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 73 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 2849		0.3 nM [Ki]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Unknown 2596

PubMed

Title	Date	PubMed
Evaluation of [(11)C]metergoline as a PET radiotracer for 5HTR in nonhuman primates.	2010-11-15	20451398
Cerebral 5-HT2A receptor and serotonin transporter binding in humans are not affected by the val66met BDNF polymorphism status or blood BDNF levels.	2010-11	20736957
Structural combination of established 5-HT(2A) receptor ligands: new aspects of the binding mode.	2010-10	20636331
Endogenous plasma estradiol in healthy men is positively correlated with cerebral cortical serotonin 2A receptor binding.	2010-10	20356681
Familial risk for mood disorder and the personality risk factor, neuroticism, interact in their association with frontolimbic serotonin 2A receptor binding.	2010-04	20043006
A nonlinear relationship between cerebral serotonin transporter and 5-HT(2A) receptor binding: an in vivo molecular imaging study in humans.	2010-03-03	20203198
Gender, personality, and serotonin-2A receptor binding in healthy subjects.	2010-01-30	19959344
Decreased frontal serotonin2A receptor binding in antipsychotic-naive patients with first-episode schizophrenia.	2010-01	20048218
Time-efficient and convenient synthesis of [(18)F]altanserin for human PET imaging by a new work-up procedure.	2009-11	19692252
Gender and the use of hormonal contraception in women are not associated with cerebral cortical 5-HT 2A receptor binding.	2009-10-06	19559762
Regional distribution and behavioral correlates of 5-HT(2A) receptors in Alzheimer's disease with [(18)F]deuteroaltanserin and PET.	2009-09-30	19682865
Test-retest variability of high resolution positron emission tomography (PET) imaging of cortical serotonin (5HT2A) receptors in older, healthy adults.	2009-07-06	19580676
Nigrostriatal upregulation of 5-HT2A receptors correlates with motor dysfunction in progressive supranuclear palsy.	2009-06-15	19353726
Synthesis and in vitro affinities of various MDL 100907 derivatives as potential 18F-radioligands for 5-HT2A receptor imaging with PET.	2009-04-15	19329329
GMP-compliant radiosynthesis of [18F]altanserin and human plasma metabolite studies.	2009-04	19162492
Reduced 5-HT(2A) receptor signaling following selective bilateral amygdala damage.	2009-03	19015089
A PET [18F]altanserin study of 5-HT2A receptor binding in the human brain and responses to painful heat stimulation.	2009-02-01	19007894
Longitudinal assessment of cerebral 5-HT2A receptors in healthy elderly volunteers: an [18F]-altanserin PET study.	2009-02	18828013
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
Cortical and subcortical 5-HT2A receptor binding in neuroleptic-naive first-episode schizophrenic patients.	2008-09	18288096
The 5-HT2A receptor binding pattern in the human brain is strongly genetically determined.	2008-04-15	18291676
Frontolimbic serotonin 2A receptor binding in healthy subjects is associated with personality risk factors for affective disorder.	2008-03-15	17884017
Total synthesis and evaluation of [18F]MHMZ.	2008-02-15	18187324
5-HT2A receptor density is decreased in the at-risk mental state.	2008-01	17899021
5HT2A receptor binding is increased in borderline personality disorder.	2007-09-15	17448449
Reproducibility of 5-HT2A receptor measurements and sample size estimations with [18F]altanserin PET using a bolus/infusion approach.	2007-06	17195073
Exaggerated 5-HT1A but normal 5-HT2A receptor activity in individuals ill with anorexia nervosa.	2007-05-01	17241616
Cerebral 5-HT2A receptor binding is increased in patients with Tourette's syndrome.	2007-04	16945163
Acute S-ketamine application does not alter cerebral [18F]altanserin binding: a pilot PET study in humans.	2007	17541696
No-carrier-added nucleophilic 18F-labelling in an electrochemical cell exemplified by the routine production of [18F]altanserin.	2006-09	16829074
Binding characteristics of the 5-HT2A receptor antagonists altanserin and MDL 100907.	2005-12-15	16206185
Decreased prefrontal 5-HT2A receptor binding in subjects at enhanced risk for schizophrenia.	2005-12	16187138
Patients with obsessive-compulsive disorder have increased 5-HT2A receptor binding in the caudate nuclei.	2005-09	15801987
Motion artifact reduction on parametric PET images of neuroreceptor binding.	2005-06	15937320
MR-based automatic delineation of volumes of interest in human brain PET images using probability maps.	2005-02-15	15670674
Decreased hippocampal 5-HT(2A) receptor binding in older depressed patients using [18F]altanserin positron emission tomography.	2004-12	15367923
Estradiol effects on the postmenopausal brain.	2004-11	15514428
[18F]altanserin binding to human 5HT2A receptors is unaltered after citalopram and pindolol challenge.	2004-09	15356424
Altered 5-HT(2A) receptor binding after recovery from bulimia-type anorexia nervosa: relationships to harm avoidance and drive for thinness.	2004-06	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.	2004-03	15006678
Decreased hippocampal 5-HT2A receptor binding in major depressive disorder: in vivo measurement with [18F]altanserin positron emission tomography.	2004-02-01	14744461
Cluster analysis in kinetic modelling of the brain: a noninvasive alternative to arterial sampling.	2004-02	14980551
Widespread increases of cortical serotonin type 2A receptor availability after hormone therapy in euthymic postmenopausal women.	2003-09	12969697
Quantification of 5-HT2A receptors in the human brain using [18F]altanserin-PET and the bolus/infusion approach.	2003-08	12902843
Increase in prefrontal cortex serotonin 2A receptors following estrogen treatment in postmenopausal women.	2003-08	12900319
Influence of synaptic serotonin level on [18F]altanserin binding to 5HT2 receptors in man.	2003-02-17	12642173
Reduced 5-HT2A receptor binding after recovery from anorexia nervosa.	2002-11-01	12399143
Distribution of 5HT2A receptors in the human brain: comparison of data in vivo and post mortem.	2002	12224404
Disturbance of serotonin 5HT2 receptors in remitted patients suffering from hereditary depressive disorder.	2001-08	11556203
Altered serotonin 2A receptor activity in women who have recovered from bulimia nervosa.	2001-07	11431241

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 `Mon Mar 31 18:00:39 GMT 2025` Edited by `admin` on `Mon Mar 31 18:00:39 GMT 2025`
Record UNII	9P204CHE8J
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

R-53,200

Preferred Name

English

ALTANSERIN TARTRATE

Official Name

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