5.04594

Gemcitabine, HCl

• 別名: 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
• 実験式（ヒル表記法）: C₉H₁₁F₂N₃O₄ · xHCl
• CAS番号: 122111-03-9
• 分子量: 263.20 (free base basis)
• MDL番号: MFCD01735988
• UNSPSCコード: 12352200
• NACRES: NA.77

特性

• アッセイ: ≥99% (HPLC)
• 品質水準: 100
• 形状: powder
• メーカー／製品名: Calbiochem^®
• 保管条件: OK to freeze; desiccated (hygroscopic); protect from light
• 色: white
• 溶解性: water: 25 mg/mL
• 保管温度: 2-8°C
• 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
• InChI Key: OKKDEIYWILRZIA-OSZBKLCCSA-N

詳細

詳細

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).

生物化学的／生理学的作用

Cell permeable: yes

Primary Target
DNA

Reversible: no

Secondary Target
DNA polymerase

包装

Packaged under inert gas

警告

Toxicity: Carcinogenic / Teratogenic (D)

再構成

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

その他情報

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.

法的情報

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

安全性情報

• ピクトグラム: GHS08
• シグナルワード: Danger
• 危険有害性情報: H360
• 注意書き: P201 - P202 - P280 - P308 + P313 - P405 - P501
• 危険有害性の分類: Repr. 1B
• 保管分類コード: 6.1C - Combustible, acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects
• WGK: WGK 3
• 引火点(°F): Not applicable
• 引火点(℃): Not applicable