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Namespace Prefixes

PrefixIRI
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Statements

Subject Item
n2:DB01101
rdf:type
n3:Drug
n3:description
Capecitabine 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 fluorouracil (antimetabolite) in the tumor, where it inhibits DNA synthesis and slows growth of tumor tissue.
n3:dosage
n11:271B3F35-363D-11E5-9242-09173F13E4C5 n11:271B3F36-363D-11E5-9242-09173F13E4C5 n11:271B3F33-363D-11E5-9242-09173F13E4C5 n11:271B3F34-363D-11E5-9242-09173F13E4C5
n3:generalReferences
# Walko CM, Lindley C: Capecitabine: a review. Clin Ther. 2005 Jan;27(1):23-44. "Pubmed":http://www.ncbi.nlm.nih.gov/pubmed/15763604 # Wagstaff AJ, Ibbotson T, Goa KL: Capecitabine: a review of its pharmacology and therapeutic efficacy in the management of advanced breast cancer. Drugs. 2003;63(2):217-36. "Pubmed":http://www.ncbi.nlm.nih.gov/pubmed/12515569 # Koukourakis GV, Kouloulias V, Koukourakis MJ, Zacharias GA, Zabatis H, Kouvaris J: Efficacy of the oral fluorouracil pro-drug capecitabine in cancer treatment: a review. Molecules. 2008 Aug 27;13(8):1897-922. "Pubmed":http://www.ncbi.nlm.nih.gov/pubmed/18794792 # Twelves C: Vision of the future: capecitabine. Oncologist. 2001;6 Suppl 4:35-9. "Pubmed":http://www.ncbi.nlm.nih.gov/pubmed/11585973 # Milano G, Ferrero JM, Francois E: Comparative pharmacology of oral fluoropyrimidines: a focus on pharmacokinetics, pharmacodynamics and pharmacomodulation. Br J Cancer. 2004 Aug 16;91(4):613-7. "Pubmed":http://www.ncbi.nlm.nih.gov/pubmed/15280932 # de Bono JS, Twelves CJ: The oral fluorinated pyrimidines. Invest New Drugs. 2001;19(1):41-59. "Pubmed":http://www.ncbi.nlm.nih.gov/pubmed/11291832
n3:group
investigational approved
n3:halfLife
45-60 minutes for capecitabine and its metabolites.
n3: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.
owl:sameAs
n13:DB01101 n22:DB01101
dcterms:title
Capecitabine
adms:identifier
n10:Capecitabine n23:PA448771 n24:60953 n25:D01223 n26:0004-1100-20 n27:46508686 n28:31348 n29:C12650 n30:54916 n31:DB01101
n3:mechanismOfAction
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-fluorouridine triphosphate (FUTP), within normal and tumour cells. These metabolites cause cell injury by two different mechanisms. First, FdUMP and the folate cofactor, N5-10-methylenetetrahydrofolate, bind to thymidylate synthase (TS) to form a covalently bound ternary complex. This binding inhibits the formation of thymidylate from 2'-deaxyuridylate. Thymidylate is the necessary precursor of thymidine triphosphate, which is essential for the synthesis of DNA, therefore a deficiency of this compound can inhibit cell division. Secondly, nuclear transcriptional enzymes can mistakenly incorporate FUTP in place of uridine triphosphate (UTP) during the synthesis of RNA. This metabolic error can interfere with RNA processing and protein synthesis through the production of fraudulent RNA.
n3:packager
n14:271B3F2F-363D-11E5-9242-09173F13E4C5 n14:271B3F30-363D-11E5-9242-09173F13E4C5 n14:271B3F2E-363D-11E5-9242-09173F13E4C5
n3:patent
n19:1327358 n19:4966891 n19:2103324 n19:5472949
n3:routeOfElimination
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.
n3:synonym
Capecitabin Pentyl [1-(5-deoxy-beta-D-ribofuranosyl)-5-fluoro-2-oxo-1,2-dihydropyrimidin-4-yl]carbamate Capecitabinum (1-(5-Deoxy-beta-D-ribofuranosyl)-5-fluoro-1,2-dihydro-2-oxo-4-pyrimidinyl)-carbamic acid pentyl ester Pentyl 1-(5-deoxy-beta-D-ribofuranosyl)-5-fluoro-1,2-dihydro-2-oxo-4-pyrimidinecarbamate Capecitabina Xeloda
n7:hasAHFSCode
n8:10-00-00
n3:foodInteraction
Take 12 hours apart, within 30 minutes of the end of breakfast and dinner to reduce nausea.
n3:proteinBinding
< 60% (mainly albumin)
n3:synthesisReference
"DrugSyn.org":http://www.drugsyn.org/Capecitabine.htm
n17:hasConcept
n18:M0287377
foaf:page
n6:capecitabine.html n21:capecitabine.htm
n3:IUPAC-Name
n4:271B3F3B-363D-11E5-9242-09173F13E4C5
n3:InChI
n4:271B3F41-363D-11E5-9242-09173F13E4C5
n3:Molecular-Formula
n4:271B3F40-363D-11E5-9242-09173F13E4C5
n3:Molecular-Weight
n4:271B3F3D-363D-11E5-9242-09173F13E4C5
n3:Monoisotopic-Weight
n4:271B3F3E-363D-11E5-9242-09173F13E4C5
n3:SMILES
n4:271B3F3F-363D-11E5-9242-09173F13E4C5
n3:Water-Solubility
n4:271B3F39-363D-11E5-9242-09173F13E4C5 n4:271B3F51-363D-11E5-9242-09173F13E4C5
n3:logP
n4:271B3F53-363D-11E5-9242-09173F13E4C5 n4:271B3F3A-363D-11E5-9242-09173F13E4C5 n4:271B3F37-363D-11E5-9242-09173F13E4C5
n3:logS
n4:271B3F38-363D-11E5-9242-09173F13E4C5
n7:hasATCCode
n16:L01BC06
n3:H-Bond-Acceptor-Count
n4:271B3F47-363D-11E5-9242-09173F13E4C5
n3:H-Bond-Donor-Count
n4:271B3F48-363D-11E5-9242-09173F13E4C5
n3:InChIKey
n4:271B3F42-363D-11E5-9242-09173F13E4C5
n3:Polar-Surface-Area--PSA-
n4:271B3F43-363D-11E5-9242-09173F13E4C5
n3:Polarizability
n4:271B3F45-363D-11E5-9242-09173F13E4C5
n3:Refractivity
n4:271B3F44-363D-11E5-9242-09173F13E4C5
n3:Rotatable-Bond-Count
n4:271B3F46-363D-11E5-9242-09173F13E4C5
n3:absorption
Readily absorbed through the GI tract (~70%)
n3:affectedOrganism
Humans and other mammals
n3:casRegistryNumber
154361-50-9
n3:category
n3:containedIn
n20:271B3F31-363D-11E5-9242-09173F13E4C5 n20:271B3F32-363D-11E5-9242-09173F13E4C5
n3:Bioavailability
n4:271B3F4D-363D-11E5-9242-09173F13E4C5
n3:Ghose-Filter
n4:271B3F4F-363D-11E5-9242-09173F13E4C5
n3:MDDR-Like-Rule
n4:271B3F50-363D-11E5-9242-09173F13E4C5
n3:Melting-Point
n4:271B3F52-363D-11E5-9242-09173F13E4C5
n3:Number-of-Rings
n4:271B3F4C-363D-11E5-9242-09173F13E4C5
n3:Physiological-Charge
n4:271B3F4B-363D-11E5-9242-09173F13E4C5
n3:Rule-of-Five
n4:271B3F4E-363D-11E5-9242-09173F13E4C5
n3:Traditional-IUPAC-Name
n4:271B3F3C-363D-11E5-9242-09173F13E4C5
n3:pKa--strongest-acidic-
n4:271B3F49-363D-11E5-9242-09173F13E4C5
n3:pKa--strongest-basic-
n4:271B3F4A-363D-11E5-9242-09173F13E4C5