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

General Information of Drug (ID: DR1643)
Drug Name
Trifluridine
Synonyms
Trifluoromethyldeoxyuridine; Trifluridina; Trifluridina [INN-Spanish]; Trifluridine; Trifluridine [USAN:INN]; Trifluridinum; Trifluridinum [INN-Latin]; Fluridine; TRIFLUOROTHYMIDINE; Virophta; Viroptic; 1-((2R,4S,5R)-4-Hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-5-(trifluoromethyl)pyrimidine-2,4(1H,3H)-dione; 2'-Deoxy-5-(trifluoromethyl)uridine; 5-(Trifluoromethyl)deoxyuridine; 5-Trifluoro-2'-deoxythymidine; 5-Trifluoromethyl-2-deoxyuridine; 5-Trifluorothymidine; 70-00-8; F3DThd; F3TDR; TFDU
Indication Herpes simplex virus infection [ICD11: 1F00] Approved [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 296.2 Topological Polar Surface Area 99.1
Heavy Atom Count 20 Rotatable Bond Count 2
Hydrogen Bond Donor Count 3 Hydrogen Bond Acceptor Count 8
Cross-matching ID
PubChem CID
6256
PubChem SID
626314 ; 7847457 ; 7980831 ; 8139891 ; 8153936 ; 12014784 ; 12149237 ; 14751529 ; 14849367 ; 24900027 ; 29225252 ; 46506192 ; 50054714 ; 56422883 ; 57323294 ; 77174799 ; 87560183 ; 93815015 ; 103321204 ; 104023317 ; 104253375 ; 104311541 ; 118048237 ; 124757493 ; 124800643 ; 125164297 ; 126667216 ; 129521334 ; 131404691 ; 134223275 ; 134338045 ; 134971818 ; 135681084 ; 135692274 ; 136369804 ; 137000771 ; 137005241 ; 137213977 ; 144205964 ; 152058901 ; 160963778 ; 163835390 ; 170464911 ; 172092201 ; 172919625 ; 174483143 ; 175266936 ; 175612130 ; 176484794 ; 179116934
ChEBI ID
CHEBI:75179
CAS Number
70-00-8
TTD Drug ID
D05RHI
Formula
C10H11F3N2O5
Canonical SMILES
C1C(C(OC1N2C=C(C(=O)NC2=O)C(F)(F)F)CO)O
InChI
1S/C10H11F3N2O5/c11-10(12,13)4-2-15(9(19)14-8(4)18)7-1-5(17)6(3-16)20-7/h2,5-7,16-17H,1,3H2,(H,14,18,19)/t5-,6+,7+/m0/s1
InChIKey
VSQQQLOSPVPRAZ-RRKCRQDMSA-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-(trifluoromethyl) uracil DM002392
5899
Unclear 1 [3]
5-carboxy-2'-deoxyuridine DM002391
10492375
Unclear 1 [4]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR002453 Trifluridine 5-carboxy-2'-deoxyuridine Unclear Unclear [4]
MR002454 Trifluridine 5-(trifluoromethyl) uracil Unclear TYMP [3]
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Thymidine phosphorylase (TYMP) DME0092 Homo sapiens
TYPH_HUMAN
2.4.2.4
[2]
References
1 Trifluridine was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 Phase I clinical study of three times a day oral administration of TAS-102 in patients with solid tumors. Cancer Invest. 2008 Oct;26(8):794-9.
3 New bioanalytical microemulsion Electrokinetic chromatography method for the simultaneous determination of Trifluridine with its metabolites and Tipiracil in rat plasma: Application to pharmacokinetic studies Saudi Pharm J. 2019 Dec;27(8):1075-1084. doi: 10.1016/j.jsps.2019.09.004.
4 Intraocular penetration of trifluridine Am J Ophthalmol. 1979 Jun;87(6):814-8. doi: 10.1016/0002-9394(79)90360-x.

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