CAS Number154361-50-9
Synonyms1-(5-Deoxypentofuranosyl)-5-fluoro-4-{[(pentyloxy)carbonyl]amino}-2(1H)-pyrimidinone; 5'-Deoxy-5-fluoro-N-[(pentyloxy)carbonyl]cytidine; Capecitabine; 5'-Deoxy-5-fluoro-N4-[(pentyloxy)carbonyl]cytidine; Capecytabine; Ro 09-1978; Captabin; MFCD00930626; XELODA; RO-9-1978; Cpecitabine; Capecitibine; 1-(5-deoxypentofuranosyl)-5-fluoro-4-{[(pentyloxy)carbonyl]amino}pyrimidin-2(1h)-one
Molecular FormulaC15H22FN3O6
Molecular Weight359.35
Purity99%
Density1.5±0.1 g/cm3
Boiling Point517.6±60.0 °C at 760 mmHg
Melting Point110-121°C
Appearancecolorless solid
Symbol
Signal WordWarning
| Chemical & Physical Properties | |
|---|---|
| CAS Number | 154361-50-9 |
| Catalog No. | 2A-9009561 |
| Chinese Name | 卡培他滨 |
| Synonyms | 1-(5-Deoxypentofuranosyl)-5-fluoro-4-{[(pentyloxy)carbonyl]amino}-2(1H)-pyrimidinone; 5'-Deoxy-5-fluoro-N-[(pentyloxy)carbonyl]cytidine; Capecitabine; 5'-Deoxy-5-fluoro-N4-[(pentyloxy)carbonyl]cytidine; Capecytabine; Ro 09-1978; Captabin; MFCD00930626; XELODA; RO-9-1978; Cpecitabine; Capecitibine; 1-(5-deoxypentofuranosyl)-5-fluoro-4-{[(pentyloxy)carbonyl]amino}pyrimidin-2(1h)-one |
| Molecular Formula | C15H22FN3O6 |
| Molecular Weight | 359.35 |
| Purity | 99 |
| Density | 1.5±0.1 g/cm3 |
| Boiling Point | 517.6±60.0 °C at 760 mmHg |
| Melting Point | 110-121°C |
| Appearance | colorless solid |
| Water Solubility | Water solubility: slightly soluble; water solubili |
| Storage Condition | -20°C Freezer |
| Application | Capecitabine is an orally available prodrug that is catalyzed by thymidine phosphorylase to its active metabolite fluorouracil (FU). |
| HTC | 2934999090 |
| PubChem ID | 329823378 |
| MDL Number | MFCD00930626 |
| SMILES | 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 |
| NACRES Code | NA.24 |
| UNSPSC | 41116107 |
| Hazard Symbols | Transport |
| MSDS | msds/9561_1_154361_50_9.pdf |
| Bioactivity | Capecitabine is an oral prodrug that is converted to its active metabolite, fluorouracil (FU), by thymidine phosphorylase. Related Catalog Signaling Pathways >> Cell Cycle/DNA Damage >> DNA/RNA Synthesis Signaling Pathways >> Cell Cycle/DNA Damage >> Nucleoside Antimetabolite/Analog Research Areas >> Cancer Target DNA/RNA Synthesis[1] In Vitro Capecitabine is an anti-cancer chemotherapy drug. It is classified as an antimetabolite. Capecitabine is converted into 5′-deoxy-5-fluorocytidine (5′DFCR), 5′-deoxy-5-fluorouridine (5′DFUR) and 5-fluorouracil (5-FU) by carboxylesterases (CES1 and 2), cytidine deaminase (CDD), and thymidine phosphorylase (TP), in both liver and tumour. Capecitabine induces a significant cytotoxic effect in vitro only at high concentrations. Mean IC50 values vary from 860 μM in COLO205 cells to 6000 μM in HCT8 cells[2]. In Vivo A pharmacokinetic/pharmacodynamic study is carried out in mice bearing HCT 116 xenografts receiving 0.52 and 2.1 mmol/kg/d of Capecitabine by oral gavage. Capecitabine administered at 0.52 mmol/kg/day induces partial control of HCT 116 xenografts tumour growth: growth rate =7.5±0.5 on day 21. Capecitabine 2.1 mmol/kg/day achieves complete control of tumor growth during the treatment period: growth rate =1±0.2 on day 21[2]. Cell Assay HCT 116, HCT8, HCT15, HT29, SW620 and COLO205 human colon cancer cells are used. Cells are plated on day 1 in 96-well plates at a density of 2500 cells/well for HCT 116, 3500 cells/well for HCT8 and HT29, 5000 cells/well for HCT15, 6000 cells/well for SW620 and 7000 cells/wells for COLO205 in a volume of 150 μL/well. All cell lines are treated on day 2 with increasing concentrations of Capecitabine (0.1-10 mM), 5′DFCR (10 nM-100 μM), 5′DFUR (2.5-500 μM) or 5-FU (0.5-250 μM) for 24 h. After drug exposure, cells are washed once with cold PBS and placed in 200 μL of drug-free medium for 72 h after the end of drug exposure. The cells are then fixed with trichloroacetic acid and stained with sulforhodamine B. Optical densities are measured at 540 nm with a Biohit BP-800. The results are based on three independent experiments performed in triplicate[2]. Animal Admin Mice[2] Six-week-old C57/Bl6 Nu/Nu mice are used. Bilateral HCT 116 xenografts are obtained by subcutaneous injection of 107 cells/flank. Animals bearing HCT 116 xenografts are treated with vehicle or Capecitabine 0.52 or 2.1 mmol/kg (563 and 2250 mg/m2, respectively) given once daily for 5 consecutive days/week by oral gavage for 3 weeks (days 0-4, 7-11, 14-18). Animals are culled on day 0 at 15, 30 min, 1, 2, 4, 8 and 24 h, and prior to planned treatment on days 7 and 14 after the start of treatment. Three animals per time-point are analysed. At the time of collection, blood is collected in heparin, and plasma isolated and stored at −80°C. The liver is removed immediately and stored in RNAlater solution. Tumours are macro-dissected to remove fibrotic tissue and blood vessels and snap-frozen in liquid nitrogen. References [1]. PharmD CM, et al. Capecitabine: A review. Clinical Therapeutics. 2005 Jan; 27(1): 23-44. [2]. Guichard SM, et al. Gene expression predicts differential capecitabine metabolism, impacting on both pharmacokinetics and antitumour activity. Eur J Cancer. 2008 Jan;44(2):310-7. Chemical & Physical Properties Density 1.5±0.1 g/cm3 Boiling Point 517.6±60.0 °C at 760 mmHg Melting Point 110-121°C Molecular Formula C15H22FN3O6 Molecular Weight 359.350 Flash Point 266.8±32.9 °C Exact Mass 359.149261 PSA 122.91000 LogP 0.97 Vapour Pressure 0.0±3.1 mmHg at 25°C Index of Refraction 1.600 InChIKey GAGWJHPBXLXJQN-UORFTKCHSA-N SMILES CCCCCOC(=O)Nc1nc(=O)n(C2OC(C)C(O)C2O)cc1F Storage condition -20°C Freezer |
| Use of | Capecitabine is an oral prodrug that is converted to its active metabolite, fluorouracil (FU), by thymidine phosphorylase. Properties Articles84 Name capecitabine Synonym More Synonyms Capecitabine Biological Activity Description Capecitabine is an oral prodrug that is converted to its active metabolite, fluorouracil (FU), by thymidine phosphorylase. Related Catalog Signaling Pathways >> Cell Cycle/DNA Damage >> DNA/RNA Synthesis Signaling Pathways >> Cell Cycle/DNA Damage >> Nucleoside Antimetabolite/Analog Research Areas >> Cancer DNA/RNA Synthesis[1] References [1]. PharmD CM, et al. Capecitabine: A review. Clinical Therapeutics. 2005 Jan; 27(1): 23-44. [2]. Guichard SM, et al. Gene expression predicts differential capecitabine metabolism, impacting on both pharmacokinetics and antitumour activity. Eur J Cancer. 2008 Jan;44(2):310-7. Chemical & Physical Properties Molecular Formula C15H22FN3O6 Exact Mass 359.149261 PSA 122.91000 Index of Refraction 1.600 InChIKey GAGWJHPBXLXJQN-UORFTKCHSA-N SMILES CCCCCOC(=O)Nc1nc(=O)n(C2OC(C)C(O)C2O)cc1F |
| Tax Rebate | 13.0% |
| Supervision | None. MFN tariff: 6.5%. Ordinary tariff: 20.0% |
| Transport Info | Shipping Name: UN |
| MSDS Transport Info | Module 14. Shipping information 14.1 United Nations number European Land Transport Dangerous Regulations: -International Maritime Dangerous Regulations: -International Air Transport Dangerous Regulations: - 14.2 United Nations shipping name European Land Transport Dangerous Regulations: Non-dangerous goods IMDG Code: Non-dangerous goods International air transport dangerous goods regulations: non-dangerous goods 14.3 Transport hazard categories European Land Transport Dangerous Regulations: -International Maritime Dangerous Regulations: -International Air Transport Dangerous Regulations: - 14.4 Package group European Land Transport Dangerous Regulations: -International Maritime Dangerous Regulations: -International Air Transport Dangerous Regulations: - 14.5 Environmental hazards European Land Transport Danger Regulations: No International Maritime Danger Regulations International Air Transport Danger Regulations: No Marine pollutants (yes/no): No 14.6 Special precautions No data available |
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