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Substance Name: Capecitabine [USAN:USP:INN:BAN]
RN: 154361-50-9
UNII: 6804DJ8Z9U
InChIKey: GAGWJHPBXLXJQN-UORFTKCHSA-N

Notes

  • A deoxycytidine derivative and fluorouracil PRODRUG that is used as an ANTINEOPLASTIC ANTIMETABOLITE in the treatment of COLON CANCER; BREAST CANCER and GASTRIC CANCER.
  • A fluorouracil prodrug; Xeloda is tradename.

    NCI: A fluoropyrimidine carbamate belonging to the class of antineoplastic agents called antimetabolites. As a prodrug, capecitabine is selectively activated by tumor cells to its cytotoxic moiety, 5-fluorouracil (5-FU); subsequently, 5-FU is metabolized to two active metabolites, 5-fluoro-2-deoxyuridine monophosphate (FdUMP) and 5-fluorouridine triphosphate (FUTP) by both tumor cells and normal cells. FdUMP inhibits DNA synthesis and cell division by reducing normal thymidine production, while FUTP inhibits RNA and protein synthesis by competing with uridine triphosphate for incorporation into the RNA strand.(NCI Thesaurus)

Molecular Formula

  • C15-H22-F-N3-O6

Molecular Weight

  • 359.3518
 

Classification Codes

  • Antimetabolites
  • Antimetabolites, Antineoplastic
  • Antineoplastic
  • Antineoplastic Agents
  • Noxae

Names and Synonyms

Name of Substance

  • Capecitabine
  • Capecitabine [USAN:USP:INN:BAN]

MeSH Heading

  • Capecitabine

Synonyms

  • 5'-Deoxy-5-fluoro-N-((pentyloxy)carbonyl)cytidine
  • Capecitabine
  • Capiibine
  • Carbamic acid, (1-(5-deoxy-beta-D-ribofuranosyl)-5-fluoro-1,2-dihydro-2-oxo-4-pyrimidinyl)-, pentyl ester
  • Caxeta
  • HSDB 7656
  • N(4)-Pentyloxycarbonyl-5'-deoxy-5-fluorocytidine
  • Pentyl 1-(5-deoxy-beta-D-ribofuranosyl)-5-fluoro-1,2-dihydro-2-oxo-4-pyrimidinecarbamate
  • Ro 09-1978
  • Ro 09-1978/000
  • UNII-6804DJ8Z9U
  • Xabine
  • Xeloda

Systematic Name

  • Cytidine, 5'-deoxy-5-fluoro-N-((pentyloxy)carbonyl)-

Registry Numbers

CAS Registry Number

  • 154361-50-9

FDA UNII

  • 6804DJ8Z9U

Other Registry Numbers

  • 158798-73-3
  • 958887-39-3

System Generated Number

  • 0154361509

Structure Descriptors

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

InChIKey

GAGWJHPBXLXJQN-UORFTKCHSA-N

Smiles

CCCCCOC(=O)Nc1c(cn(c(=O)n1)[C@H]2[C@@H]([C@@H]([C@H](O2)C)O)O)F

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
women TDLo oral 2120mg/kg/28D (2120mg/kg) SENSE ORGANS AND SPECIAL SENSES: CORNEAL DAMAGE: EYE

SENSE ORGANS AND SPECIAL SENSES: VISUAL FIELD CHANGES: EYE
New England Journal of Medicine. Vol. 343, Pg. 740, 2000.