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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:
Molecular Weight:
359.35
UNSPSC Code:
12352200
PubChem Substance ID:
NACRES:
NA.77
MDL number:
Assay:
≥98% (HPLC)
Form:
powder
Quality level:
Technical Service
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Product Name

Capecitabine, ≥98% (HPLC)

Quality Level

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)

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.


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pictograms

Health hazard

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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Francesco Giotta et al.
Tumori, 99(6), 278e-281e (2014-02-08)
We present the case of a 58-year-old woman with breast cancer metastasizing to the liver after adjuvant chemotherapy. A liver biopsy confirmed metastatic lesions from breast cancer that were immunohistochemically positive for estrogen/progesterone receptors and HER2. After first-line treatment with
Karen-Lise G Spindler et al.
Anticancer research, 34(2), 845-850 (2014-02-11)
We investigated the efficacy and safety of capecitabine and gemcitabin (GemCap) in heavily pre-treated, therapy-resistant metastatic colorectal cancer (mCRC) patients and the clinical importance of cell-free DNA (cfDNA) measurement. Patients' inclusion criteria included histopathologically-verified mCRC refractory to standard chemotherapy, adequate
Dermatomyositis associated with capecitabine in the setting of malignancy.
Frank W Chen et al.
Journal of the American Academy of Dermatology, 70(2), e47-e48 (2014-01-21)



Global Trade Item Number

SKUGTIN
SML0653-10MG04061833025765
SML0653-50MG04061837101229