Details of the Drug

General Information of Drug (ID: DM31ZQM)

Drug Name
Tegafur
Synonyms Tegafur (Fluoropyrimidine)
Indication
Disease Entry ICD 11 Status REF
Solid tumour/cancer 2A00-2F9Z Approved [1]
Drug Type
Small molecular drug
Structure
3D MOL 2D MOL
#Ro5 Violations (Lipinski): 0 Molecular Weight (mw) 200.17
Logarithm of the Partition Coefficient (xlogp) -0.3
Rotatable Bond Count (rotbonds) 1
Hydrogen Bond Donor Count (hbonddonor) 1
Hydrogen Bond Acceptor Count (hbondacc) 4
ADMET Property
Absorption Tmax
The time to maximum plasma concentration (Tmax) is 1-2 h [2]
Clearance
The drug present in the plasma can be removed from the body at the rate of 0.95 mL/min/kg [3]
Elimination
About less 20% of total dose is excreted unchanged in the urine [2]
Half-life
The concentration or amount of drug in body reduced by one-half in 11 hours [2]
Metabolism
The drug is metabolized via the hepatic [4]
Vd
Fluid volume that would be required to contain the amount of drug present in the body at the same concentration as in the plasma 0.62 L/kg [3]
Chemical Identifiers
Formula
C8H9FN2O3
IUPAC Name
5-fluoro-1-(oxolan-2-yl)pyrimidine-2,4-dione
Canonical SMILES
C1CC(OC1)N2C=C(C(=O)NC2=O)F
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)
InChIKey
WFWLQNSHRPWKFK-UHFFFAOYSA-N
Cross-matching ID
PubChem CID
5386
ChEBI ID
CHEBI:32188
CAS Number
17902-23-7
DrugBank ID
DB09256
TTD ID
D0F3SY
INTEDE ID
DR1539
Combinatorial Drugs (CBD) Click to Jump to the Detailed CBD Information of This Drug

Molecular Interaction Atlas of This Drug


Drug-Metabolizing Enzyme (DME)
DME Name DME ID UniProt ID MOA REF
Cytochrome P450 2E1 (CYP2E1) DEVDYN7 CP2E1_HUMAN Substrate [5]
Cytochrome P450 2A6 (CYP2A6) DEJVYAZ CP2A6_HUMAN Substrate [6]
Cytochrome P450 1A2 (CYP1A2) DEJGDUW CP1A2_HUMAN Substrate [7]
Cytochrome P450 3A5 (CYP3A5) DEIBDNY CP3A5_HUMAN Substrate [5]
Cytochrome P450 2C8 (CYP2C8) DES5XRU CP2C8_HUMAN Substrate [5]

Drug Off-Target (DOT)
DOT Name DOT ID UniProt ID Interaction REF
Cellular tumor antigen p53 (TP53) OTIE1VH3 P53_HUMAN Drug Response [8]
Cytidine deaminase (CDA) OT3HXP6N CDD_HUMAN Drug Response [9]
Cytochrome P450 2A6 (CYP2A6) OT52TWG3 CP2A6_HUMAN Drug Response [10]
Dihydropyrimidine dehydrogenase (DPYD) OTWRF2NR DPYD_HUMAN Drug Response [9]
Thymidylate synthase OTXTG0C7 TYSY_HUMAN Drug Response [11]
Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction Atlas of This Drug

References

1 Drugs@FDA. U.S. Food and Drug Administration. U.S. Department of Health & Human Services. 2015
2 UFT (uracil/tegafur) capsules_Product information
3 Trend Analysis of a Database of Intravenous Pharmacokinetic Parameters in Humans for 1352 Drug Compounds
4 Goldman JL, Leeder JS, Van Haandel L, Pearce RE: In Vitro Hepatic Oxidative Biotransformation of Trimethoprim. Drug Metab Dispos. 2015 Sep;43(9):1372-80. doi: 10.1124/dmd.115.065193. Epub 2015 Jul 2.
5 Roles of cytochromes P450 1A2, 2A6, and 2C8 in 5-fluorouracil formation from tegafur, an anticancer prodrug, in human liver microsomes. Drug Metab Dispos. 2000 Dec;28(12):1457-63.
6 Rapid development of S-1 in the west for therapy of advanced gastric carcinoma. Gan To Kagaku Ryoho. 2006 Jun;33 Suppl 1:117-20.
7 Summary of information on human CYP enzymes: human P450 metabolism data. Drug Metab Rev. 2002 Feb-May;34(1-2):83-448.
8 Dependence of chemotherapy response on p53 mutation status in a panel of human cancer lines maintained in nude mice. Cancer Sci. 2004 Jun;95(6):541-6. doi: 10.1111/j.1349-7006.2004.tb03246.x.
9 Dihydropyrimidine dehydrogenases and cytidine-deaminase gene polymorphisms as outcome predictors in resected gastric cancer patients treated with fluoropyrimidine adjuvant chemotherapy. J Surg Oncol. 2008 Aug 1;98(2):130-4.
10 Cyp2a6 is a principal enzyme involved in hydroxylation of 1,7-dimethylxanthine, a main caffeine metabolite, in humans. Drug Metab Dispos. 2005 Sep;33(9):1361-6. doi: 10.1124/dmd.105.004796. Epub 2005 Jun 24.
11 [Thymidylate synthase gene promoter polymorphism in patients with advanced head and neck cancer treated by radio- and 5-fluorouracil chemotherapy]. Magy Onkol. 2006;50(1):33-7. Epub 2006 Apr 17.