Tezacitabine

HCID 6435808CAS 130306-02-4

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Grundinformationen

Standard-SMILES: Nc1ccn([C@@H]2O[C@H](CO)[C@@H](O)/C2=C\F)c(=O)n1
InChIKey: GFFXZLZWLOBBLO-ASKVSEFXSA-N
Summenformel: C10H12FN3O4
Durchschnittliche Molmasse: 257,22 g/mol
Monoisotopische Masse: 257,08118403

Namen und Bezeichner

Bevorzugter Name: Tezacitabine
IUPAC: 4-amino-1-[(2R,3E,4S,5R)-3-(fluoromethylidene)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrimidin-2-one
Englischer Name: (E)-2'-DEOXY-2'-(FLUOROMETHYLENE) CYTIDINE
Summenformel: C10H12FN3O4
Molmasse: 257.22

Namen und Synonyme

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

Weitere Namen anzeigen

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

Datenbank-Bezeichner

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

Eigenschaften

Berechnete Struktureigenschaften

XLogP: -2,3
Polarare Oberfläche (TPSA): 108 Å²
H-Brücken-Donoren: 3
H-Brücken-Akzeptoren: 5
Frei drehbare Bindungen: 2
Schwere Atome: 18
Formalladung: 0
Komplexität: 448

Physikochemische Eigenschaften

Siedepunkt: 512.5 · 512.5±60.0 °C(Predicted)
Dichte: 1.71 · 1.71±0.1 g/cm3(Predicted)
storage temp.: -80 °C · -80°C
Löslichkeit: 200 mg/mL · DMSO : 200 mg/mL (777.54 mM; Need ultrasonic)
Aggregatzustand: Solid
pka: 12.5 · 12.50±0.60(Predicted)
Farbe: Off-white to light yellow

Chemie und Industrie

Pharmakologische Informationen

Mechanism of Action · 1 Eintrag

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 Einträge

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.