ALTANSERIN TARTRATE

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 Search

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

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
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
Analyses of [(18)F] altanserin bolus injection PET data. I: consideration of radiolabeled metabolites in baboons.	2001 Jul	11354008
Distribution of 5HT2A receptors in the human brain: comparison of data in vivo and post mortem.	2002	12224404
Reduced 5-HT2A receptor binding after recovery from anorexia nervosa.	2002 Nov 1	12399143
Quantification of 5-HT2A receptors in the human brain using [18F]altanserin-PET and the bolus/infusion approach.	2003 Aug	12902843
Increase in prefrontal cortex serotonin 2A receptors following estrogen treatment in postmenopausal women.	2003 Aug	12900319
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-HT2A receptor binding in major depressive disorder: in vivo measurement with [18F]altanserin positron emission tomography.	2004 Feb 1	14744461
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
[18F]altanserin binding to human 5HT2A receptors is unaltered after citalopram and pindolol challenge.	2004 Sep	15356424
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
5HT2A receptor binding is increased in borderline personality disorder.	2007 Sep 15	17448449
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
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
A PET [18F]altanserin study of 5-HT2A receptor binding in the human brain and responses to painful heat stimulation.	2009 Feb 1	19007894
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
Structural combination of established 5-HT(2A) receptor ligands: new aspects of the binding mode.	2010 Oct	20636331

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 `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

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