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

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Synonyme: 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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504594
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Übersicht

Replacement Information

Key Spec Table

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

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      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
      Bestellnummer GTIN
      5045940001 04055977243895

      Documentation

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

      Titel

      Sicherheitsdatenblatt (SDB) 

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

      TitelChargennummer
      504594

      Literatur

      Übersicht
      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.
      Datenblatt

      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.