An active metabolite of NUC-1031 and gemcitabine elaidate and a prodrug form of gemcitabine diphosphate and gemcitabine triphosphate
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Gemcitabine (hydrochloride)

Item No. 9003096

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
2'-deoxy-2',2'-difluoro-cytidine, monohydrochloride
CAS Number
122111-03-9
Synonyms
  • DDFC
  • dFdC
  • LY 188011
Molecular Formula
C9H11F2N3O4 • HCl
Formula Weight
299.7
Purity
≥98%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
PBS (pH 7.2): 10 mg/ml
λmax
272 nm
SMILES
OC[C@H]1O[C@@H](N2C=CC(N)=NC2=O)C(F)(F)[C@@H]1O.Cl
InChi Code
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
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    25 mg

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    50 mg

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    100 mg

    $280

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    Product Description

    Gemcitabine is an active metabolite of the gemcitabine prodrugs NUC-1031 (Item No. 9003247) and gemcitabine elaidate (Item No. 28303) and a prodrug form of gemcitabine di- and triphosphates.1,2,3 Gemcitabine is phosphorylated by intracellular kinases to the intermediate metabolite gemcitabine monophosphate (Item No. 31726) and the active di- and triphosphate forms.3 It is cytotoxic to HepG2 hepatocellular carcinoma and A549 non-small cell lung cancer (NSCLC) cells (IC50s = 5.2 and 16 nM, respectively) and inhibits tumor growth in various breast, colon, lung, and pancreatic cancer mouse xenograft models.4 Gemcitabine (12 mg/kg) sensitizes tumors to antibodies targeting programmed cell death protein 1 (PD-1), decreases the number of tumor-infiltrating regulatory T cells (Tregs), and increases survival in an MC-38 syngeneic mouse model of colon carcinoma.5 Formulations containing gemcitabine have been used in the treatment of cancer.

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Slusarczyk, M., Lopez, M.H., Balzarini, J., et al. Application of ProTide technology to gemcitabine: A successful approach to overcome the key cancer resistance mechanisms leads to a new agent (NUC-1031) in clinical development. J. Med. Chem. 57(4), 1531-1542 (2014).

    2. Bergman, A.M., Adema, A.D., Balzarini, J., et al. Antiproliferative activity, mechanism of action and oral antitumor activity of CP-4126, a fatty acid derivative of gemcitabine, in in vitro and in vivo tumor models. Invest. New Drugs 29(3), 456-466 (2011).

    3. Veltkamp, S.A., Pluim, D., van Eijndhoven, M.A.J., et al. New insights into the pharmacology and cytotoxicity of gemcitabine and 2',2'-difluorodeoxyuridine. Mol. Cancer Ther. 7(8), 2415-2425 (2008).

    4. Merriman, R.L., Hertel, L.W., Schultz, R.M., et al. Comparison of the antitumor activity of gemcitabine and ara-C in a panel of human breast, colon, lung and pancreatic xenograft models. Invest. New. Drugs 14(3), 243-247 (1996).

    5. Obradovic, A., Ager, C., Turunen, M., et al. Systematic elucidation and pharmacological targeting of tumor-infiltrating regulatory T cell master regulators. Cancer Cell 41(5), 933-949 (2023).

    Product Citations

    Gallo, D., Young, J.T.F., Fourtounis, J., et al. CCNE1 amplification is synthetic lethal with PKMYT1 kinase inhibition. Nature 604(7907), 749-756 (2022).