Capecitabine

Capecitabine

Clinical data
Pregnancy category	AU: D US: D (Evidence of risk)
Routes of administration	Oral
ATC code	L01BC06 (WHO)
Legal status
Legal status	AU: S4 (Prescription only) UK: POM (Prescription only) US: ℞-only
Pharmacokinetic data
Bioavailability	Extensive
Protein binding	< 60%
Metabolism	Hepatic, to 5'-DFCR, 5'-DFUR (inactive); neoplastic tissue, 5'-DFUR to active fluorouracil
Elimination half-life	38–45 minutes
Excretion	Renal 95.5%, faecal 2.6%
Identifiers
IUPAC name pentyl[1-(3,4-dihydroxy-5-methyl-tetrahydrofuran-2-yl)- 5-fluoro-2-oxo-1H-pyrimidin- 4-yl]aminomethanoate
CAS Number	154361-50-9
PubChem CID	60953
DrugBank	APRD00203
E number	{{#property:P628}}
ECHA InfoCard	{{#property:P2566}}
Chemical and physical data
Formula	C15H22FN3O6
Molar mass	359.35 g/mol

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Overview

Capecitabine (INN) (IPA: Template:IPA) is an orally-administered chemotherapeutic agent used in the treatment of metastatic breast and colorectal cancers. Capecitabine is a prodrug, that is enzymatically converted to 5-fluorouracil in the tumor, where it inhibits DNA synthesis and slows growth of tumor tissue. The activation of capecitabine follows a pathway with three enzymatic steps and two intermediary metabolites, 5'-deoxy-5-fluorocytidine (5'-DFCR) and 5'-deoxy-5-fluorouridine (5'-DFUR), to form 5-fluorouracil. Capecitabine is marketed under the trade name Xeloda (Roche).

Indications

Capecitabine is FDA-approved for:

• Adjuvant in colorectal cancer Stage III Dukes' C - used as first-line monotherapy.
• Metastatic colorectal cancer - used as first-line monotherapy, if appropriate.
• Metastatic breast cancer - used in combination with docetaxel, after failure of anthracycline-based treatment. Also as monotherapy, if the patient has failed paclitaxel-based treatment, and if anthracycline-based treatment has either failed or cannot be continued for other reasons (i.e., the patient has already received the maximum lifetime dose of an anthracycline).

In the UK, capecitabine is approved by the National Institute for Health and Clinical Excellence (NICE) for colon and colorectal cancer, and locally advanced or metastatic breast cancer[2].

Dose

The usual starting dose is 2,500 mg/m2/day in two divided doses, 12 hours apart. One cycle includes two weeks of treatment followed by one week without treatment. Cycles can be repeated every three weeks.

Dose adjustments

• For mild renal dysfunction (creatinine clearance 30-50 mL/min), it is recommended to reduce dose by 25%.
• For severe renal dysfunction (creatinine clearance <30 mL/min), treatment is not recommended.
• There is no recommendation for hepatic dysfunction.
• For elderly patients, lower doses may be required due to higher incidences of serious adverse reactions.

Side effects

Potential major adverse reactions include:

• Cardiovascular: EKG changes, myocardial infarction, angina (these may be more common in patients with pre-existing coronary artery disease)
• Dermatological: Hand-foot syndrome (numbness, tingling, pain, redness, or blistering of the palms of the hands and soles of the feet)
• Gastrointestinal: Diarrhea (sometimes severe), nausea, stomatitis
• Hematological: Neutropenia, anemia, thrombocytopenia
• Hepatic: Hyperbilirubinemia

Drug interactions

• May interact with warfarin and increase bleeding risk.
• May inhibit cytochrome CYP2C9 enzyme, and therefore increase levels of substrates such as phenytoin and other substrates of CYP2C9.
• Much as fluorouracil, the concomitant use of leucovorin may increase both the efficacy and the toxicity of capecitabine.

Xeloda Logo

Formulation

Capecitabine (as brand-name Xeloda®) is available in light peach 150 mg tablets and peach 500 mg tablets.

References

• Lacy, Charles F; Armstrong, Lora L; Goldman, Morton P; Lance, Leonard L (2004). Lexi-Comp's Drug Information Handbook (12th Edition). Lexi-Comp Inc. ISBN 1-59195-083-X
• Fischer, David S; Knobf, M Tish; Durivage, Henry J; Beaulieu, Nancy J (2003). The Cancer Chemotherapy Handbook (6th Edition). Mosby. ISBN 0-323-01890-4
• Thomson Centerwatch: Drugs Approved by the FDA (Xeloda) Retrieved 6/05

External links

• Xeloda.com(patient information, tools, and resources)
• [3] (patient information)