Capecitabine

Capecitabine
Clinical data
Pronunciation/kæpɪˈsaɪtəbiːn/
Trade namesXeloda, Xitabin, Kapetral, others
AHFS/Drugs.comMonograph
MedlinePlusa699003
Pregnancy
category
  • AU: D
Routes of
administration		By mouth
Drug classAntineoplastic agent
ATC code
Legal status
Legal status
Pharmacokinetic data
BioavailabilityExtensive
Protein binding< 60%
Metabolismliver, to 5'-DFCR, 5'-DFUR (inactive); neoplastic tissue, 5'-DFUR to active fluorouracil
Elimination half-life38–45 minutes
Excretionkidney (95.5%), faecal (2.6%)
Identifiers
  • Pentyl [1-(3,4-dihydroxy-5-methyltetrahydrofuran-2-yl)-5-fluoro-2-oxo-1H-pyrimidin-4-yl]carbamate
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.112.980 Edit this at Wikidata
Chemical and physical data
FormulaC15H22FN3O6
Molar mass359.354 g·mol−1
3D model (JSmol)
  • FC=1\C(=N/C(=O)N(C=1)[C@@H]2O[C@@H]([C@@H](O)[C@H]2O)C)\NC(=O)OCCCCC
  • 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 checkY
  • Key:GAGWJHPBXLXJQN-UORFTKCHSA-N checkY
  (verify)

Capecitabine, sold under the brand name Xeloda among others, is a anticancer medication used to treat breast cancer, gastric cancer and colorectal cancer.[3] For breast cancer it is often used together with docetaxel.[4] It is taken by mouth.[4]

Common side effects include abdominal pain, vomiting, diarrhea, weakness, and rashes.[4] Other severe side effects include blood clotting problems, allergic reactions, heart problems such as cardiomyopathy, and low blood cell counts.[4] Use during pregnancy may result in harm to the fetus.[4] Capecitabine, inside the body, is converted to 5-fluorouracil (5-FU) through which it acts.[4] It belongs to the class of medications known as fluoropyrimidines, which also includes 5-FU and tegafur.[5]

Capecitabine was patented in 1992 and approved for medical use in 1998.[6] It is on the World Health Organization's List of Essential Medicines.[7]

  1. ^ "FDA-sourced list of all drugs with black box warnings (Use Download Full Results and View Query links.)". nctr-crs.fda.gov. FDA. Retrieved 22 October 2023.
  2. ^ "Xeloda EPAR". European Medicines Agency. 2 February 2001. Retrieved 2 July 2024.
  3. ^ British national formulary : BNF 69 (69 ed.). British Medical Association. 2015. pp. 585, 588. ISBN 9780857111562.
  4. ^ a b c d e f "Capecitabine". The American Society of Health-System Pharmacists. Archived from the original on 15 April 2016. Retrieved 8 December 2016.
  5. ^ Caudle KE, Thorn CF, Klein TE, Swen JJ, McLeod HL, Diasio RB, et al. (December 2013). "Clinical Pharmacogenetics Implementation Consortium guidelines for dihydropyrimidine dehydrogenase genotype and fluoropyrimidine dosing". Clinical Pharmacology and Therapeutics. 94 (6): 640–645. doi:10.1038/clpt.2013.172. PMC 3831181. PMID 23988873.
  6. ^ Fischer J, Ganellin CR (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 511. ISBN 9783527607495. Archived from the original on 12 January 2023. Retrieved 30 August 2017.
  7. ^ World Health Organization (2019). World Health Organization model list of essential medicines: 21st list 2019. Geneva: World Health Organization. hdl:10665/325771. WHO/MVP/EMP/IAU/2019.06. License: CC BY-NC-SA 3.0 IGO.