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

MSDS (material safety data sheet) or SDS, CoA and CoQ, dossiers, brochures and other available documents.

Synonyms: Ribonucleotide 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

Primary Target: DNA
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Overview

Replacement Information

Key Specifications Table

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

Products

Catalog 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
Applications
Biological Information
Primary TargetDNA
Secondary targetDNA polymerase
Purity≥99% by HPLC
Physicochemical Information
Cell permeableY
Dimensions
Materials Information
Toxicological Information
Safety Information according to GHS
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.
Product Usage Statements
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
Transport Information
Supplemental Information
Specifications
Global Trade Item Number
Catalog Number GTIN
5.04594.0001 04055977243895

Documentation

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

Title

Safety Data Sheet (SDS) 

Gemcitabine, HCl - CAS 122111-03-9 - Calbiochem Certificates of Analysis

TitleLot Number
504594

References

Reference overview
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.
Data Sheet

Note that this data sheet is not lot-specific and is representative of the current specifications for this product. Please consult the vial label and the certificate of analysis for information on specific lots. Also note that shipping conditions may differ from storage conditions.

Revision01-July-2013 JSW
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
DescriptionA 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).
FormWhite powder
Intert gas (Yes/No) Packaged under inert gas
CAS number122111-03-9
Chemical formulaC₉H₁₁F₂N₃O₄ • HCl
Purity≥99% by HPLC
SolubilityH₂O (25 mg/ml)
Storage Protect from light
+2°C to +8°C
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.
Toxicity Carcinogenic / Teratogenic
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.