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130306-02-4 , Tezacitabine, CAS:130306-02-4

130306-02-4 , Tezacitabine,
CAS:130306-02-4
C10H12FN3O4 / 257.218
MFCD00893181

Tezacitabine

Tezacitabine is a synthetic pyrimidine 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. This agent is relatively resistant to metabolic deactivation by cytidine deaminase. RNR catalyzes the conversion of ribonucleoside 5'-diphosphates to deoxyribonucleoside 5'-diphosphates necessary for DNA synthesis and is overexpressed in many tumor types.

Tezacitabine Anhydrous is the anhydrous form of tezacitabine, a synthetic pyrimidine 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 eventually tumor cell apoptosis. Tezacitabine triphosphate acts as a substrate for DNA polymerase, thereby further inhibiting DNA replication. RNR catalyzes the conversion of ribonucleoside 5'-diphosphates to deoxyribonucleoside 5'-diphosphates, a necessary step for DNA synthesis, and is overexpressed in many tumor cell types.

A synthetic purine nucleoside analogue with potential antineoplastic activity.

(E)-2'-Deoxy-2'-(fluoromethylene)cytidine is a cytostatic compound that inhibits DNA synthesis in tumor cells. It has been shown to be more potent than tezacitabine and hl-60 cells, as well as being less toxic than benzimidazole compounds. This analog of cytosine has been shown to have potent antitumor activity against carcinoma cell lines and myeloid leukemia cell lines. The oral prodrug form of this drug has been shown to be an effective treatment for myeloid leukemia in mice.

CAS Number

130306-02-4

Product Name

Tezacitabine

IUPAC Name

4-amino-1-[(2R,3E,4S,5R)-3-(fluoromethylidene)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrimidin-2-one

Molecular Formula

C10H11FN2O4

Molecular Weight

257.218 g/mol

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

InChI Key

CXVQYURZKMJITE-JZUREZDFSA-N

SMILES

C1=CN(C(=O)N=C1N)C2C(=CF)C(C(O2)CO)O

Solubility

Soluble in DMSO, not in water

Synonyms

2'-deoxy-2'-(fluoromethylene)cytidine, MDL 101,731, MDL 101731, MDL-101,731, MDL-101731, tezacitabine

Canonical SMILES

C1=CN(C(=O)N=C1N)C2C(=CF)C(C(O2)CO)O

Isomeric SMILES

C1=CN(C(=O)N=C1N)[C@H]2/C(=C/F)/[C@@H]([C@H](O2)CO)O


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