Mr. Ibrahem/Capecitabine
Clinical data
Pronunciation/kæpɪˈstəbn/
Trade namesXeloda, Xitabin, Kapetral, others
AHFS/Drugs.comMonograph
MedlinePlusa699003
License data
Pregnancy
category
  • AU: D
Routes of
administration
By mouth
Drug classChemotherapy agent
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
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 chemotherapy medication used to treat breast cancer, gastric cancer, and colorectal cancer.[1] For breast cancer it is often used together with docetaxel.[2] It is taken by mouth.[2]

Common side effects include abdominal pain, vomiting, diarrhea, weakness, and rashes.[2] Other severe side effects include blood clotting problems, allergic reactions, heart problems such as cardiomyopathy, and low blood cell counts.[2] It is not recommended in people with kidney problems.[2] Use during pregnancy may result in harm to the baby.[2] Capecitabine, inside the body, is converted to 5-fluorouracil (5-FU) through which it acts.[2] It belongs to the class of medications known as fluoropyrimidines, which also includes 5-fluorouracil and tegafur.[4]

Capecitabine was patented in 1992 and approved for medical use in 1998.[5] It is on the World Health Organization's List of Essential Medicines.[6] The wholesale cost in the developing world is about US$122.64–195.66 per cycle of medication.[7] In the United Kingdom it costs the NHS about £210.67 per cycle.[1] In the United States it costs about $1,892.00 as of 2016.[8]

References

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  1. ^ a b c British national formulary : BNF 69 (69 ed.). British Medical Association. 2015. pp. 585, 588. ISBN 9780857111562.
  2. ^ a b c d e f g h "Capecitabine". The American Society of Health-System Pharmacists. Archived from the original on 15 April 2016. Retrieved 8 December 2016.
  3. ^ Cite error: The named reference who was invoked but never defined (see the help page).
  4. ^ Caudle KE, Thorn CF, Klein TE, Swen JJ, McLeod HL, Diasio RB, Schwab M (December 2013). "Clinical Pharmacogenetics Implementation Consortium guidelines for dihydropyrimidine dehydrogenase genotype and fluoropyrimidine dosing". Clinical Pharmacology and Therapeutics. 94 (6): 640–5. doi:10.1038/clpt.2013.172. PMC 3831181. PMID 23988873.
  5. ^ Fischer, Janos; Ganellin, C. Robin (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 511. ISBN 9783527607495. Archived from the original on 2020-12-06. Retrieved 2017-08-30.
  6. ^ 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.
  7. ^ "Capecitabine". International Drug Price Indicator Guide. Archived from the original on 22 January 2018. Retrieved 8 December 2016.
  8. ^ "NADAC as of 2016-12-07 | Data.Medicaid.gov". Centers for Medicare and Medicaid Services. Archived from the original on 21 December 2016. Retrieved 19 December 2016.