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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 of ALTANSERIN

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

Molecular Formula C22H22FN3O2S
Molecular Weight 411.492
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

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.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Target ID: P28223
Gene ID: 3356.0
Gene Symbol: HTR2A
Target Organism: Homo sapiens (Human)
0.3 nM [Ki]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
PubMed

PubMed

TitleDatePubMed
Disturbance of serotonin 5HT2 receptors in remitted patients suffering from hereditary depressive disorder.
2001 Aug
Altered serotonin 2A receptor activity in women who have recovered from bulimia nervosa.
2001 Jul
Analyses of [(18)F] altanserin bolus injection PET data. I: consideration of radiolabeled metabolites in baboons.
2001 Jul
Distribution of 5HT2A receptors in the human brain: comparison of data in vivo and post mortem.
2002
Quantification of 5-HT2A receptors in the human brain using [18F]altanserin-PET and the bolus/infusion approach.
2003 Aug
Increase in prefrontal cortex serotonin 2A receptors following estrogen treatment in postmenopausal women.
2003 Aug
Widespread increases of cortical serotonin type 2A receptor availability after hormone therapy in euthymic postmenopausal women.
2003 Sep
Cluster analysis in kinetic modelling of the brain: a noninvasive alternative to arterial sampling.
2004 Feb
Decreased hippocampal 5-HT2A receptor binding in major depressive disorder: in vivo measurement with [18F]altanserin positron emission tomography.
2004 Feb 1
[18F]altanserin binding to human 5HT2A receptors is unaltered after citalopram and pindolol challenge.
2004 Sep
Decreased prefrontal 5-HT2A receptor binding in subjects at enhanced risk for schizophrenia.
2005 Dec
Binding characteristics of the 5-HT2A receptor antagonists altanserin and MDL 100907.
2005 Dec 15
MR-based automatic delineation of volumes of interest in human brain PET images using probability maps.
2005 Feb 15
Motion artifact reduction on parametric PET images of neuroreceptor binding.
2005 Jun
No-carrier-added nucleophilic 18F-labelling in an electrochemical cell exemplified by the routine production of [18F]altanserin.
2006 Sep
Acute S-ketamine application does not alter cerebral [18F]altanserin binding: a pilot PET study in humans.
2007
Exaggerated 5-HT1A but normal 5-HT2A receptor activity in individuals ill with anorexia nervosa.
2007 May 1
The 5-HT2A receptor binding pattern in the human brain is strongly genetically determined.
2008 Apr 15
5-HT2A receptor density is decreased in the at-risk mental state.
2008 Jan
Cortical and subcortical 5-HT2A receptor binding in neuroleptic-naive first-episode schizophrenic patients.
2008 Sep
Assessment of the Potential Role of Tryptophan as the Precursor of Serotonin and Melatonin for the Aged Sleep-wake Cycle and Immune Function: Streptopelia Risoria as a Model.
2009
Longitudinal assessment of cerebral 5-HT2A receptors in healthy elderly volunteers: an [18F]-altanserin PET study.
2009 Feb
A PET [18F]altanserin study of 5-HT2A receptor binding in the human brain and responses to painful heat stimulation.
2009 Feb 1
Test-retest variability of high resolution positron emission tomography (PET) imaging of cortical serotonin (5HT2A) receptors in older, healthy adults.
2009 Jul 6
Nigrostriatal upregulation of 5-HT2A receptors correlates with motor dysfunction in progressive supranuclear palsy.
2009 Jun 15
Time-efficient and convenient synthesis of [(18)F]altanserin for human PET imaging by a new work-up procedure.
2009 Nov
Gender and the use of hormonal contraception in women are not associated with cerebral cortical 5-HT 2A receptor binding.
2009 Oct 6
Regional distribution and behavioral correlates of 5-HT(2A) receptors in Alzheimer's disease with [(18)F]deuteroaltanserin and PET.
2009 Sep 30
Gender, personality, and serotonin-2A receptor binding in healthy subjects.
2010 Jan 30
A nonlinear relationship between cerebral serotonin transporter and 5-HT(2A) receptor binding: an in vivo molecular imaging study in humans.
2010 Mar 3
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
Evaluation of [(11)C]metergoline as a PET radiotracer for 5HTR in nonhuman primates.
2010 Nov 15
Structural combination of established 5-HT(2A) receptor ligands: new aspects of the binding mode.
2010 Oct
Patents

Patents

Sample Use Guides

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
Substance Class Chemical
Created
by admin
on Thu Jul 06 22:00:12 UTC 2023
Edited
by admin
on Thu Jul 06 22:00:12 UTC 2023
Record UNII
5015H744JQ
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
ALTANSERIN
INN   WHO-DD  
INN  
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
Created by admin on Thu Jul 06 22:00:13 UTC 2023 , Edited by admin on Thu Jul 06 22:00:13 UTC 2023
Code System Code Type Description
NCI_THESAURUS
C77258
Created by admin on Thu Jul 06 22:00:13 UTC 2023 , Edited by admin on Thu Jul 06 22:00:13 UTC 2023
PRIMARY
EVMPD
SUB05375MIG
Created by admin on Thu Jul 06 22:00:13 UTC 2023 , Edited by admin on Thu Jul 06 22:00:13 UTC 2023
PRIMARY
MESH
C071983
Created by admin on Thu Jul 06 22:00:13 UTC 2023 , Edited by admin on Thu Jul 06 22:00:13 UTC 2023
PRIMARY
ChEMBL
CHEMBL62919
Created by admin on Thu Jul 06 22:00:13 UTC 2023 , Edited by admin on Thu Jul 06 22:00:13 UTC 2023
PRIMARY
INN
5395
Created by admin on Thu Jul 06 22:00:13 UTC 2023 , Edited by admin on Thu Jul 06 22:00:13 UTC 2023
PRIMARY
ECHA (EC/EINECS)
278-422-1
Created by admin on Thu Jul 06 22:00:13 UTC 2023 , Edited by admin on Thu Jul 06 22:00:13 UTC 2023
PRIMARY
FDA UNII
5015H744JQ
Created by admin on Thu Jul 06 22:00:13 UTC 2023 , Edited by admin on Thu Jul 06 22:00:13 UTC 2023
PRIMARY
CAS
76330-71-7
Created by admin on Thu Jul 06 22:00:13 UTC 2023 , Edited by admin on Thu Jul 06 22:00:13 UTC 2023
PRIMARY
PUBCHEM
3033677
Created by admin on Thu Jul 06 22:00:13 UTC 2023 , Edited by admin on Thu Jul 06 22:00:13 UTC 2023
PRIMARY
SMS_ID
100000087474
Created by admin on Thu Jul 06 22:00:13 UTC 2023 , Edited by admin on Thu Jul 06 22:00:13 UTC 2023
PRIMARY
EPA CompTox
DTXSID5043891
Created by admin on Thu Jul 06 22:00:13 UTC 2023 , Edited by admin on Thu Jul 06 22:00:13 UTC 2023
PRIMARY
WIKIPEDIA
ALTANSERIN
Created by admin on Thu Jul 06 22:00:13 UTC 2023 , Edited by admin on Thu Jul 06 22:00:13 UTC 2023
PRIMARY
Related Record Type Details
LABELED -> NON-LABELED
LABELED -> NON-LABELED
SALT/SOLVATE -> PARENT
Related Record Type Details
ACTIVE MOIETY