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Capecitabine
drug data and news
Capecitabine drug data, resources, and news articles (when available). Onconews.org provides news on cancer research. This section, which includes profiles on medicines that may or not be cancer-related is in beta form. If things run smoothly we will be releasing a new format late in the summer of 2006.
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| Generic name | Capecitabine | ||
| Brand Names/Synonyms | CAPECITABINE; Capecitabine; Capecitabine [Usan]; Xeloda | ||
| Indication | For the treatment of patients with metastatic breast cancer resistant to both paclitaxel and an anthracycline-containing chemotherapy regimen | ||
| Sponsored links | Description | Not Available | |
| Pharmacology | Capecitabine is a fluoropyrimidine carbamate with antineoplastic activity indicated for the treatment of patients with metastatic breast cancer. It is an orally administered systemic prodrug of 5'-deoxy-5-fluorouridine (5'-DFUR) which is converted to 5-fluorouracil. | ||
| Mechanism Of Action | Capecitabine is a prodrug that is selectively tumour-activated to its cytotoxic moiety, fluorouracil, by thymidine phosphorylase. Fluorouracil is further metabolized to two active metabolites, 5-fluoro-2-deoxyuridine monophosphate (FdUMP) and 5-fluorouridine triphosphate (FUTP), within normal and tumour cells. FdUMP inhibits DNA synthesis by reducing normal thymidine production, while FUTP inhibits RNA and protein synthesis by competing with uridine triphosphate.3 The active moiety of capecitabine, fluorouracil, is cell cycle phase-specific (Sphase). Both normal and tumor cells metabolize 5-FU to 5-fluoro-2-deoxyuridine monophosphate (FdUMP) and 5-fluorouridine triphosphate (FUTP). 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, so that a deficiency of this compound can inhibit cell division. Second 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. | ||
| Capecitabine News (When available) |
Various Forms of Life in Antineutrophil Cytoplasmic Antibody ... 06 Mar 2006 International Approvals: Rotarix, Hycamtin, Pulmicort HFA 06 Mar 2006 Q&A: Breast Cancer During Pregnancy 06 Mar 2006 Adjuvant Taxotere® and Herceptin® Effective for Breast Cancer ... 06 Mar 2006 Liposomal Doxorubicin Plus Cyclophosphamide Shows Promise in ... Feb 3, 2006 Cyclophosphamide Aids Fludarabine Against Leukemia Feb 18, 2006 Addition of Cyclophosphamide to Fludarabine Improves Progression ... Jan 31, 2006 ZIOPHARM Presents ZIO-201 Preclinical Kidney Toxicity Data at Bone ... Feb 21, 2006 Genasense(R) New Drug Application Accepted for Review by FDA Mar 1, 2006 AIDS-related Lymphoma Outcome Improved By Combination Therapy Mar 2, 2006 FDA accepts Genta's application Mar 1, 2006 Today's Early Winners and Losers Mar 1, 2006 FDA Approves Rituxan for Refractory Rheumatoid Arthritis Mar 1, 2006 Optimising Herceptin-based Therapy in HER2-positive Metastatic ... Feb 22, 2006 Anti-angiogenesis Therapy With Avastin (Bevacizumab): Presented at ... Feb 21, 2006 FDA to review Genta drug in leukemia indication Mar 2, 2006 What Can Xeloda (capecitabine) Add to Neoadjuvant Chemotherapy? ... Feb 22, 2006 CHOP Plus HAART Improves Outcome of AIDS-Related Lymphoma Feb 28, 2006 La Jolla Pharmaceutical Company Reports Fourth Quarter and Year ... Mar 2, 2006 Genta leukemia drug accepted for review Mar 1, 2006 Simultaneous HIV therapy and chemotherapy for lymphoma effective ... Feb 28, 2006 Interim Combined Analysis Shows Benefits of Adjuvant trastuzumab ... Feb 20, 2006 Autologous Hematopoietic Stem Cell Transplantation Shows Benefit ... Feb 21, 2006 Ziopharm compound shows potential for bone marrow transplants Feb 21, 2006 Sequential High-Dose Chemotherapy with Stem Cell Support Promising ... Feb 21, 2006 PDL's Potent Pick-Me-Up Feb 27, 2006 Genentech, Biogen Idec Gain Approval Of Rituxan In RA Mar 1, 2006 Randomized Trial Shows Ganite(R) Effective When Compared with a ... Mar 2, 2006 Genta to have Genasense decision by fall Mar 1, 2006 YM's Breast-Cancer Drug is Fast-Tracked Feb 13, 2006 Intensive Therapy May Benefit Women With Breast Cancer of a Poor ... Feb 14, 2006 The antioxidant herb Feb 25, 2006 Xeloda Shows Benefits as First Choice for Metastatic Breast Cancer ... Feb 22, 2006 YM BioSciences Receives FDA Fast Track Designation for Tesmilifene ... Feb 13, 2006 Adjuvant Docetaxel More Effective Than Vinorelbine for Early ... Feb 23, 2006 Xeloda Expands Options in Adjuvant Treatment of Breast Cancer ... Feb 21, 2006 BCIRG 006 Shows Trastuzumab (Herceptin) Improves Disease-free ... Feb 20, 2006 ZIOPHARM Presents ZIO-201 Preclinical Data at Bone Marrow ... Feb 17, 2006 Adjuvant Docetaxel or Vinorelbine with or without Trastuzumab for ... Feb 22, 2006 RITUXAN: FIRST FDA-APPROVED TREATMENT TO IMPROVE SURVIVAL FOR ... Feb 22, 2006 Unrelated BMT is feasible for adult T-cell leukemia/lymphoma ... Feb 23, 2006 Treatment Response Linked with Symptom Improvement in CLL Feb 22, 2006 Topotecan/Cytarabine Regimen May Be Effective Alternative for MDS Feb 22, 2006 Genentech Submits Supplemental Biologics License Application for ... Feb 15, 2006 Recurrence-Free Survival Improved with Taxotere® Compared to ... Feb 23, 2006 Clinical Benefit Analysis of Genasense plus Chemotherapy Reported ... Feb 15, 2006 Botox Could Help Target Resistant Tumors For Chemotherapy And ... Feb 20, 2006 Rituxan Gets Added Clearance Feb 13, 2006 Rituximab maintenance therapy dramatically improves survival for ... Feb 15, 2006 | ||
| Dosage Forms | TABLET | ||
| Drug_Category | Prodrugs; Antimetabolites; Antineoplastic Agents; ATC:L01BC06 | ||
| Absorption | Not Available | ||
| Interactions |
-->Interactions for Capecitabine: Antacid The effect of an aluminum hydroxide- and magnesium hydroxide-containing antacid (Maalox)* on the pharmacokinetics of capecitabine was investigated in 12 cancer patients. There was a small increase in plasma concentrations of capecitabine and one metabolite (5'-DFCR); there was no effect on the 3 major metabolites (5'-DFUR, 5-FU and FBAL). Coumarin Anticoagulants Altered coagulation parameters and/or bleeding have been reported in patients taking capecitabine concomitantly with coumarin-derivative anticoagulants such as warfarin and phenprocoumon. Patients taking coumarin-derivative anticoagulants concomitantly with capecitabine should be monitored regularly for alterations in their coagulation parameters (PT or INR). Leucovorin The concentration of 5-fluorouracil is increased and its toxicity may be enhanced by leucovorin. Deaths from severe enterocolitis, diarrhea, and dehydration have been reported in elderly patients receiving weekly leucovorin and fluorouracil. | ||
| Toxicity | Not Available | ||
| Organisms Affected | Humans and other mammals | ||
| Chemical IUPAC Name | pentyl[1-(3,4-dihydroxy-5-methyl-tetrahydrofuran-2-yl)-5-fluoro-2-oxo-1H-pyrimidin-4-yl]aminomethanoate | ||
| Chemical Formula | C15H22FN3O6 | ||
| Molecular Weight | 359.35 g/mol | ||
| Smiles String | CCCCCOC(=O)NC1=NC(=O)N(C=C1F)C2C(C(C(O2)C)O)O | ||
| Melting Point | 110-121 °C | ||
| Water Solubility | 26 mg/mL | ||
| State | Solid (white to off-white powder) | ||
| LogP/Hphobicity | 0.043 | ||
| Isoelectric Point | Not Available | ||
| Biotransformation | Metabolized by thymidine phosphorylase to fluoruracil | ||
| Half Life | 0.75 hours | ||
| Protein Binding [%] | < 60% | ||
| RxList Link | RXlist | ||
| Sponsored links | |||
| Drug Reference |
http://www.drugs.com/cons/Capecitabine.html http://www.rxlist.com/cgi/generic3/capecitabine.htm | ||
| Drug Type | Approved Drug | ||
| Accession No | APRD00203 | ||
| CAS Registry Number | 154361-50-9 | ||
| KEGG Compound ID | C12650 | ||
| PubChem ID | SID:197173 | ||
| PharmGKB ID | PA448771 | ||
| SwissProt ID | Not Available | ||
| GenBank ID | Not Available | ||
| Drug ID Number [DIN] | 2238454 |
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