Pagoclone

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C23H22ClN3O2
Molecular Weight	407.893
Optical Activity	( + )
Defined Stereocenters	1 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CC(C)CCC(=O)C[C@@H]1N(C(=O)C2=CC=CC=C12)C3=CC=C4C=CC(Cl)=NC4=N3

InChI

InChIKey=HIUPRQPBWVEQJJ-IBGZPJMESA-N

InChI=1S/C23H22ClN3O2/c1-14(2)7-10-16(28)13-19-17-5-3-4-6-18(17)23(29)27(19)21-12-9-15-8-11-20(24)25-22(15)26-21/h3-6,8-9,11-12,14,19H,7,10,13H2,1-2H3/t19-/m0/s1

HIDE SMILES / InChI

Molecular Formula	C23H22ClN3O2
Molecular Weight	407.893
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/15926867
Curator's Comment: description was created based on several sources, including https://www.drugbank.ca/drugs/DB04903 | https://www.ncbi.nlm.nih.gov/pubmed/?term=18728798

Pagoclone is an anxiolytic agent from the cyclopyrrolone family, related to better-known drugs such as the sleeping medication zopiclone. It binds with the roughly equivalent high affinity (0.7–9.1 nM) to the benzodiazepine binding site of human GABAA receptors containing either a α1, α2, α3 or α5 subunit. It is a partial agonist at α1-, α2- and α5-containing GABAA receptors and a full agonist at receptors containing a α3 subunit. Pagoclone produces anxiolytic effects with little sedative or amnestic actions at low doses.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
GABA-A receptor; anion channel 202 Target ID: CHEMBL1907607 Sources: https://www.ncbi.nlm.nih.gov/pubmed/12871032	Partial Agonist 290

Conditions

Condition	Modality	Targets	Highest Phase	Product
Stuttering 1 Sources: https://clinicaltrials.gov/ct2/show/NCT00830154	Primary		Phase III 656	Unknown Approved Use Unknown
Premature ejaculation 3 Sources: https://clinicaltrials.gov/ct2/show/NCT00370981	Primary		Phase II 1132	Unknown Approved Use Unknown

Sourcing

Vendor/Aggregator	ID	URL
3B Scientific (Wuhan) Corp	3B2-1121	http://www.3bsc.com/index/pro_info.php?id=54837
AA Blocks	AA009ADA	https://www.aablocks.com/goods/Goods/detail?id=AA009ADA
AHH Chemical co.,ltd	MT-57621	http://www.ahhchemical.com/product/MT-57621.html
Angel Pharmatech	AG316726	http://www.angelpharmatech.com/133737-32-3.html
Axon MedChem	1594	https://www.axonmedchem.com/product/1594
BOC Sciences	133737-32-3	https://www.bocsci.com/pagoclone-cas-133737-32-3-item-57535.html
BioChemPartner	BCP28850	http://www.biochempartner.com/133737-32-3-BCP28850
BioSynth	J-690132	https://www.biosynth.com/en/products/all-products/products/J-690150.html
Chem Scene	CS-6427	http://www.chemscene.com/133737-32-3.html
ChemMol	99041250	http://www.chemmol.com/chemmol/99041250.html
ChemShuttle	169603	http://www.chemshuttle.com/catalogsearch/result/?q=133737-32-3&cat=
Chemspace	CSSB00000054307	https://chem-space.com/CSSB00000054307
Combi-Blocks	QV-6895	http://www.combi-blocks.com/cgi-bin/find.cgi?QV-6895
DC Chemicals	DC10292	http://www.dcchemicals.com/product_show-FITM.html
Debye Scientific	DA-45926	http://www.debyesci.com/cas_133737-32-3.html
Excenen	EX-A896	http://www.excenen.com/searchresultlist.php?id=133737-32-3
Finetech	FT-0700167	http://www.finetechnology-ind.com/prod/detail/pub/133737-32-3.html
Finetech	FT-0763408	http://www.finetechnology-ind.com/prod/detail/pub/133737-48-1.html
Lab Network	LN02195770	https://labnetwork.com/frontend-app/p/#!/moleculedetails/LN02195770
MedChem Express	HY-101665	https://www.medchemexpress.com/Pagoclone.html
MolPort	MolPort-005-932-428	https://www.molport.com/shop/molecule-link/MolPort-005-932-428
MuseChem	M110788	https://www.musechem.com/product/M110788.html
MuseChem	M116989	https://www.musechem.com/product/M116989.html
Smolecule	S538531	http://www.smolecule.com/products/s538531
Synblock Inc	SB17133	http://www.synblock.com/product/133737-32-3.html
Syntharise	Pagoclone	http://syntharise.com/products-page/pagoclone/pagoclone-250mg/
THE BioTek	bt-278632	https://www.thebiotek.com/product/inhibitors/bt-278632
abcr GmbH	AB460677	http://www.abcr.de/shop/en/AB460677
eNovation Chemicals	D548229	https://www.enovationchem.com/ProductDetails.asp?ProductID=D548229
iChemical	EBD4053815	http://www.ichemical.com/products/133737-48-1.html?utm_source=PubChem&utm_medium=website&utm_campaign=product%20catalogs

PubMed

Title	Date	PubMed
		252160283
Crossover trial of pagoclone and placebo in patients with DSM-IV panic disorder.	2001 Sep	11565630
Psychopharmacology of anxiety disorders.	2002 Sep	22033867
Anxioselective compounds acting at the GABA(A) receptor benzodiazepine binding site.	2003 Aug	12871032
Pagoclone Indevus.	2003 Jan	12625036
Gateways to clinical trials.	2004 Apr	15148527
A proof-of-concept study using [11C]flumazenil PET to demonstrate that pagoclone is a partial agonist.	2005 Aug	15986186
The benzodiazepine binding site of GABA(A) receptors as a target for the development of novel anxiolytics.	2005 May	15926867
Evaluation of the abuse potential of pagoclone, a partial GABAA agonist.	2006 Jun	16702891
The in vivo properties of pagoclone in rat are most likely mediated by 5'-hydroxy pagoclone.	2006 May	16430927
Gateways to clinical trials.	2007 Mar	17440629
Preliminary effects of pagoclone, a partial GABA(A) agonist, on neuropsychological performance.	2008 Feb	18728798
Exploratory randomized clinical study of pagoclone in persistent developmental stuttering: the EXamining Pagoclone for peRsistent dEvelopmental Stuttering Study.	2010 Feb	20075648
Gateways to clinical trials.	2010 Jun	20664824
Comments on article by Maguire et al: pagoclone trial: questionable findings for stuttering treatment.	2010 Oct	20841975

Patents

Sample Use Guides

In Vivo Use Guide

Subjects received 0.15 mg (low), 0.30 mg (medium), or 0.60 mg (high) oral doses of pagoclone every 12 hours for seven days with a seven-day washout between periods.

Route of Administration: Oral

In Vitro Use Guide

Pagoclone binds with roughly equivalent high affinity (0.7–9.1 nM) to the benzodiazepine binding site of human GABAA receptors containing either an α1, α2, α3 or α5 subunit.

Substance Class	Chemical Created by `admin` on `Fri Dec 15 16:47:13 GMT 2023` Edited by `admin` on `Fri Dec 15 16:47:13 GMT 2023`
Record UNII	38VAG2SA33
Record Status	`Validated (UNII)`
Record Version

Download

Name

Type

Language

Pagoclone

Official Name

English

pagoclone [INN]

Common Name

English

PAGOCLONE [USAN]

Common Name

English

1H-Isoindol-1-one, 2-(7-chloro-1,8-naphthyridin-2-yl)-2,3-dihydro-3-(5-methyl-2-oxohexyl)-, (3S)-

Systematic Name

English

(3S)-2-(7-Chloro-1,8-naphthyridin-2-yl)-2,3-dihydro-3-(5-methyl-2-oxohexyl)-1H-isoindol-1-one

Systematic Name

English

CI-1043

Code

English

IP-456

Code

English

RP62955

Code

English

PAGOCLONE [MI]

Common Name

English

(+)-2-(7-chloro-1,8-naphthyridin-2-yl)-3S-(5- methyl-2-oxohexyl)-1-isoindolinone

Systematic Name

English

IP456

Code

English

RP-62955

Code

English

1H-Isoindol-1-one, 2-(7-chloro-1,8-naphthyridin-2-yl)-2,3-dihydro-3-(5-methyl-2-oxohexyl)-, (+)-

Systematic Name

English

Classification Tree Code System Code

NCI_THESAURUS

C28197