An active metabolite of NUC-1031 and gemcitabine elaidate and a prodrug form of gemcitabine diphosphate and gemcitabine triphosphate
Technical Support & Resources

Information provided in the product description is from published literature. Due to the nature of scientific experimentation, your results (e.g., selectivity and effective concentrations) or specific application for this product may differ. If you have questions about how this product fits your application, please contact our technical support staff.

Visit our FAQ

Contact Us

Toll Free Phone (USA and Canada Only): (888) 526-5351
Direct Phone: (734) 975-3888

Request Technical Support

Technical Support Request

To streamline the process attach the appropriate questionnaire to your inquiry.

Download IHC QuestionnaireDownload WB Questionnaire

View Our Privacy Statement for details on how we use and protect your data. In addition, this site is protected by hCaptcha and its Privacy Policy and Terms of Service apply.

Gemcitabine

Item No. 11690

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
2'-deoxy-2',2'-difluoro-cytidine
CAS Number
95058-81-4
Synonyms
  • DDFC
  • dFdC
  • LY 188011
  • NSC 613327
Molecular Formula
C9H11N3O4F2
Formula Weight
263.2
Purity
≥98%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 0.1 mg/mlDMSO: 5 mg/mlEthanol: 0.2 mg/mlPBS (pH 7.2): 1 mg/ml
λmax
243, 269 nm
SMILES
O=C1N=C(N)C=CN1[C@H]2C(F)(F)[C@H](O)[C@@H](CO)O2
InChi Code
InChI=1S/C9H11F2N3O4/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)/t4-,6-,7-/m1/s1
InChi Key
SDUQYLNIPVEERB-QPPQHZFASA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
Recommended Products

Certificates of Analysis & Batch Specific Data

Provide batch numbers separated by commas to download or request available product inserts, QC sheets, certificates of analysis, data packs, and GC-MS data.

Download most recent Certificate of Analysis for this product

    10 mg

    $47

    Add

    25 mg

    $87

    Add

    50 mg

    $162

    Add

    100 mg

    $301

    Add
    Cayman Chemical
    Visit Our Cancer Resource Center
    Find Tools & Resources to Study the Hallmarks of Cancer
    • Cancer cell signaling & regulation
    • Cancer metabolism
    • Tumor microenvironment
    EXPLORE NOW
    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

    Kremer, D.M., Nelson, B.S., Lin, L., et al. GOT1 inhibition primes pancreatic cancer for ferroptosis through the autophagic release of labile iron. bioRxiv (2020).