A prodrug of 5-fluorouracil
Related Products
Active Metabolite(s)
144165-Fluorouracil
Labeled Version(s)
10010681Capecitabine-d11
Metabolite(s)
100106825'-deoxy-5-Fluorocytidine 10253Doxifluridine
Technical Support & Resources

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Capecitabine

Item No. 10487

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
5'-deoxy-5-fluoro-N-[(pentyloxy)carbonyl]-cytidine
CAS Number
154361-50-9
Synonyms
  • Ro 09-1978
Molecular Formula
C15H22FN3O6
Formula Weight
359.4
Purity
≥98%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 14 mg/mlDMSO: 12.5 mg/mlEthanol: 5 mg/mlPBS (pH 7.2): 0.15 mg/ml
λmax
215, 243, 308 nm
SMILES
O=C1N([C@@H]2O[C@H](C)[C@@H](O)[C@H]2O)C=C(F)C(NC(OCCCCC)=O)=N1
InChi Code
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
InChi Key
GAGWJHPBXLXJQN-UORFTKCHSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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Certificates of Analysis & Batch Specific Data

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    500 mg

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    Product Description

    Capecitabine is a prodrug of 5-fluorouracil (5-FU; Item No. 14416).1 It is converted to 5-FU via several enzymatic steps beginning in the liver and ending with conversion in tumor tissue by thymidine phosphorylase, an enzyme that is more concentrated in tumor tissue compared with normal tissue. Capecitabine is cytotoxic only at high concentrations in Scaber, SIHA, and MKN45 cells (IC50s = 97, 578, and 994 µM, respectively) and is inactive in a variety of cancer cell lines, including COLO205, HCT116, and MCF-7 cells (IC50s = >1,000 µM).

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Miwa, M., Ura, M., Nishida, M., et al. Design of a novel oral fluoropyrimidine carbamate, capecitabine, which generates 5-fluorouracil selectively in tumours by enzymes concentrated in human liver and cancer tissue. Eur. J. Cancer 34(8), 1274-1281 (1998).