uses/Sources

For 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.

Minimum Risk Level

Not Available

Health Effects

Not Available

Symptoms

Not Available

Treatment

Not Available

Concentrations

Not Available

External Links

DrugBank ID

DB00544

HMDB ID

HMDB0014684

FooDB ID

Not Available

Phenol Explorer ID

Not Available

KNApSAcK ID

Not Available

BiGG ID

Not Available

BioCyc ID

Not Available

METLIN ID

Not Available

PDB ID

Not Available

Wikipedia Link

Chemspider ID

ChEBI ID

PubChem Compound ID

Kegg Compound ID

YMDB ID

Not Available

ECMDB ID

M2MDB004605

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.

MSDS

Link

General References

1. Longley DB, Harkin DP, Johnston PG: 5-fluorouracil: mechanisms of action and clinical strategies. Nat Rev Cancer. 2003 May;3(5):330-8.

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.

3. https://www.ncbi.nlm.nih.gov/pubmed/?term=11356943

4. https://www.ncbi.nlm.nih.gov/pubmed/?term=12520460

5. https://www.ncbi.nlm.nih.gov/pubmed/?term=14769231

6. https://www.ncbi.nlm.nih.gov/pubmed/?term=19023200

Fluorouracil (CHEM003733)

Structure for CHEM003733: Fluorouracil