ALTANSERIN

Details

Stereochemistry	ACHIRAL
Molecular Formula	C22H22FN3O2S
Molecular Weight	411.492
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

FC1=CC=C(C=C1)C(=O)C2CCN(CCN3C(=S)NC4=C(C=CC=C4)C3=O)CC2

InChI

InChIKey=SMYALUSCZJXWHG-UHFFFAOYSA-N

InChI=1S/C22H22FN3O2S/c23-17-7-5-15(6-8-17)20(27)16-9-11-25(12-10-16)13-14-26-21(28)18-3-1-2-4-19(18)24-22(26)29/h1-8,16H,9-14H2,(H,24,29)

HIDE SMILES / InChI

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/21996132

Altanserin is a potent and selective 5-HT2A receptor antagonist. Serotonin (5-HT) system functioning have been proposed for a variety of psychiatric disorders, but a direct method quantitatively assessing 5-HT release capacity in the living human brain is still lacking. It was suggested that the combination of a dexfenfluramine-induced 5-HT release and subsequent assessment of 5-HT(2A) receptor availability with [(18)F]altanserin by positron emission tomography (PET) was suitable to measure cortical 5-HT release capacity in the human brain. Besides human neuroimaging studies altanserin has also been used in the study of rats.

CNS Activity

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/15006678	Antagonist 2778		0.3 nM [Ki]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Unknown 2578

PubMed

Title	Date	PubMed
Disturbance of serotonin 5HT2 receptors in remitted patients suffering from hereditary depressive disorder.	2001 Aug	11556203
Altered serotonin 2A receptor activity in women who have recovered from bulimia nervosa.	2001 Jul	11431241
Analyses of [(18)F]altanserin bolus injection PET data. II: consideration of radiolabeled metabolites in humans.	2001 Jul	11354009
Reduced 5-HT2A receptor binding after recovery from anorexia nervosa.	2002 Nov 1	12399143
Influence of synaptic serotonin level on [18F]altanserin binding to 5HT2 receptors in man.	2003 Feb 17	12642173
Estradiol effects on the postmenopausal brain.	2004 Nov	15514428
The 5-HT2A receptor binding pattern in the human brain is strongly genetically determined.	2008 Apr 15	18291676
Total synthesis and evaluation of [18F]MHMZ.	2008 Feb 15	18187324
5-HT2A receptor density is decreased in the at-risk mental state.	2008 Jan	17899021
Cortical and subcortical 5-HT2A receptor binding in neuroleptic-naive first-episode schizophrenic patients.	2008 Sep	18288096
Synthesis and in vitro affinities of various MDL 100907 derivatives as potential 18F-radioligands for 5-HT2A receptor imaging with PET.	2009 Apr 15	19329329
Longitudinal assessment of cerebral 5-HT2A receptors in healthy elderly volunteers: an [18F]-altanserin PET study.	2009 Feb	18828013
Regional distribution and behavioral correlates of 5-HT(2A) receptors in Alzheimer's disease with [(18)F]deuteroaltanserin and PET.	2009 Sep 30	19682865
Cerebral 5-HT2A receptor and serotonin transporter binding in humans are not affected by the val66met BDNF polymorphism status or blood BDNF levels.	2010 Nov	20736957

Patents

Sample Use Guides

In Vivo Use Guide

Thirteen healthy male subjects received placebo and single oral doses of 40 mg (n = 6) or 60 mg (n = 7) of the potent 5-HT releaser dexfenfluramine separated by an interval of 14 days. Three further subjects received placebo on both days. Two hours after placebo/drug administration, 250 MBq of the 5-HT(2A) receptor selective PET-radiotracer [(18)F]altanserin was administered intravenously as a 30s bolus.

Route of Administration: Intravenous

In Vitro Use Guide

Unknown

Name

Type

Language

ALTANSERIN

Official Name

English

3-(2-(4-(P-FLUOROBENZOYL)PIPERIDINO)ETHYL)-2-THIO-2,4(1H,3H)-QUINAZOLINEDIONE

Common Name

English

Altanserin [WHO-DD]

Common Name

English

4(1H)-QUINAZOLINONE, 3-(2-(4-(4-FLUOROBENZOYL)-1-PIPERIDINYL)ETHYL)-2,3-DIHYDRO-2-THIOXO-

Systematic Name

English

altanserin [INN]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C66885