Tezacitabine

HCID 6435808CAS 130306-02-4

Substructure search Find similar structures

Basic information

Standard SMILES: Nc1ccn([C@@H]2O[C@H](CO)[C@@H](O)/C2=C\F)c(=O)n1
InChIKey: GFFXZLZWLOBBLO-ASKVSEFXSA-N
Molecular formula: C10H12FN3O4
Average molar mass: 257.22 g/mol
Monoisotopic mass: 257.08118403

Names & identifiers

Preferred name: Tezacitabine
IUPAC: 4-amino-1-[(2R,3E,4S,5R)-3-(fluoromethylidene)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrimidin-2-one
English name: (E)-2'-DEOXY-2'-(FLUOROMETHYLENE) CYTIDINE
Molecular formula: C10H12FN3O4
Molecular weight: 257.22

Names & synonyms

TezacitabineMDL-1017312'-Deoxy-2'-(fluoromethylene)cytidinetezacitabinaDTXSID10156446Cytidine, 2'-deoxy-2'-(fluoromethylene)-, (2E)-171176-43-5DTXSID001690204-amino-1-[(2R,3E,4S,5R)-3-(fluoromethylidene)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-1,2-dihydropyrimidin-2-onetezacitabinum4-amino-1-((2R,3E,4S,5R)-3-(fluoromethylidene)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl)-1,2-dihydropyrimidin-2-oneMDL-101,731

Show more names

tezaciabine(E)-2'-Deoxy-2'-(fluoromethylene)cytidine(E)-2'-DEOXY-2'-(FLUOROMETHYLENE) CYTIDINE2'-deoxy-2'-(fluoromethylene)-(2E)CytidineCytidine, 2'-deoxy-2'-(fluoromethylene)-, (2'E)-

RefChem:188974DTXCID5091511DTXCID7078937AnhydrousCytidine, 2'-deoxy-2'-(fluoromethylene)-, monohydrate, (2'E)-FMD-CFMdCTezacitabine monohydrate

Database identifiers

CAS: 130306-02-4、171176-43-5
PubChem CID: 6435808
DTXSID: DTXSID10156446
ChEMBL: CHEMBL2105467、CHEMBL3989496
ChEBI: CHEBI:230773
UNII: 7607Y95N9S
Nikkaji: J579.163D、J898.249J

Properties

Computed structural properties

XLogP: -2.3
Topological polar surface area: 108 Å²
Hydrogen bond donors: 3
Hydrogen bond acceptors: 5
Rotatable bonds: 2
Heavy atoms: 18
Formal charge: 0
Complexity: 448

Physicochemical properties

Boiling point: 512.5 · 512.5±60.0 °C(Predicted)
Density: 1.71 · 1.71±0.1 g/cm3(Predicted)
storage temp.: -80 °C · -80°C
solubility: 200 mg/mL · DMSO : 200 mg/mL (777.54 mM; Need ultrasonic)
form: Solid
pka: 12.5 · 12.50±0.60(Predicted)
color: Off-white to light yellow
FDA UNII: 7607 Y95N9S · 7607Y95N9S

Chemistry & industry

Pharmacology

Mechanism of Action · 1 item

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.

MeSH Pharmacological Classification · 3 items

Substances that inhibit or prevent the proliferation of NEOPLASMS.

Compounds or agents that combine with an enzyme in such a manner as to prevent the normal substrate-enzyme combination and the catalytic reaction.

Drugs used to potentiate the effectiveness of radiation therapy in destroying unwanted cells.