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Merck
CN

5.04594

Gemcitabine, HCl

别名:

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

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关于此项目

经验公式（希尔记法）:
C9H11F2N3O4 · xHCl
化学文摘社编号:
122111-03-9
分子量:
263.20 (free base basis)
MDL编号:
MFCD01735988
UNSPSC代码:
12352200
NACRES:
NA.77

主要文件

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方案

≥99% (HPLC)

质量水平

100

表单

powder

制造商/商品名称

Calbiochem®

储存条件

OK to freeze
desiccated (hygroscopic)
protect from light

颜色

white

溶解性

water: 25 mg/mL

储存温度

2-8°C

SMILES字符串

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

InChI key

OKKDEIYWILRZIA-OSZBKLCCSA-N

一般描述

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).

生化/生理作用

Cell permeable: yes
Primary Target
DNA
Reversible: no
Secondary Target
DNA polymerase

包装

Packaged under inert gas

制备说明

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

其他说明

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.

法律信息

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

免责声明

Toxicity: Carcinogenic / Teratogenic (D)

象形图

Health hazard
GHS08

警示用语：

Danger

危险声明

H360

危险分类

Repr. 1B

储存分类代码

6.1C - Combustible, acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

WGK

WGK 3

闪点(°F)

Not applicable

闪点(°C)

Not applicable

法规信息

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H Eda et al.
Cancer research, 58(6), 1165-1169 (1998-03-27)
We showed that the efficacy of the new 2'-deoxycytidine (2'-dCyd) analogue antimetabolite 2'-deoxy-2'-methylidenecytidine (DMDC) correlates well with tumor levels of cytidine (Cyd) deaminase in human cancer xenograft models. DMDC was highly effective in tumors with higher levels of Cyd deaminase
H A Burris et al.
Journal of clinical oncology : official journal of the American Society of Clinical Oncology, 15(6), 2403-2413 (1997-06-01)
Most patients with advanced pancreas cancer experience pain and must limit their daily activities because of tumor-related symptoms. To date, no treatment has had a significant impact on the disease. In early studies with gemcitabine, patients with pancreas cancer experienced
Sau Wai Hung et al.
Cancer letters, 320(2), 138-149 (2012-03-20)
Clinical refractoriness to nucleoside analogs (e.g., gemcitabine, capecitabine) is a major scientific problem and is one of the main reasons underlying the extremely poor prognostic state of pancreatic cancer. The drugs' effects are suboptimal partly due to cellular mechanisms limiting
J R Mackey et al.
Cancer research, 58(19), 4349-4357 (1998-10-10)
Gemcitabine (2',2'-difluorodeoxycytidine) is a novel pyrimidine nucleoside drug with clinical efficacy in several common epithelial cancers. We have proposed that gemcitabine requires nucleoside transporter (NT) proteins to permeate the plasma membrane and to exhibit pharmacological activity. In humans, there are
V Heinemann et al.
Cancer research, 52(3), 533-539 (1992-02-01)
2',2'-Difluorodeoxycytidine (dFdC, Gemcitabine) is a deoxycytidine analogue which, after phosphorylation to the 5'-di- and 5'-triphosphate (dFdCTP), induces inhibition of DNA synthesis and cell death. We examined the values for elimination kinetics of cellular dFdCTP and found they were dependent on
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