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

General Information of Drug (ID: DR1539)
Drug Name
Tegafur
Prodrug Info Tegafur is the prodrug of 5'-hydroxytegafur
Synonyms
Tefsiel C; Tegafurum [INN-Latin]; Citofur; Coparogin; Exonal; Fental; Florafur; Fluorafur; Fluorofur; Franroze; Ftorafur; Fulfeel; Furafluor; Furflucil; Furofutran; Futraful; Lifril; MJF-12264; Neberk; Nitobanil; Phthorafur; Phthorafur [Czech]; Racemic Ftorafur; Sinoflurol; Sunfral; tegafur; 1-(2-Tetrahydrofuryl)-5-fluorouracil; 17902-23-7; 2,4(1H,3H)-Pyrimidinedione, 5-fluoro-1-(tetrahydro-2-furanyl)-; 5-Fluoro-1-(tetrahydro-2-furyl)uracil; 5-fluoro-1-(tetrahydrofuran-2-yl)pyrimidine-2,4(1H,3H)-dione; C8H9FN2O3; FT-207; Lamar; Riol
Indication Colon cancer [ICD11: 2B90] Phase 4 [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 200.17 Topological Polar Surface Area 58.6
Heavy Atom Count 14 Rotatable Bond Count 1
Hydrogen Bond Donor Count 1 Hydrogen Bond Acceptor Count 4
Cross-matching ID
PubChem CID
5386
ChEBI ID
CHEBI:32188
CAS Number
17902-23-7
TTD Drug ID
D0F3SY
Formula
C8H9FN2O3
Canonical SMILES
C1CC(OC1)N2C=C(C(=O)NC2=O)F
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
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
5'-hydroxytegafur DM004889 N. A. Oxidation - 5-hydroxylation 1 [2] , [4]
Fluorouracil DM000190
3385
Other reaction - Degradation 2 [2] , [4]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR005269 Tegafur 5'-hydroxytegafur Oxidation - 5-hydroxylation CYP2A6 [2], [4]
MR005270 5'-hydroxytegafur Fluorouracil Other reaction - Degradation CYP3A5 ... [2], [4]
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Cytochrome P450 1A2 (CYP1A2) DME0003 Homo sapiens
CP1A2_HUMAN
1.14.14.1
[2]
Cytochrome P450 2A6 (CYP2A6) DME0005 Homo sapiens
CP2A6_HUMAN
1.14.14.1
[3]
Cytochrome P450 2C8 (CYP2C8) DME0018 Homo sapiens
CP2C8_HUMAN
1.14.14.1
[4]
Cytochrome P450 2E1 (CYP2E1) DME0013 Homo sapiens
CP2E1_HUMAN
1.14.14.1
[4]
Cytochrome P450 3A5 (CYP3A5) DME0012 Homo sapiens
CP3A5_HUMAN
1.14.14.1
[4]
Unclear metabolic mechanism (DME-unclear) DME1275 Lactobacillus johnsonii Not Available Not Available [5]
⏷ Show the Full List of 6  DME(s)
References
1 ClinicalTrials.gov (NCT02887365) A Phase II Study of Tegafur-Uracil as Maintenance Chemotherapy in Patients With Stage II of Colon Cancer.
2 Summary of information on human CYP enzymes: human P450 metabolism data. Drug Metab Rev. 2002 Feb-May;34(1-2):83-448.
3 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.
4 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.
5 Activation of multiple chemotherapeutic prodrugs by the natural enzymolome of tumour-localised probiotic bacteria. J Control Release. 2016 Jan 28;222:9-17.

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