Capecitabine Inhibitor CAS No. 154361-50-9

Cat. No.	Name	Size	Price	Add Cart
KI0297	Capecitabine	50 mg	$154

Chemical Characteristic

Product Name	Capecitabine
Synonyms	Xeloda
CAS No.	154361-50-9
Molecular Weight	359.35
Formula	C₁₅H₂₂FN₃O₆
Chemical Name	pentyl 1-((2R,3R,4S,5R)-3,4-dihydroxy-5-methyl-tetrahydrofuran-2-yl)-5-fluoro-2-oxo-1,2-dihydropyrimidin-4-ylcarbamate
Smiles	C(=O)(OCCCCC)Nc1nc(=O)n(cc1F)C1OC(C(C1O)O)C
Chemical Structure

Biological activities

Capecitabine is a new oral chemotherapeutic agent used in the treatment of metastatic breast cancers, colorectal cancers and gastric cancers. As a prodrug, capecitabine is enzymatically from fluoropyrimidine converted to 5-fluorouracil (5-FU) by thymidine phosphory in the tumor, where it inhibits DNA synthesis. The converting pathway includes three enzymatic steps and two intermediary metabolites, 5'-deoxy-5-fluorocytidine (5'-DFCR) and 5'-deoxy-5-fluorouridine (5'-DFUR). As thymidine phosphory is preferentially expressed by tumor cells, capecitabine is considered to exert a selective antitumoral action.^[1] Capecitabine has a bioavailability of approximately 100% with a C_{max of 3.9 mg/L, T_{max of 1.5 to 2 hour, and AUC of 5.96 mg.h/L in adults.^[2] HepG2 and LS174T cells treated with capecitabine have a bystander effect. Although little cell death occurs in LS174T cells exposed to capecitabine, both early and late apoptosis are increased by 244 and 262%, respectively, in the LS174T-c2 subclone. Furthermore, thymidine phosphorylase plays a key role in the capecitabine activity and the Fas/FasL system can be a new determinant for capecitabine efficacy.^[3] HCC xenografts treated with capecitabine may result to high concentration of 5-FU in tumors converted by platelet-derived endothelial cell growth factor (PD-ECGF) and inhibit tumor growth and lung metastasis in LCI-D20 mice.^[4] Besides, in tests with various human cancer xenograft models, capecitabine is more efficacious at wider dose ranges than either 5-FU or 5'-DFUR and is significantly less toxic to the intestinal tract than the others in monkeys.^[5]}}

Protocols

Capecitabine is dissolved in 40 mM citrate buffer (pH 6.0) containing 5% Arabic gum .^[4]

References

[1] Dooley M, et al.Capecitabine. Drugs. 1999, 58(1): 69-76. [2] Walko CM, et al. Capecitabine: a review. Clin Ther. 2005, 27(1): 23-44. [3] Ciccolini J, et al. Transmission of apoptosis in human colorectal tumor cells exposed to capecitabine, Xeloda, is mediated via Fas. Mol Cancer Ther. 2002, 1(11): 923-927. [4] Zhou J et al. Capecitabine inhibits postoperative recurrence and metastasis after liver cancer resection in nude mice with relation to the expression of platelet-derived endothelial cell growth factor. Clin Cancer Res. 2003, 9(16 Pt 1): 6030-6037. [5] Shimma N, et al. The design and synthesis of a new tumor-selective fluoropyrimidine carbamate, capecitabine. Bioorg Med Chem. 2000, 8(7): 1697-1706.

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