PRUVANSERIN HYDROCHLORIDE

Investigational

Details

Stereochemistry	ACHIRAL
Molecular Formula	C22H21FN4O.ClH
Molecular Weight	412.888
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

Cl.FC1=CC=C(CCN2CCN(CC2)C(=O)C3=CC=CC4=C3NC=C4C#N)C=C1

InChI

InChIKey=UYGNZRVLPYZLTF-UHFFFAOYSA-N

InChI=1S/C22H21FN4O.ClH/c23-18-6-4-16(5-7-18)8-9-26-10-12-27(13-11-26)22(28)20-3-1-2-19-17(14-24)15-25-21(19)20;/h1-7,15,25H,8-13H2;1H

HIDE SMILES / InChI

Molecular Formula	C22H21FN4O
Molecular Weight	376.4267
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Molecular Formula	ClH
Molecular Weight	36.461
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description
Sources: http://adisinsight.springer.com/drugs/800024525
Curator's Comment: Description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/12892843

Pruvanserin (EMD 281014, LY-2422347) is a selective serotonin 5-HT2A receptor antagonist. Pruvanserin was originated by Merck KGaA. Eli Lilly had been developing pruvanserin, under a global licence from Merck KGaA, for the treatment of primary insomnia and major depressive disorder. Phase II trials were completed in the US, Hungary and Spain. However, development appears to have been discontinued.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Serotonin 2a (5-HT2a) receptor 237 Target ID: CHEMBL224 Sources: https://www.ncbi.nlm.nih.gov/pubmed/12892843	Antagonist 2849		0.35 nM [IC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Primary insomnia 5 Sources: http://adisinsight.springer.com/drugs/800024525	Primary		Phase II 1147	Unknown Approved Use Unknown
Major depressive disorder 179 Sources: http://adisinsight.springer.com/drugs/800024525	Primary		Phase II 1147	Unknown Approved Use Unknown

Sourcing

Vendor/Aggregator	ID	URL
Compound Cloud	6433122
Compound Cloud	9887933
eMolecules	48884680	https://orderbb.emolecules.com/search/#?query=48884680
eMolecules	72980624	https://orderbb.emolecules.com/search/#?query=72980624
Hangzhou Yuhao Chemical Technology	RT9796
Molnova	M14512	https://www.molnova.com/en/serch-list.html?keywords=M14512
Molnova	M14513	https://www.molnova.com/en/serch-list.html?keywords=M14513
MolPort	MolPort-035-765-739	https://www.molport.com/shop/molecule-link/MolPort-035-765-739
MuseChem	R042206	https://www.musechem.com/product/R042206.html
Tocris	4470	https://www.tocris.com/search.php?Type=QuickSearch&Value=4470
Toronto Research Chemicals	P839050	https://www.trc-canada.com/product-detail/?CatNum=P839050

PubMed

Title	Date	PubMed
5-HT(2A) inverse-agonists for the treatment of insomnia.	2008	18673166
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.	2006-12-28	17059817
Selective serotonin 5-HT2A receptor antagonist EMD 281014 improves delayed matching performance in young and aged rhesus monkeys.	2005-06	15619109
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.	2004-11-03	15507224
EMD 281014, a specific and potent 5HT2 antagonist in humans: a dose-finding PET study.	2004-09	15007535
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.	2004-04	14755634
EMD 281014, a new selective serotonin 5-HT2A receptor antagonist.	2003-07-25	12892843

Patents

Sample Use Guides

In Vivo Use Guide

Eli Lilly had completed a multicentre phase II trial of pruvanserin in the US (9951; H9U-MC-MDBD; NCT00259311). The trial assessed the safety and efficacy of 5 and 15mg doses versus placebo in approximately 400 patients with primary insomnia.

Route of Administration: Oral

In Vitro Use Guide

Pruvanserin (EMD 281014, LY-2422347) (10–40 nM) dose-dependently inhibited human platelet aggregation in vitro

Substance Class	Chemical Created by `admin` on `Mon Mar 31 17:58:48 GMT 2025` Edited by `admin` on `Mon Mar 31 17:58:48 GMT 2025`
Record UNII	AWA682DH9Z
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

PRUVANSERIN HYDROCHLORIDE

Official Name

English

EMD-281014

Preferred Name

English

7-{4-[2-(4-fluorophenyl)ethyl]piperazine-1-carbonyl}-1H-indole-3-carbonitrile, monohydrochloride

Systematic Name

English

7-(4-(2-(4-FLUOROPHENYL)ETHYL)PIPERAZINE-1-YLCARBONYL)-1H-INDOLE-3-CARBONITRILE HYDROCHLORIDE

Systematic Name

English

LSN-2420586

Code

English

PRUVANSERIN HYDROCHLORIDE [USAN]

Common Name

English

LY-2422347 HYDROCHLORIDE

Code

English

LSN2420586

Code

English

LY-2422347 HCL

Code

English

PRUVANSERIN HCL

Common Name

English

PIPERAZINE, 1-((3-CYANO-1H-INDOL-7-YL)CARBONYL)-4-(2-(4-FLUOROPHENYL)ETHYL)-, MONOHYDROCHLORIDE

Systematic Name

English

LY2422347 HCL

Code

English

Classification Tree Code System Code

NCI_THESAURUS

C66885