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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

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

Storage Class Code

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

Certificates of Analysis (COA)

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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
Valentina Sini et al.
Tumori, 99(6), 273e-277e (2014-02-08)
This report describes a case of ab initio metastatic HER2-positive breast cancer in a very young patient. The onset of breast cancer at such a young age is uncommon and could delay the diagnosis with unquestionable impact on the prognosis.
Takahiro Yamanashi et al.
Gan to kagaku ryoho. Cancer & chemotherapy, 41(1), 107-112 (2014-01-16)
A 77-year-old man who complained of melena was admitted to our department. Colonoscopy revealed a type 2 tumor in the hepatic flexure of the ascending colon. Biopsy examination revealed a poorly differentiated adenocarcinoma. Abdominal computed tomography(CT)revealed 3 tumors within the
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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