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

General Information of Drug (ID: DR0020)
Drug Name
Fluorouracilo
Synonyms
Fluoroblastin; Fluoroplex; Fluorouracilo; Fluorouracilum; Fluracil; Fluracilum; Fluril; Fluro Uracil; Fluroblastin; Ftoruracil; 5-Fluorouracil; Kecimeton; Phthoruracil; Phtoruracil; Queroplex; Timazin; fluorouracil; 2,4(1H,3H)-Pyrimidinedione, 5-fluoro-; 2,4-Dihydroxy-5-fluoropyrimidine; 5 Fluorouracil; 5-FU; 5-Fluoracil; 5-Fluoro-2,4(1H,3H)-pyrimidinedione; 5-fluoro-1H-pyrimidine-2,4-dione; 5-fluoropyrimidine-2,4(1H,3H)-dione; 51-21-8; Carac; Fluri; Ulup; Adrucil; Arumel; Carzonal; Effluderm (free base); Efudex; Efudix; Efurix
Indication Stomach cancer [ICD11: 2B72] Approved [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 130.08 Topological Polar Surface Area 58.2
Heavy Atom Count 9 Rotatable Bond Count 0
Hydrogen Bond Donor Count 2 Hydrogen Bond Acceptor Count 3
Cross-matching ID
PubChem CID
3385
PubChem SID
9851 ; 82653 ; 595836 ; 603131 ; 841046 ; 3139714 ; 5132902 ; 5367838 ; 7847650 ; 7891022 ; 7978600 ; 8139872 ; 8149350 ; 8152156 ; 10524722 ; 11111190 ; 11335229 ; 11360468 ; 11363735 ; 11366297 ; 11368859 ; 11371368 ; 11374392 ; 11377021 ; 11406045 ; 11461440 ; 11484027 ; 11487892 ; 11490250 ; 11492372 ; 11494655 ; 11538022 ; 15218968 ; 17389875 ; 17405099 ; 22391543 ; 24276773 ; 24278439 ; 24871165 ; 24894963 ; 25346604 ; 25621761 ; 26611750 ; 26679238 ; 26697058 ; 26747342 ; 26747343 ; 26747344 ; 26752979 ; 26758708
ChEBI ID
ChEBI:46345
CAS Number
51-21-8
TTD Drug ID
D05LEO
Formula
C4H3FN2O2
Canonical SMILES
C1=C(C(=O)NC(=O)N1)F
InChI
1S/C4H3FN2O2/c5-2-1-6-4(9)7-3(2)8/h1H,(H2,6,7,8,9)
InChIKey
GHASVSINZRGABV-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
FdUMP DM006276
8642
Unclear 1 [9]
FUrd DM006272
9427
Unclear 1 [9]
FUMP DM006273
54609526
Unclear 2 [9]
FUDP DM006274
444503
Unclear 3 [9]
FdUDP DM006275
53882537
Unclear 4 [9]
FUTP DM006277
1025548
Unclear 4 [9]
FdUMP DM006276
8642
Unclear 5 [9]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR006748 5-FU FUrd Unclear Unclear [9]
MR006754 5-FU FdUMP Unclear Unclear [9]
MR006749 FUrd FUMP Unclear Unclear [9]
MR006750 FUMP FUDP Unclear Unclear [9]
MR006751 FUDP FdUDP Unclear Unclear [9]
MR006753 FUDP FUTP Unclear Unclear [9]
MR006752 FdUDP FdUMP Unclear Unclear [9]
⏷ Show the Full List of 7 MR(s)
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Amidophosphoribosyltransferase (GPAT) DME0136 Homo sapiens
PUR1_HUMAN
2.4.2.14
[2]
Cytochrome P450 1A2 (CYP1A2) DME0003 Homo sapiens
CP1A2_HUMAN
1.14.14.1
[3]
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
[3]
Dihydrothymine dehydrogenase (DPYD) DME0053 Homo sapiens
DPYD_HUMAN
1.3.1.2
[4]
Methylenetetrahydrofolate reductase (MTHFR) DME0083 Homo sapiens
MTHR_HUMAN
1.5.1.20
[5]
Thymidine phosphorylase (TYMP) DME0092 Homo sapiens
TYPH_HUMAN
2.4.2.4
[5]
Thymidylate synthase (TYMS) DME0137 Homo sapiens
TYSY_HUMAN
2.1.1.45
[5]
Uracil phosphoribosyltransferase (UPRT) DME0428 Homo sapiens
UPP_HUMAN
2.4.2.9
[6]
Uridine 5'-monophosphate synthase (UMPS) DME0138 Homo sapiens
UMPS_HUMAN
4.1.1.23
[7]
Uridine phosphorylase 1 (UPP1) DME0139 Homo sapiens
UPP1_HUMAN
2.4.2.3
[8]
Uridine phosphorylase 2 (UPP2) DME0140 Homo sapiens
UPP2_HUMAN
2.4.2.3
[8]
⏷ Show the Full List of 12  DME(s)
References
1 5-Fluorouracil was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 PharmGKB: A worldwide resource for pharmacogenomic information. Wiley Interdiscip Rev Syst Biol Med. 2018 Jul;10(4):e1417. (ID: PA150653776)
3 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.
4 5-Fluorouracil toxicity-attributable IVS14 + 1G > A mutation of the dihydropyrimidine dehydrogenase gene in Polish colorectal cancer patients. Pharmacol Rep. 2008 Mar-Apr;60(2):238-42.
5 5-Fluorouracil pharmacogenomics: still rocking after all these years? Pharmacogenomics. 2011 Feb;12(2):251-65.
6 Combined suicide gene therapy for human colon cancer cells using adenovirus-mediated transfer of escherichia coli cytosine deaminase gene and Escherichia coli uracil phosphoribosyltransferase gene with 5-fluorocytosine. Cancer Gene Ther. 2000 Jul;7(7):1015-22.
7 Orotate phosphoribosyltransferase is overexpressed in malignant pleural mesothelioma: Dramatically responds one case in high OPRT expression. Rare Dis. 2016 Apr 5;4(1):e1165909.
8 Uridine phosphorylase in breast cancer: a new prognostic factor? Front Biosci. 2006 Sep 1;11:2759-66.
9 Study of the metabolism of flucytosine in Aspergillus species by 19F nuclear magnetic resonance spectroscopy

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