Ciproxifan

Ciproxifan
Clinical data
ATC code	none;
Identifiers
	IUPAC name cyclopropyl 4-(3-(1H-imidazol-4-yl)propyloxy)phenyl ketone;
CAS Number	184025-19-2 ;
PubChem CID	6422124;
IUPHAR/BPS	1265;
ChemSpider	4927646 ;
UNII	5EVQ7IRG99;
ChEMBL	ChEMBL14638 ;
CompTox Dashboard (EPA)	DTXSID50171532 ;
Chemical and physical data
Formula	C16H18N2O2
Molar mass	270.332 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES C1CC1C(=O)C2=CC=C(C=C2)OCCCC3=CN=CN3;
	InChI InChI=1S/C16H18N2O2/c19-16(12-3-4-12)13-5-7-15(8-6-13)20-9-1-2-14-10-17-11-18-14/h5-8,10-12H,1-4,9H2,(H,17,18) ; Key:ACQBHJXEAYTHCY-UHFFFAOYSA-N ;
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Ciproxifan is an extremely potent histamine H₃ inverse agonist/antagonist.

The histamine H₃ receptor is an inhibitory autoreceptor located on histaminergic nerve terminals, and is believed to be involved in modulating the release of histamine in the brain. Histamine has an excitatory effect in the brain via H₁ receptors in the cerebral cortex, and so drugs such as ciproxifan which block the H₃ receptor and consequently allow more histamine to be released have an alertness-promoting effect.

Ciproxifan produces wakefulness and attentiveness in animal studies, and produced cognitive enhancing effects without prominent stimulant effects at relatively low levels of receptor occupancy, and pronounced wakefulness at higher doses. It has therefore been proposed as a potential treatment for sleep disorders such as narcolepsy and to improve vigilance in old age, particularly in the treatment of conditions such as Alzheimer's disease. It also potentiated the effects of antipsychotic drugs, and has been suggested as an adjuvant treatment for schizophrenia.

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