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

General Information of Drug (ID: DR0266)
Drug Name
Capecitabine
Prodrug Info Capecitabine is the prodrug of Fluorouracil
Synonyms
Capecitibine; Capiibine; Captabin; Ro 09-1978; Ro 09-1978/000; Xeloda; 154361-50-9; 5'-Deoxy-5-fluoro-N-((pentyloxy)carbonyl)cytidine; CAPECITABINE; 5'-deoxy-5-fluoro-N-[(pentyloxy)carbonyl]cytidine; Cytidine, 5'-deoxy-5-fluoro-N-[(pentyloxy)carbonyl]-; N(4)-Pentyloxycarbonyl-5'-deoxy-5-fluorocytidine; Pentyl 1-(5-deoxy-beta-D-ribofuranosyl)-5-fluoro-1,2-dihydro-2-oxo-4-pyrimidinecarbamate; R340; UNII-6804DJ8Z9U
Indication Colon cancer [ICD11: 2B90] Approved [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 359.35 Topological Polar Surface Area 121
Heavy Atom Count 25 Rotatable Bond Count 7
Hydrogen Bond Donor Count 3 Hydrogen Bond Acceptor Count 7
Cross-matching ID
PubChem CID
60953
PubChem SID
583040 ; 7848286 ; 7978485 ; 8187136 ; 12014895 ; 14828191 ; 14925873 ; 29214852 ; 43118267 ; 46508686 ; 49960125 ; 53790473 ; 57314195 ; 71821403 ; 74459733 ; 99436918 ; 103724218 ; 104322032 ; 117506114 ; 117673331 ; 118048469 ; 119526524 ; 124757042 ; 125163846 ; 126653765 ; 126671131 ; 127925204 ; 134338046 ; 134358377 ; 135017419 ; 135693779 ; 135723537 ; 136368008 ; 136375551 ; 136949108 ; 137005622 ; 140014282 ; 143493385 ; 144115785 ; 144205751 ; 152059549 ; 152235778 ; 152258963 ; 160647810 ; 160964435 ; 162011675 ; 163304897 ; 164175281 ; 164194987 ; 165245546
ChEBI ID
ChEBI:31348
CAS Number
154361-50-9
TTD Drug ID
D00HCQ
Formula
C15H22FN3O6
Canonical SMILES
CCCCCOC(=O)NC1=NC(=O)N(C=C1F)C2C(C(C(O2)C)O)O
InChI
1S/C15H22FN3O6/c1-3-4-5-6-24-15(23)18-12-9(16)7-19(14(22)17-12)13-11(21)10(20)8(2)25-13/h7-8,10-11,13,20-21H,3-6H2,1-2H3,(H,17,18,22,23)/t8-,10-,11-,13-/m1/s1
InChIKey
GAGWJHPBXLXJQN-UORFTKCHSA-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'-DFCR DM000544
10037499
Hydrolysis - Hydrolysis 1 [6] , [7]
5'-DFUR DM000545
18343
Unclear 2 [6] , [7]
Fluorouracil DM000190
3385
Hydrolysis - Hydrolysis 3 [6] , [7]
FUH2 DM020033
121997
Reduction - Reduction 4 [7]
FUPA DM004893
151244
Hydrolysis - Hydrolysis 5 [7]
FBAL DM000193
13351
Hydrolysis - Amide Hydrolysis 6 [7]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR002523 Capecitabine 5'-DFCR Hydrolysis - Hydrolysis CES1 [6], [7]
MR002521 5'-DFCR 5'-DFUR Unclear cdd [6], [7]
MR002522 5'-DFUR 5-fluorouracil Hydrolysis - Hydrolysis TYMP [6], [7]
MR002524 5-fluorouracil FUH2 Reduction - Reduction DPYD [7]
MR002525 FUH2 FUPA Hydrolysis - Hydrolysis DPYS [7]
MR002526 FUPA FBAL Hydrolysis - Amide Hydrolysis UPB1 [7]
⏷ Show the Full List of 6 MR(s)
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]
Carboxylesterase 1 (CES1) DME0054 Homo sapiens
EST1_HUMAN
3.1.1.1
[2]
Cytidine aminohydrolase (CDA) DME0080 Homo sapiens
CDD_HUMAN
3.5.4.5
[3]
Cytidine deaminase (cdd) DME1055 Escherichia coli
CDD_ECOLI
3.5.4.5
[2]
Dihydropyrimidinase (DPYS) DMEN004 Homo sapiens
DPYS_HUMAN
2.7.1.113
[2]
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]
Unclear metabolic mechanism (DME-unclear) DME1406 Collinsella aerofaciens Not Available Not Available [5]
Unclear metabolic mechanism (DME-unclear) DME1462 Salmonella enterica Not Available Not Available [5]
⏷ Show the Full List of 9  DME(s)
References
1 Capecitabine was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 LABEL: RIZATRIPTAN BENZOATE
3 Augmentation of the antitumor activity of capecitabine by a tumor selective dihydropyrimidine dehydrogenase inhibitor, RO0094889. Int J Cancer. 2003 Sep 20;106(5):799-805.
4 Induction of thymidine phosphorylase in both irradiated and shielded, contralateral human U87MG glioma xenografts: implications for a dual modality treatment using capecitabine and irradiation. Mol Cancer Ther. 2002 Oct;1(12):1139-45.
5 Mapping human microbiome drug metabolism by gut bacteria and their genes. Nature. 2019 Jun;570(7762):462-467.
6 EUCRISA? (crisaborole) ointment, 2%, for topical use
7 A new, validated HPLC-MS/MS method for the simultaneous determination of the anti-cancer agent capecitabine and its metabolites: 5'-deoxy-5-fluorocytidine, 5'-deoxy-5-fluorouridine, 5-fluorouracil and 5-fluorodihydrouracil, in human plasma

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