Name: Fluphenazine-N-2-chloroethane (hydrochloride)
Rating: 5 (10 reviews)

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HIT ID:HIT104084347
Cas No:3892-78-2
常用名:Fluphenazine-N-2-chloroethane (hydrochloride)
常用名:Fluphenazine-N-2-chloroethane (hydrochloride)
IUPAC:10-{3-[4-(2-chloroethyl)piperazin-1-yl]propyl}-2-(trifluoromethyl)-10H-phenothiazine dihydrochloride
IUPAC:10-{3-[4-(2-chloroethyl)piperazin-1-yl]propyl}-2-(trifluoromethyl)-10H-phenothiazine dihydrochloride
InChI key:OAWAULFIPAZCMH-UHFFFAOYSA-N

分子式:C22H27Cl3F3N3S
分子量:528.88
氢键供体数 (HBD):0
氢键受体数 (HBA):3
LogP:5.267
SMILES:Cl.Cl.FC(F)(F)c1ccc2Sc3ccccc3N(CCCN3CCN(CCCl)CC3)c2c1
SMILES:Cl.Cl.FC(F)(F)c1ccc2Sc3ccccc3N(CCCN3CCN(CCCl)CC3)c2c1

Fluphenazine is a traditional antipsychotic compound that tightly binds the dopamine D2 receptor (Ki = 0.55 nM) and also reversibly inhibits calmodulin at micromolar concentrations. Fluphenazine-N-2-chloroethane is a derivative of fluphenazine that contains an alkylating chlorethylamine chain, which produces irreversible protein binding. It is a relatively selective, irreversible antagonist of D2 receptors both in vitro (IC50 = 100 nM) and in vivo, inactivating approximately 90% of D2 receptors in mice within 4 hours of treatment. Through this action, fluphenazine-B-2-chloroethane can be used to induce catalepsy in mice. It irreversibly inhibits calmodulin at higher doses (IC50 = 10 μM), which can sensitize cancer cells to TRAIL-induced apoptosis.

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