|Systematic (IUPAC) name|
|Protein binding||< 60%|
|Metabolism||Hepatic, to 5'-DFCR, 5'-DFUR (inactive); neoplastic tissue, 5'-DFUR to active fluorouracil|
|Excretion||Renal (95.5%), faecal (2.6%)|
|Mol. mass||359.35 g/mol|
|(what is this?)|
Capecitabine (INN) // (Xeloda, Roche) is an orally-administered chemotherapeutic agent used in the treatment of numerous cancers. Capecitabine is a prodrug, that is enzymatically converted to 5-fluorouracil (5-FU) in the body.
- Colorectal cancer (either as neoadjuvant therapy with radiation, adjuvant therapy or for metastatic cases)
- Breast cancer (metastatic or as monotherapy/combotherapy; this is licensed as a second-line treatment in the UK)
- Gastric cancer (off-label in the US; this is a licensed indication in the UK)
- Oesophageal cancer (off-label in the US)
- Very common (>10% frequency)
Notes on adverse effects:
- History of hypersensitivity to fluorouacil, capecitabine or any of its excipients.
- Patients with DPD deficiency
- Pregnancy and lactation
- Patients with pre-existing blood dyscrasias
- Patients with severe hepatic impairment or severe renal impairment
- Treatment with sorivudine or its chemically related analogues, such as brivudine
Drugs it is known to interact with includes:
- Sorivudine or its analogues, such as, brivudine.
- Allopurinol as it decreases the efficacy of 5-FU.
- CYP2C9 substrates, including, warfarin and other coumarin-derivatives anticoagulants
- Phenytoin, as it increases the plasma concentrations of phenytoin.
- Calcium folinate may enhance the therapeutic effects of capecitabine by means of synergising with its metabolite, 5-FU. It may also induce more severe diarrhoea by means of this synergy.
Mechanism of action
Click on genes, proteins and metabolites below to link to respective articles. [§ 1]
- The interactive pathway map can be edited at WikiPathways: "FluoropyrimidineActivity_WP1601".
Capecitabine is metabolised to 5-FU which in turn is a thymidylate synthase inhibitor, hence inhibiting the synthesis of thymidine monophosphate (ThMP), the active form of thymidine which is required for the de novo synthesis of DNA and RNA during gene expression.
- Rossi, S, ed. (2013). Australian Medicines Handbook (2013 ed.). Adelaide: The Australian Medicines Handbook Unit Trust. ISBN 978-0-9805790-9-3.
- "Xeloda (capecitabine) dosing, indications, interactions, adverse effects, and more". Medscape Reference. WebMD. 25 January 2014.
- Joint Formulary Committee (2013). British National Formulary (BNF) (65 ed.). London, UK: Pharmaceutical Press. ISBN 978-0-85711-084-8.
- "XELODA (capecitabine) tablet, film coated [Genentech, Inc.]". DailyMed. Genentech, Inc. December 2013. Retrieved 25 January 2014.
- "Capecitabine Teva : EPAR - Product Information" (PDF). European Medicines Agency. Teva Pharma B.V. 10 January 2014. Retrieved 25 January 2014.
- "Capecitabine 150mg - Summary of Product Characteristics (SPC)". electronic Medicines Compendium. Zentiva. 23 December 2013. Retrieved 25 January 2014.
- "NAME OF THE MEDICINE XELODA® Capecitabine" (PDF). TGA eBusiness Services. Roche Products Pty Limited. 5 December 2013. Retrieved 25 January 2014.
- Reddening, swelling, numbness and desquamation on palms and soles