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
Disturbance of serotonin 5HT2 receptors in remitted patients suffering from hereditary depressive disorder.	2001 Aug	11556203
Distribution of 5HT2A receptors in the human brain: comparison of data in vivo and post mortem.	2002	12224404
Altered 5-HT(2A) receptor binding after recovery from bulimia-type anorexia nervosa: relationships to harm avoidance and drive for thinness.	2004 Jun	15054474
Decreased prefrontal 5-HT2A receptor binding in subjects at enhanced risk for schizophrenia.	2005 Dec	16187138
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
The 5-HT2A receptor binding pattern in the human brain is strongly genetically determined.	2008 Apr 15	18291676
5-HT2A receptor density is decreased in the at-risk mental state.	2008 Jan	17899021
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
A PET [18F]altanserin study of 5-HT2A receptor binding in the human brain and responses to painful heat stimulation.	2009 Feb 1	19007894
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
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