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154361-50-9

154361-50-9 structure
154361-50-9 structure
Name capecitabine
Synonyms 2(1H)-Pyrimidinone, 1-(5-deoxypentofuranosyl)-5-fluoro-4-[[(pentyloxy)carbonyl]amino]-
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
Ro 09-1978/000
Description Capecitabine is an oral prodrug that is converted to its active metabolite, fluorouracil (FU), by thymidine phosphorylase.
Related Catalog
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.
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
Storage condition -20°C Freezer
Symbol GHS08
GHS08
Signal Word Danger
Hazard Statements H341-H350-H360FD
Precautionary Statements P201-P308 + P313
Hazard Codes T
Risk Phrases 45-60-61-68
Safety Phrases 53-22-36/37-45
RIDADR NONH for all modes of transport
WGK Germany 3
HS Code 2934999090
HS Code 2934999090
Summary 2934999090. other heterocyclic compounds. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0%

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