LGM Pharma

Capecitabine

CAS No: 154361-50-9

Capecitabine

LGM Pharma is a Capecitabine 154361-50-9 active pharmaceutical ingredient supplier distributor, based in the USA.

Questions? Call our customer API support number 1-(800)-881-8210.

LGM Pharma offers this active ingredient but not the finished dosage forms.

Inquire about Capecitabine

Product Details:

CAS No: 154361-50-9
AHFS Codes: 10:00.00
Synonyms:
  • R340
ATC code: L01BC06
Molecular Weight: 359.3501 g/mol
PubChem: 60953
Chemical Formula: C19H15NO6
DrugBank: DB01101 (APRD00203)
Assay/Purity: Typically NLT 98%
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[C,H](C)[C,,H](O)[C,H]1O
InChl: GAGWJHPBXLXJQN-UORFTKCHSA-N

Additional Details: [+]

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.
Pharmacodynamics: 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. Fluorouracil it then metabolized both normal and tumor cells to 5-fluoro-2_-deoxyuridine 5_-monophosphate (FdUMP) and 5-fluorouridine triphosphate (FUTP).
Mode 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-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.
Metabolism: Metabolized by thymidine phosphorylase to fluoruracil.
General Reference:
  1. Walko CM, Lindley C: Capecitabine: a review. Clin Ther. 2005 Jan;27(1):23-44. Pubmed
  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
  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
  4. Twelves C: Vision of the future: capecitabine. Oncologist. 2001;6 Suppl 4:35-9. Pubmed
  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
  6. de Bono JS, Twelves CJ: The oral fluorinated pyrimidines. Invest New Drugs. 2001;19(1):41-59. Pubmed

Capecitabine News:

  • Capecitabine is also known by the trade name Xeloda, which is used to treat both metastatic breast and colorectal cancers.
  • Capecitabine was the first oral chemotherapy drug approved in the United States for breast and colorectal cancer, as well as Dukesê C Stage III colon cancer.
  • Typically prescribed twice daily, to be taken in the morning and in the evening, capecitabine is commonly taken for two weeks and is followed with a one week break.
  • Results released from Phase 1 trials at Georgetown University Medical Center were positive, and examined the use of both temsirolimus and capecitabine to treat patients with advanced malignancies.

Products currently covered by valid US Patents are offered for R&D use in accordance with 35 USC 271(e)+A13(1).
Any patent infringement and resulting liability is solely at buyer risk.