Capecitabine
Capecitabine is a fluoropyrimidine carbamate belonging to the class of antineoplastic agents called antimetabolites. As a prodrug, capecitabine is selectively activated by carboxylesterases of tumor cells to its cytotoxic moiety, 5-fluorouracil (5-FU); subsequently, 5-FU is metabolized to two active metabolites, 5-fluoro-2-deoxyuridine monophosphate (FdUMP) and 5-fluorouridine triphosphate (FUTP) by both tumor cells and normal cells. FdUMP inhibits DNA synthesis and cell division by reducing normal thymidine production, while FUTP inhibits RNA and protein synthesis by competing with uridine triphosphate for incorporation into the RNA strand
General
Type : Drug, Carbamate, Pyrimidine, Pro-Drug
Chemical_Nomenclature : pentyl N-[1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-methyloxolan-2-yl]-5-fluoro-2-oxopyrimidin-4-yl]carbamate
Canonical SMILES : CCCCCOC(=O)NC1=NC(=O)N(C=C1F)C2C(C(C(O2)C)O)O
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
InChIKey : GAGWJHPBXLXJQN-UORFTKCHSA-N
Other name(s) : Xeloda || capecitabina || capecitabinum || Capecitabin || Capecitibine || Capiibine || Caxeta || Xabine
MW : 359.35
Formula : C15H22FN3O6
CAS_number : 154361-50-9
PubChem : 60953
UniChem : GAGWJHPBXLXJQN-UORFTKCHSA-N
Wikipedia : Capecitabine
Target
Structures : No structure
Families : Carboxylesterase, Carb_B_Chordata
References (16)
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| Author(s) : de With M , van Doorn L , Maasland DC , Mulder TAM , Oomen-de Hoop E , Mostert B , Homs MYV , El Bouazzaoui S , Mathijssen RHJ , van Schaik RHN , Bins S |
| Ref : Biomed Pharmacother , 159 :114232 , 2023 |
| Abstract : |
| PubMedSearch : de With_2023_Biomed.Pharmacother_159_114232 |
| PubMedID: 36630849 |
| Title : Assessment of drug-drug interaction and optimization in capecitabine and irinotecan combination regimen using a physiologically based pharmacokinetic model - Sakai_2021_J.Pharm.Sci__ |
| Author(s) : Sakai S , Kobuchi S , Ito Y , Sakaeda T |
| Ref : J Pharm Sci , : , 2021 |
| Abstract : |
| PubMedSearch : Sakai_2021_J.Pharm.Sci__ |
| PubMedID: 34965386 |
| Title : Novel Genetic Variants in Carboxylesterase 1 Predict Severe Early-Onset Capecitabine-Related Toxicity - Hamzic_2017_Clin.Pharmacol.Ther_102_796 |
| Author(s) : Hamzic S , Kummer D , Milesi S , Mueller D , Joerger M , Aebi S , Amstutz U , Largiader CR |
| Ref : Clinical Pharmacology & Therapeutics , 102 :796 , 2017 |
| Abstract : |
| PubMedSearch : Hamzic_2017_Clin.Pharmacol.Ther_102_796 |
| PubMedID: 28139840 |
| Gene_locus related to this paper: human-CES1 |
| Title : A Simple Method for Comparing Enzymatic Capecitabine Activation in Various Mono- and Combination Chemotherapies - Buchner_2015_Pharmacology_95_29 |
| Author(s) : Buchner P , Sahmanovic A , Schreiber V , Baroian N , Dittrich C , Czejka M |
| Ref : Pharmacology , 95 :29 , 2015 |
| Abstract : |
| PubMedSearch : Buchner_2015_Pharmacology_95_29 |
| PubMedID: 25591914 |
| Title : Standard versus continuous administration of capecitabine in metastatic breast cancer (GEICAM\/2009-05): a randomized, noninferiority phase II trial with a pharmacogenetic analysis - Martin_2015_Oncologist_20_111 |
| Author(s) : Martin M , Martinez N , Ramos M , Calvo L , Lluch A , Zamora P , Munoz M , Carrasco E , Caballero R , Garcia-Saenz JA , Guerra E , Caronia D , Casado A , Ruiz-Borrego M , Hernando B , Chacon JI , De la Torre-Montero JC , Jimeno MA , Heras L , Alonso R , De la Haba J , Pita G , Constenla M , Gonzalez-Neira A |
| Ref : Oncologist , 20 :111 , 2015 |
| Abstract : |
| PubMedSearch : Martin_2015_Oncologist_20_111 |
| PubMedID: 25601966 |
| Title : ZRX1, the first EGFR inhibitor-capecitabine based combi-molecule, requires carboxylesterase-mediated hydrolysis for optimal activity - Ait-Tihyaty_2013_Invest.New.Drugs_31_1409 |
| Author(s) : Ait-Tihyaty M , Rachid Z , Larroque-Lombard AL , Jean-Claude BJ |
| Ref : Invest New Drugs , 31 :1409 , 2013 |
| Abstract : |
| PubMedSearch : Ait-Tihyaty_2013_Invest.New.Drugs_31_1409 |
| PubMedID: 23959266 |
| Title : Higher capecitabine AUC in elderly patients with advanced colorectal cancer (SWOGS0030) - Louie_2013_Br.J.Cancer_109_1744 |
| Author(s) : Louie SG , Ely B , Lenz HJ , Albain KS , Gotay C , Coleman D , Raghavan D , Shields AF , Gold PJ , Blanke CD |
| Ref : Br J Cancer , 109 :1744 , 2013 |
| Abstract : |
| PubMedSearch : Louie_2013_Br.J.Cancer_109_1744 |
| PubMedID: 24022189 |
| Title : Phase II and gene expression analysis trial of neoadjuvant capecitabine plus irinotecan followed by capecitabine-based chemoradiotherapy for locally advanced rectal cancer: Hoosier Oncology Group GI03-53 - Chiorean_2012_Cancer.Chemother.Pharmacol_70_25 |
| Author(s) : Chiorean EG , Sanghani S , Schiel MA , Yu M , Burns M , Tong Y , Hinkle DT , Coleman N , Robb B , LeBlanc J , Clark R , Bufill J , Curie C , Loehrer PJ , Cardenes H |
| Ref : Cancer Chemother Pharmacol , 70 :25 , 2012 |
| Abstract : |
| PubMedSearch : Chiorean_2012_Cancer.Chemother.Pharmacol_70_25 |
| PubMedID: 22610353 |
| Title : A polymorphism in the cytidine deaminase promoter predicts severe capecitabine-induced hand-foot syndrome - Caronia_2011_Clin.Cancer.Res_17_2006 |
| Author(s) : Caronia D , Martin M , Sastre J , de la Torre J , Garcia-Saenz JA , Alonso MR , Moreno LT , Pita G , Diaz-Rubio E , Benitez J , Gonzalez-Neira A |
| Ref : Clin Cancer Research , 17 :2006 , 2011 |
| Abstract : |
| PubMedSearch : Caronia_2011_Clin.Cancer.Res_17_2006 |
| PubMedID: 21325291 |
| Title : Capecitabine, oxaliplatin and radiotherapy: a phase IB neoadjuvant study for esophageal cancer with gene expression analysis - Javle_2009_Cancer.Invest_27_193 |
| Author(s) : Javle MM , Yang G , Nwogu CE , Wilding GE , O'Malley L , Vinjamaram S , Schiff MD , Nava HR , LeVea C , Clark KR , Prey JD , Smith PF , Pendyala L |
| Ref : Cancer Invest , 27 :193 , 2009 |
| Abstract : |
| PubMedSearch : Javle_2009_Cancer.Invest_27_193 |
| PubMedID: 19235592 |
| Title : A carboxylesterase 2 gene polymorphism as predictor of capecitabine on response and time to progression - Ribelles_2008_Curr.Drug.Metab_9_336 |
| Author(s) : Ribelles N , Lopez-Siles J , Sanchez A , Gonzalez E , Sanchez MJ , Carabantes F , Sanchez-Rovira P , Marquez A , Duenas R , Sevilla I , Alba E |
| Ref : Curr Drug Metab , 9 :336 , 2008 |
| Abstract : |
| PubMedSearch : Ribelles_2008_Curr.Drug.Metab_9_336 |
| PubMedID: 18473752 |
| Title : Capecitabine-induced severe hypertriglyceridemia: report of two cases - Kurt_2006_Ann.Pharmacother_40_328 |
| Author(s) : Kurt M , Babaoglu MO , Yasar U , Shorbagi A , Guler N |
| Ref : Annals of Pharmacotherapy , 40 :328 , 2006 |
| Abstract : |
| PubMedSearch : Kurt_2006_Ann.Pharmacother_40_328 |
| PubMedID: 16391007 |
| Title : Mammalian carboxylesterases: from drug targets to protein therapeutics - Redinbo_2005_Drug.Discov.Today_10_313 |
| Author(s) : Redinbo MR , Potter PM |
| Ref : Drug Discov Today , 10 :313 , 2005 |
| Abstract : |
| PubMedSearch : Redinbo_2005_Drug.Discov.Today_10_313 |
| PubMedID: 15749280 |
| Title : Hydrolysis of capecitabine to 5'-deoxy-5-fluorocytidine by human carboxylesterases and inhibition by loperamide - Quinney_2005_J.Pharmacol.Exp.Ther_313_1011 |
| Author(s) : Quinney SK , Sanghani SP , Davis WI , Hurley TD , Sun Z , Murry DJ , Bosron WF |
| Ref : Journal of Pharmacology & Experimental Therapeutics , 313 :1011 , 2005 |
| Abstract : |
| PubMedSearch : Quinney_2005_J.Pharmacol.Exp.Ther_313_1011 |
| PubMedID: 15687373 |
| Gene_locus related to this paper: human-CES1 , human-CES2 , human-CES3 |
| Title : Capecitabine in the treatment of metastatic renal cell carcinoma failing immunotherapy - Wenzel_2002_Am.J.Kidney.Dis_39_48 |
| Author(s) : Wenzel C , Locker GJ , Schmidinger M , Mader R , Kramer G , Marberger M , Rauchenwald M , Zielinski CC , Steger GG |
| Ref : Am J Kidney Dis , 39 :48 , 2002 |
| Abstract : |
| PubMedSearch : Wenzel_2002_Am.J.Kidney.Dis_39_48 |
| PubMedID: 11774101 |
| Title : Design of a novel oral fluoropyrimidine carbamate, capecitabine, which generates 5-fluorouracil selectively in tumours by enzymes concentrated in human liver and cancer tissue - Miwa_1998_Eur.J.Cancer_34_1274 |
| Author(s) : Miwa M , Ura M , Nishida M , Sawada N , Ishikawa T , Mori K , Shimma N , Umeda I , Ishitsuka H |
| Ref : Eur J Cancer , 34 :1274 , 1998 |
| Abstract : |
| PubMedSearch : Miwa_1998_Eur.J.Cancer_34_1274 |
| PubMedID: 9849491 |