EPLIVANSERIN FUMARATE

Investigational

Details

Stereochemistry	ACHIRAL
Molecular Formula	2C19H21FN2O2.C4H4O4
Molecular Weight	772.8334
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	5
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

OC(=O)\C=C\C(O)=O.CN(C)CCO\N=C(\C=C\C1=CC=C(O)C=C1)C2=CC=CC=C2F.CN(C)CCO\N=C(\C=C\C3=CC=C(O)C=C3)C4=CC=CC=C4F

InChI

InChIKey=RNLKLYQQDLHHBH-ABDBJYMXSA-N

InChI=1S/2C19H21FN2O2.C4H4O4/c2*1-22(2)13-14-24-21-19(17-5-3-4-6-18(17)20)12-9-15-7-10-16(23)11-8-15;5-3(6)1-2-4(7)8/h2*3-12,23H,13-14H2,1-2H3;1-2H,(H,5,6)(H,7,8)/b2*12-9+,21-19-;2-1+

HIDE SMILES / InChI

Molecular Formula	C4H4O4
Molecular Weight	116.0722
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	1
Optical Activity	NONE

Molecular Formula	C19H21FN2O2
Molecular Weight	328.3806
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	2
Optical Activity	NONE

Description
Sources: https://adisinsight.springer.com/drugs/800001948 | https://www.ncbi.nlm.nih.gov/pubmed/1501121 | https://www.ncbi.nlm.nih.gov/pubmed/23616706

Eplivanserin (SR 46349) is an antagonist of serotonin 2A receptor. Eplivanserin was previously in development by Sanofi-aventis in an effort to educate the public regarding this new mechanism of action for sleep aids. Eplivanserin was reviewed by the FDA as a potential treatment for patients with chronic insomnia, but the FDA requested additional information regarding benefit-risk and development of the drug has 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/18673166 \| https://www.ncbi.nlm.nih.gov/pubmed/1501121	Antagonist 2849

PubMed

Title	Date	PubMed
Biochemical and pharmacological properties of SR 46349B, a new potent and selective 5-hydroxytryptamine2 receptor antagonist.	1992-08	1501121

Patents

Sample Use Guides

In Vivo Use Guide

Phase III study: 5 mg/day for 12 weeks

Route of Administration: Oral

Substance Class	Chemical Created by `admin` on `Mon Mar 31 18:05:53 GMT 2025` Edited by `admin` on `Mon Mar 31 18:05:53 GMT 2025`
Record UNII	BT8UYC46KA
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

EPLIVANSERIN FUMARATE

Official Name

English

EPLIVANSERIN HEMIFUMARATE

Preferred Name

English

SR46349B

Code

English

(1Z,2E)-1-(2-FLUOROPHENYL)-3-(4-HYDROXYPHENYL)PROP-2-EN-1-ONE O-(2-(DIMETHYLAMINO)ETHYL)OXIME (2E)-BUT-2-ENEDIOATE (2:1) (SALT)

Systematic Name

English

EPLIVANSERIN FUMARATE [USAN]

Common Name

English

SR-46349B

Code

English

(4-((1E,3Z)-3-((2-(DIMETHYLAMINO)ETHOXY)IMINO)-3-(2-FLUOROPHENYL)PROP-1- ENYL)PHENOL)(2E)-2-BUTENEDIOATE (2:1)

Systematic Name

English

2-PROPEN-1-ONE, 1-(2-FLUOROPHENYL)-3-(4-HYDROXYPHENYL)-, O-(2- (DIMETHYLAMINO)ETHYL)OXIME, (1Z,2E)-, (2E)-2-BUTENEDIOATE (2:1)

Systematic Name

English

Classification Tree Code System Code

NCI_THESAURUS

C66885