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Journal of Thermal Analysis and Calorimetry
Authors: M. Łaszcz, K. Trzcińska, K. Filip, A. Szyprowska, M. Mucha, and P. Krzeczyński

Introduction Capecitabine ((pentyl[1-(3,4-dihydroxy-5-methyl-tetrahydrofuran-2-yl)-5-fluoro-2-oxo-1H-pyrimidin-4-yl]aminomethanoate)) (Xeloda ® , Roche) is an oral carbamate of fluoropyrimidine, a precursor of 5-fluorouracil

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Summary

Five new peaks of potential impurities, ranging from 0.05 to 0.12% on an area-percent basis, have been observed in reversed-phase high-performance liquid chromatography of capecitabine drug substance. On the basis of comparison of relative retention times and mass values two of the impurities were identified as intermediates in the process used for synthesis of capecitabine and were characterized as (2-(4-amino-5-fluoro-2-oxopyrimidin-1(2H)-yl)-5-methyltetrahydrofuran-3,4-diyl diacetate and 2-(5-fluoro-2-oxo-4-(pentyloxycarbonylamino)pyrimidin-1(2H)-yl)-5-methyl tetrahydrofuran-3,4-diyl diacetate. The area percentages of two of the other peaks increased substantially when the drug was treated with acid and base. The three compounds other than the two intermediates were isolated by preparative HPLC with gradient elution and were characterized by use of spectroscopic techniques, viz. MS-MS, FTIR, and NMR (1H, 13C and DEPT). On the basis of the spectral data, the structures 5′-deoxy-5-fluorocytidine, 5′-deoxy-5-fluorouridine, and 2-(4-(bis(pentyloxycarbonyl)amino)-5-fluoro-2-oxopyrimidin-(2H)-yl)-5-methyltetrahydrofuran-3,4-diyl diacetate were proposed for the three impurities.

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II study of capecitabine in taxane-pretreated metastatic breast carcinoma patients Cancer 92 1759 1768 . 3. JL

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Cameron , D , Casey , M , Press , M et al. 2008 A phase III randomized comparison of lapatinib plus capecitabine alone in women with advanced breast cancer that has progressed on trastuzumab: updated efficacy and biomarker analyses Breast Cancer Res

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predicts response to capecitabine in advanced colorectal cancer. Int J Colorectal Dis. 2002; 17: 46–49. 22 Leicher LW, Lammertink MH, Offerman SR, et al. Consequences of testing

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.: First-line chemotherapy with capecitabine and temozolomide in patients with metastatic pancreatic endocrine carcinomas. Cancer, 2011, 117 , 268–275. Choi J. First-line chemotherapy

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A Kubicka 2005 Infusional 5-fluorouracil/folinic acid plus oxaliplatin (FUFOX) versus capecitabine plus oxaliplatin (CAPOX) as first line treatment of metastatic colorectal cancer (MCRC

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Toniolo 2003 Capecitabine© and irinotecan (I)(CAPIRI): A good combination in elderly patients (pts) with advanced colorectal cancer (ACRC) as first-line chemotherapy (CT). Preliminary results of a phase II

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lapatinib plus capecitabine in patients with HER2-positive metastatic breast cancer and central nervous system metastases: a retrospective, exploratory analysis in EMILIA. Ann. Oncol., 2015, 26

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. 2010 AVAGAST: A randomized, double-blind, placebo-controlled, phase III study of first-line capecitabine and cisplatin plus bevacizumab or placebo in patients with advanced gastric cancer (AGC) J Clin Oncol 28 18s

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