2-[4-(3,4-Dimethylphenyl)piperazin-1-ylmethyl]-1H benzoimidazole (A-381393), a selective dopamine D4 receptor antagonist

Neuropharmacology. 2005 Jul;49(1):112-21. doi: 10.1016/j.neuropharm.2005.02.004. Epub 2005 Apr 1.

Abstract

2-[4-(3,4-Dimethylphenlyl)piperazin-1-ylmethyl]-1H benzoimidazole (A-381393) was identified as a potent dopamine D4 receptor antagonist with excellent receptor selectivity. [3H]-spiperone competition binding assays showed that A-381393 potently bound to membrane from cells expressing recombinant human dopamine D4.4 receptor (Ki=1.5 nM), which was 20-fold higher than that of clozapine (Ki=30.4 nM). A-381393 exhibited highly selective binding for the dopamine D4.4 receptor (>2700-fold) when compared to D1, D2, D3 and D5 dopamine receptors. Furthermore, in comparison to clozapine and L-745870, A-381393 exhibits better receptor selectivity, showing no affinity up to 10 microM for a panel of more than 70 receptors and channels, with the exception of moderate affinity for 5-HT2A (Ki=370 nM). A-381393 potently inhibited the functional activity of agonist-induced GTP-gamma-S binding assay and 1 microM dopamine induced-Ca2+ flux in human dopamine D4.4 receptor expressing cells, but not in human dopamine D2L or D3 receptor cells. In contrast to L-745870, A-381393 did not exhibit any significant intrinsic activity in a D4.4 receptor. In vivo, A-381393 has good brain penetration after subcutaneous administration. A-381393 inhibited penile erection induced by the selective D4 agonist PD168077 in conscious rats. Thus, A-381393 is a novel selective D4 antagonist that will enhance the ability to study dopamine D4 receptors both in vitro and in vivo.

Publication types

  • Comparative Study

MeSH terms

  • Animals
  • Benzamides / pharmacology
  • Benzimidazoles / chemical synthesis
  • Benzimidazoles / pharmacokinetics
  • Benzimidazoles / pharmacology
  • Binding, Competitive / drug effects
  • Calcium / metabolism
  • Cell Line
  • Clozapine / pharmacokinetics
  • Dopamine / metabolism
  • Dopamine Antagonists / chemical synthesis*
  • Dopamine Antagonists / chemistry
  • Dopamine Antagonists / pharmacology*
  • Dose-Response Relationship, Drug
  • Drug Administration Routes
  • Drug Interactions
  • Europium / pharmacokinetics
  • Fluorometry / methods
  • GABA Antagonists / pharmacokinetics
  • Guanosine Triphosphate / pharmacokinetics
  • Humans
  • Male
  • Penile Erection / drug effects
  • Piperazines / chemical synthesis
  • Piperazines / pharmacokinetics
  • Piperazines / pharmacology
  • Pyridines / pharmacokinetics
  • Pyrroles / pharmacokinetics
  • Radioligand Assay / methods
  • Rats
  • Rats, Sprague-Dawley
  • Rats, Wistar
  • Spiperone / pharmacokinetics
  • Time Factors
  • Tritium / pharmacokinetics

Substances

  • 2-(4-(3,4-dimethylphenyl)piperazin-1-ylmethyl)-1H-benzimidazole
  • 3-((4-(4-chlorophenyl)piperazin-1-yl)methyl)-1H-pyrrolo(2,3-b)pyridine
  • Benzamides
  • Benzimidazoles
  • Dopamine Antagonists
  • GABA Antagonists
  • N-((4-(2-cyanophenyl)-1-piperazinyl)methyl)-3-methylbenzamide
  • Piperazines
  • Pyridines
  • Pyrroles
  • Tritium
  • Europium
  • Spiperone
  • Guanosine Triphosphate
  • Clozapine
  • Calcium
  • Dopamine