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Details

Stereochemistry ACHIRAL
Molecular Formula C20H19ClN2O3S
Molecular Weight 402.894
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of A-867744

SMILES

CCC(=O)C1=C(C)N(C(=C1)C2=CC=C(Cl)C=C2)C3=CC=C(C=C3)S(N)(=O)=O

InChI

InChIKey=ABACVOXFUHDKNZ-UHFFFAOYSA-N
InChI=1S/C20H19ClN2O3S/c1-3-20(24)18-12-19(14-4-6-15(21)7-5-14)23(13(18)2)16-8-10-17(11-9-16)27(22,25)26/h4-12H,3H2,1-2H3,(H2,22,25,26)

HIDE SMILES / InChI
Molecular Formula C20H19ClN2O3S
Molecular Weight 402.894
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description

Targeting alpha7 neuronal acetylcholine receptors (nAChRs) with selective agonists and positive allosteric modulators (PAMs) is considered a therapeutic approach for managing cognitive deficits in schizophrenia and Alzheimer's disease. A-867744 is a novel type II positive allosteric modulator of α7 nAChR, which was developed by Abbott Laboratories, and has a good potency and selectivity.

CNS Activity

CNS Penetrant
2554
Curator's Comment: Known to be CNS penetrant in rat Human data not available

Originator

Approval Year

Unknown
139594
Targets

Targets

Primary TargetPharmacologyConditionPotency
Positive Allosteric Modulator
179
 0.98 µM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Basic research
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Positive allosteric modulation of alpha7 neuronal nicotinic acetylcholine receptors: lack of cytotoxicity in PC12 cells and rat primary cortical neurons.
2009 Dec
Patents

Patents

07741364
1
08609713
1
20080064695
3
20100216748
1

Sample Use Guides

In Vivo Use Guide
Unknown
Route of Administration: Unknown
In Vitro Use Guide
In oocytes expressing alpha7 neuronal acetylcholine receptors (nAChRs), A-867744 potentiated acetylcholine (ACh)-evoked currents, with an EC(50) value of approximately 1 uM. In the presence of A-867744, ACh concentration responses were potentiated by increases in potency, Hill slope, and maximal efficacy. When examined in rat hippocampus CA1 stratum radiatum interneurons or dentate gyrus granule cells, A-867744 (10 uM) increased choline-evoked alpha7 currents and recovery from inhibition/desensitization, and enhanced spontaneous inhibitory postsynaptic current activity.
Substance Class Chemical
Created
by admin
on Sat Dec 16 10:57:39 GMT 2023
Edited
by admin
on Sat Dec 16 10:57:39 GMT 2023
Record UNII
O6NW23A765
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
A-867744
Common Name English
BENZENESULFONAMIDE, 4-(5-(4-CHLOROPHENYL)-2-METHYL-3-(1-OXOPROPYL)-1H-PYRROL-1-YL)-
Systematic Name English
4-(5-(4-CHLOROPHENYL)-2-METHYL-3-PROPIONYLPYRROL-1-YL)BENZENESULFONAMIDE
Systematic Name English
Code System Code Type Description
PUBCHEM
23642319
Created by admin on Sat Dec 16 10:57:39 GMT 2023 , Edited by admin on Sat Dec 16 10:57:39 GMT 2023
PRIMARY
EPA CompTox
DTXSID20142875
Created by admin on Sat Dec 16 10:57:39 GMT 2023 , Edited by admin on Sat Dec 16 10:57:39 GMT 2023
PRIMARY
FDA UNII
O6NW23A765
Created by admin on Sat Dec 16 10:57:39 GMT 2023 , Edited by admin on Sat Dec 16 10:57:39 GMT 2023
PRIMARY
CAS
1000279-69-5
Created by admin on Sat Dec 16 10:57:39 GMT 2023 , Edited by admin on Sat Dec 16 10:57:39 GMT 2023
PRIMARY
Related Record Type Details
Structure of A-867744
ACTIVE MOIETY
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