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 2737		0.3 nM [Ki]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Unknown 2554

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
Influence of synaptic serotonin level on [18F]altanserin binding to 5HT2 receptors in man.	2003 Feb 17	12642173
Widespread increases of cortical serotonin type 2A receptor availability after hormone therapy in euthymic postmenopausal women.	2003 Sep	12969697
Decreased hippocampal 5-HT(2A) receptor binding in older depressed patients using [18F]altanserin positron emission tomography.	2004 Dec	15367923
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
Estradiol effects on the postmenopausal brain.	2004 Nov	15514428
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
Patients with obsessive-compulsive disorder have increased 5-HT2A receptor binding in the caudate nuclei.	2005 Sep	15801987
No-carrier-added nucleophilic 18F-labelling in an electrochemical cell exemplified by the routine production of [18F]altanserin.	2006 Sep	16829074
Cerebral 5-HT2A receptor binding is increased in patients with Tourette's syndrome.	2007 Apr	16945163
Exaggerated 5-HT1A but normal 5-HT2A receptor activity in individuals ill with anorexia nervosa.	2007 May 1	17241616
Total synthesis and evaluation of [18F]MHMZ.	2008 Feb 15	18187324
Cortical and subcortical 5-HT2A receptor binding in neuroleptic-naive first-episode schizophrenic patients.	2008 Sep	18288096
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
Reduced 5-HT(2A) receptor signaling following selective bilateral amygdala damage.	2009 Mar	19015089
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
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 `Sun Dec 18 18:43:54 UTC 2022` Edited by `admin` on `Sun Dec 18 18:43:54 UTC 2022`
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