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QuickView for Capecitabine (compound)

Name: capecitabine
PubChem Compound ID: 10861706
Molecular formula: C15H22FN3O7
Molecular weight: 375.35 g/mol
Name: capecitabine
Name (isomeric): DB01101
Drug Type: small molecule
Brand: Xeloda
Category: Antimetabolites, Prodrugs, Antimetabolites, Antineoplastic, Antineoplastic Agents
CAS number: 154361-50-9
Indication: For the treatment of patients with metastatic breast cancer resistant to both paclitaxel and an anthracycline-containing chemotherapy regimen. May also be used in combination with docetaxel for the treatment of metastatic breast cancer in patients who have failed to respond to, or recurred or relasped during or following anthracycline-containing chemotherapy. Capecitabine is used alone as an adjuvant therapy following the complete resection of primary tumor in patients with stage III colon cancer when monotherapy with fluroprymidine is preferred. The use or capecitabine in combination regimens for advanced gastric cancer is currently being investigated.
Capecitabine is a fluoropyrimidine carbamate with antineoplastic activity indicated for the treatment of metastatic breast cancer and colon cancer. It is an orally administered systemic prodrug that has little pharmacologic activity until it is converted to fluorouracil by enzymes that are expressed in higher concentrations in many tumors. Fluorour...
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Mechanism of Action:
Capecitabine is a prodrug that is selectively tumour-activated to its cytotoxic moiety, fluorouracil, by thymidine phosphorylase, an enzyme found in higher concentrations in many tumors compared to normal tissues or plasma. Fluorouracil is further metabolized to two active metabolites, 5-fluoro-2'-deoxyuridine 5'-monophosphate (FdUMP) and 5-fluorou...
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Absorption: Readily absorbed through the GI tract (~70%)
Protein binding: < 60% (mainly albumin)
Biotransformation: Metabolized by thymidine phosphorylase to fluoruracil.
Route of elimination: Capecitabine and its metabolites are predominantly excreted in urine; 95.5% of administered capecitabine dose is recovered in urine. Fecal excretion is minimal (2.6%). The major metabolite excreted in urine is FBAL which represents 57% of the administered dose.About 3% of the administered dose is excreted in urine as unchanged drug.
Half Life: 45-60 minutes for capecitabine and its metabolites.
Affected organisms: Humans and other mammals
Food interaction:
Take 12 hours apart, within 30 minutes of the end of breakfast and dinner to reduce nausea.
Drug interaction:
EthotoinCapecitabine increases the effect of hydantoin
AcenocoumarolCapecitabine may increase the anticoagulant effect of acenocoumarol by increasing its serum concentration.
WarfarinCapecitabine may increase the serum concentration of warfarin by decreasing its metabolism. Monitor for changes in prothrombin time and therapeutic effects of warfarin if capecitabine is initiated or discontinued. Subsequent cycles of capecitabine may increase this effect.
TrimethoprimThe strong CYP2C9 inhibitor, Capecitabine, may decrease the metabolism and clearance of Trimethoprim, a CYP2C9 substrate. Consider alternate therapy or monitor for changes in therapeutic and adverse effects of Trimethoprim if Capecitabine is initiated, discontinued or dose changed.
MephenytoinCapecitabine increases the effect of hydantoin
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