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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 of Alnespirone

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
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 1 / 1
E/Z Centers 0
Optical Activity UNSPECIFIED

Description

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

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
Record UNII
34E28BM822
Record Status Validated (UNII)
Record Version