5.04594

Gemcitabine, HCl

• Synonyme(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
• Formule empirique (notation de Hill) : C₉H₁₁F₂N₃O₄ · xHCl
• CAS Number: 122111-03-9
• Poids moléculaire : 263.20 (free base basis)
• Numéro MDL: MFCD01735988
• Code UNSPSC : 12352200
• Nomenclature NACRES : NA.77

Propriétés

• Essai: ≥99% (HPLC)
• Niveau de qualité: 100
• Forme: powder
• Fabricant/nom de marque: Calbiochem^®
• Conditions de stockage: OK to freeze; desiccated (hygroscopic); protect from light
• Couleur: white
• Solubilité: water: 25 mg/mL
• Température de stockage: 2-8°C
• Chaîne 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
• Clé InChI: OKKDEIYWILRZIA-OSZBKLCCSA-N

Description

Description générale

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).

Actions biochimiques/physiologiques

Cell permeable: yes

Primary Target
DNA

Reversible: no

Secondary Target
DNA polymerase

Conditionnement

Packaged under inert gas

Avertissement

Toxicity: Carcinogenic / Teratogenic (D)

Reconstitution

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

Autres remarques

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.

Informations légales

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

Informations sur la sécurité

• Pictogrammes: GHS08
• Mention d'avertissement: Danger
• Mentions de danger: H360
• Conseils de prudence: P201 - P202 - P280 - P308 + P313 - P405 - P501
• Classification des risques: Repr. 1B
• Code de la classe de stockage: 6.1C - Combustible, acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects
• Classe de danger pour l'eau (WGK): WGK 3
• Point d'éclair (°F): Not applicable
• Point d'éclair (°C): Not applicable