Bifeprunox

Names

[ Name ]:
Bifeprunox

[Synonym ]:
Bifeprunox [INN]
UNII-AP69E83Z79
Bifeprunoxum
Bifeprunox (USAN/INN)
bifeprunox base
Bifeprunoxum [INN-Latin]
2-[4-[4-(5-fluoro-1H-indol-3-yl)-3,6-dihydro-1(2H)-pyridinyl]butyl]-1H-isoindole-1,3(2H)-dione
Bifeprunox
7-[4-[(3-phenylphenyl)methyl]piperazin-1-yl]-3H-benzooxazol-2-one
7-[4-([1,1'-biphenyl]-3-ylmethyl)-1-piperazinyl]-2(3H)-benzoxa-zolone

Biological Activity

[Description]:

Bifeprunox is a potent dopamine D2-like and 5-HT1A receptor partial agonist with pKis of 7.19 and 8.83 for cortex 5-HT1A and striatum D2, and a pEC50 of 6.37 for hippocampus 5-HT1A, respectively. Bifeprunox is an antipsychotic for the research of schizophrenia[1][2].

[Related Catalog]:

Signaling Pathways >> GPCR/G Protein >> Dopamine Receptor

Signaling Pathways >> Neuronal Signaling >> Dopamine Receptor

Research Areas >> Neurological Disease

Signaling Pathways >> GPCR/G Protein >> 5-HT Receptor

Signaling Pathways >> Neuronal Signaling >> 5-HT Receptor

[Target]

5-HT1A Receptor:7.19 (pKi, cortex)

D2 Receptor:8.83 (pKi, striatum)

5-HT1A Receptor:6.37 (pEC50, hippocampus)

[In Vitro]

Bifeprunox has a pKi of 8 at h5-HT1A receptors, with an Emax of 70%[1].

[In Vivo]

Bifeprunox (0.001-2.5 mg/kg) reduces marble burying in mice[2]. Bifeprunox (4-250 μg/kg) influences nicotine-seeking behaviour in response to drug-associated stimuli in rats[3]. Animal Model: Male NMRI mice (weighing 20-22 g)[2] Dosage: 0.001, 0.0025, 0.01, 0.04, 0.16, 0.63, and 2.5 mg/kg Administration: I.p. Result: Reduced marble burying. Potently active from 0.0025 mg/kg. Animal Model: Naïve male Wistar rats (weighing 250-275 g)[3] Dosage: 4, 16, 64 and 250 μg/kg Administration: Injected s.c. 30 minutes before testing Result: 4-16 μg/kg dose-dependently attenuated the responsereinstating effects of nicotine-associated cues. Higher doses (64-250 μg/kg, s.c.) reduced spontaneous locomotor activity and suppressed operant responding induced by sucrose-associated cues and by the primary reinforcing properties of nicotine or sucrose.

[References]

[1]. Newman-Tancredi A, et al. Novel antipsychotics activate recombinant human and native rat serotonin 5-HT1A receptors: affinity, efficacy and potential implications for treatment of schizophrenia. Int J Neuropsychopharmacol. 2005 Sep;8(3):341-56.

[2]. Bruins Slot LA, et al. Effects of antipsychotics and reference monoaminergic ligands on marble burying behavior in mice. Behav Pharmacol. 2008 Mar;19(2):145-52.

[3]. Di Clemente A, et al. Bifeprunox: a partial agonist at dopamine D2 and serotonin 1A receptors, influences nicotine-seeking behaviour in response to drug-associated stimuli in rats. Addict Biol. 2012 Mar;17(2):274-86.

Chemical & Physical Properties

[ Density]:
1.247g/cm3

[ Molecular Formula ]:
C₂₄H₂₃N₃O₂

[ Molecular Weight ]:
385.45800

[ Exact Mass ]:
385.17900

[ PSA ]:
52.48000

[ LogP ]:
4.11320

[ Index of Refraction ]:
1.643

Safety Information

[ HS Code ]:
2934999090

Customs

[ HS Code ]: 2934999090

[ Summary ]:
2934999090. other heterocyclic compounds. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0%