You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on DrugBank.
Identification
NameCapecitabine
Accession NumberDB01101  (APRD00203)
TypeSmall Molecule
GroupsApproved, Investigational
DescriptionCapecitabine 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.
Structure
Thumb
Synonyms
(1-(5-Deoxy-beta-D-ribofuranosyl)-5-fluoro-1,2-dihydro-2-oxo-4-pyrimidinyl)-carbamic acid pentyl ester
Capecitabin
Capecitabina
Capecitabinum
Pentyl [1-(5-deoxy-beta-D-ribofuranosyl)-5-fluoro-2-oxo-1,2-dihydropyrimidin-4-yl]carbamate
Pentyl 1-(5-deoxy-beta-D-ribofuranosyl)-5-fluoro-1,2-dihydro-2-oxo-4-pyrimidinecarbamate
Xeloda
External Identifiers
  • R340
Approved Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Ach-capecitabinetablet150 mgoralAccord Healthcare Inc2014-09-19Not applicableCanada
Ach-capecitabinetablet500 mgoralAccord Healthcare Inc2014-09-19Not applicableCanada
Sandoz Capecitabinetablet150 mgoralSandoz Canada Incorporated2014-07-23Not applicableCanada
Sandoz Capecitabinetablet500 mgoralSandoz Canada Incorporated2014-07-23Not applicableCanada
Teva-capecitabinetablet150 mgoralTeva Canada Limited2013-08-19Not applicableCanada
Teva-capecitabinetablet500 mgoralTeva Canada Limited2013-08-19Not applicableCanada
Xelodatablet, film coated150 mg/1oralGenentech, Inc.1998-04-30Not applicableUs
Xelodatablet, film coated500 mg/1oralPhysicians Total Care, Inc.2005-06-28Not applicableUs
Xelodatablet, film coated500 mg/1oralGenentech, Inc.1998-04-30Not applicableUs
Xelodatablet150 mgoralHoffmann La Roche Limited1998-09-10Not applicableCanada
Xelodatablet, film coated500 mg/1oralState of Florida DOH Central Pharmacy2009-07-01Not applicableUs
Xelodatablet500 mgoralHoffmann La Roche Limited1998-09-10Not applicableCanada
Xelodatablet, film coated150 mg/1oralPhysicians Total Care, Inc.2005-02-20Not applicableUs
Approved Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Apo-capecitabinetablet150 mgoralApotex IncNot applicableNot applicableCanada
Apo-capecitabinetablet500 mgoralApotex IncNot applicableNot applicableCanada
Capecitabinetablet, film coated500 mg/1oralNorthstar Rx LLC2015-11-01Not applicableUs
Capecitabinetablet, film coated150 mg/1oralTeva Pharmaceuticals USA Inc2014-03-07Not applicableUs
Capecitabinetablet, film coated500 mg/1oralAccord Healthcare Inc.2015-05-20Not applicableUs
Capecitabinetablet, film coated500 mg/1oralAmerican Health Packaging2015-10-01Not applicableUs
Capecitabinetablet, film coated150 mg/1oralMylan Pharmaceuticals Inc.2014-08-08Not applicableUs
Capecitabinetablet, film coated150 mg/1oralAv Kare, Inc.2015-03-20Not applicableUs
Capecitabinetablet, film coated500 mg/1oralTeva Pharmaceuticals USA Inc2014-03-07Not applicableUs
Capecitabinetablet, film coated500 mg/1oralMylan Pharmaceuticals Inc.2014-08-08Not applicableUs
Capecitabinetablet, film coated500 mg/1oralAv Kare, Inc.2015-03-20Not applicableUs
Capecitabinetablet, film coated500 mg/1oralKAISER FOUNDATION HOSPITALS2014-05-14Not applicableUs
Capecitabinetablet, film coated150 mg/1oralNorthstar Rx LLC2015-11-01Not applicableUs
Capecitabinetablet, film coated500 mg/1oralMylan Institutional Inc.2014-08-23Not applicableUs
Capecitabinetablet, film coated500 mg/1oralKAISER FOUNDATION HOSPITALS2015-12-02Not applicableUs
Capecitabinetablet, film coated150 mg/1oralAccord Healthcare Inc.2015-05-22Not applicableUs
Capecitabine AccordFilm-coated tablet300 mgOral useAccord Healthcare Ltd2012-04-20Not applicableEu
Capecitabine AccordFilm-coated tablet300 mgOral useAccord Healthcare Ltd2012-04-20Not applicableEu
Capecitabine AccordFilm-coated tablet500 mgOral useAccord Healthcare Ltd2012-04-20Not applicableEu
Capecitabine AccordFilm-coated tablet300 mgOral useAccord Healthcare Ltd2012-04-20Not applicableEu
Capecitabine AccordFilm-coated tablet500 mgOral useAccord Healthcare Ltd2012-04-20Not applicableEu
Capecitabine AccordFilm-coated tablet150 mgOral useAccord Healthcare Ltd2012-04-20Not applicableEu
Capecitabine AccordFilm-coated tablet150 mgOral useAccord Healthcare Ltd2012-04-20Not applicableEu
Capecitabine AccordFilm-coated tablet300 mgOral useAccord Healthcare Ltd2012-04-20Not applicableEu
Capecitabine AccordFilm-coated tablet300 mgOral useAccord Healthcare Ltd2012-04-20Not applicableEu
Capecitabine AccordFilm-coated tablet500 mgOral useAccord Healthcare Ltd2012-04-20Not applicableEu
Capecitabine AccordFilm-coated tablet150 mgOral useAccord Healthcare Ltd2012-04-20Not applicableEu
Capecitabine AccordFilm-coated tablet300 mgOral useAccord Healthcare Ltd2012-04-20Not applicableEu
Capecitabine AccordFilm-coated tablet500 mgOral useAccord Healthcare Ltd2012-04-20Not applicableEu
Capecitabine AccordFilm-coated tablet150 mgOral useAccord Healthcare Ltd2012-04-20Not applicableEu
Capecitabine AccordFilm-coated tablet150 mgOral useAccord Healthcare Ltd2012-04-20Not applicableEu
Capecitabine AccordFilm-coated tablet300 mgOral useAccord Healthcare Ltd2012-04-20Not applicableEu
Capecitabine AccordFilm-coated tablet300 mgOral useAccord Healthcare Ltd2012-04-20Not applicableEu
Capecitabine AccordFilm-coated tablet150 mgOral useAccord Healthcare Ltd2012-04-20Not applicableEu
Capecitabine AccordFilm-coated tablet500 mgOral useAccord Healthcare Ltd2012-04-20Not applicableEu
Capecitabine AccordFilm-coated tablet500 mgOral useAccord Healthcare Ltd2012-04-20Not applicableEu
Capecitabine AccordFilm-coated tablet150 mgOral useAccord Healthcare Ltd2012-04-20Not applicableEu
Capecitabine AccordFilm-coated tablet150 mgOral useAccord Healthcare Ltd2012-04-20Not applicableEu
Capecitabine AccordFilm-coated tablet300 mgOral useAccord Healthcare Ltd2012-04-20Not applicableEu
Capecitabine AccordFilm-coated tablet500 mgOral useAccord Healthcare Ltd2012-04-20Not applicableEu
Capecitabine AccordFilm-coated tablet150 mgOral useAccord Healthcare Ltd2012-04-20Not applicableEu
Capecitabine AccordFilm-coated tablet500 mgOral useAccord Healthcare Ltd2012-04-20Not applicableEu
Capecitabine AccordFilm-coated tablet500 mgOral useAccord Healthcare Ltd2012-04-20Not applicableEu
Capecitabine MedacFilm-coated tablet500 mgOral useMedac Gesellschaft Für Klinische Spezialpräparate Mb H2012-11-19Not applicableEu
Capecitabine MedacFilm-coated tablet150 mgOral useMedac Gesellschaft Für Klinische Spezialpräparate Mb H2012-11-19Not applicableEu
Capecitabine MedacFilm-coated tablet300 mgOral useMedac Gesellschaft Für Klinische Spezialpräparate Mb H2012-11-19Not applicableEu
Capecitabine MedacFilm-coated tablet300 mgOral useMedac Gesellschaft Für Klinische Spezialpräparate Mb H2012-11-19Not applicableEu
Capecitabine MedacFilm-coated tablet500 mgOral useMedac Gesellschaft Für Klinische Spezialpräparate Mb H2012-11-19Not applicableEu
Capecitabine MedacFilm-coated tablet150 mgOral useMedac Gesellschaft Für Klinische Spezialpräparate Mb H2012-11-19Not applicableEu
Capecitabine MedacFilm-coated tablet150 mgOral useMedac Gesellschaft Für Klinische Spezialpräparate Mb H2012-11-19Not applicableEu
Capecitabine MedacFilm-coated tablet500 mgOral useMedac Gesellschaft Für Klinische Spezialpräparate Mb H2012-11-19Not applicableEu
Capecitabine MedacFilm-coated tablet150 mgOral useMedac Gesellschaft Für Klinische Spezialpräparate Mb H2012-11-19Not applicableEu
Capecitabine MedacFilm-coated tablet300 mgOral useMedac Gesellschaft Für Klinische Spezialpräparate Mb H2012-11-19Not applicableEu
Capecitabine MedacFilm-coated tablet500 mgOral useMedac Gesellschaft Für Klinische Spezialpräparate Mb H2012-11-19Not applicableEu
Capecitabine MedacFilm-coated tablet150 mgOral useMedac Gesellschaft Für Klinische Spezialpräparate Mb H2012-11-19Not applicableEu
Capecitabine MedacFilm-coated tablet300 mgOral useMedac Gesellschaft Für Klinische Spezialpräparate Mb H2012-11-19Not applicableEu
Capecitabine MedacFilm-coated tablet500 mgOral useMedac Gesellschaft Für Klinische Spezialpräparate Mb H2012-11-19Not applicableEu
Capecitabine MedacFilm-coated tablet150 mgOral useMedac Gesellschaft Für Klinische Spezialpräparate Mb H2012-11-19Not applicableEu
Capecitabine MedacFilm-coated tablet300 mgOral useMedac Gesellschaft Für Klinische Spezialpräparate Mb H2012-11-19Not applicableEu
Capecitabine MedacFilm-coated tablet500 mgOral useMedac Gesellschaft Für Klinische Spezialpräparate Mb H2012-11-19Not applicableEu
Capecitabine MedacFilm-coated tablet300 mgOral useMedac Gesellschaft Für Klinische Spezialpräparate Mb H2012-11-19Not applicableEu
Capecitabine MedacFilm-coated tablet500 mgOral useMedac Gesellschaft Für Klinische Spezialpräparate Mb H2012-11-19Not applicableEu
Capecitabine MedacFilm-coated tablet150 mgOral useMedac Gesellschaft Für Klinische Spezialpräparate Mb H2012-11-19Not applicableEu
Capecitabine MedacFilm-coated tablet300 mgOral useMedac Gesellschaft Für Klinische Spezialpräparate Mb H2012-11-19Not applicableEu
Capecitabine MedacFilm-coated tablet500 mgOral useMedac Gesellschaft Für Klinische Spezialpräparate Mb H2012-11-19Not applicableEu
Capecitabine MedacFilm-coated tablet150 mgOral useMedac Gesellschaft Für Klinische Spezialpräparate Mb H2012-11-19Not applicableEu
Capecitabine MedacFilm-coated tablet300 mgOral useMedac Gesellschaft Für Klinische Spezialpräparate Mb H2012-11-19Not applicableEu
Capecitabine MedacFilm-coated tablet500 mgOral useMedac Gesellschaft Für Klinische Spezialpräparate Mb H2012-11-19Not applicableEu
Capecitabine MedacFilm-coated tablet150 mgOral useMedac Gesellschaft Für Klinische Spezialpräparate Mb H2012-11-19Not applicableEu
Capecitabine MedacFilm-coated tablet300 mgOral useMedac Gesellschaft Für Klinische Spezialpräparate Mb H2012-11-19Not applicableEu
Capecitabine MedacFilm-coated tablet500 mgOral useMedac Gesellschaft Für Klinische Spezialpräparate Mb H2012-11-19Not applicableEu
Capecitabine MedacFilm-coated tablet150 mgOral useMedac Gesellschaft Für Klinische Spezialpräparate Mb H2012-11-19Not applicableEu
Capecitabine MedacFilm-coated tablet300 mgOral useMedac Gesellschaft Für Klinische Spezialpräparate Mb H2012-11-19Not applicableEu
Capecitabine MedacFilm-coated tablet500 mgOral useMedac Gesellschaft Für Klinische Spezialpräparate Mb H2012-11-19Not applicableEu
Capecitabine MedacFilm-coated tablet500 mgOral useMedac Gesellschaft Für Klinische Spezialpräparate Mb H2012-11-19Not applicableEu
Capecitabine MedacFilm-coated tablet150 mgOral useMedac Gesellschaft Für Klinische Spezialpräparate Mb H2012-11-19Not applicableEu
Capecitabine MedacFilm-coated tablet300 mgOral useMedac Gesellschaft Für Klinische Spezialpräparate Mb H2012-11-19Not applicableEu
Capecitabine MedacFilm-coated tablet150 mgOral useMedac Gesellschaft Für Klinische Spezialpräparate Mb H2012-11-19Not applicableEu
Capecitabine MedacFilm-coated tablet300 mgOral useMedac Gesellschaft Für Klinische Spezialpräparate Mb H2012-11-19Not applicableEu
Capecitabine MedacFilm-coated tablet150 mgOral useMedac Gesellschaft Für Klinische Spezialpräparate Mb H2012-11-19Not applicableEu
Capecitabine MedacFilm-coated tablet300 mgOral useMedac Gesellschaft Für Klinische Spezialpräparate Mb H2012-11-19Not applicableEu
Capecitabine MedacFilm-coated tablet500 mgOral useMedac Gesellschaft Für Klinische Spezialpräparate Mb H2012-11-19Not applicableEu
Capecitabine MedacFilm-coated tablet150 mgOral useMedac Gesellschaft Für Klinische Spezialpräparate Mb H2012-11-19Not applicableEu
Capecitabine MedacFilm-coated tablet300 mgOral useMedac Gesellschaft Für Klinische Spezialpräparate Mb H2012-11-19Not applicableEu
Capecitabine MedacFilm-coated tablet500 mgOral useMedac Gesellschaft Für Klinische Spezialpräparate Mb H2012-11-19Not applicableEu
Capecitabine SunFilm-coated tablet500 mgOral useSun Pharmaceutical Industries Europe B.V.2013-06-21Not applicableEu
Capecitabine SunFilm-coated tablet150 mgOral useSun Pharmaceutical Industries Europe B.V.2013-06-21Not applicableEu
Capecitabine TevaFilm-coated tablet150 mgOral useTeva Pharma B.V.2012-04-20Not applicableEu
Capecitabine TevaFilm-coated tablet500 mgOral useTeva Pharma B.V.2012-04-20Not applicableEu
EcansyaFilm-coated tablet300 mgOral useKrka, D.D., Novo Mesto2012-04-20Not applicableEu
EcansyaFilm-coated tablet150 mgOral useKrka, D.D., Novo Mesto2012-04-20Not applicableEu
EcansyaFilm-coated tablet500 mgOral useKrka, D.D., Novo Mesto2012-04-20Not applicableEu
EcansyaFilm-coated tablet500 mgOral useKrka, D.D., Novo Mesto2012-04-20Not applicableEu
EcansyaFilm-coated tablet150 mgOral useKrka, D.D., Novo Mesto2012-04-20Not applicableEu
EcansyaFilm-coated tablet300 mgOral useKrka, D.D., Novo Mesto2012-04-20Not applicableEu
EcansyaFilm-coated tablet150 mgOral useKrka, D.D., Novo Mesto2012-04-20Not applicableEu
EcansyaFilm-coated tablet500 mgOral useKrka, D.D., Novo Mesto2012-04-20Not applicableEu
EcansyaFilm-coated tablet500 mgOral useKrka, D.D., Novo Mesto2012-04-20Not applicableEu
EcansyaFilm-coated tablet300 mgOral useKrka, D.D., Novo Mesto2012-04-20Not applicableEu
EcansyaFilm-coated tablet300 mgOral useKrka, D.D., Novo Mesto2012-04-20Not applicableEu
EcansyaFilm-coated tablet150 mgOral useKrka, D.D., Novo Mesto2012-04-20Not applicableEu
EcansyaFilm-coated tablet500 mgOral useKrka, D.D., Novo Mesto2012-04-20Not applicableEu
EcansyaFilm-coated tablet300 mgOral useKrka, D.D., Novo Mesto2012-04-20Not applicableEu
EcansyaFilm-coated tablet300 mgOral useKrka, D.D., Novo Mesto2012-04-20Not applicableEu
EcansyaFilm-coated tablet150 mgOral useKrka, D.D., Novo Mesto2012-04-20Not applicableEu
EcansyaFilm-coated tablet150 mgOral useKrka, D.D., Novo Mesto2012-04-20Not applicableEu
EcansyaFilm-coated tablet500 mgOral useKrka, D.D., Novo Mesto2012-04-20Not applicableEu
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International BrandsNot Available
Brand mixturesNot Available
SaltsNot Available
Categories
UNII6804DJ8Z9U
CAS number154361-50-9
WeightAverage: 359.3501
Monoisotopic: 359.149263656
Chemical FormulaC15H22FN3O6
InChI KeyInChIKey=GAGWJHPBXLXJQN-UORFTKCHSA-N
InChI
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
IUPAC Name
pentyl N-{1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-methyloxolan-2-yl]-5-fluoro-2-oxo-1,2-dihydropyrimidin-4-yl}carbamate
SMILES
CCCCCOC(=O)NC1=NC(=O)N(C=C1F)[C@@H]1O[[email protected]](C)[C@@H](O)[[email protected]]1O
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as glycosylamines. These are compounds consisting of an amine with a beta-N-glycosidic bond to a carbohydrate, thus forming a cyclic hemiaminal ether bond (alpha-amino ether).
KingdomOrganic compounds
Super ClassOrganooxygen compounds
ClassCarbohydrates and carbohydrate conjugates
Sub ClassGlycosyl compounds
Direct ParentGlycosylamines
Alternative Parents
Substituents
  • N-glycosyl compound
  • Pyrimidone
  • Halopyrimidine
  • Aminopyrimidine
  • Imidolactam
  • Pyrimidine
  • Hydropyrimidine
  • Aryl halide
  • Aryl fluoride
  • Heteroaromatic compound
  • Oxolane
  • Secondary alcohol
  • 1,2-diol
  • Oxacycle
  • Azacycle
  • Organoheterocyclic compound
  • Monocarboxylic acid or derivatives
  • Hydrocarbon derivative
  • Organonitrogen compound
  • Organofluoride
  • Organohalogen compound
  • Alcohol
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Pharmacology
IndicationFor 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.
PharmacodynamicsCapecitabine 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. Fluorouracil it then metabolized both normal and tumor cells to 5-fluoro-2′-deoxyuridine 5′-monophosphate (FdUMP) and 5-fluorouridine triphosphate (FUTP).
Mechanism of actionCapecitabine 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.
Related Articles
AbsorptionReadily absorbed through the GI tract (~70%)
Volume of distributionNot Available
Protein binding< 60% (mainly albumin)
Metabolism

Metabolized by thymidine phosphorylase to fluoruracil.

SubstrateEnzymesProduct
Capecitabine
5’-Deoxy-5-fluorouridineDetails
5’-Deoxy-5-fluorouridine
5-fluorouracilDetails
Route of eliminationCapecitabine 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 life45-60 minutes for capecitabine and its metabolites.
ClearanceNot Available
ToxicityNot Available
Affected organisms
  • Humans and other mammals
Pathways
PathwayCategorySMPDB ID
Capecitabine Metabolism PathwayDrug metabolismSMP00607
Capecitabine Action PathwayDrug actionSMP00469
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9513
Blood Brain Barrier+0.6064
Caco-2 permeable-0.7096
P-glycoprotein substrateSubstrate0.5106
P-glycoprotein inhibitor INon-inhibitor0.8234
P-glycoprotein inhibitor IINon-inhibitor0.7514
Renal organic cation transporterNon-inhibitor0.9654
CYP450 2C9 substrateNon-substrate0.7999
CYP450 2D6 substrateNon-substrate0.864
CYP450 3A4 substrateNon-substrate0.5
CYP450 1A2 substrateNon-inhibitor0.7523
CYP450 2C9 inhibitorNon-inhibitor0.7673
CYP450 2D6 inhibitorNon-inhibitor0.8612
CYP450 2C19 inhibitorNon-inhibitor0.6569
CYP450 3A4 inhibitorNon-inhibitor0.7404
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.8484
Ames testNon AMES toxic0.6521
CarcinogenicityNon-carcinogens0.8754
BiodegradationNot ready biodegradable0.9964
Rat acute toxicity2.4690 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9759
hERG inhibition (predictor II)Non-inhibitor0.7124
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Pharmacoeconomics
ManufacturersNot Available
Packagers
Dosage forms
FormRouteStrength
Film-coated tabletOral use150 mg
Film-coated tabletOral use300 mg
Film-coated tabletOral use500 mg
Tabletoral150 mg
Tabletoral500 mg
Tablet, film coatedoral150 mg/1
Tablet, film coatedoral500 mg/1
Prices
Unit descriptionCostUnit
Xeloda 500 mg tablet28.97USD tablet
Xeloda 150 mg tablet8.69USD tablet
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)
CA1327358 No1994-03-012011-03-01Canada
CA2103324 No1997-12-232013-11-17Canada
US4966891 No1994-01-132011-01-13Us
US5472949 No1993-12-142013-12-14Us
Properties
StateSolid
Experimental Properties
PropertyValueSource
melting point110-121 °CNot Available
water solubility26 mg/mLNot Available
logP0.4Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.248 mg/mLALOGPS
logP1.17ALOGPS
logP0.77ChemAxon
logS-3.2ALOGPS
pKa (Strongest Acidic)8.23ChemAxon
pKa (Strongest Basic)-3.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area120.69 Å2ChemAxon
Rotatable Bond Count7ChemAxon
Refractivity82.75 m3·mol-1ChemAxon
Polarizability35.81 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
References
Synthesis Reference

DrugSyn.org

US5472949
General References
  1. Walko CM, Lindley C: Capecitabine: a review. Clin Ther. 2005 Jan;27(1):23-44. [PubMed:15763604 ]
  2. 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:12515569 ]
  3. 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:18794792 ]
  4. Twelves C: Vision of the future: capecitabine. Oncologist. 2001;6 Suppl 4:35-9. [PubMed:11585973 ]
  5. 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:15280932 ]
  6. de Bono JS, Twelves CJ: The oral fluorinated pyrimidines. Invest New Drugs. 2001;19(1):41-59. [PubMed:11291832 ]
External Links
ATC CodesL01BC06
AHFS Codes
  • 10:00.00
PDB EntriesNot Available
FDA labelDownload (133 KB)
MSDSNot Available
Interactions
Drug Interactions
Drug
AceclofenacThe metabolism of Aceclofenac can be decreased when combined with Capecitabine.
AcenocoumarolThe serum concentration of Acenocoumarol can be increased when it is combined with Capecitabine.
AcetaminophenThe metabolism of Acetaminophen can be decreased when combined with Capecitabine.
AcetyldigitoxinAcetyldigitoxin may decrease the cardiotoxic activities of Capecitabine.
Acetylsalicylic acidThe metabolism of Acetylsalicylic acid can be decreased when combined with Capecitabine.
AlosetronThe metabolism of Alosetron can be decreased when combined with Capecitabine.
AlprazolamThe metabolism of Alprazolam can be decreased when combined with Capecitabine.
AminophenazoneThe metabolism of Aminophenazone can be decreased when combined with Capecitabine.
AmiodaroneThe metabolism of Amiodarone can be decreased when combined with Capecitabine.
AmitriptylineThe metabolism of Amitriptyline can be decreased when combined with Capecitabine.
AmprenavirThe metabolism of Amprenavir can be decreased when combined with Capecitabine.
AntipyrineThe metabolism of Antipyrine can be decreased when combined with Capecitabine.
ApixabanThe metabolism of Apixaban can be decreased when combined with Capecitabine.
Arachidonic AcidThe metabolism of Arachidonic Acid can be decreased when combined with Capecitabine.
ArformoterolThe metabolism of Arformoterol can be decreased when combined with Capecitabine.
ArtemetherThe metabolism of Artemether can be decreased when combined with Capecitabine.
AtazanavirThe metabolism of Atazanavir can be decreased when combined with Capecitabine.
AzelastineThe metabolism of Azelastine can be decreased when combined with Capecitabine.
BevacizumabBevacizumab may increase the cardiotoxic activities of Capecitabine.
BexaroteneThe metabolism of Bexarotene can be decreased when combined with Capecitabine.
BortezomibThe metabolism of Bortezomib can be decreased when combined with Capecitabine.
BosentanThe serum concentration of Bosentan can be increased when it is combined with Capecitabine.
BrompheniramineThe metabolism of Brompheniramine can be decreased when combined with Capecitabine.
BuprenorphineThe metabolism of Buprenorphine can be decreased when combined with Capecitabine.
BupropionThe metabolism of Bupropion can be decreased when combined with Capecitabine.
CabazitaxelThe risk or severity of adverse effects can be increased when Cabazitaxel is combined with Capecitabine.
CabozantinibThe metabolism of Cabozantinib can be decreased when combined with Capecitabine.
CaffeineThe metabolism of Caffeine can be decreased when combined with Capecitabine.
CandesartanThe metabolism of Candesartan can be decreased when combined with Capecitabine.
CarbinoxamineThe metabolism of Carbinoxamine can be decreased when combined with Capecitabine.
CarvedilolThe serum concentration of Carvedilol can be increased when it is combined with Capecitabine.
CelecoxibThe metabolism of Celecoxib can be decreased when combined with Capecitabine.
ChlorpropamideThe metabolism of Chlorpropamide can be decreased when combined with Capecitabine.
CimetidineThe serum concentration of the active metabolites of Capecitabine can be increased when Capecitabine is used in combination with Cimetidine.
CinnarizineThe metabolism of Cinnarizine can be decreased when combined with Capecitabine.
CisaprideThe metabolism of Cisapride can be decreased when combined with Capecitabine.
ClopidogrelThe metabolism of Clopidogrel can be decreased when combined with Capecitabine.
ClozapineThe risk or severity of adverse effects can be increased when Capecitabine is combined with Clozapine.
CyclophosphamideCyclophosphamide may increase the cardiotoxic activities of Capecitabine.
CyclophosphamideThe metabolism of Cyclophosphamide can be decreased when combined with Capecitabine.
DapagliflozinThe metabolism of Dapagliflozin can be decreased when combined with Capecitabine.
DapsoneThe metabolism of Dapsone can be decreased when combined with Capecitabine.
DenosumabThe risk or severity of adverse effects can be increased when Denosumab is combined with Capecitabine.
DeslanosideDeslanoside may decrease the cardiotoxic activities of Capecitabine.
DextromethorphanThe metabolism of Dextromethorphan can be decreased when combined with Capecitabine.
DiazepamThe metabolism of Diazepam can be decreased when combined with Capecitabine.
DiclofenacThe serum concentration of Diclofenac can be increased when it is combined with Capecitabine.
DicoumarolThe serum concentration of Dicoumarol can be increased when it is combined with Capecitabine.
DigitoxinDigitoxin may decrease the cardiotoxic activities of Capecitabine.
DigoxinDigoxin may decrease the cardiotoxic activities of Capecitabine.
DiltiazemThe metabolism of Diltiazem can be decreased when combined with Capecitabine.
DiphenhydramineThe metabolism of Diphenhydramine can be decreased when combined with Capecitabine.
DocetaxelThe risk or severity of adverse effects can be increased when Docetaxel is combined with Capecitabine.
DolasetronThe metabolism of Dolasetron can be decreased when combined with Capecitabine.
DonepezilThe metabolism of Donepezil can be decreased when combined with Capecitabine.
DopamineThe metabolism of Dopamine can be decreased when combined with Capecitabine.
DorzolamideThe metabolism of Dorzolamide can be decreased when combined with Capecitabine.
DoxepinThe metabolism of Doxepin can be decreased when combined with Capecitabine.
DronabinolThe serum concentration of Dronabinol can be increased when it is combined with Capecitabine.
EletriptanThe metabolism of Eletriptan can be decreased when combined with Capecitabine.
EpoprostenolThe metabolism of Epoprostenol can be decreased when combined with Capecitabine.
EstradiolThe metabolism of Estradiol can be decreased when combined with Capecitabine.
EstroneThe metabolism of Estrone can be decreased when combined with Capecitabine.
EszopicloneThe metabolism of Eszopiclone can be decreased when combined with Capecitabine.
Ethyl biscoumacetateThe serum concentration of Ethyl biscoumacetate can be increased when it is combined with Capecitabine.
EtodolacThe metabolism of Etodolac can be decreased when combined with Capecitabine.
EtoricoxibThe metabolism of Etoricoxib can be decreased when combined with Capecitabine.
EtravirineThe metabolism of Etravirine can be decreased when combined with Capecitabine.
FingolimodCapecitabine may increase the immunosuppressive activities of Fingolimod.
FlunarizineThe metabolism of Flunarizine can be decreased when combined with Capecitabine.
FlunitrazepamThe metabolism of Flunitrazepam can be decreased when combined with Capecitabine.
FluoxetineThe metabolism of Fluoxetine can be decreased when combined with Capecitabine.
FlurbiprofenThe metabolism of Flurbiprofen can be decreased when combined with Capecitabine.
FluvastatinThe metabolism of Fluvastatin can be decreased when combined with Capecitabine.
FormoterolThe metabolism of Formoterol can be decreased when combined with Capecitabine.
FosphenytoinThe serum concentration of Fosphenytoin can be increased when it is combined with Capecitabine.
GavestinelThe metabolism of Gavestinel can be decreased when combined with Capecitabine.
GimeracilThe serum concentration of the active metabolites of Capecitabine can be increased when Capecitabine is used in combination with Gimeracil.
GliclazideThe metabolism of Gliclazide can be decreased when combined with Capecitabine.
GlimepirideThe metabolism of Glimepiride can be decreased when combined with Capecitabine.
GlipizideThe metabolism of Glipizide can be decreased when combined with Capecitabine.
GlyburideThe metabolism of Glyburide can be decreased when combined with Capecitabine.
GuanfacineThe metabolism of Guanfacine can be decreased when combined with Capecitabine.
HaloperidolThe metabolism of Haloperidol can be decreased when combined with Capecitabine.
HalothaneThe metabolism of Halothane can be decreased when combined with Capecitabine.
HexobarbitalThe metabolism of Hexobarbital can be decreased when combined with Capecitabine.
Histamine PhosphateThe metabolism of Histamine Phosphate can be decreased when combined with Capecitabine.
HydromorphoneThe metabolism of Hydromorphone can be decreased when combined with Capecitabine.
IbuprofenThe metabolism of Ibuprofen can be decreased when combined with Capecitabine.
IdarubicinThe metabolism of Idarubicin can be decreased when combined with Capecitabine.
IfosfamideThe metabolism of Ifosfamide can be decreased when combined with Capecitabine.
ImatinibThe metabolism of Imatinib can be decreased when combined with Capecitabine.
indisulamThe metabolism of indisulam can be decreased when combined with Capecitabine.
IndomethacinThe metabolism of Indomethacin can be decreased when combined with Capecitabine.
IrbesartanThe metabolism of Irbesartan can be decreased when combined with Capecitabine.
IxazomibThe metabolism of Ixazomib can be decreased when combined with Capecitabine.
KetamineThe metabolism of Ketamine can be decreased when combined with Capecitabine.
KetobemidoneThe metabolism of Ketobemidone can be decreased when combined with Capecitabine.
KetoprofenThe metabolism of Ketoprofen can be decreased when combined with Capecitabine.
LacosamideThe serum concentration of Lacosamide can be increased when it is combined with Capecitabine.
LansoprazoleThe metabolism of Lansoprazole can be decreased when combined with Capecitabine.
LeflunomideThe risk or severity of adverse effects can be increased when Capecitabine is combined with Leflunomide.
LesinuradThe metabolism of Lesinurad can be decreased when combined with Capecitabine.
LicofeloneThe metabolism of Licofelone can be decreased when combined with Capecitabine.
LidocaineThe metabolism of Lidocaine can be decreased when combined with Capecitabine.
LoratadineThe metabolism of Loratadine can be decreased when combined with Capecitabine.
LornoxicamThe metabolism of Lornoxicam can be decreased when combined with Capecitabine.
LosartanThe metabolism of Losartan can be decreased when combined with Capecitabine.
LumiracoxibThe metabolism of Lumiracoxib can be decreased when combined with Capecitabine.
Mefenamic acidThe metabolism of Mefenamic acid can be decreased when combined with Capecitabine.
MelatoninThe metabolism of Melatonin can be decreased when combined with Capecitabine.
MeloxicamThe metabolism of Meloxicam can be decreased when combined with Capecitabine.
MephenytoinThe metabolism of Mephenytoin can be decreased when combined with Capecitabine.
MestranolThe metabolism of Mestranol can be decreased when combined with Capecitabine.
MetamizoleThe risk or severity of adverse effects can be increased when Metamizole is combined with Capecitabine.
MethadoneThe metabolism of Methadone can be decreased when combined with Capecitabine.
MethoxyfluraneThe metabolism of Methoxyflurane can be decreased when combined with Capecitabine.
MetronidazoleThe serum concentration of the active metabolites of Capecitabine can be increased when Capecitabine is used in combination with Metronidazole.
MetronidazoleThe metabolism of Metronidazole can be decreased when combined with Capecitabine.
MirtazapineThe metabolism of Mirtazapine can be decreased when combined with Capecitabine.
MoclobemideThe metabolism of Moclobemide can be decreased when combined with Capecitabine.
MontelukastThe metabolism of Montelukast can be decreased when combined with Capecitabine.
NaproxenThe metabolism of Naproxen can be decreased when combined with Capecitabine.
NatalizumabThe risk or severity of adverse effects can be increased when Capecitabine is combined with Natalizumab.
NateglinideThe metabolism of Nateglinide can be decreased when combined with Capecitabine.
NetupitantThe metabolism of Netupitant can be decreased when combined with Capecitabine.
NevirapineThe metabolism of Nevirapine can be decreased when combined with Capecitabine.
NiclosamideThe metabolism of Niclosamide can be decreased when combined with Capecitabine.
NicotineThe metabolism of Nicotine can be decreased when combined with Capecitabine.
NortriptylineThe metabolism of Nortriptyline can be decreased when combined with Capecitabine.
OlodaterolThe metabolism of Olodaterol can be decreased when combined with Capecitabine.
OmeprazoleThe metabolism of Omeprazole can be decreased when combined with Capecitabine.
OndansetronThe metabolism of Ondansetron can be decreased when combined with Capecitabine.
OspemifeneThe serum concentration of Ospemifene can be increased when it is combined with Capecitabine.
OuabainOuabain may decrease the cardiotoxic activities of Capecitabine.
OxaprozinThe metabolism of Oxaprozin can be decreased when combined with Capecitabine.
PaclitaxelThe metabolism of Paclitaxel can be decreased when combined with Capecitabine.
PaclitaxelThe risk or severity of adverse effects can be increased when Paclitaxel is combined with Capecitabine.
ParamethadioneThe metabolism of Paramethadione can be decreased when combined with Capecitabine.
ParecoxibThe serum concentration of Parecoxib can be increased when it is combined with Capecitabine.
PerphenazineThe metabolism of Perphenazine can be decreased when combined with Capecitabine.
PhenacetinThe metabolism of Phenacetin can be decreased when combined with Capecitabine.
PhenindioneThe serum concentration of Phenindione can be increased when it is combined with Capecitabine.
PhenobarbitalThe metabolism of Phenobarbital can be decreased when combined with Capecitabine.
PhenprocoumonThe serum concentration of Phenprocoumon can be increased when it is combined with Capecitabine.
PhenylbutazoneThe metabolism of Phenylbutazone can be decreased when combined with Capecitabine.
PhenytoinThe serum concentration of Phenytoin can be increased when it is combined with Capecitabine.
PimecrolimusThe risk or severity of adverse effects can be increased when Pimecrolimus is combined with Capecitabine.
PioglitazoneThe metabolism of Pioglitazone can be decreased when combined with Capecitabine.
PiroxicamThe metabolism of Piroxicam can be decreased when combined with Capecitabine.
PitavastatinThe metabolism of Pitavastatin can be decreased when combined with Capecitabine.
PrasugrelThe metabolism of Prasugrel can be decreased when combined with Capecitabine.
PravastatinThe metabolism of Pravastatin can be decreased when combined with Capecitabine.
ProgesteroneThe metabolism of Progesterone can be decreased when combined with Capecitabine.
ProguanilThe metabolism of Proguanil can be decreased when combined with Capecitabine.
PromazineThe metabolism of Promazine can be decreased when combined with Capecitabine.
PropofolThe metabolism of Propofol can be decreased when combined with Capecitabine.
QuazepamThe metabolism of Quazepam can be decreased when combined with Capecitabine.
QuinidineThe metabolism of Quinidine can be decreased when combined with Capecitabine.
QuinineThe metabolism of Quinine can be decreased when combined with Capecitabine.
Rabies vaccineThe risk or severity of adverse effects can be increased when Capecitabine is combined with Rabies vaccine.
RamelteonThe serum concentration of Ramelteon can be increased when it is combined with Capecitabine.
RifampicinThe metabolism of Rifampicin can be decreased when combined with Capecitabine.
RofecoxibThe metabolism of Rofecoxib can be decreased when combined with Capecitabine.
RoflumilastRoflumilast may increase the immunosuppressive activities of Capecitabine.
RosiglitazoneThe metabolism of Rosiglitazone can be decreased when combined with Capecitabine.
RosuvastatinThe metabolism of Rosuvastatin can be decreased when combined with Capecitabine.
Salicylic acidThe metabolism of Salicylic acid can be decreased when combined with Capecitabine.
SelegilineThe metabolism of Selegiline can be decreased when combined with Capecitabine.
SeratrodastThe metabolism of Seratrodast can be decreased when combined with Capecitabine.
SertralineThe metabolism of Sertraline can be decreased when combined with Capecitabine.
SildenafilThe metabolism of Sildenafil can be decreased when combined with Capecitabine.
Sipuleucel-TThe therapeutic efficacy of Sipuleucel-T can be decreased when used in combination with Capecitabine.
SitaxentanThe metabolism of Sitaxentan can be decreased when combined with Capecitabine.
SulfadiazineThe metabolism of Sulfadiazine can be decreased when combined with Capecitabine.
SulfamethoxazoleThe metabolism of Sulfamethoxazole can be decreased when combined with Capecitabine.
SulfamoxoleThe metabolism of Sulfamoxole can be decreased when combined with Capecitabine.
SulfinpyrazoneThe metabolism of Sulfinpyrazone can be decreased when combined with Capecitabine.
SulfisoxazoleThe metabolism of Sulfisoxazole can be decreased when combined with Capecitabine.
SuprofenThe metabolism of Suprofen can be decreased when combined with Capecitabine.
TacrolimusThe risk or severity of adverse effects can be increased when Tacrolimus is combined with Capecitabine.
TamoxifenThe metabolism of Tamoxifen can be decreased when combined with Capecitabine.
TapentadolThe metabolism of Tapentadol can be decreased when combined with Capecitabine.
TemazepamThe metabolism of Temazepam can be decreased when combined with Capecitabine.
TenoxicamThe metabolism of Tenoxicam can be decreased when combined with Capecitabine.
TerbinafineThe metabolism of Terbinafine can be decreased when combined with Capecitabine.
TerfenadineThe metabolism of Terfenadine can be decreased when combined with Capecitabine.
TestosteroneThe metabolism of Testosterone can be decreased when combined with Capecitabine.
ThalidomideThe metabolism of Thalidomide can be decreased when combined with Capecitabine.
TheophyllineThe metabolism of Theophylline can be decreased when combined with Capecitabine.
ThiamylalThe metabolism of Thiamylal can be decreased when combined with Capecitabine.
TofacitinibCapecitabine may increase the immunosuppressive activities of Tofacitinib.
TolbutamideThe metabolism of Tolbutamide can be decreased when combined with Capecitabine.
TolterodineThe metabolism of Tolterodine can be decreased when combined with Capecitabine.
TorasemideThe metabolism of Torasemide can be decreased when combined with Capecitabine.
TrabectedinThe metabolism of Trabectedin can be decreased when combined with Capecitabine.
TrastuzumabTrastuzumab may increase the neutropenic activities of Capecitabine.
TreprostinilThe metabolism of Treprostinil can be decreased when combined with Capecitabine.
TretinoinThe metabolism of Tretinoin can be decreased when combined with Capecitabine.
TrimethadioneThe metabolism of Trimethadione can be decreased when combined with Capecitabine.
TrimethoprimThe metabolism of Trimethoprim can be decreased when combined with Capecitabine.
TrimipramineThe metabolism of Trimipramine can be decreased when combined with Capecitabine.
TroglitazoneThe metabolism of Troglitazone can be decreased when combined with Capecitabine.
ValdecoxibThe metabolism of Valdecoxib can be decreased when combined with Capecitabine.
Valproic AcidThe metabolism of Valproic Acid can be decreased when combined with Capecitabine.
ValsartanThe metabolism of Valsartan can be decreased when combined with Capecitabine.
VenlafaxineThe metabolism of Venlafaxine can be decreased when combined with Capecitabine.
VerapamilThe metabolism of Verapamil can be decreased when combined with Capecitabine.
VicrivirocThe metabolism of Vicriviroc can be decreased when combined with Capecitabine.
VismodegibThe metabolism of Vismodegib can be decreased when combined with Capecitabine.
VoriconazoleThe metabolism of Voriconazole can be decreased when combined with Capecitabine.
VortioxetineThe metabolism of Vortioxetine can be decreased when combined with Capecitabine.
WarfarinThe serum concentration of Warfarin can be increased when it is combined with Capecitabine.
XimelagatranThe metabolism of Ximelagatran can be decreased when combined with Capecitabine.
ZafirlukastThe metabolism of Zafirlukast can be decreased when combined with Capecitabine.
ZalcitabineThe metabolism of Zalcitabine can be decreased when combined with Capecitabine.
ZaltoprofenThe metabolism of Zaltoprofen can be decreased when combined with Capecitabine.
ZidovudineThe metabolism of Zidovudine can be decreased when combined with Capecitabine.
ZileutonThe metabolism of Zileuton can be decreased when combined with Capecitabine.
ZolpidemThe metabolism of Zolpidem can be decreased when combined with Capecitabine.
ZopicloneThe metabolism of Zopiclone can be decreased when combined with Capecitabine.
Food Interactions
  • Take 12 hours apart, within 30 minutes of the end of breakfast and dinner to reduce nausea.

Targets

Kind
Protein
Organism
Human
Pharmacological action
yes
Actions
inhibitor
General Function:
Thymidylate synthase activity
Specific Function:
Contributes to the de novo mitochondrial thymidylate biosynthesis pathway.
Gene Name:
TYMS
Uniprot ID:
P04818
Molecular Weight:
35715.65 Da
References
  1. Patel A, Pluim T, Helms A, Bauer A, Tuttle RM, Francis GL: Enzyme expression profiles suggest the novel tumor-activated fluoropyrimidine carbamate capecitabine (Xeloda) might be effective against papillary thyroid cancers of children and young adults. Cancer Chemother Pharmacol. 2004 May;53(5):409-14. [PubMed:15132128 ]
  2. Eliason JF, Megyeri A: Potential for predicting toxicity and response of fluoropyrimidines in patients. Curr Drug Targets. 2004 May;5(4):383-8. [PubMed:15134221 ]
  3. Carlini LE, Meropol NJ, Bever J, Andria ML, Hill T, Gold P, Rogatko A, Wang H, Blanchard RL: UGT1A7 and UGT1A9 polymorphisms predict response and toxicity in colorectal cancer patients treated with capecitabine/irinotecan. Clin Cancer Res. 2005 Feb 1;11(3):1226-36. [PubMed:15709193 ]
  4. Li KM, Rivory LP, Clarke SJ: Rapid quantitation of plasma 2'-deoxyuridine by high-performance liquid chromatography/atmospheric pressure chemical ionization mass spectrometry and its application to pharmacodynamic studies in cancer patients. J Chromatogr B Analyt Technol Biomed Life Sci. 2005 Jun 5;820(1):121-30. Epub 2005 Apr 19. [PubMed:15866500 ]
  5. Fischel JL, Ciccolini J, Formento P, Ferrero JM, Milano G: Synergistic cytotoxic interaction in hormone-refractory prostate cancer with the triple combination docetaxel-erlotinib and 5-fluoro-5'-deoxyuridine. Anticancer Drugs. 2006 Aug;17(7):807-13. [PubMed:16926630 ]
  6. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]
2. DNA
Kind
Nucleotide
Organism
Human
Pharmacological action
yes
Actions
incorporation into and destabilization
General Function:
Used for biological information storage.
Specific Function:
DNA contains the instructions needed for an organism to develop, survive and reproduce.
Molecular Weight:
2.15 x 1012 Da
References
  1. Walko CM, Lindley C: Capecitabine: a review. Clin Ther. 2005 Jan;27(1):23-44. [PubMed:15763604 ]
  2. Thomas DM, Zalcberg JR: 5-fluorouracil: a pharmacological paradigm in the use of cytotoxics. Clin Exp Pharmacol Physiol. 1998 Nov;25(11):887-95. [PubMed:9807659 ]
  3. Wyatt MD, Wilson DM 3rd: Participation of DNA repair in the response to 5-fluorouracil. Cell Mol Life Sci. 2009 Mar;66(5):788-99. doi: 10.1007/s00018-008-8557-5. [PubMed:18979208 ]
  4. Ghoshal K, Jacob ST: An alternative molecular mechanism of action of 5-fluorouracil, a potent anticancer drug. Biochem Pharmacol. 1997 Jun 1;53(11):1569-75. [PubMed:9264308 ]
  5. Longley DB, Harkin DP, Johnston PG: 5-fluorouracil: mechanisms of action and clinical strategies. Nat Rev Cancer. 2003 May;3(5):330-8. [PubMed:12724731 ]
  6. Petty RD, Cassidy J: Novel fluoropyrimidines: improving the efficacy and tolerability of cytotoxic therapy. Curr Cancer Drug Targets. 2004 Mar;4(2):191-204. [PubMed:15032669 ]
3. RNA
Kind
Nucleotide
Organism
Human
Pharmacological action
yes
Actions
incorporation into and destabilization
References
  1. Walko CM, Lindley C: Capecitabine: a review. Clin Ther. 2005 Jan;27(1):23-44. [PubMed:15763604 ]
  2. Thomas DM, Zalcberg JR: 5-fluorouracil: a pharmacological paradigm in the use of cytotoxics. Clin Exp Pharmacol Physiol. 1998 Nov;25(11):887-95. [PubMed:9807659 ]
  3. Wyatt MD, Wilson DM 3rd: Participation of DNA repair in the response to 5-fluorouracil. Cell Mol Life Sci. 2009 Mar;66(5):788-99. doi: 10.1007/s00018-008-8557-5. [PubMed:18979208 ]
  4. Ghoshal K, Jacob ST: An alternative molecular mechanism of action of 5-fluorouracil, a potent anticancer drug. Biochem Pharmacol. 1997 Jun 1;53(11):1569-75. [PubMed:9264308 ]
  5. Longley DB, Harkin DP, Johnston PG: 5-fluorouracil: mechanisms of action and clinical strategies. Nat Rev Cancer. 2003 May;3(5):330-8. [PubMed:12724731 ]
  6. Petty RD, Cassidy J: Novel fluoropyrimidines: improving the efficacy and tolerability of cytotoxic therapy. Curr Cancer Drug Targets. 2004 Mar;4(2):191-204. [PubMed:15032669 ]

Enzymes

Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrate
General Function:
Transferase activity, transferring pentosyl groups
Specific Function:
May have a role in maintaining the integrity of the blood vessels. Has growth promoting activity on endothelial cells, angiogenic activity in vivo and chemotactic activity on endothelial cells in vitro.Catalyzes the reversible phosphorolysis of thymidine. The produced molecules are then utilized as carbon and energy sources or in the rescue of pyrimidine bases for nucleotide synthesis.
Gene Name:
TYMP
Uniprot ID:
P19971
Molecular Weight:
49954.965 Da
References
  1. de Bono JS, Twelves CJ: The oral fluorinated pyrimidines. Invest New Drugs. 2001;19(1):41-59. [PubMed:11291832 ]
  2. Tsukamoto Y, Kato Y, Ura M, Horii I, Ishitsuka H, Kusuhara H, Sugiyama Y: A physiologically based pharmacokinetic analysis of capecitabine, a triple prodrug of 5-FU, in humans: the mechanism for tumor-selective accumulation of 5-FU. Pharm Res. 2001 Aug;18(8):1190-202. [PubMed:11587492 ]
  3. Blanquicett C, Gillespie GY, Nabors LB, Miller CR, Bharara S, Buchsbaum DJ, Diasio RB, Johnson MR: Induction of thymidine phosphorylase in both irradiated and shielded, contralateral human U87MG glioma xenografts: implications for a dual modality treatment using capecitabine and irradiation. Mol Cancer Ther. 2002 Oct;1(12):1139-45. [PubMed:12481438 ]
  4. Ishitsuka H, Shimma N, Horii I: [Discovery and development of novel anticancer drug capecitabine]. Yakugaku Zasshi. 1999 Dec;119(12):881-97. [PubMed:10630095 ]
  5. Ishitsuka H: Capecitabine: preclinical pharmacology studies. Invest New Drugs. 2000 Nov;18(4):343-54. [PubMed:11081570 ]
  6. Endo M, Miwa M, Eda H, Ura M, Tanimura H, Ishikawa T, Miyazaki-Nose T, Hattori K, Shimma N, Yamada-Okabe H, Ishitsuka H: Augmentation of the antitumor activity of capecitabine by a tumor selective dihydropyrimidine dehydrogenase inhibitor, RO0094889. Int J Cancer. 2003 Sep 20;106(5):799-805. [PubMed:12866042 ]
  7. Schuller J, Cassidy J, Dumont E, Roos B, Durston S, Banken L, Utoh M, Mori K, Weidekamm E, Reigner B: Preferential activation of capecitabine in tumor following oral administration to colorectal cancer patients. Cancer Chemother Pharmacol. 2000;45(4):291-7. [PubMed:10755317 ]
  8. Patel A, Pluim T, Helms A, Bauer A, Tuttle RM, Francis GL: Enzyme expression profiles suggest the novel tumor-activated fluoropyrimidine carbamate capecitabine (Xeloda) might be effective against papillary thyroid cancers of children and young adults. Cancer Chemother Pharmacol. 2004 May;53(5):409-14. [PubMed:15132128 ]
  9. Eliason JF, Megyeri A: Potential for predicting toxicity and response of fluoropyrimidines in patients. Curr Drug Targets. 2004 May;5(4):383-8. [PubMed:15134221 ]
  10. Fischel JL, Ciccolini J, Formento P, Ferrero JM, Milano G: Synergistic cytotoxic interaction in hormone-refractory prostate cancer with the triple combination docetaxel-erlotinib and 5-fluoro-5'-deoxyuridine. Anticancer Drugs. 2006 Aug;17(7):807-13. [PubMed:16926630 ]
  11. Walko CM, Lindley C: Capecitabine: a review. Clin Ther. 2005 Jan;27(1):23-44. [PubMed:15763604 ]
  12. Ranieri G, Roccaro AM, Vacca A, Ribatti D: Thymidine phosphorylase (platelet-derived endothelial cell growth factor) as a target for capecitabine: from biology to the bedside. Recent Pat Anticancer Drug Discov. 2006 Jun;1(2):171-83. [PubMed:18221035 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrate
General Function:
Triglyceride lipase activity
Specific Function:
Involved in the detoxification of xenobiotics and in the activation of ester and amide prodrugs. Hydrolyzes aromatic and aliphatic esters, but has no catalytic activity toward amides or a fatty acyl-CoA ester. Hydrolyzes the methyl ester group of cocaine to form benzoylecgonine. Catalyzes the transesterification of cocaine to form cocaethylene. Displays fatty acid ethyl ester synthase activity,...
Gene Name:
CES1
Uniprot ID:
P23141
Molecular Weight:
62520.62 Da
References
  1. de Bono JS, Twelves CJ: The oral fluorinated pyrimidines. Invest New Drugs. 2001;19(1):41-59. [PubMed:11291832 ]
  2. Tsukamoto Y, Kato Y, Ura M, Horii I, Ishitsuka H, Kusuhara H, Sugiyama Y: A physiologically based pharmacokinetic analysis of capecitabine, a triple prodrug of 5-FU, in humans: the mechanism for tumor-selective accumulation of 5-FU. Pharm Res. 2001 Aug;18(8):1190-202. [PubMed:11587492 ]
  3. Ishitsuka H, Shimma N, Horii I: [Discovery and development of novel anticancer drug capecitabine]. Yakugaku Zasshi. 1999 Dec;119(12):881-97. [PubMed:10630095 ]
  4. Ishitsuka H: Capecitabine: preclinical pharmacology studies. Invest New Drugs. 2000 Nov;18(4):343-54. [PubMed:11081570 ]
  5. Endo M, Miwa M, Eda H, Ura M, Tanimura H, Ishikawa T, Miyazaki-Nose T, Hattori K, Shimma N, Yamada-Okabe H, Ishitsuka H: Augmentation of the antitumor activity of capecitabine by a tumor selective dihydropyrimidine dehydrogenase inhibitor, RO0094889. Int J Cancer. 2003 Sep 20;106(5):799-805. [PubMed:12866042 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrate
General Function:
Protein homodimerization activity
Specific Function:
Involved in pyrimidine base degradation. Catalyzes the reduction of uracil and thymine. Also involved the degradation of the chemotherapeutic drug 5-fluorouracil.
Gene Name:
DPYD
Uniprot ID:
Q12882
Molecular Weight:
111400.32 Da
References
  1. Tsukamoto Y, Kato Y, Ura M, Horii I, Ishitsuka H, Kusuhara H, Sugiyama Y: A physiologically based pharmacokinetic analysis of capecitabine, a triple prodrug of 5-FU, in humans: the mechanism for tumor-selective accumulation of 5-FU. Pharm Res. 2001 Aug;18(8):1190-202. [PubMed:11587492 ]
  2. Blanquicett C, Gillespie GY, Nabors LB, Miller CR, Bharara S, Buchsbaum DJ, Diasio RB, Johnson MR: Induction of thymidine phosphorylase in both irradiated and shielded, contralateral human U87MG glioma xenografts: implications for a dual modality treatment using capecitabine and irradiation. Mol Cancer Ther. 2002 Oct;1(12):1139-45. [PubMed:12481438 ]
  3. de Bono JS, Twelves CJ: The oral fluorinated pyrimidines. Invest New Drugs. 2001;19(1):41-59. [PubMed:11291832 ]
  4. Gross E, Seck K, Neubauer S, Mayr J, Hellebrand H, Ratanaphan A, Lutz V, Stockinger H, Kiechle M: High-throughput genotyping by DHPLC of the dihydropyrimidine dehydrogenase gene implicated in (fluoro)pyrimidine catabolism. Int J Oncol. 2003 Feb;22(2):325-32. [PubMed:12527930 ]
  5. Ishitsuka H: Capecitabine: preclinical pharmacology studies. Invest New Drugs. 2000 Nov;18(4):343-54. [PubMed:11081570 ]
  6. Endo M, Miwa M, Eda H, Ura M, Tanimura H, Ishikawa T, Miyazaki-Nose T, Hattori K, Shimma N, Yamada-Okabe H, Ishitsuka H: Augmentation of the antitumor activity of capecitabine by a tumor selective dihydropyrimidine dehydrogenase inhibitor, RO0094889. Int J Cancer. 2003 Sep 20;106(5):799-805. [PubMed:12866042 ]
  7. Patel A, Pluim T, Helms A, Bauer A, Tuttle RM, Francis GL: Enzyme expression profiles suggest the novel tumor-activated fluoropyrimidine carbamate capecitabine (Xeloda) might be effective against papillary thyroid cancers of children and young adults. Cancer Chemother Pharmacol. 2004 May;53(5):409-14. [PubMed:15132128 ]
  8. Eliason JF, Megyeri A: Potential for predicting toxicity and response of fluoropyrimidines in patients. Curr Drug Targets. 2004 May;5(4):383-8. [PubMed:15134221 ]
  9. Walko CM, Lindley C: Capecitabine: a review. Clin Ther. 2005 Jan;27(1):23-44. [PubMed:15763604 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrate
General Function:
Zinc ion binding
Specific Function:
This enzyme scavenges exogenous and endogenous cytidine and 2'-deoxycytidine for UMP synthesis.
Gene Name:
CDA
Uniprot ID:
P32320
Molecular Weight:
16184.545 Da
References
  1. de Bono JS, Twelves CJ: The oral fluorinated pyrimidines. Invest New Drugs. 2001;19(1):41-59. [PubMed:11291832 ]
  2. Tsukamoto Y, Kato Y, Ura M, Horii I, Ishitsuka H, Kusuhara H, Sugiyama Y: A physiologically based pharmacokinetic analysis of capecitabine, a triple prodrug of 5-FU, in humans: the mechanism for tumor-selective accumulation of 5-FU. Pharm Res. 2001 Aug;18(8):1190-202. [PubMed:11587492 ]
  3. Ishitsuka H, Shimma N, Horii I: [Discovery and development of novel anticancer drug capecitabine]. Yakugaku Zasshi. 1999 Dec;119(12):881-97. [PubMed:10630095 ]
  4. Ishitsuka H: Capecitabine: preclinical pharmacology studies. Invest New Drugs. 2000 Nov;18(4):343-54. [PubMed:11081570 ]
  5. Endo M, Miwa M, Eda H, Ura M, Tanimura H, Ishikawa T, Miyazaki-Nose T, Hattori K, Shimma N, Yamada-Okabe H, Ishitsuka H: Augmentation of the antitumor activity of capecitabine by a tumor selective dihydropyrimidine dehydrogenase inhibitor, RO0094889. Int J Cancer. 2003 Sep 20;106(5):799-805. [PubMed:12866042 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
inhibitor
General Function:
Steroid hydroxylase activity
Specific Function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. This enzyme contributes to the wide pharmacokinetics variability of the metabolism of drugs such as S-warfarin, diclofenac, phenyto...
Gene Name:
CYP2C9
Uniprot ID:
P11712
Molecular Weight:
55627.365 Da
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
Comments
comments powered by Disqus
Drug created on June 13, 2005 07:24 / Updated on August 17, 2016 12:23