Tegafur

Status : approved

Therapeutic Classification

ANTIMETABOLITES

ANTINEOPLASTIC AND IMMUNOMODULATING AGENTS
ANTINEOPLASTIC AGENTS
ANTIMETABOLITES

Description

Tegafur (INN, BAN, USAN) is a chemotherapeutic fluorouracil prodrug used in the treatment of cancers. It is a component of the combination drugs tegafur/uracil and tegafur/gimeracil/oteracil. When metabolised, it becomes 5-fluorouracil.

Used

For the treatment of cancer.

Chemical Classification

This compound 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.

Halopyrimidines

Organic compounds

Organoheterocyclic compounds

Diazines

Pyrimidines and pyrimidine derivatives

Calculated Property

kind Value Source
logP -0.09 ALOGPS
logS -1.2 ALOGPS
Water Solubility 1.40e+01 g/l ALOGPS
logP 0.024 ChemAxon
IUPAC Name 5-fluoro-1-(oxolan-2-yl)-1,2,3,4-tetrahydropyrimidine-2,4-dione ChemAxon
Traditional IUPAC Name tegafur ChemAxon
Molecular Weight 200.169 ChemAxon
Monoisotopic Weight 200.059720321 ChemAxon
SMILES FC1=CN(C2CCCO2)C(=O)NC1=O ChemAxon
Molecular Formula C8H9FN2O3 ChemAxon
InChI 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) ChemAxon
InChIKey WFWLQNSHRPWKFK-UHFFFAOYSA-N ChemAxon
Polar Surface Area (PSA) 58.64 ChemAxon
Refractivity 44.5 ChemAxon
Polarizability 17.52 ChemAxon
Rotatable Bond Count 1 ChemAxon
H Bond Acceptor Count 3 ChemAxon
H Bond Donor Count 1 ChemAxon
pKa (strongest acidic) 8.08 ChemAxon
pKa (strongest basic) -4.3 ChemAxon
Physiological Charge 0 ChemAxon
Number of Rings 2 ChemAxon
Bioavailability 1 ChemAxon
Rule of Five 1 ChemAxon
Ghose Filter 1 ChemAxon
MDDR-Like Rule 0 ChemAxon