Details of the Drug Metabolized by Drug-Metabolizing Enzyme (DME)

General Information of Drug (ID: DR1540)
Drug Name
Tegafur-uracil
Synonyms
Tegafur - uracil mixture; Tegafur / uracil; Tegafur mixt. with uracil (1:4); Tegafur-Uracil; Uracil mixt. with FT (4:1); Uracil mixt. with tegafur (4:1); Uracil-Tegafur; FT mixt. with uracil (1:4); Youfuding; 1-(2-Tetrahydrofuryl)-5-fluorouracil mixt. with uracil (1:4); 1-Uft protocol; 74578-38-4; UFT; Ufur; Uracil mixt. with 1-(2-tetrahydrofuryl)-5-fluorouracil (4:1); Uracil, 5-fluoro-1-(tetrahydro-2-furyl)- mixt. with uracil (1:4); orzel
Indication Colon cancer [ICD11: 2B90] Phase 4 [1]
Structure
3D MOL is unavailable 2D MOL
Pharmaceutical Properties Molecular Weight 312.25 Topological Polar Surface Area 117
Heavy Atom Count 22 Rotatable Bond Count 1
Hydrogen Bond Donor Count 3 Hydrogen Bond Acceptor Count 6
Cross-matching ID
PubChem CID
104747
CAS Number
74578-38-4
TTD Drug ID
D0Y8PT
Formula
C12H13FN4O5
Canonical SMILES
C1CC(OC1)N2C=C(C(=O)NC2=O)F.C1=CNC(=O)NC1=O
InChI
1S/C8H9FN2O3.C4H4N2O2/c9-5-4-11(6-2-1-3-14-6)8(13)10-7(5)12;7-3-1-2-5-4(8)6-3/h4,6H,1-3H2,(H,10,12,13);1-2H,(H2,5,6,7,8)
InChIKey
DHMYGZIEILLVNR-UHFFFAOYSA-N
The Metabolic Roadmap of This Drug
The Full List of Drug Metabolites (DM) of This Drug
DM Name DM ID PubChem ID Reaction DM Level REF
3-hydroxytegafur DM004897
139593699
Oxidation - Hydrolyzationn 1 [2]
4-hydroxytegafur DM004898
559992
Oxidation - Hydrolyzationn 1 [2]
5-hydroxytegafur DM004891 N. A. Oxidation - Hydrolyzationn 1 [2]
Dihydrotegafur DM004899
71369791
Oxidation - Hydrolyzationn 1 [4] , [5] , [6]
Fluorouracil DM000190
3385
Multi-steps Reaction - Hydrolysis; oxidation 2 [2]
5-fluorodeoxyuridine-monophosphate DM004895
1816
Conjugation - Phosphorylation 3 [2]
5-fluorouridine-triphosphate DM004896
53936407
Conjugation - Phosphorylation 3 [2]
5-FUH2 DM000191
121997
Oxidation - Dehydrogenation 3 [2]
FUPA DM004893
151244
Hydrolysis - Hydrolysis 4 [2]
FBAL DM000193
13351
Hydrolysis - Hydrolysis 5 [2]
Urea DM001344
1176
Hydrolysis - Hydrolysis 5 [2]
⏷ Show the Full List of 11  DM(s)
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR005271 Tegafur-uracil 5-hydroxytegafur Oxidation - Hydrolyzationn CYP2A6 [2]
MR005279 Tegafur-uracil 3-hydroxytegafur Oxidation - Hydrolyzationn CYP2A6 [2]
MR005280 Tegafur-uracil 4-hydroxytegafur Oxidation - Hydrolyzationn CYP2A6 [2]
MR005281 Tegafur-uracil Dihydrotegafur Oxidation - Hydrolyzationn CYP2A6 [4], [5], [6]
MR005272 5-hydroxytegafur Fluorouracil Multi-steps Reaction - Hydrolysis; oxidation Unclear [2]
MR005273 Fluorouracil 5-FUH2 Oxidation - Dehydrogenation DPYD [2]
MR005277 Fluorouracil 5-fluorodeoxyuridine-monophosphate Conjugation - Phosphorylation Unclear [2]
MR005278 Fluorouracil 5-fluorouridine-triphosphate Conjugation - Phosphorylation Unclear [2]
MR005274 5-FUH2 FUPA Hydrolysis - Hydrolysis DPYSL2 [2]
MR005275 FUPA FBAL Hydrolysis - Hydrolysis BUP-1 [2]
MR005276 FUPA Urea Hydrolysis - Hydrolysis BUP-1 [2]
⏷ Show the Full List of 11 MR(s)
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Beta-Ureidopropionase (BUP-1) DMEN070 . Not Available Not Available [2]
Cytochrome P450 2A6 (CYP2A6) DME0005 Homo sapiens
CP2A6_HUMAN
1.14.14.1
[3]
Dihydropyrimidinase-related protein 2 (DPYSL2) DMEN246 Homo sapiens
DPYL2_HUMAN
Not Available [2]
Dihydrothymine dehydrogenase (DPYD) DME0053 Homo sapiens
DPYD_HUMAN
1.3.1.2
[2]
References
1 ClinicalTrials.gov (NCT02887365) A Phase II Study of Tegafur-Uracil as Maintenance Chemotherapy in Patients With Stage II of Colon Cancer.
2 DrugBank(Pharmacology-Metabolism):Tegafur-uracil
3 UFT Capsules (uracil-tegafur).
4 Summary of information on human CYP enzymes: human P450 metabolism data. Drug Metab Rev. 2002 Feb-May;34(1-2):83-448.
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 Comparative pharmacology of oral fluoropyrimidines: a focus on pharmacokinetics, pharmacodynamics and pharmacomodulation

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