For research use only. Not for therapeutic Use.
Tezacitabine is a synthetic purine nucleoside analogue with potential antineoplastic activity. Phosphorylated by cellular kinases, tezacitabine is converted into its active diphosphate and triphosphate metabolites. Tezacitabine diphosphate binds to and irreversibly inhibits the activity of the enzyme ribonucleotide reductase (RNR), which may result in the inhibition of DNA synthesis in tumor cells and tumor cell apoptosis. Tezacitabine triphosphate acts as a substrate for DNA polymerase, further compromising DNA replication.
| Catalog Number | M117139 |
| CAS Number | 130306-02-4 |
| Molecular Formula | C10H12FN3O4 |
| Purity | ≥95% |
| Target | ribonucleoside-diphosphate reductase inhibitor |
| Storage | -20°C |
| IUPAC Name | 4-amino-1-[(2R,3E,4S,5R)-3-(fluoromethylidene)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrimidin-2-one |
| InChI | InChI=1S/C10H12FN3O4/c11-3-5-8(16)6(4-15)18-9(5)14-2-1-7(12)13-10(14)17/h1-3,6,8-9,15-16H,4H2,(H2,12,13,17)/b5-3+/t6-,8+,9-/m1/s1 |
| InChIKey | GFFXZLZWLOBBLO-ASKVSEFXSA-N |
| SMILES | C1=CN(C(=O)N=C1N)C2C(=CF)C(C(O2)CO)O |
| Reference | </br>1: Taverna P, Rendahl K, Jekic-McMullen D, Shao Y, Aardalen K, Salangsang F, Doyle L, Moler E, Hibner B. Tezacitabine enhances the DNA-directed effects of fluoropyrimidines in human colon cancer cells and tumor xenografts. Biochem Pharmacol. 2007 Jan 1;73(1):44-55. Epub 2006 Sep 16. PubMed PMID: 17046720.</br>2: Skierski JS, Koronkiewicz M, Grieb P. Tezacitabine blocks tumor cells in G1 and S phases of the cell cycle and induces apoptotic cell death. Acta Pol Pharm. 2005 May-Jun;62(3):195-205. PubMed PMID: 16193812.</br>3: Stachnik K, Grieb P, Skierski JS. Cytotoxic effects of cladribine and tezacitabine toward HL-60. Acta Biochim Pol. 2005;52(2):561-5. Epub 2005 May 31. PubMed PMID: 15933759.</br>4: Bendell JC, Eder JP, Clark JW, Fidias P, Lynch TJ, Seiden MV, Ryan DP. Phase I dose-escalation study of tezacitabine in combination with 5-fluorouracil in patients with advanced solid tumors. Cancer. 2005 May 1;103(9):1925-31. PubMed PMID: 15772958.</br>5: Flaherty KT, Stevenson JP, Gallagher M, Giantonio B, Algazy KM, Sun W, Haller DG, O/’Dwyer PJ. Dose escalation study of tezacitabine in combination with cisplatin in patients with advanced cancer. Cancer. 2003 Apr 15;97(8):1985-90. PubMed PMID: 12673728.</br>6: Rodriguez GI, Jones RE, Orenberg EK, Stoltz ML, Brooks DJ. Phase I clinical trials of tezacitabine [(E)-2/’-deoxy-2/’-(fluoromethylene)cytidine] in patients with refractory solid tumors. Clin Cancer Res. 2002 Sep;8(9):2828-34. PubMed PMID: 12231523.</br>7: Seley KL. Tezacitabine Hoechst Marion Roussel. Curr Opin Investig Drugs. 2000 Sep;1(1):135-40. Review. PubMed PMID: 11249589.</br> |
