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

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

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
Comparison of [(18)F]altanserin and [(18)F]deuteroaltanserin for PET imaging of serotonin(2A) receptors in baboon brain: pharmacological studies.	2001 Apr	11323237
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
Analyses of [(18)F] altanserin bolus injection PET data. I: consideration of radiolabeled metabolites in baboons.	2001 Jul	11354008
Increase in prefrontal cortex serotonin 2A receptors following estrogen treatment in postmenopausal women.	2003 Aug	12900319
Cluster analysis in kinetic modelling of the brain: a noninvasive alternative to arterial sampling.	2004 Feb	14980551
Decreased hippocampal 5-HT2A receptor binding in major depressive disorder: in vivo measurement with [18F]altanserin positron emission tomography.	2004 Feb 1	14744461
Altered 5-HT(2A) receptor binding after recovery from bulimia-type anorexia nervosa: relationships to harm avoidance and drive for thinness.	2004 Jun	15054474
A database of [(18)F]-altanserin binding to 5-HT(2A) receptors in normal volunteers: normative data and relationship to physiological and demographic variables.	2004 Mar	15006678
Decreased prefrontal 5-HT2A receptor binding in subjects at enhanced risk for schizophrenia.	2005 Dec	16187138
Binding characteristics of the 5-HT2A receptor antagonists altanserin and MDL 100907.	2005 Dec 15	16206185
MR-based automatic delineation of volumes of interest in human brain PET images using probability maps.	2005 Feb 15	15670674
Motion artifact reduction on parametric PET images of neuroreceptor binding.	2005 Jun	15937320
No-carrier-added nucleophilic 18F-labelling in an electrochemical cell exemplified by the routine production of [18F]altanserin.	2006 Sep	16829074
Acute S-ketamine application does not alter cerebral [18F]altanserin binding: a pilot PET study in humans.	2007	17541696
Cerebral 5-HT2A receptor binding is increased in patients with Tourette's syndrome.	2007 Apr	16945163
Reproducibility of 5-HT2A receptor measurements and sample size estimations with [18F]altanserin PET using a bolus/infusion approach.	2007 Jun	17195073
Exaggerated 5-HT1A but normal 5-HT2A receptor activity in individuals ill with anorexia nervosa.	2007 May 1	17241616
5HT2A receptor binding is increased in borderline personality disorder.	2007 Sep 15	17448449
5-HT2A receptor density is decreased in the at-risk mental state.	2008 Jan	17899021
Frontolimbic serotonin 2A receptor binding in healthy subjects is associated with personality risk factors for affective disorder.	2008 Mar 15	17884017
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	22084580
GMP-compliant radiosynthesis of [18F]altanserin and human plasma metabolite studies.	2009 Apr	19162492
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
A PET [18F]altanserin study of 5-HT2A receptor binding in the human brain and responses to painful heat stimulation.	2009 Feb 1	19007894
Test-retest variability of high resolution positron emission tomography (PET) imaging of cortical serotonin (5HT2A) receptors in older, healthy adults.	2009 Jul 6	19580676
Nigrostriatal upregulation of 5-HT2A receptors correlates with motor dysfunction in progressive supranuclear palsy.	2009 Jun 15	19353726
Time-efficient and convenient synthesis of [(18)F]altanserin for human PET imaging by a new work-up procedure.	2009 Nov	19692252
Gender and the use of hormonal contraception in women are not associated with cerebral cortical 5-HT 2A receptor binding.	2009 Oct 6	19559762
Regional distribution and behavioral correlates of 5-HT(2A) receptors in Alzheimer's disease with [(18)F]deuteroaltanserin and PET.	2009 Sep 30	19682865
Familial risk for mood disorder and the personality risk factor, neuroticism, interact in their association with frontolimbic serotonin 2A receptor binding.	2010 Apr	20043006
Decreased frontal serotonin2A receptor binding in antipsychotic-naive patients with first-episode schizophrenia.	2010 Jan	20048218
Gender, personality, and serotonin-2A receptor binding in healthy subjects.	2010 Jan 30	19959344
A nonlinear relationship between cerebral serotonin transporter and 5-HT(2A) receptor binding: an in vivo molecular imaging study in humans.	2010 Mar 3	20203198
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
Evaluation of [(11)C]metergoline as a PET radiotracer for 5HTR in nonhuman primates.	2010 Nov 15	20451398
Structural combination of established 5-HT(2A) receptor ligands: new aspects of the binding mode.	2010 Oct	20636331
Endogenous plasma estradiol in healthy men is positively correlated with cerebral cortical serotonin 2A receptor binding.	2010 Oct	20356681

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

Substance Class	Chemical Created by `admin` on `Sat Dec 16 16:31:32 GMT 2023` Edited by `admin` on `Sat Dec 16 16:31:32 GMT 2023`
Record UNII	5015H744JQ
Record Status	`Validated (UNII)`
Record Version

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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