ABECARNIL

Details

Stereochemistry	ACHIRAL
Molecular Formula	C24H24N2O4
Molecular Weight	404.4584
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

COCC1=C(N=CC2=C1C3=C(N2)C=CC(OCC4=CC=CC=C4)=C3)C(=O)OC(C)C

InChI

InChIKey=RLFKILXOLJVUNF-UHFFFAOYSA-N

InChI=1S/C24H24N2O4/c1-15(2)30-24(27)23-19(14-28-3)22-18-11-17(29-13-16-7-5-4-6-8-16)9-10-20(18)26-21(22)12-25-23/h4-12,15,26H,13-14H2,1-3H3

HIDE SMILES / InChI

Molecular Formula	C24H24N2O4
Molecular Weight	404.4584
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/1970361 | https://www.ncbi.nlm.nih.gov/pubmed/7908435 | https://www.ncbi.nlm.nih.gov/pubmed/9829018 | https://adisinsight.springer.com/drugs/800000651

Abecarnil (isopropyl 6-benzyloxy-4-methoxymethyl-beta-carboline-3-carboxylate) is a nonselective mixed full agonist/partial agonist at GABA(A) receptor subtypes. Abecarnil possesses anxiolytic and anticonvulsant properties. Abecarnil has been studied in the treatment of anxiety disorders however its development has been discontinued.

CNS Activity

Originator

Approval Year

PubMed

Title	Date	PubMed
Pharmacology of gamma-aminobutyric acidA receptor complex after the in vivo administration of the anxioselective and anticonvulsant beta-carboline derivative abecarnil.	1992 Dec	1361574
Antagonism of isoniazid-induced convulsions by abecarnil in mice tolerant to diazepam.	1995 Oct	8577786
Abecarnil, a beta-carboline derivative, does not exhibit anticonvulsant tolerance or withdrawal effects in mice.	1996 Nov	8938660
Use of negatively reinforcing electrical brain stimulation to detect conventional and nonconventional anxiolytics as well as an anxiogenic drug.	2001 Jan	11274705
Functional pharmacology of GABA(A) receptors containing the chicken brain gamma 4 subunit.	2001 May 4	11348623
Synthesis of beta- and gamma-carbolines by the palladium-catalyzed iminoannulation of alkynes.	2002 Dec 27	12492334
5-ethoxymethyl-7-fluoro-3-oxo-1,2,3,5-tetrahydrobenzo[4,5]imidazo[1,2a]pyridine-4-N-(2-fluorophenyl)carboxamide (RWJ-51204), a new nonbenzodiazepine anxiolytic.	2002 Nov	12388665
Psychopharmacology of anxiety disorders.	2002 Sep	22033867
Anxioselective compounds acting at the GABA(A) receptor benzodiazepine binding site.	2003 Aug	12871032
Discriminative stimulus effects of positive GABAA modulators and other anxiolytics, sedatives, and anticonvulsants in untreated and diazepam-treated monkeys.	2003 Jan	12490581
Generalised anxiety disorder.	2003 Jun	12967407
Treating generalised anxiety disorder.	2003 Mar 29	12663409
Neuroanatomical and pharmacological evidence for a functional interaction between GABAergic and NPY-Y1 transmission in the amygdala of Y1R/LacZ transgenic mice.	2004	15581397
Generalised anxiety disorder.	2004 Jun	15652060
Anxioselective anxiolytics: can less be more?	2004 Oct 1	15464051
The benzodiazepine binding site of GABA(A) receptors as a target for the development of novel anxiolytics.	2005 May	15926867
Anticipation and consumption of food each increase the concentration of neuroactive steroids in rat brain and plasma.	2006 Sep	16938341
The point mutation gamma 2F77I changes the potency and efficacy of benzodiazepine site ligands in different GABAA receptor subtypes.	2010 Jun 25	20303942

Substance Class	Chemical Created by `admin` on `Fri Dec 15 15:57:25 GMT 2023` Edited by `admin` on `Fri Dec 15 15:57:25 GMT 2023`
Record UNII	IZM1PNJ3JL
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

ABECARNIL

Official Name

English

ABECARNIL [MI]

Common Name

English

Abecarnil [WHO-DD]

Common Name

English

ZK-112119

Code

English

ABECARNIL [MART.]

Common Name

English

abecarnil [INN]

Common Name

English

ISOPROPYL 6-(BENZYLOXY)-4-(METHOXYMETHYL)-9H-PYRIDO(3,4-B)INDOLE-3-CARBOXYLATE

Systematic Name

English

9H-PYRIDO(3,4-B)INDOLE-3-CARBOXYLIC ACID, 4-(METHOXYMETHYL)-6-(PHENYLMETHOXY)-, 1-METHYLETHYL ESTER

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C28197