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Details

Stereochemistry ABSOLUTE
Molecular Formula C22H22FN3O2S.C4H6O6
Molecular Weight 561.579
Optical Activity UNSPECIFIED
Defined Stereocenters 2 / 2
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of ALTANSERIN TARTRATE

SMILES

O[C@H]([C@@H](O)C(O)=O)C(O)=O.FC1=CC=C(C=C1)C(=O)C2CCN(CCN3C(=S)NC4=C(C=CC=C4)C3=O)CC2

InChI

InChIKey=VZGOQPXIRAHJLV-LREBCSMRSA-N
InChI=1S/C22H22FN3O2S.C4H6O6/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;5-1(3(7)8)2(6)4(9)10/h1-8,16H,9-14H2,(H,24,29);1-2,5-6H,(H,7,8)(H,9,10)/t;1-,2-/m.1/s1

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

Molecular Formula C4H6O6
Molecular Weight 150.0868
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 2 / 2
E/Z Centers 0
Optical Activity UNSPECIFIED

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
Altered serotonin 2A receptor activity in women who have recovered from bulimia nervosa.
2001 Jul
Reduced 5-HT2A receptor binding after recovery from anorexia nervosa.
2002 Nov 1
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
Influence of synaptic serotonin level on [18F]altanserin binding to 5HT2 receptors in man.
2003 Feb 17
Widespread increases of cortical serotonin type 2A receptor availability after hormone therapy in euthymic postmenopausal women.
2003 Sep
Estradiol effects on the postmenopausal brain.
2004 Nov
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
Patients with obsessive-compulsive disorder have increased 5-HT2A receptor binding in the caudate nuclei.
2005 Sep
Cerebral 5-HT2A receptor binding is increased in patients with Tourette's syndrome.
2007 Apr
Reproducibility of 5-HT2A receptor measurements and sample size estimations with [18F]altanserin PET using a bolus/infusion approach.
2007 Jun
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
Synthesis and in vitro affinities of various MDL 100907 derivatives as potential 18F-radioligands for 5-HT2A receptor imaging with PET.
2009 Apr 15
Longitudinal assessment of cerebral 5-HT2A receptors in healthy elderly volunteers: an [18F]-altanserin PET study.
2009 Feb
Nigrostriatal upregulation of 5-HT2A receptors correlates with motor dysfunction in progressive supranuclear palsy.
2009 Jun 15
Reduced 5-HT(2A) receptor signaling following selective bilateral amygdala damage.
2009 Mar
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
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 Fri Dec 15 15:32:39 GMT 2023
Edited
by admin
on Fri Dec 15 15:32:39 GMT 2023
Record UNII
9P204CHE8J
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
ALTANSERIN TARTRATE
USAN  
USAN  
Official Name English
R-53,200
Code English
4(1H)-QUINAZOLINONE, 3-(2-(4-(4-FLUOROBENZOYL)-1-PIPERIDINYL)ETHYL)-2,3-DIHYDRO-2-THIOXO-, (R-(R*,R*))-2,3-DIHYDROXYBUTANEDIOATE
Common Name English
3-(2-(4-(P-FLUOROBENZOYL)PIPERIDINO)ETHYL)-2-THIO-2,4(1H,3H)-QUINAZOLINEDIONE L-(+)-TARTRATE (1:1)
Common Name English
R-53200
Code English
ALTANSERIN TARTRATE [USAN]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C66885
Created by admin on Fri Dec 15 15:32:39 GMT 2023 , Edited by admin on Fri Dec 15 15:32:39 GMT 2023
Code System Code Type Description
PUBCHEM
3033676
Created by admin on Fri Dec 15 15:32:39 GMT 2023 , Edited by admin on Fri Dec 15 15:32:39 GMT 2023
PRIMARY
ECHA (EC/EINECS)
279-159-5
Created by admin on Fri Dec 15 15:32:39 GMT 2023 , Edited by admin on Fri Dec 15 15:32:39 GMT 2023
PRIMARY
ChEMBL
CHEMBL62919
Created by admin on Fri Dec 15 15:32:39 GMT 2023 , Edited by admin on Fri Dec 15 15:32:39 GMT 2023
PRIMARY
EPA CompTox
DTXSID20229675
Created by admin on Fri Dec 15 15:32:39 GMT 2023 , Edited by admin on Fri Dec 15 15:32:39 GMT 2023
PRIMARY
CAS
79449-96-0
Created by admin on Fri Dec 15 15:32:39 GMT 2023 , Edited by admin on Fri Dec 15 15:32:39 GMT 2023
PRIMARY
NCI_THESAURUS
C79965
Created by admin on Fri Dec 15 15:32:39 GMT 2023 , Edited by admin on Fri Dec 15 15:32:39 GMT 2023
PRIMARY
FDA UNII
9P204CHE8J
Created by admin on Fri Dec 15 15:32:39 GMT 2023 , Edited by admin on Fri Dec 15 15:32:39 GMT 2023
PRIMARY
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