Pruvanserin

Pruvanserin
Clinical data
Routes of; administration	Oral
ATC code	none;
Legal status
Legal status	In general: uncontrolled;
Identifiers
	IUPAC name 7-({4-[2-(4-fluorophenyl)ethyl]piperazin-1-yl}carbonyl)-1H-indole-3-carbonitrile;
CAS Number	443144-26-1 ; 443144-27-2 (hydrochloride);
PubChem CID	6433122;
ChemSpider	4938310;
UNII	UL09X1D9EM;
ChEMBL	ChEMBL1215661;
CompTox Dashboard (EPA)	DTXSID40196133 ;
Chemical and physical data
Formula	C22H21FN4O
Molar mass	376.435 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES N#Cc2c1cccc(c1[nH]c2)C(=O)N4CCN(CCc3ccc(F)cc3)CC4;

Pruvanserin (EMD-281,014, LY-2,422,347) is a selective 5-HT_2A receptor antagonist which was under development by Eli Lilly and Company for the treatment of insomnia.^[1]^[2] It was in phase II clinical trials in 2008 but appears to have been discontinued as it is no longer in the company's development pipeline.^[3]^[4] In addition to its sleep-improving properties,^[5]^[6] pruvanserin has also been shown to have antidepressant, anxiolytic, and working memory-enhancing effects in animal studies.^[7]^[8]^[9]

References

^ Bartoszyk GD, van Amsterdam C, Böttcher H, Seyfried CA (July 2003). "EMD 281014, a new selective serotonin 5-HT2A receptor antagonist". European Journal of Pharmacology. 473 (2–3): 229–30. doi:10.1016/S0014-2999(03)01992-7. PMID 12892843.
^ Teegarden BR, Al Shamma H, Xiong Y (2008). "5-HT(2A) inverse-agonists for the treatment of insomnia". Current Topics in Medicinal Chemistry. 8 (11): 969–76. doi:10.2174/156802608784936700. PMID 18673166.
^ "Efficacy Study of LY2422347 to Treat Insomnia - Full Text View - ClinicalTrials.gov". 24 January 2007.
^ "Eli Lilly and Company » Research Pipeline".
^ Monti JM, Jantos H (September 2006). "Effects of activation and blockade of 5-HT2A/2C receptors in the dorsal raphe nucleus on sleep and waking in the rat". Progress in Neuro-psychopharmacology & Biological Psychiatry. 30 (7): 1189–95. doi:10.1016/j.pnpbp.2006.02.013. PMID 16713054. S2CID 12837755.
^ Monti JM, Jantos H (December 2006). "Effects of the serotonin 5-HT2A/2C receptor agonist DOI and of the selective 5-HT2A or 5-HT2C receptor antagonists EMD 281014 and SB-243213, respectively, on sleep and waking in the rat". European Journal of Pharmacology. 553 (1–3): 163–70. doi:10.1016/j.ejphar.2006.09.027. PMID 17059817.
^ Patel JG, Bartoszyk GD, Edwards E, Ashby CR (April 2004). "The highly selective 5-hydroxytryptamine (5-HT)2A receptor antagonist, EMD 281014, significantly increases swimming and decreases immobility in male congenital learned helpless rats in the forced swim test". Synapse. 52 (1): 73–5. doi:10.1002/syn.10308. PMID 14755634. S2CID 21941333.
^ Adamec R, Creamer K, Bartoszyk GD, Burton P (November 2004). "Prophylactic and therapeutic effects of acute systemic injections of EMD 281014, a selective serotonin 2A receptor antagonist on anxiety induced by predator stress in rats". European Journal of Pharmacology. 504 (1–2): 79–96. doi:10.1016/j.ejphar.2004.09.017. PMID 15507224.
^ Terry AV, Buccafusco JJ, Bartoszyk GD (June 2005). "Selective serotonin 5-HT2A receptor antagonist EMD 281014 improves delayed matching performance in young and aged rhesus monkeys". Psychopharmacology. 179 (4): 725–32. doi:10.1007/s00213-004-2114-1. PMID 15619109. S2CID 30366683.

[pmid12892843-1] Bartoszyk GD, van Amsterdam C, Böttcher H, Seyfried CA (July 2003). "EMD 281014, a new selective serotonin 5-HT2A receptor antagonist". European Journal of Pharmacology. 473 (2–3): 229–30. doi:10.1016/S0014-2999(03)01992-7. PMID 12892843.

[pmid18673166-2] Teegarden BR, Al Shamma H, Xiong Y (2008). "5-HT(2A) inverse-agonists for the treatment of insomnia". Current Topics in Medicinal Chemistry. 8 (11): 969–76. doi:10.2174/156802608784936700. PMID 18673166.

[urlEfficacy_Study_of_LY2422347_to_Treat_Insomnia_-_Full_Text_View_-_ClinicalTrials.gov-3] "Efficacy Study of LY2422347 to Treat Insomnia - Full Text View - ClinicalTrials.gov". 24 January 2007.

[urlEli_Lilly_and_Company_»_Research_Pipeline-4] "Eli Lilly and Company » Research Pipeline".

[pmid16713054-5] Monti JM, Jantos H (September 2006). "Effects of activation and blockade of 5-HT2A/2C receptors in the dorsal raphe nucleus on sleep and waking in the rat". Progress in Neuro-psychopharmacology & Biological Psychiatry. 30 (7): 1189–95. doi:10.1016/j.pnpbp.2006.02.013. PMID 16713054. S2CID 12837755.

[pmid17059817-6] Monti JM, Jantos H (December 2006). "Effects of the serotonin 5-HT2A/2C receptor agonist DOI and of the selective 5-HT2A or 5-HT2C receptor antagonists EMD 281014 and SB-243213, respectively, on sleep and waking in the rat". European Journal of Pharmacology. 553 (1–3): 163–70. doi:10.1016/j.ejphar.2006.09.027. PMID 17059817.

[pmid14755634-7] Patel JG, Bartoszyk GD, Edwards E, Ashby CR (April 2004). "The highly selective 5-hydroxytryptamine (5-HT)2A receptor antagonist, EMD 281014, significantly increases swimming and decreases immobility in male congenital learned helpless rats in the forced swim test". Synapse. 52 (1): 73–5. doi:10.1002/syn.10308. PMID 14755634. S2CID 21941333.

[pmid15507224-8] Adamec R, Creamer K, Bartoszyk GD, Burton P (November 2004). "Prophylactic and therapeutic effects of acute systemic injections of EMD 281014, a selective serotonin 2A receptor antagonist on anxiety induced by predator stress in rats". European Journal of Pharmacology. 504 (1–2): 79–96. doi:10.1016/j.ejphar.2004.09.017. PMID 15507224.

[pmid15619109-9] Terry AV, Buccafusco JJ, Bartoszyk GD (June 2005). "Selective serotonin 5-HT2A receptor antagonist EMD 281014 improves delayed matching performance in young and aged rhesus monkeys". Psychopharmacology. 179 (4): 725–32. doi:10.1007/s00213-004-2114-1. PMID 15619109. S2CID 30366683.

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See also

References