capecitabine   Click here for help

GtoPdb Ligand ID: 6799

Synonyms: Ro-09-1978-000 | Ro-091978000 | Xeloda®
Approved drug
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
Click here for help
Click here for structure editor
Physico-chemical Properties
Click here for help
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
Click here for help
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 Click here for help
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 Click here for help
pentyl N-[1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-methyloxolan-2-yl]-5-fluoro-2-oxopyrimidin-4-yl]carbamate
International Nonproprietary Names Click here for help
INN number INN
7317 capecitabine
Synonyms Click here for help
Ro-09-1978-000 | Ro-091978000 | Xeloda®
Database Links Click here for help
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
Search Google for chemical match using the InChIKey GAGWJHPBXLXJQN-UORFTKCHSA-N
Search Google for chemicals with the same backbone GAGWJHPBXLXJQN
Search PubMed clinical trials capecitabine
Search PubMed titles capecitabine
Search PubMed titles/abstracts capecitabine
Search UniChem for chemical match using the InChIKey GAGWJHPBXLXJQN-UORFTKCHSA-N
Search UniChem for chemicals with the same backbone GAGWJHPBXLXJQN
Wikipedia Capecitabine

Product suppliers

View disclaimer

Tocris
Capecitabine
Cat. No. 4799