Floxuridine

• CAT Number: A000292
• CAS Number: 50-91-9
• Molecular Formula: C9H11FN2O5
• Molecular Weight: 246.2
• Purity: ≥95%
• Target: DNA Synthesis
• Solubility: >12.3mg/mL in DMSO
• Storage: -20°C
• InChI: 1S/C9H11FN2O5/c10-4-2-12(9(16)11-8(4)15)7-1-5(14)6(3-13)17-7/h2,5-7,13-14H,1,3H2,(H,11,15,16)/t5-,6+,7+/m0/s1
• InChIKey: ODKNJVUHOIMIIZ-RRKCRQDMSA-N
• SMILES: C1C(C(OC1N2C=C(C(=O)NC2=O)F)CO)O

Floxuridine is a fluorinated pyrimidine monophosphate analogue of 5-fluoro-2/’-deoxyuridine-5/’-phosphate (FUDR-MP) with antineoplastic activity. As an antimetabolite, floxuridine inhibits thymidylate synthetase, resulting in disruption of DNA synthesis and cytotoxicity. This agent is also metabolized to fluorouracil and other metabolites that can be incorporated into RNA and inhibit the utilization of preformed uracil in RNA synthesis. Check for active clinical trials or closed clinical trials using this agent. (NCI Thesaurus).

Reference

1: Liang X, Gao C, Cui L, Wang S, Wang J, Dai Z. Self-Assembly of an Amphiphilic
Janus Camptothecin-Floxuridine Conjugate into Liposome-Like Nanocapsules for More
Efficacious Combination Chemotherapy in Cancer. Adv Mater. 2017 Oct;29(40). doi:
10.1002/adma.201703135. Epub 2017 Sep 11. PubMed PMID: 28891273.

2: Mou Q, Ma Y, Pan G, Xue B, Yan D, Zhang C, Zhu X. DNA Trojan Horses:
Self-Assembled Floxuridine-Containing DNA Polyhedra for Cancer Therapy. Angew
Chem Int Ed Engl. 2017 Oct 2;56(41):12528-12532. doi: 10.1002/anie.201706301.
Epub 2017 Sep 5. PubMed PMID: 28806476.

3: Baehr CA, Huntoon CJ, Hoang SM, Jerde CR, Karnitz LM. Glycogen Synthase Kinase
3 (GSK-3)-mediated Phosphorylation of Uracil N-Glycosylase 2 (UNG2) Facilitates
the Repair of Floxuridine-induced DNA Lesions and Promotes Cell Survival. J Biol
Chem. 2016 Dec 23;291(52):26875-26885. doi: 10.1074/jbc.M116.746081. Epub 2016
Nov 14. PubMed PMID: 27875297; PubMed Central PMCID: PMC5207193.

4: Yang J, Xiang Y, Wan X, Feng F, Ren T. Primary treatment of stage IV
gestational trophoblastic neoplasia with floxuridine, dactinomycin, etoposide and
vincristine (FAEV): A report based on our 10-year clinical experiences. Gynecol
Oncol. 2016 Oct;143(1):68-72. doi: 10.1016/j.ygyno.2016.07.099. Epub 2016 Jul 15.
PubMed PMID: 27426306.

5: Datta A, Dey S, Das P, Alam SK, Roychoudhury S. Transcriptome profiling
identifies genes and pathways deregulated upon floxuridine treatment in
colorectal cancer cells harboring GOF mutant p53. Genom Data. 2016 Mar
17;8:47-51. doi: 10.1016/j.gdata.2016.03.003. eCollection 2016 Jun. PubMed PMID:
27114909; PubMed Central PMCID: PMC4832042.

6: Hu M, Huang P, Wang Y, Su Y, Zhou L, Zhu X, Yan D. Synergistic Combination
Chemotherapy of Camptothecin and Floxuridine through Self-Assembly of Amphiphilic
Drug-Drug Conjugate. Bioconjug Chem. 2015 Dec 16;26(12):2497-506. doi:
10.1021/acs.bioconjchem.5b00513. Epub 2015 Nov 5. PubMed PMID: 26497258.

7: Zhang T, Huang P, Shi L, Su Y, Zhou L, Zhu X, Yan D. Self-Assembled
Nanoparticles of Amphiphilic Twin Drug from Floxuridine and Bendamustine for
Cancer Therapy. Mol Pharm. 2015 Jul 6;12(7):2328-36. doi:
10.1021/acs.molpharmaceut.5b00005. Epub 2015 Jun 3. PubMed PMID: 25996874.

8: Weiss JT, Carragher NO, Unciti-Broceta A. Palladium-mediated dealkylation of
N-propargyl-floxuridine as a bioorthogonal oxygen-independent prodrug strategy.
Sci Rep. 2015 Mar 19;5:9329. doi: 10.1038/srep09329. PubMed PMID: 25788464;
PubMed Central PMCID: PMC4365405.

9: Huczyński A, Antoszczak M, Kleczewska N, Lewandowska M, Maj E, Stefańska J,
Wietrzyk J, Janczak J, Celewicz L. Synthesis and biological activity of
salinomycin conjugates with floxuridine. Eur J Med Chem. 2015 Mar 26;93:33-41.
doi: 10.1016/j.ejmech.2015.01.045. Epub 2015 Jan 27. PubMed PMID: 25644674.

10: Vivian D, Polli JE. Synthesis and in vitro evaluation of bile acid prodrugs
of floxuridine to target the liver. Int J Pharm. 2014 Nov 20;475(1-2):597-604.
doi: 10.1016/j.ijpharm.2014.09.014. Epub 2014 Sep 16. PubMed PMID: 25219859;
PubMed Central PMCID: PMC4319323.