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SML0653

Sigma-Aldrich

Capecitabine

≥98% (HPLC)

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
MDL number:
MFCD00930626
UNSPSC Code:
12352200
PubChem Substance ID:
329825576
NACRES:
NA.77

Quality Level

100

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)

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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. 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

Signal Word

Danger

Hazard Statements

H341,H350,H360FD

Hazard Classifications

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

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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)
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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
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
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