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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
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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
- NSC 759853
- 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
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/s1InChIKey
GAGWJHPBXLXJQN-UORFTKCHSA-NSmiles
CCCCCOC(=O)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. |