fdcyd Report issue

Small molecule Experimental
AACT DrugBank MeSH PubChem

Active Ingredient History

NOW
  • Now
Capecitabine is a fluoropyrimidine carbamate with antineoplastic activity. It is an orally administered systemic prodrug which is converted to 5-fluorouracil (5-FU). 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’-deoxyuridylate. 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. Most common adverse reactions (≥30%) were diarrhea, hand-and-foot syndrome, nausea, vomiting, abdominal pain, fatigue/weakness, and hyperbilirubinemia. The concentration of 5-fluorouracil is increased and its toxicity may be enhanced by leucovorin.   NCATS

Chemistry

  • SMILES: C[C@H]1O[C@H]([C@H](O)[C@@H]1O)N2C=C(F)C(N)=NC2=O
  • InChIKey: YSNABXSEHNLERR-ZIYNGMLESA-N
  • Mol. Mass: 245.2077
  • ALogP: Missing data
  • ChEMBL Molecules: Missing data
More Chemistry

Pharmacology

Alternative names

2'-deoxy-5-fluorocytidine | 5-fluoro-2-deoxycytidine | 5-fluoro-2'-deoxycytidine | 5-fluorodeoxycytidine | fdcyd

Organizations (2)

Research & Development (2)

Organization Org Type FDA approvals Clinical Trials involvement Org ID Force Sort

Marketing (0)

Organization Org Type FDA approvals Clinical Trials involvement Org ID Force Sort

Indications (10)

Approved Indications (4)


 

Breast Neoplasms (approved 1998)

Colorectal Neoplasms (approved 1998)

Esophageal Neoplasms

Pancreatic Neoplasms

Experimental Indications - Clinical Trial Phases 1-4 (7)


 

Breast Neoplasms (Phase 2)

Head and Neck Neoplasms (Phase 2)

Leukemia, Myeloid, Acute (Phase 1)

Lung Neoplasms (Phase 2)

Myelodysplastic Syndromes (Phase 1)

Neoplasms (Phase 1)

Urinary Bladder Neoplasms (Phase 2)

Overview

  • Highest Phase: Phase 2
  • # of Trials: 4
  • # of Trial Organizations: 2

Trials by Phase

Trial Phase Start Date Organizations Indications

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