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]
Affected Organisms
Humans and other mammals
ATC Code
L01BC03: Tegafur
L01BC: Pyrimidine analogues
L01B: ANTIMETABOLITES
L01: ANTINEOPLASTIC AGENTS
L: ANTINEOPLASTIC AND IMMUNOMODULATING AGENTS
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
UNII
1548R74NSZ
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.