capecitabine   

GtoPdb Ligand ID: 6799

Synonyms: Ro-09-1978-000 | Ro-091978000 | Xeloda®
capecitabine is an approved drug (FDA (1998), EMA (2001))
Compound class: Synthetic organic
Comment: Capecitabine is a prodrug, that is enzymatically converted to 5-fluorouracil (active agent). It is a thymidylate synthase inhibitor.
2D Structure
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Physico-chemical Properties
Hydrogen bond acceptors 8
Hydrogen bond donors 3
Rotatable bonds 8
Topological polar surface area 122.91
Molecular weight 359.15
XLogP 2.04
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
Canonical SMILES CCCCCOC(=O)Nc1nc(=O)n(cc1F)C1OC(C(C1O)O)C
Isomeric SMILES CCCCCOC(=O)Nc1nc(=O)n(cc1F)[C@@H]1O[C@@H]([C@H]([C@H]1O)O)C
InChI 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
InChI Key GAGWJHPBXLXJQN-UORFTKCHSA-N
Classification
Compound class Synthetic organic
Approved drug? Yes (FDA (1998), EMA (2001))
WHO Essential Medicine WHO Model List of Essential Medicines (21st List, 2019). Access PDF version.
Is prodrug? Yes
Active form 5-fluorouracil
IUPAC Name
pentyl N-[1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-methyloxolan-2-yl]-5-fluoro-2-oxopyrimidin-4-yl]carbamate
International Nonproprietary Names
INN number INN
7317 capecitabine
Synonyms
Ro-09-1978-000 | Ro-091978000 | Xeloda®
Database Links
CAS Registry No. 154361-50-9
ChEBI CHEBI:31348
ChEMBL Ligand CHEMBL1773
DrugBank Ligand DB01101
DrugCentral Ligand 480
GtoPdb PubChem SID 178103405
PubChem CID 60953
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Wikipedia Capecitabine

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Tocris
Capecitabine
Cat. No. 4799