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Merck

SML0653

Capecitabine

≥98% (HPLC), DNA/RNA synthesis inhibitor, powder

Synonym(s):

5′-Deoxy-5-fluoro-N-[(pentyloxy)carbonyl]cytidine, Ro-9-1978

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About This Item

Empirical Formula (Hill Notation):
C15H22FN3O6
CAS Number:
154361-50-9
Molecular Weight:
359.35
UNSPSC Code:
12352200
PubChem Substance ID:
329825576
NACRES:
NA.77
MDL number:
MFCD00930626

Key Documents

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Product Name

Capecitabine, ≥98% (HPLC)

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 key

GAGWJHPBXLXJQN-UORFTKCHSA-N

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

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

Quality Level

100

Gene Information

human ... TYMS(7298)

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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.
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.

pictograms

Health hazard
GHS08

signalword

Danger

Hazard Classifications

Carc. 1B - Muta. 2 - Repr. 1B

Storage Class

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

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Certificates of Analysis (COA)

Lot/Batch Number
0000521662
0000521662
0000511613
0000511613
0000475189

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Tim Meyer et al.
European journal of cancer (Oxford, England : 1990), 50(5), 902-911 (2014-01-22)
Cytotoxic chemotherapy is widely used for advanced, unresectable pancreatic and other gastrointestinal foregut neuroendocrine tumours (NETs) and the most commonly used regimen combines 5-fluorouracil with streptozocin. The NET01 trial was designed to investigate whether capecitabine combined with streptozocin was an
Mitsuhiro Tomoda et al.
Anticancer research, 34(1), 191-194 (2014-01-10)
Unresectable metastatic colorectal cancer with very slow tumour growth rate does not necessarily require for strong short-interval chemotherapy. In the present study, we administered monthly chemotherapy and aimed to evaluate the usefulness of the specific treatment schedule in patients with
Ferdinando Riccardi et al.
Tumori, 99(6), 257e-260e (2014-02-08)
Targeted therapies against HER2 (trastuzumab, lapatinib) have improved the efficacy of treatment and the outcome of patients with HER2-positive breast cancer. Lapatinib is a tyrosine kinase inhibitor targeting EGFR1 and HER2: it binds the intracellular domain of these receptors and
Nestor F Esnaola et al.
International journal of radiation oncology, biology, physics, 88(4), 837-844 (2014-03-13)
To evaluate, in a phase 2 study, the safety and efficacy of induction gemcitabine, oxaliplatin, and cetuximab followed by selective capecitabine-based chemoradiation in patients with borderline resectable or unresectable locally advanced pancreatic cancer (BRPC or LAPC, respectively). Patients received gemcitabine
Moyuru Yamada et al.
Nihon Shokakibyo Gakkai zasshi = The Japanese journal of gastro-enterology, 111(3), 521-528 (2014-03-07)
A woman in her 60s was referred to our department with advanced rectal cancer and multiple unresectable metastases of the liver and peritoneum. She had been diagnosed with idiopathic thrombocytopenic purpura (ITP) in her 20s, with a platelet count maintained
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