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Details

Stereochemistry ABSOLUTE
Molecular Formula C26H38N2O4.ClH
Molecular Weight 479.052
Optical Activity ( + )
Defined Stereocenters 1 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of Alnespirone hydrochloride

SMILES

Cl.CCCN(CCCCN1C(=O)CC2(CCCC2)CC1=O)[C@@H]3COC4=CC=CC(OC)=C4C3

InChI

InChIKey=QYFHCFNBYQZGKW-BDQAORGHSA-N
InChI=1S/C26H38N2O4.ClH/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;1H/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 ( + )

Molecular Formula ClH
Molecular Weight 36.461
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

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.

Approval Year

PubMed

PubMed

TitleDatePubMed
In vivo comparison of two 5-HT1A receptors agonists alnespirone (S-20499) and buspirone on locus coeruleus neuronal activity.
2003 Jan 10
5-HT1A and 5-HT1B receptor agonists and aggression: a pharmacological challenge of the serotonin deficiency hypothesis.
2005 Dec 5
Patents

Sample Use Guides

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 19:39:23 GMT 2023
Edited
by admin
on Fri Dec 15 19:39:23 GMT 2023
Record UNII
5CPK6K625T
Record Status Validated (UNII)
Record Version
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Name Type Language
Alnespirone hydrochloride
Common Name English
8-Azaspiro[4.5]decane-7,9-dione, 8-[4-[[(3S)-3,4-dihydro-5-methoxy-2H-1-benzopyran-3-yl]propylamino]butyl]-, monohydrochloride
Common Name English
8-Azaspiro[4.5]decane-7,9-dione, 8-[4-[(3,4-dihydro-5-methoxy-2H-1-benzopyran-3-yl)propylamino]butyl]-, monohydrochloride, (S)-
Common Name English
(+)-S 20499
Code English
Code System Code Type Description
PUBCHEM
9826391
Created by admin on Fri Dec 15 19:39:23 GMT 2023 , Edited by admin on Fri Dec 15 19:39:23 GMT 2023
PRIMARY
EPA CompTox
DTXSID90931874
Created by admin on Fri Dec 15 19:39:23 GMT 2023 , Edited by admin on Fri Dec 15 19:39:23 GMT 2023
PRIMARY
CAS
143413-69-8
Created by admin on Fri Dec 15 19:39:23 GMT 2023 , Edited by admin on Fri Dec 15 19:39:23 GMT 2023
PRIMARY
FDA UNII
5CPK6K625T
Created by admin on Fri Dec 15 19:39:23 GMT 2023 , Edited by admin on Fri Dec 15 19:39:23 GMT 2023
PRIMARY
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ACTIVE MOIETY