ContaminantDB: Tegafur

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-05-22 03:31:03 UTC

Update Date

2016-11-09 01:15:23 UTC

Accession Number

CHEM016419

Identification

Common Name

Tegafur

Class

Small Molecule

Description

Tegafur (INN, BAN, USAN) is a prodrug of [DB00544] (5-FU), an antineoplastic agent used as the treatment of various cancers such as advanced gastric and colorectal cancers. It is a pyrimidine analogue used in combination therapies as an active chemotherapeutic agent in conjunction with [DB09257] and [DB03209], or along with [DB00544] as [DB09327]. Tegafur is usually given in combination with other drugs that enhance the bioavailability of the 5-FU by blocking the enzyme responsible for its degradation, or serves to limit the toxicity of 5-FU by ensuring high concentrations of 5-FU at a lower dose of tegafur [L933]. When converted and bioactivated to 5-FU, the drug mediates an anticancer activity by inhibiting thymidylate synthase (TS) during the pyrimidine pathway involved in DNA synthesis. 5-FU is listed on the World Health Organization's List of Essential Medicines.

Contaminant Sources

STOFF IDENT Compounds
ToxCast & Tox21 Chemicals

Contaminant Type

Not Available

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
Atillon	Kegg
1-(2-Tetrahydrofuryl)-5-fluorouracil	MeSH
Uftoral	MeSH
Fluorofur	MeSH
N1-(2'-Tetrahydrofuryl)-5-fluorouracil	MeSH
Futraful	MeSH
Sunfural S	MeSH
1-(Tetrahydro-2-furanyl)-5-fluorouracil	MeSH
Utefos	MeSH
5-Fluoro-1-(tetrahydro-2-furanyl)-2,4-pyrimidinedione	MeSH
Ftorafur	MeSH
Florafur	MeSH

Chemical Formula

C₈H₉FN₂O₃

Average Molecular Mass

200.169 g/mol

Monoisotopic Mass

200.060 g/mol

CAS Registry Number

37076-68-9

IUPAC Name

5-fluoro-1-(oxolan-2-yl)-1,2,3,4-tetrahydropyrimidine-2,4-dione

Traditional Name

tegafur

SMILES

FC1=CN(C2CCCO2)C(=O)NC1=O

InChI Identifier

InChI=1S/C8H9FN2O3/c9-5-4-11(6-2-1-3-14-6)8(13)10-7(5)12/h4,6H,1-3H2,(H,10,12,13)

InChI Key

WFWLQNSHRPWKFK-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

Halopyrimidine
Pyrimidone
Aryl fluoride
Aryl halide
Hydropyrimidine
Tetrahydrofuran
Vinylogous amide
Heteroaromatic compound
Urea
Lactam
Azacycle
Oxacycle
Organic nitrogen compound
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Organofluoride
Organohalogen compound
Organic oxide
Organopnictogen compound
Organic oxygen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

pyrimidines (CHEBI:32188 )
organohalogen compound (CHEBI:32188 )

Biological Properties

Status

Detected and Not Quantified

Origin

Not Available

Cellular Locations

Not Available

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Physical Properties

State

Not Available

Appearance

Not Available

Experimental Properties

Property	Value
Melting Point	Not Available
Boiling Point	Not Available
Solubility	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	14 g/L	ALOGPS
logP	-0.09	ALOGPS
logP	0.024	ChemAxon
logS	-1.2	ALOGPS
pKa (Strongest Acidic)	8.08	ChemAxon
pKa (Strongest Basic)	-4.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	58.64 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	44.5 m³·mol⁻¹	ChemAxon
Polarizability	17.42 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-00di-9010000000-09f17e43065fd7cafc97	Spectrum
GC-MS	GC-MS Spectrum - CI-B (Non-derivatized)	splash10-0089-6900000000-0edac06a6aa07cfd4b9f	Spectrum
GC-MS	GC-MS Spectrum - CI-B (Non-derivatized)	splash10-0udi-2190000000-6638249408dce3b6c1ee	Spectrum
GC-MS	GC-MS Spectrum - CI-B (Non-derivatized)	splash10-014i-0090000000-dc47df1bb362c454d07d	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-004l-8900000000-e49614f77c1ff16cc175	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 35V, Positive	splash10-023r-6900000000-188214f26a1d69ed533a	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-001i-0900000000-47ca8a935d89153a5208	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-001i-2900000000-dd4508f1cfd9f5e41985	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-03di-9300000000-cf6a12090561a84535cb	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0zfv-3900000000-540b2f444a8582b4b2b7	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-003s-3900000000-719cd08b446e321daa4b	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9100000000-0b2c9c62c17aafd3f041	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0fk9-9100000000-a6c03573064f47986545	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0fl3-9310000000-3a526507aebf2916c0ad	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-03di-9400000000-8d25616295ea8c4d4076	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0002-0900000000-3c6d5eb6120100ac538d	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0007-9600000000-dcbdad1ff740f61bef21	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9000000000-076a20100044fff1134a	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum

Toxicity Profile

Route of Exposure

Not Available

Mechanism of Toxicity

Not Available

Metabolism

Not Available

Toxicity Values

Not Available

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

Not Available

Uses/Sources

Not Available

Minimum Risk Level

Not Available

Health Effects

Not Available

Symptoms

Not Available

Treatment

Not Available

Concentrations

Not Available

External Links

DrugBank ID

DB09256

HMDB ID

HMDB0246215

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

Tegafur

Chemspider ID

5193

ChEBI ID

Not Available

PubChem Compound ID

Not Available

Kegg Compound ID

C12673

YMDB ID

Not Available

ECMDB ID

Not Available

References

Synthesis Reference

Not Available

MSDS

Not Available

General References

Not Available

Tegafur (CHEM016419)

Structure for CHEM016419: Tegafur