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
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
| 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.
CNS Activity
Approval Year
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 |
|
| Altered serotonin 2A receptor activity in women who have recovered from bulimia nervosa. | 2001 Jul |
|
| Analyses of [(18)F]altanserin bolus injection PET data. II: consideration of radiolabeled metabolites in humans. | 2001 Jul |
|
| Analyses of [(18)F] altanserin bolus injection PET data. I: consideration of radiolabeled metabolites in baboons. | 2001 Jul |
|
| Distribution of 5HT2A receptors in the human brain: comparison of data in vivo and post mortem. | 2002 |
|
| Reduced 5-HT2A receptor binding after recovery from anorexia nervosa. | 2002 Nov 1 |
|
| 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 |
|
| Altered 5-HT(2A) receptor binding after recovery from bulimia-type anorexia nervosa: relationships to harm avoidance and drive for thinness. | 2004 Jun |
|
| 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 |
|
| Estradiol effects on the postmenopausal brain. | 2004 Nov |
|
| [18F]altanserin binding to human 5HT2A receptors is unaltered after citalopram and pindolol challenge. | 2004 Sep |
|
| 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 |
|
| No-carrier-added nucleophilic 18F-labelling in an electrochemical cell exemplified by the routine production of [18F]altanserin. | 2006 Sep |
|
| Acute S-ketamine application does not alter cerebral [18F]altanserin binding: a pilot PET study in humans. | 2007 |
|
| 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 |
|
| Exaggerated 5-HT1A but normal 5-HT2A receptor activity in individuals ill with anorexia nervosa. | 2007 May 1 |
|
| 5HT2A receptor binding is increased in borderline personality disorder. | 2007 Sep 15 |
|
| The 5-HT2A receptor binding pattern in the human brain is strongly genetically determined. | 2008 Apr 15 |
|
| Total synthesis and evaluation of [18F]MHMZ. | 2008 Feb 15 |
|
| 5-HT2A receptor density is decreased in the at-risk mental state. | 2008 Jan |
|
| Frontolimbic serotonin 2A receptor binding in healthy subjects is associated with personality risk factors for affective disorder. | 2008 Mar 15 |
|
| 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 |
|
| GMP-compliant radiosynthesis of [18F]altanserin and human plasma metabolite studies. | 2009 Apr |
|
| 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 |
|
| A PET [18F]altanserin study of 5-HT2A receptor binding in the human brain and responses to painful heat stimulation. | 2009 Feb 1 |
|
| Test-retest variability of high resolution positron emission tomography (PET) imaging of cortical serotonin (5HT2A) receptors in older, healthy adults. | 2009 Jul 6 |
|
| 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 |
|
| Familial risk for mood disorder and the personality risk factor, neuroticism, interact in their association with frontolimbic serotonin 2A receptor binding. | 2010 Apr |
|
| Decreased frontal serotonin2A receptor binding in antipsychotic-naive patients with first-episode schizophrenia. | 2010 Jan |
|
| Gender, personality, and serotonin-2A receptor binding in healthy subjects. | 2010 Jan 30 |
|
| A nonlinear relationship between cerebral serotonin transporter and 5-HT(2A) receptor binding: an in vivo molecular imaging study in humans. | 2010 Mar 3 |
|
| 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 |
|
| Endogenous plasma estradiol in healthy men is positively correlated with cerebral cortical serotonin 2A receptor binding. | 2010 Oct |
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
| Substance Class |
Chemical
Created
by
admin
on
Edited
Fri Dec 15 15:32:39 GMT 2023
by
admin
on
Fri Dec 15 15:32:39 GMT 2023
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| Record UNII |
9P204CHE8J
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| Record Status |
Validated (UNII)
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| Record Version |
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C66885
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3033676
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279-159-5
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CHEMBL62919
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DTXSID20229675
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79449-96-0
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C79965
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9P204CHE8J
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ACTIVE MOIETY |