View source for It07:Capecitabine

=Capecitabine=

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! {{chembox header}} | General
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| [http://en.wikipedia.org/wiki/IUPAC Systematic name]
| pentyl N-[1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-methyloxolan-2-yl]-5-fluoro-2-oxopyrimidin-4-yl]carbamate

|-
| Other names
| Xeloda
|-
| [http://en.wikipedia.org/wiki/Chemical_formula Molecular formula]
|C15H22FN3O6
|-
| [http://en.wikipedia.org/wiki/Chemical_file_format SMILES] <!-- mostly for organic compounds, omit otherwise -->
| CCCCCOC(=O)NC1=NC(=O)N(C=C1F)C2C(C(C(O2)C)O)O
|-
| [http://en.wikipedia.org/wiki/Molar_mass Molar mass]
| 359.350083 g/mol
|-
| [http://en.wikipedia.org/wiki/CAS_registry_number CAS number]
| 154361-50-9
|-
{{Chem-Data_Structure}}

==3D Structure==
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==Capecitabine==

Capecitabine, trade name Xeloda, is an orally administered prodrug (drug which is administered in an inactive form and is metabolised in vivo to an active metabolite) of Fluoroacil (FU), one of the most frequently used anti tumour agents for treating solid tumours. Capecitabine is used in the treatment of colorectal and metastatic breast cancer. It can be used in monotherapy or more commonly in combination therapy usually with doxcetaxel.

Capecitabine is ingested and only gets converted to its active metabolite (FU) by thymidine phosphorylase.<ref>Walko CM, Lindley C. Capecitabine:a review Clin Ther. 2005;27(1):23-44</ref>  This is useful as higher levels of this enzyme are found in tumours and the liver as opposed to normal healthy tissue.

The most common side effects occurring in patients receiving monotherapy are:

*Lymphopenia
*Anaemia
*Diarrhoea
*Hand and Foot syndrome
*Nausea
*Fatigue
*Hyperbilirubinaemia
*Dermatitis
*Vomiting


==Synthesis==


[[Image:Capecitabine_synthesis.jpg]]



The synthesis takes place in three steps <ref>N. Shimma et al Bioorg. Med. Chem. 8 (2000)</ref> 

#Glycosidation of 11 with 1,2,3-tri-O-acetyl-5-deoxyribose with stannic tetrachloride in dichloromethane.
#Acylation of the N4 amino group with acid chlorides in pyridine/dichloromethane.
#Alkaline Hydrolysis of the acetyl group

In the reaction scheme above R = O(CH<sub>2</sub>)<sub>4</sub>CH<sub>3</sub>
==Dose==

Combination Therapy with Capecitabine 1,250 mg/m(2) twice daily for two weeks then a week of no treatment. This is a cycle of treatment. On the first day of each cycle a intravenous docextaxel dose of 75mg/m(2) is given. <ref>Wagstaff AJ, Ibbotson T, Goa KL. Drugs. 2003;63(2):217-36</ref>


==References==

<references/>