ABT-239

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C22H22N2O
Molecular Weight	330.4229
Optical Activity	UNSPECIFIED
Defined Stereocenters	1 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

C[C@@H]1CCCN1CCC2=CC3=CC(=CC=C3O2)C4=CC=C(C=C4)C#N

InChI

InChIKey=KFHYZKCRXNRKRC-MRXNPFEDSA-N

InChI=1S/C22H22N2O/c1-16-3-2-11-24(16)12-10-21-14-20-13-19(8-9-22(20)25-21)18-6-4-17(15-23)5-7-18/h4-9,13-14,16H,2-3,10-12H2,1H3/t16-/m1/s1

HIDE SMILES / InChI

Molecular Formula	C22H22N2O
Molecular Weight	330.4229
Charge	0
Count

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

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/15608077
Curator's Comment: description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/15608078

ABT-239 is a selective, nonimidazole H3 receptor antagonist/inverse agonist, which was investigated by Abbott laboratory as a potential drug for treatment of a variety of cognitive disorders including attention deficit/hyperactivity disorder, Alzheimer's disease, and schizophrenia.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Histamine H3 receptor 44 Target ID: CHEMBL264 Sources: https://www.ncbi.nlm.nih.gov/pubmed/15608078	Antagonist 2778		9.4 null [pKi]

Conditions

Condition	Modality	Highest Phase	Product
Attention deficit hyperactivity disorder 68 Sources: https://www.ncbi.nlm.nih.gov/pubmed/15608077	Primary	Preclinical	Unknown Approved Use Unknown
Alzheimer’s disease 272 Sources: https://www.ncbi.nlm.nih.gov/pubmed/15608077	Primary	Preclinical	Unknown Approved Use Unknown
Schizophrenia 298 Sources: https://www.ncbi.nlm.nih.gov/pubmed/15608077	Primary	Preclinical	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed

Patents

Sample Use Guides

In Vivo Use Guide

oral: dog, monkey: 1 mg/kg; rat: 1, 10.30.60 mg/kg intravenous: dog, monkey: 1 mg/kg; rat: 1, 5 mg/kg

Route of Administration: Other

In Vitro Use Guide

ABT-239 is a potent H3 receptor antagonist at recombinant human and rat receptors, reversing agonist-induced changes in cAMP formation (pK(b) = 7.9 and 7.6, respectively), guanosine 5'-O-(3-[35S]thio) triphosphate ([35S]GTPgammaS) binding (pK(b) = 9.0 and 8.3, respectively), and calcium mobilization (human pK(b) = 7.9). ABT-239 also competitively reversed histamine-mediated inhibition of [3H]histamine release from rat brain cortical synaptosomes (pK(b) = 7.7) and agonist-induced inhibition of contractile responses in electric field stimulated guinea pig ileal segments (pA2 = 8.7). Additionally, ABT-239 is a potent inverse agonist, inhibiting constitutive [35S]GTPgammaS binding at both rat and human H3 receptors with respective pEC50 values of 8.9 and 8.2.

Substance Class	Chemical Created by `admin` on `Sat Dec 16 09:52:44 UTC 2023` Edited by `admin` on `Sat Dec 16 09:52:44 UTC 2023`
Record UNII	86H6B395PI
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

ABT-239

Common Name

English

BENZONITRILE, 4-(2-(2-((2R)-2-METHYL-1-PYRROLIDINYL)ETHYL)-5-BENZOFURANYL)-

Systematic Name

English

(R)-4-(2-(2-(2-METHYLPYRROLIDINYL)ETHYL)BENZOFURAN-5-YL)BENZONITRILE

Systematic Name

English

Code System Code Type Description

PUBCHEM

9818903