ADATANSERIN HYDROCHLORIDE

Possibly Marketed Outside US

Details

Stereochemistry	ACHIRAL
Molecular Formula	C21H31N5O.ClH
Molecular Weight	405.965
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

Cl.O=C(NCCN1CCN(CC1)C2=NC=CC=N2)C34CC5CC(CC(C5)C3)C4

InChI

InChIKey=PPHCXMVJHQJEAK-UHFFFAOYSA-N

InChI=1S/C21H31N5O.ClH/c27-19(21-13-16-10-17(14-21)12-18(11-16)15-21)22-4-5-25-6-8-26(9-7-25)20-23-2-1-3-24-20;/h1-3,16-18H,4-15H2,(H,22,27);1H

HIDE SMILES / InChI

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

Molecular Formula	C21H31N5O
Molecular Weight	369.5037
Charge	0
Count

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

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/10602693 | https://adisinsight.springer.com/drugs/800001485

Adatanserin is an adamantyl piperazine derivative a partial agonist of 5-HT1A receptors and antagonist of 5-HT2A and 5-HT2C receptors. Adatanserin demonstrated activity in vivo in rat serotonin syndrome, quipazine- and DOI-induced head shake experiments, and anxiolytic activity in animal conflict model. It was developed by Wyeth for the treatment of depression. The compound was investigated in phase II clinical trials in anxiety disorders and major depressive disorders, but no results were reported, and the development of adatanserin was discontinued.

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
5-hydroxytryptamine receptor 2A 73 Target ID: P28223 Gene ID: 3356.0 Gene Symbol: HTR2A Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/8632301	Antagonist 2849
5-hydroxytryptamine receptor 2C 29 Target ID: P28335 Gene ID: 3358.0 Gene Symbol: HTR2C Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/8632301	Antagonist 2849
5-hydroxytryptamine receptor 1A 58 Target ID: P08908 Gene ID: 3350.0 Gene Symbol: HTR1A Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/8632301	Partial Agonist 297

PubMed

Title	Date	PubMed
Adamantane-1-thio-amide.	2009-07-18	21583581
Attenuation of ischemic efflux of endogenous amino acids by the novel 5-HT(1A)/5-HT(2) receptor ligand adatanserin.	2002-03	11741003
An intelligent data acquisition system for simultaneous screening of microsomal stability and metabolite profiling by liquid chromatography/mass spectrometry.	2001-09	11599083
Simultaneous screen for microsomal stability and metabolite profile by direct injection turbulent-laminar flow LC-LC and automated tandem mass spectrometry.	2001-05-01	11354502

Substance Class	Chemical Created by `admin` on `Mon Mar 31 18:01:50 GMT 2025` Edited by `admin` on `Mon Mar 31 18:01:50 GMT 2025`
Record UNII	48BX75B06D
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

WY 50324 HCL

Preferred Name

English

ADATANSERIN HYDROCHLORIDE

Official Name

English

ADATANSERIN HCL

Common Name

English

WY-50324-HCL

Code

English

TRICYCLO(3.3.1.1(SUP 3,7))DECANE-1-CARBOXAMIDE, N-(2-(4-(2-PYRIMIDINYL)-1-PIPERAZINYL)ETHYL)-, MONOHYDROCHLORIDE

Common Name

English

N-[2-[4-(2-Pyrimidinyl)-1-piperazinyl]ethyl]-1-adamantanecarboxamide monohydrochloride

Systematic Name

English

WY-50324 HCL

Code

English

ADATANSERIN HYDROCHLORIDE [USAN]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C66885