A prodrug form of gemcitabine
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Active Metabolite(s)
11690Gemcitabine 9003096Gemcitabine (hydrochloride)
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NUC-1031

Item No. 9003247

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
N-(2'-deoxy-2',2'-difluoro-P-phenyl-5'-cytidylyl)-L-alanine, phenylmethyl ester
CAS Number
840506-29-8
Molecular Formula
C25H27F2N4O8P
Formula Weight
580.5
Purity
≥98% (mixture of diastereomers)
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 12 mg/mLDMSO: 14 mg/mLDMSO:PBS (pH 7.2) (1:1): 0.5 mg/mLEthanol: 10 mg/mL
λmax
245 nm
SMILES
O[C@H]1C(F)(F)[C@H](N2C(N=C(N)C=C2)=O)O[C@@H]1COP(N[C@@H](C)C(OCC3=CC=CC=C3)=O)(OC4=CC=CC=C4)=O
InChi Code
InChI=1S/C25H27F2N4O8P/c1-16(22(33)36-14-17-8-4-2-5-9-17)30-40(35,39-18-10-6-3-7-11-18)37-15-19-21(32)25(26,27)23(38-19)31-13-12-20(28)29-24(31)34/h2-13,16,19,21,23,32H,14-15H2,1H3,(H,30,35)(H2,28,29,34)/t16-,19+,21+,23+,40?/m0/s1
InChi Key
NHTKGYOMICWFQZ-KKQYNPQSSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    Product Description

    NUC-1031 is a prodrug form of the anticancer nucleoside analog gemcitabine (Item No. 11690).1,2 NUC-1031 is more lipophilic than gemcitabine and enters cells through passive diffusion.1 It inhibits the growth of L1210, CEM, MP-2, and BxPC-3 cancer cells in vitro (IC50 = 35, 30, 60, and 40 nM, respectively).2 NUC-1031 (0.076 mmol/kg) reduces tumor growth in Mia-PaCa-2 and BxPC-3 mouse xenograft models, which are partially responsive and resistant to gemcitabine, respectively.3

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Thornton, P.J., Kadri, H., Miccoli, A., et al. Nucleoside phosphate and phosphonate prodrug clinical candidates. J. Med. Chem. 59(23), 10400-10410 (2016).

    2. 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).

    3. McGuigan, C., Habib, N.A., Wasan, H.S., et al. A phosphoramidate ProTide (NUC-1031) and acquired and intrinsic resistance to gemcitabine. J. Clin. Oncol. 29(15_suppl), e13540 (2016).