Alnespirone

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C26H38N2O4
Molecular Weight	442.5909
Optical Activity	( + )
Defined Stereocenters	1 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CCCN(CCCCN1C(=O)CC2(CCCC2)CC1=O)[C@@H]3COC4=C(C3)C(OC)=CC=C4

InChI

InChIKey=DLLULNTXJPATBC-FQEVSTJZSA-N

InChI=1S/C26H38N2O4/c1-3-13-27(20-16-21-22(31-2)9-8-10-23(21)32-19-20)14-6-7-15-28-24(29)17-26(18-25(28)30)11-4-5-12-26/h8-10,20H,3-7,11-19H2,1-2H3/t20-/m0/s1

HIDE SMILES / InChI

Molecular Formula	C26H38N2O4
Molecular Weight	442.5909
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	1 / 1
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://adisinsight.springer.com/drugs/800001421 | https://www.ncbi.nlm.nih.gov/pubmed/9600628

Alnespirone [S 20499] is a potent and full agonist at pre- and postsynaptic serotonin 1A receptors. Alnespirone is the (+)-enantiomer, S 20244 is the racemate. In animal models, alnespirone demonstrated both anxiolytic and antidepressant activity and was undergoing phase II trials in these indications with Servier in France. However, development of Alnespirone was discontinued for anxiety disorders and major depressive disorder.

CNS Activity

Originator

Approval Year

PubMed

Title	Date	PubMed
Enhanced sensitivity of postsynaptic serotonin-1A receptors in rats and mice with high trait aggression.	2001 Sep 1-15	11564470
Activation of serotonergic neurotransmission during the performance of aggressive behavior in rats.	2003 Aug	12931952
In vivo comparison of two 5-HT1A receptors agonists alnespirone (S-20499) and buspirone on locus coeruleus neuronal activity.	2003 Jan 10	12505530
5-HT1A agonists: alcohol drinking in rats and squirrel monkeys.	2003 May	12658527
5-HT1A and 5-HT1B receptor agonists and aggression: a pharmacological challenge of the serotonin deficiency hypothesis.	2005 Dec 5	16310183
Efficient single nucleotide polymorphism discovery in laboratory rat strains using wild rat-derived SNP candidates.	2005 Nov 29	16316463
Serotonin synthesis, release and reuptake in terminals: a mathematical model.	2010 Aug 19	20723248

Patents

Sample Use Guides

In Vivo Use Guide

Rat model of depression: Alnespirone was administered twice daily via the oral route (2.5, 5, 10, 20 mg kg(-1) day(-1)). It was shown to protect against the elevation in escape failures caused by exposure to the uncontrollable aversive situation at 5 and 10 mg kg(-1) day(-1) p.o. (13+/-2 and 10+/-3 escape failures, respectively, vs. 9+/-2 escape failures in control rats).

Route of Administration: Oral

In Vitro Use Guide

Alnespirone bound with a high affinity (Kd = 0.36 nM) to a homogeneous class of sites in rat hippocampal membranes.

Substance Class	Chemical Created by `admin` on `Fri Dec 15 16:05:53 UTC 2023` Edited by `admin` on `Fri Dec 15 16:05:53 UTC 2023`
Record UNII	34E28BM822
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

Alnespirone

Official Name

English

alnespirone [INN]

Common Name

English

S20499

Code

English

S-20499

Code

English

(+)-(S)-N-(4-((5-METHOXY-3-CHROMANYL)PROPYLAMINO)BUTYL)-1,1-CYCLOPENTANEDIACETIMIDE

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C28197