ADATANSERIN

Possibly Marketed Outside US

Details

Stereochemistry	ACHIRAL
Molecular Formula	C21H31N5O
Molecular Weight	369.5037
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

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

InChI

InChIKey=HPFLVTSWRFCPCV-UHFFFAOYSA-N

InChI=1S/C21H31N5O/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)

HIDE SMILES / InChI

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 69 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 2778
5-hydroxytryptamine receptor 2C 26 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 2778
5-hydroxytryptamine receptor 1A 54 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 290

PubMed

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

Substance Class	Chemical Created by `admin` on `Fri Dec 15 16:02:09 UTC 2023` Edited by `admin` on `Fri Dec 15 16:02:09 UTC 2023`
Record UNII	W5U6WQM26H
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

ADATANSERIN

Official Name

English

WY-50324

Code

English

TRICYCLO(3.3.1.13,7)DECANE-1-CARBOXAMIDE, N-(2-(4-(2-PYRIMIDINYL)-1-PIPERAZINYL)ETHYL)

Systematic Name

English

adatanserin [INN]

Common Name

English

N-(2-(4-(2-PYRIMIDINYL)-1-PIPERAZINYL)ETHYL)-1-ADAMANTANECARBOXAMIDE

Systematic Name

English

N-(2-(4-(2-PYRIMIDINYL)-1-PIPERAZINYL)ETHYL)TRICYCLO(3.3.1.1(SUP (3.7))DECANE-1-CARBOXAMIDE

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C66885