capecitabine capecitabine capecitabine, sold under the brand name xeloda among others, is a anticancer 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. capecitabineclinical datapronunciation/kæpɪˈsaɪtəbiːn/ trade namesxeloda, xitabin, kapetral, othersahfs/drugs.commonographmedlineplusa699003license data eu ema: by inn pregnancycategory au: d routes ofadministrationby mouthdrug classchemotherapy agentatc codel01bc06 (who) legal statuslegal status au: s4 (prescription only) ca: ℞-only uk: pom (prescription only) us: ℞-only eu: rx-only pharmacokinetic databioavailabilityextensiveprotein binding< 60%metabolismliver, to 5'-dfcr, 5'-dfur (inactive); neoplastic tissue, 5'-dfur to active fluorouracilelimination half-life38–45 minutesexcretionkidney (95.5%), faecal (2.6%)identifiers iupac name pentyl carbamate cas number154361-50-9 ypubchem cid60953iuphar/bps6799drugbankdb01101 ychemspider54916 yunii6804dj8z9ukeggd01223 ychebichebi:31348 ychemblchembl1773 ycomptox dashboard (epa)dtxsid3046451 echa infocard100.112.980 chemical and physical dataformulac15h22fn3o6molar mass359.354 g·mol−13d model (jsmol)interactive image smiles fc=1\c(=n/c(=o)n(c=1)2o((o)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 ykey:gagwjhpbxlxjqn-uorftkchsa-n y (verify) common side effects include abdominal pain, vomiting, diarrhea, weakness, and rashes. other severe side effects include blood clotting problems, allergic reactions, heart problems such as cardiomyopathy, and low blood cell counts. use during pregnancy may result in harm to the fetus. capecitabine, inside the body, is converted to 5-fluorouracil (5-fu) through which it acts. it belongs to the class of medications known as fluoropyrimidines, which also includes 5-fu and tegafur. capecitabine was patented in 1992 and approved for medical use in 1998. it is on the world health organization's list of essential medicines. medical uses capecitabine is indicated for adjuvant treatment of people with stage iii colon cancer as a single agent or as a component of a combination chemotherapy regimen; perioperative treatment of adults with locally advanced rectal cancer as a component of chemoradiotherapy; treatment of people with unresectable or metastatic colorectal cancer as a single agent or as a component of a combination chemotherapy regimen; treatment of people with advanced or metastatic breast cancer as a single agent if an anthracycline- or taxane-containing chemotherapy is not indicated; treatment of people with advanced or metastatic breast cancer in combination with docetaxel after disease progression on prior anthracycline-containing chemotherapy; treatment of adults with unresectable or metastatic gastric, esophageal, or gastroesophageal junction cancer as a component of a combination chemotherapy regimen; treatment of adults with her2-overexpressing metastatic gastric or gastroesophageal junction adenocarcinoma who have not received prior treatment for metastatic disease as a component of a combination regimen; adjuvant treatment of adults with pancreatic adenocarcinoma as a component of a combination chemotherapy regimen. adverse effects adverse effects by frequency: very common (>10% frequency) appetite loss diarrhea vomiting nausea stomatitis abdominal pain fatigue weakness hand-foot syndrome oedema fever pain headache hair loss dermatitis indigestion shortness of breath eye irritation myelosuppression notes on adverse effects: includes: anaemia, lymphopenia, neutropenia and thrombocytopenia contraindications contraindications include: history of hypersensitivity to fluorouracil, capecitabine or any of its excipients dpd deficiency (see pharmacogenetics) pregnancy and lactation severe leucopenia, neutropenia, or thrombocytopenia severe hepatic impairment or severe renal impairment treatment with sorivudine or its chemically related analogues, such as brivudine drug interactions drugs it is known to interact with include: sorivudine or its analogues, such as, brivudine. 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. pharmacogenetics 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. mechanism of action click on genes, proteins and metabolites below to link to respective articles. [[file: |alt=fluorouracil (5-fu) activity edit]] fluorouracil (5-fu) activity edit 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. drug synthesis society and culture brand names one of the brand names is xeloda, marketed by genentech. others include xitabin, capcibin, kapetral and pecaset by eurolab.