Capecitabine

Capecitabine
Clinical data
Pronunciation	/kæpɪˈsaɪtəbiːn/
Trade names	Xeloda, Xitabin, Kapetral, others
AHFS/Drugs.com	Monograph
MedlinePlus	a699003
Pregnancy; category	AU: D;
Routes of; administration	By mouth
Drug class	Antineoplastic agent
ATC code	L01BC06 (WHO) ;
Legal status
Legal status	AU: S4 (Prescription only); CA: ℞-only; UK: POM (Prescription only); US: ℞-only; EU: Rx-only;
Pharmacokinetic data
Bioavailability	Extensive
Protein binding	< 60%
Metabolism	liver, to 5'-DFCR, 5'-DFUR (inactive); neoplastic tissue, 5'-DFUR to active fluorouracil
Elimination half-life	38–45 minutes
Excretion	kidney (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 ;
PubChem CID	60953;
IUPHAR/BPS	6799;
DrugBank	DB01101 ;
ChemSpider	54916 ;
UNII	6804DJ8Z9U;
KEGG	D01223 ;
ChEBI	CHEBI:31348 ;
ChEMBL	ChEMBL1773 ;
CompTox Dashboard (EPA)	DTXSID3046451 ;
ECHA InfoCard	100.112.980
Chemical and physical data
Formula	C15H22FN3O6
Molar mass	359.354 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 ; Key:GAGWJHPBXLXJQN-UORFTKCHSA-N ;
	(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]

^ "Xeloda EPAR". European Medicines Agency. 2 February 2001. Retrieved 2 July 2024.
^ British national formulary : BNF 69 (69 ed.). British Medical Association. 2015. pp. 585, 588. ISBN 9780857111562.
^ ^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.
^ 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.
^ 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.
^ 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.

[1] "Xeloda EPAR". European Medicines Agency. 2 February 2001. Retrieved 2 July 2024.

[BNF69-2] British national formulary : BNF 69 (69 ed.). British Medical Association. 2015. pp. 585, 588. ISBN 9780857111562.

[AHFS2016-3] ^ ^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.

[pmid23988873-4] 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.

[Fis2006-5] 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.

[WHO21st-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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