SML0653

Capecitabine

≥98% (HPLC)

• Synonym(s): 5′-Deoxy-5-fluoro-N-[(pentyloxy)carbonyl]cytidine, Ro-9-1978
• Empirical Formula (Hill Notation): C₁₅H₂₂FN₃O₆
• CAS Number: 154361-50-9
• Molecular Weight: 359.35
• MDL number: MFCD00930626
• UNSPSC Code: 12352200
• PubChem Substance ID: 329825576
• NACRES: NA.77

Properties

• Assay: ≥98% (HPLC)
• form: powder
• optical activity: [α]/D +80 to +100°, c = 0.5 in methanol
• color: white to beige
• solubility: H₂O: 10 mg/mL, clear (warmed)
• storage temp.: 2-8°C
• SMILES string: O[C@H]1[C@@H](O)[C@H](N2C(N=C(NC(OCCCCC)=O)C(F)=C2)=O)O[C@@H]1C
• 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
• InChI key: GAGWJHPBXLXJQN-UORFTKCHSA-N
• Gene Information: human ... TYMS(7298)

Description

Application

Capecitabine has been used:

• in combination with gemcitabine to achieve glutamine deprivation by enhancing the sensitivity of expression in pancreatic ductal adenocarcinoma (PDAC) cells to inhibitors of glutamine metabolism and study its effect on PDAC cell survival
• to study the drug metabolic function in a two-organ microfluidic system
• as an anti-cancer agent to study its cytotoxic activity alone or in combination with B87 on cancer cells

Biochem/physiol Actions

Capecitabine is an anti-cancer drug, a prodrug of doxifluridine, metabolized to 5-fluorouracil at the tumor site. The activation of capecitabine follows a pathway with three enzymatic steps and two intermediary metabolites, 5′-Deoxy-5-fluorocytidine (5′-DFCR) and 5′-Deoxy-5-fluorouridine (5′-DFUR), to form 5-fluorouracil.

Safety Information

• Pictograms: GHS08
• Signal Word: Danger
• Hazard Statements: H341,H350,H360FD
• Precautionary Statements: P201 - P202 - P280 - P308 + P313 - P405 - P501
• Hazard Classifications: Carc. 1B - Muta. 2 - Repr. 1B
• Storage Class Code: 6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects
• WGK: WGK 3
• Flash Point(F): Not applicable
• Flash Point(C): Not applicable