Capecitabine

Modify Date: 2024-01-01 17:27:44

Capecitabine Structure
Capecitabine structure
 Common Name Capecitabine
CAS Number 154361-50-9 Molecular Weight 359.350
Density 1.5±0.1 g/cm3 Boiling Point 517.6±60.0 °C at 760 mmHg
Molecular Formula C15H22FN3O6 Melting Point 110-121°C
MSDS Chinese USA Flash Point 266.8±32.9 °C
Symbol GHS08
GHS08		 Signal Word Danger

 Use of Capecitabine


Capecitabine is an oral prodrug that is converted to its active metabolite, fluorouracil (FU), by thymidine phosphorylase.

 Names

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
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
Storage condition -20°C Freezer

 Safety Information

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

 Customs

HS Code 2934999090
Summary 2934999090. other heterocyclic compounds. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0%

 Articles84

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[A case of S-1/CDDP-resistant recurrent gastric cancer responsive to capecitabine/CDDP].

Gan To Kagaku Ryoho. 41(5) , 649-51, (2014)

We present a case of recurrent gastric cancer in which stable disease status was achieved for four months due to treatment with capecitabine/cisplatin (CDDP)after the failure of multiple anticancer dr...

Genetic markers of toxicity from capecitabine and other fluorouracil-based regimens: investigation in the QUASAR2 study, systematic review, and meta-analysis.

J. Clin. Oncol. 32(10) , 1031-9, (2014)

Fluourouracil (FU) is a mainstay of chemotherapy, although toxicities are common. Genetic biomarkers have been used to predict these adverse events, but their utility is uncertain.We tested candidate ...

 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
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