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Capecitabine information


Capecitabine
Clinical data
Pronunciation/kæpɪˈstəbn/
Trade namesXeloda, Xitabin, Kapetral, others
AHFS/Drugs.comMonograph
MedlinePlusa699003
License data
  • EU EMA: by INN
Pregnancy
category
  • AU: D
Routes of
administration
By mouth
Drug classchemotherapy agent
ATC code
  • L01BC06 (WHO)
Legal status
Legal status
  • AU: S4 (Prescription only)
  • CA: ℞-only
  • UK: POM (Prescription only)
  • US: WARNING[1]Rx-only
  • EU: Rx-only
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
IUPAC name
  • Pentyl [1-(3,4-dihydroxy-5-methyltetrahydrofuran-2-yl)-5-fluoro-2-oxo-1H-pyrimidin-4-yl]carbamate
CAS Number
  • 154361-50-9 checkY
PubChem CID
  • 60953
IUPHAR/BPS
  • 6799
DrugBank
  • DB01101 checkY
ChemSpider
  • 54916 checkY
UNII
  • 6804DJ8Z9U
KEGG
  • D01223 checkY
ChEBI
  • CHEBI:31348 checkY
ChEMBL
  • ChEMBL1773 checkY
CompTox Dashboard (EPA)
  • DTXSID3046451 Edit this at Wikidata
ECHA InfoCard100.112.980 Edit this at Wikidata
Chemical and physical data
FormulaC15H22FN3O6
Molar mass359.354 g·mol−1
3D model (JSmol)
  • Interactive image
SMILES
  • 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
  • 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.[2] For breast cancer it is often used together with docetaxel.[3] It is taken by mouth.[3]

Common side effects include abdominal pain, vomiting, diarrhea, weakness, and rashes.[3] Other severe side effects include blood clotting problems, allergic reactions, heart problems such as cardiomyopathy, and low blood cell counts.[3] Use during pregnancy may result in harm to the fetus.[3] Capecitabine, inside the body, is converted to 5-fluorouracil (5-FU) through which it acts.[3] It belongs to the class of medications known as fluoropyrimidines, which also includes 5-FU 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]

  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. ^ British national formulary : BNF 69 (69 ed.). British Medical Association. 2015. pp. 585, 588. ISBN 9780857111562.
  3. ^ 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.
  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): 640–645. doi:10.1038/clpt.2013.172. PMC 3831181. PMID 23988873.
  5. ^ 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.
  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.

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