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

General Information of Drug (ID: DR1754)
Drug Name
Floxuridine
Synonyms
Floxuridine; 5-Fluorodeoxyuridine; 2'-Deoxy-5-fluorouridine; Fluorodeoxyuridine; FUDR; Floxuridin; Deoxyfluorouridine; Fluoruridine deoxyribose; 5-Fluoro-2'-deoxyuridine; 5FdU; Floxuridinum; Floxiridina; 5-Fluoro-2-desoxyuridine; FdUrd; 5 Fluorodeoxyuridine; beta-5-Fluoro-2'-deoxyuridine; Floxuridinum [INN-Latin]; 5-Fluorouracil 2'-deoxyriboside; Floxiridina [INN-Spanish]; 5-fluoro-1-((2r,4s,5r)-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)pyrimidine-2,4(1h,3h)-dione; 5-Fluoro-2-deoxyuridine; 5-Fluorouracil deoxyriboside; 5-FdUrd; 1-(2-Deoxy-beta-D-ribofuranosyl)-5-fluorouracil; 1beta-D-2'-Deoxyribofuranosyl-5-flurouracil; 1-beta-D-2'-Deoxyribofuranosyl-5-flurouracil; Uridine, 2'-deoxy-5-fluoro-; NSC-27640; FDUR; UNII-039LU44I5M; 5-fluoro-1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-1,2,3,4-tetrahydropyrimidine-2,4-dione; (+)-5-fluoro-2'-deoxyuridine; CHEBI:60761; HSDB 3227; 5-FUDR; EINECS 200-072-5; (+)-5-fluorodeoxyuridine; CHEMBL917; BRN 0090221; AI3-50691; MLS000069439; 039LU44I5M; NSC 27640; Uridine, 2'-deoxy-5'-fluoro-; NCGC00023722-05; SMR000059051; DSSTox_CID_3057; 5-Fluor-1-(beta-2'-deoxyribofuranosyl)pyrimidin-2,4(1H,3H)-dion [Czech]; Ro 5-0360; DSSTox_RID_76855; DSSTox_GSID_23057; FdU; Uridine, 2'-deoxy-5-fluoro; (+)-5-Fluoro-2 -deoxyuridine; CAS-50-91-9; Floxuridine [USAN:INN]; FUDR (TN); 5-Fluoro-2'-deoxy-beta-uridine; floxidine; Fluoxuridine; NSC27640; Floxuridine [USAN:USP:INN]; 5-floxuridine; Floxuridine,(S); 5-Fluoro-dUrd; MFCD00006530; Floxuridine (Fludara); Floxuridine (USP/INN); 50-91-9
Indication Hepatocellular carcinoma [ICD11: 2C12] Approved [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 246.19 Topological Polar Surface Area 99.1
Heavy Atom Count 17 Rotatable Bond Count 2
Hydrogen Bond Donor Count 3 Hydrogen Bond Acceptor Count 6
Cross-matching ID
PubChem CID
5790
PubChem SID
13901 ; 603423 ; 855946 ; 3139662 ; 7978599 ; 8153561 ; 12146088 ; 14749704 ; 14749705 ; 24894724 ; 25622076 ; 29215018 ; 29215019 ; 29224824 ; 46508645 ; 47206143 ; 48416016 ; 49693295 ; 49833282 ; 50061739 ; 50104188 ; 50895505 ; 56459391 ; 57322956 ; 85279351 ; 87568673 ; 92309168 ; 92714934 ; 93576919 ; 103158493 ; 103240093 ; 104310265 ; 117613653 ; 124558526 ; 124799590 ; 126623741 ; 126943727 ; 127301295 ; 127301296 ; 127301297 ; 127301298 ; 127301299 ; 127301300 ; 127301301 ; 127301302 ; 127301303 ; 127301304 ; 127301305 ; 127301306 ; 127301307
ChEBI ID
ChEBI:60761
CAS Number
50-91-9
TTD Drug ID
D0TS1Z
Formula
C9H11FN2O5
Canonical SMILES
C1C(C(OC1N2C=C(C(=O)NC2=O)F)CO)O
InChI
1S/C9H11FN2O5/c10-4-2-12(9(16)11-8(4)15)7-1-5(14)6(3-13)17-7/h2,5-7,13-14H,1,3H2,(H,11,15,16)/t5-,6+,7+/m0/s1
InChIKey
ODKNJVUHOIMIIZ-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
Fluorouracil DM000190
3385
Unclear 1 [4] , [3]
5-FUH2 DM000191
121997
Reduction - Reduction 2 [4] , [3]
Fluoro-beta-ureidopropionate DM000192 N. A. Hydrolysis - Hydrolysis 3 [4] , [3]
FBAL DM000193
13351
Hydrolysis - Hydrolysis 4 [4] , [3]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR001058 Floxuridine 5-fluorouracil Unclear TYMP [4], [3]
MR001055 5-fluorouracil 5,6-Dihydro-5-fluorouracil Reduction - Reduction DPYD [4], [3]
MR001056 5,6-Dihydro-5-fluorouracil Fluoro-beta-ureidopropionate Hydrolysis - Hydrolysis DPYS [4], [3]
MR001057 Fluoro-beta-ureidopropionate Alpha-Fluoro-beta-alanine Hydrolysis - Hydrolysis UPB1 [4], [3]
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Beta-ureidopropionase (UPB1) DMEN028 Homo sapiens
BUP1_HUMAN
Not Available [2]
Dihydropyrimidinase (DPYS) DMEN004 Homo sapiens
DPYS_HUMAN
2.7.1.113
[3]
Dihydrothymine dehydrogenase (DPYD) DME0053 Homo sapiens
DPYD_HUMAN
1.3.1.2
[2]
Thymidine phosphorylase (TYMP) DME0092 Homo sapiens
TYPH_HUMAN
2.4.2.4
[4]
References
1 Floxuridine was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 Enhanced cancer cell growth inhibition by dipeptide prodrugs of floxuridine: increased transporter affinity and metabolic stability Mol Pharm. 2008 Sep-Oct;5(5):717-27. doi: 10.1021/mp800008c.
3 The achievement of mass balance by simultaneous quantification of floxuridine prodrug, floxuridine, 5-fluorouracil, 5-dihydrouracil, -fluoro--ureidopropionate, -fluoro--alanine using LC-MS J Chromatogr B Analyt Technol Biomed Life Sci. 2011 Apr 15;879(13-14):915-20. doi: 10.1016/j.jchromb.2011.02.045.
4 Enhanced cancer cell growth inhibition by dipeptide prodrugs of floxuridine: increased transporter affinity and metabolic stability. Mol Pharm. 2008 Sep-Oct;5(5):717-27.

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