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Ciproxifan

Names

[ CAS No. ]:
184025-18-1

[ Name ]:
Ciproxifan

[Synonym ]:
Ciproxifan
cyclopropyl 4-(3-(1H-imidazol-4-yl)propyloxy)phenyl ketone
Methanone, cyclopropyl[4-[3-(1H-imidazol-4-yl)propoxy]phenyl]-
Cyclopropylpyrrol4-[3-(1H-imidazol-4-yl)propoxy] phenylmorphomethanone
Cyclopropyl{4-[3-(1H-imidazol-4-yl)propoxy]phenyl}methanone
FUB-359
cyclopropyl 4-(3-(1H-imidazol-4-yl)propyloxy)phenyl methanone

Biological Activity

[Description]:

Ciproxifan(FUB-359) is a highly potent and selective histamin H3-receptor antagonist with IC50 of 9.2 nM, with low apparent affinity at other receptor subtypes.IC50 value: 9.2 nM(Ki)Target: H3 receptorIn vitro, Ciproxifan behaved as a competitive antagonist at the H3 autoreceptor controlling 3H histamine release from synaptosomes and displayed similar Ki values (0.5-1.9 nM) at the H3 receptor controlling the electrically-induced contraction of guinea pig ileum or at the brain H3 receptor labeled with 125I-iodoproxyfan. This appears to be an orally bioavailable, extremely selective and potent H3-receptor antagonist whose vigilance- and attention-promoting effects are promising for therapeutic applications in aging disorders.

[Related Catalog]:

Signaling Pathways >> GPCR/G Protein >> Histamine Receptor
Signaling Pathways >> Immunology/Inflammation >> Histamine Receptor
Research Areas >> Neurological Disease

[References]

[1]. Motawaj M, Arrang JM. Ciproxifan, a histamine H?-receptor antagonist?/?inverse agonist, modulates methamphetamine-induced sensitization in mice. Eur J Neurosci. 2011 Apr;33(7):1197-204. doi: 10.1111/j.1460-9568.2011.07618.x.

[2]. Bardgett ME, et al. Ciproxifan, an H3 receptor antagonist, alleviates hyperactivity and cognitive deficits in the APP Tg2576 mouse model of Alzheimer's disease. Neurobiol Learn Mem. 2011 Jan;95(1):64-72.

[3]. Bardgett ME, et al. The H3 antagonist, ciproxifan, alleviates the memory impairment but enhances the motor effects of MK-801 (dizocilpine) in rats. Neuropharmacology. 2010 Nov;59(6):492-502.

[4]. Day M, et al. Differential effects of ciproxifan and nicotine on impulsivity and attention measures in the 5-choice serial reaction time test. Biochem Pharmacol. 2007 Apr 15;73(8):1123-34.

[5]. Pillot C, et al. Ciproxifan, a histamine H3-receptor antagonist/inverse agonist, modulates the effects of methamphetamine on neuropeptide mRNA expression in rat striatum. Eur J Neurosci. 2003 Jan;17(2):307-14.


[Related Small Molecules]

Loratadine | Histamine | Pitolisant hydrochloride | Cimetidine | Osthole | Clemastine fumarate | Ebrotidine | JNJ-7777120 | Famotidine | Cetirizine Dihydrochloride | Desloratadine | Ketotifen fumarate | Lodoxamide | Meclizine dihydrochloride | Chlorpheniramine maleate

Chemical & Physical Properties

[ Density]:
1.2±0.1 g/cm3

[ Boiling Point ]:
526.9±35.0 °C at 760 mmHg

[ Molecular Formula ]:
C16H18N2O2

[ Molecular Weight ]:
270.326

[ Flash Point ]:
272.5±25.9 °C

[ Exact Mass ]:
270.136841

[ PSA ]:
54.98000

[ LogP ]:
2.29

[ Appearance of Characters ]:
solid | white

[ Vapour Pressure ]:
0.0±1.4 mmHg at 25°C

[ Index of Refraction ]:
1.613

[ Storage condition ]:
-20℃

[ Water Solubility ]:
H2O: insoluble

Safety Information

[ Hazard Codes ]:
Xn

[ Risk Phrases ]:
22-36/37/38-43

[ Safety Phrases ]:
26-36/37/39

[ WGK Germany ]:
3

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Related Compounds