Capecitabine

Capecitabine
Clinical data


Pronunciation	/kæpᵻˈsaɪtəbin/
Trade names	Xeloda, others
AHFS/Drugs.com	Monograph
MedlinePlus	a699003
Pregnancy category	AU: D US: D (Evidence of risk)
Routes of administration	by mouth
Drug class	chemotherapy agent
ATC code	L01BC06 (WHO)
Legal status
Legal status	AU: S4 (Prescription only) UK: POM (Prescription only) US: ℞-only
Pharmacokinetic data
Bioavailability	Extensive
Protein binding	< 60%
Metabolism	lilver, to 5'-DFCR, 5'-DFUR (inactive); neoplastic tissue, 5'-DFUR to active fluorouracil
Biological 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^Y
PubChem (CID)	60953
IUPHAR/BPS	6799
DrugBank	DB01101^Y
ChemSpider	54916^Y
UNII	6804DJ8Z9U^Y
KEGG	D01223^Y
ChEBI	CHEBI:31348^Y
ChEMBL	CHEMBL1773^Y
ECHA InfoCard	100.112.980
Chemical and physical data
Formula	C₁₅H₂₂FN₃O₆
Molar mass	359.35 g/mol
3D model (Jmol)	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^Y Key:GAGWJHPBXLXJQN-UORFTKCHSA-N^Y

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

Common side effects include abdominal pain, vomiting, diarrhea, weakness, and rashes. Other severe side effects include blood clotting problems, allergic reactions, heart problems, and low blood cell counts. It is not recommended in people with kidney problems. Use during pregnancy may result in harm to the baby. Capecitabine, inside the body, is converted to 5-fluorouracil (5-FU) through which it acts.

Capecitabine was patented in 1992 and approved for medical use in 1998. It is on the World Health Organization's List of Essential Medicines, the most effective and safe medicines needed in a health system. The wholesale cost in the developing world is about 122.64 to 195.66 USD per cycle of medication. In the United Kingdom it costs the NHS about £210.67 per cycle. In the United States it costs about 1,892.00 USD as of 2016.

It is used in the treatment of the following cancers:

Adverse effects by frequency:

Notes on adverse effects:

Contraindications include:

Drugs it is known to interact with include:

The dihydropyrimidine dehydrogenase (DPD) enzyme is responsible for the detoxifying metabolism of fluoropyrimidines, a class of drugs that includes capecitabine, 5-fluorouracil and tegafur.Genetic variations within the DPD gene (DPYD) can lead to reduced or absent DPD activity, and individuals who are heterozygous or homozygous for these variations may have partial or complete DPD deficiency; an estimated 0.2% of individuals have complete DPD deficiency. Those with partial or complete DPD deficiency have a significantly increased risk of severe or even fatal drug toxicities when treated with fluoropyrimidines; examples of toxicities include myelosuppression, neurotoxicity and hand-foot syndrome.

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