5.04594

Gemcitabine, HCl

• Sinônimo(s): Gemcitabine, HCl, 2ʹ,2ʹ-Difluoro-2ʹ-deoxycytidine, HCl, 2ʹ-Deoxy-2ʹ,2ʹ-difluorocytidine, HCl, 4-Amino-1-((2R,5S)-3,3-difluoro-5-(hydroxymethyl)tetrahydrofuran-2-yl)pyrimidin-2(1H)-one, HCl, LY188011, dFdC, dFdCyd, Ribonucleotide Reductase Inhibitor II, RNR Inhibitor II, LY188011, dFdC, dFdCyd, 2ʹ,2ʹ-Difluoro-2ʹ-deoxycytidine, HCl, 2ʹ-Deoxy-2ʹ,2ʹ-difluorocytidine, HCl, 4-Amino-1-((2R,5S)-3,3-difluoro-5-(hydroxymethyl)tetrahydrofuran-2-yl)pyrimidin-2(1H)-one, HCl, Ribonucleotide
• Fórmula empírica (Notação de Hill): C₉H₁₁F₂N₃O₄ · xHCl
• Número CAS: 122111-03-9
• Peso molecular: 263.20 (free base basis)
• Número MDL: MFCD01735988
• Código UNSPSC: 12352200
• NACRES: NA.77

Propriedades

• Ensaio: ≥99% (HPLC)
• Nível de qualidade: 100
• Formulário: powder
• fabricante/nome comercial: Calbiochem^®
• condição de armazenamento: OK to freeze; desiccated (hygroscopic); protect from light
• cor: white
• solubilidade: water: 25 mg/mL
• temperatura de armazenamento: 2-8°C
• cadeia de caracteres SMILES: FC1([C@@H](O[C@@H]([C@H]1O)CO)[n]2[c](nc(cc2)N)=O)F.Cl
• InChI: 1S/C9H11F2N3O4.ClH/c10-9(11)6(16)4(3-15)18-7(9)14-2-1-5(12)13-8(14)17;/h1-2,4,6-7,15-16H,3H2,(H2,12,13,17);1H/t4-,6-,7-;/m1./s1
• chave InChI: OKKDEIYWILRZIA-OSZBKLCCSA-N

Descrição

Descrição geral

A bioavailable, moderately toxic, deoxyctytidine analog with anti-metabolite and anti-tumor properties. Shown to be effective against a variety of tumors and blocks the growth of cancer cells in culture (IC ₅₀ = 8.7, 57, 3.7, and 36 nM for L1210, CEM, Caco2, and HeLa cells, respectively). Following its uptake into cells by nucleoside transporters it is phosphorylated to its mono (dFdCMP), di (dFdCDP), and triphosphorylated (dFdCTP) forms by deoxycytidine kinase. dFdCDP and dFdCTP are reported to inhibit the activity of ribonucleotide reductase and impede DNA synthesis and repair mechanisms and induce cell death. Blocks the progression of cells through the G1/S phase. The dFdCTP is shown to compete with endogenous deoxycytidine triphosphate (dCTP) for incorporation into DNA and against CTP into RNA. Gemcitabine is also shown to block mitochondrial DNA polymerase γ. Works synergistically with other chemotherapeutic agents to enhance their cytotoxicity. Its half life is reported to be 42 to 94 min (depending upon the age and sex of the individual).

Ações bioquímicas/fisiológicas

Cell permeable: yes

Primary Target
DNA

Reversible: no

Secondary Target
DNA polymerase

Embalagem

Packaged under inert gas

Advertência

Toxicity: Carcinogenic / Teratogenic (D)

Reconstituição

Following reconstitution, aliquot and freeze (-20°C). Stock solutions are stable for up to 6 months at -20°C.

Outras notas

Hung, S.W., et al. 2012. Cancer Lett.320, 138.
Fowler, J.D., et al. 2008. J. Biol. Chem.283, 15339.
Mackey, J.R., et al. 1998. Cancer Res.58, 4349.
Eda, H., et al. 1998. Cancer Res.58, 1165.
Burris III, H.A., et al. 1997. J. Clin. Oncol.15, 2403.
Heinemann, V., et al. 1992. Cancer Res.52, 533.
Hertel, L.W., et al. 1990. Cancer Res.50, 4417.

Informações legais

CALBIOCHEM is a registered trademark of Merck KGaA, Darmstadt, Germany

Informações de segurança

• Pictogramas: GHS08
• Palavra indicadora: Danger
• Frases de perigo: H360
• Declarações de precaução: P201 - P202 - P280 - P308 + P313 - P405 - P501
• Classificações de perigo: Repr. 1B
• Código de classe de armazenamento: 6.1C - Combustible, acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects
• Classe de risco de água (WGK): WGK 3
• Ponto de fulgor (°F): Not applicable
• Ponto de fulgor (°C): Not applicable