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504594 Gemcitabine, HCl - CAS 122111-03-9 - Calbiochem

Overview

Key Spec Table

CAS #Empirical Formula
122111-03-9C₉H₁₁F₂N₃O₄ • HCl

Products

Catalogue NumberPackaging Qty/Pack
5.04594.0001 Glass bottle 50 mg
Description
OverviewA 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).
Catalogue Number504594
Brand Family Calbiochem®
SynonymsRibonucleotide Reductase Inhibitor II, RNR Inhibitor II, 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
References
ReferencesHung, 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.
Product Information
CAS number122111-03-9
FormWhite powder
Hill FormulaC₉H₁₁F₂N₃O₄ • HCl
Chemical formulaC₉H₁₁F₂N₃O₄ • HCl
Hygroscopic Hygroscopic
ReversibleN
Quality LevelMQ100
Biological Information
Primary TargetDNA
Secondary targetDNA polymerase
Purity≥99% by HPLC
Physicochemical Information
Cell permeableY
Safety Information
R PhraseR: 62-63

Possible risk of impaired fertility.
Possible risk of harm to the unborn child.
S PhraseS: 36/37-53

Wear suitable protective clothing and gloves.
Avoid exposure - obtain special instructions before use.
Storage and Shipping Information
Ship Code Ambient Temperature Only
Toxicity Carcinogenic / Teratogenic
Storage +2°C to +8°C
Protect from Light Protect from light
Hygroscopic Hygroscopic
Do not freeze Ok to freeze
Special InstructionsFollowing reconstitution, aliquot and freeze (-20°C). Stock solutions are stable for up to 6 months at -20°C.
Packaging Information
Packaged under inert gas Packaged under inert gas
Global Trade Item Number
Catalogue Number GTIN
5.04594.0001 04055977243895