PANADIPLON

Details

Stereochemistry	ACHIRAL
Molecular Formula	C18H17N5O2
Molecular Weight	335.3599
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CC(C)N1C(=O)C2=C(N=CN2C3=C1C=CC=C3)C4=NOC(=N4)C5CC5

InChI

InChIKey=ZGEGOFCLSWVVKG-UHFFFAOYSA-N

InChI=1S/C18H17N5O2/c1-10(2)23-13-6-4-3-5-12(13)22-9-19-14(15(22)18(23)24)16-20-17(25-21-16)11-7-8-11/h3-6,9-11H,7-8H2,1-2H3

HIDE SMILES / InChI

Molecular Formula	C18H17N5O2
Molecular Weight	335.3599
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/1681085 | https://www.ncbi.nlm.nih.gov/pubmed/9881933

Panadiplon (previously known as U-78875) was investigated as a compound with a high affinity for the benzodiazepine receptors. It was studied as a unique anxiolytic agent with a minimum of central nervous system depression for the treatment of anxiety disorders. However, panadiplon was dropped from clinical development due to unexpected hepatic toxicity in human volunteers. It was shown that the drug-induced mitochondrial dysfunction in the liver, and suggested that this dysfunction could be attributed to the carboxylic acid metabolite.

Originator

Approval Year

PubMed

Title	Date	PubMed
Discriminative stimulus effects of panadiplon (U-78875), a partial agonist at the benzodiazepine site, in pentobarbital-trained rhesus monkeys.	2001 Feb 1	11164687
Metabolic, idiosyncratic toxicity of drugs: overview of the hepatic toxicity induced by the anxiolytic, panadiplon.	2001 May 16	11336974
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
Contribution of alpha 1GABAA and alpha 5GABAA receptor subtypes to the discriminative stimulus effects of ethanol in squirrel monkeys.	2005 May	15650112
Metabolomics in drug intolerance.	2009 Nov	20214587

Substance Class	Chemical Created by `admin` on `Fri Dec 15 15:33:47 UTC 2023` Edited by `admin` on `Fri Dec 15 15:33:47 UTC 2023`
Record UNII	V4PW0S7ZP7
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

PANADIPLON

Official Name

English

IMIDAZO(1,5-A)QUINOXALIN-4(5H)-ONE, 3-(5-CYCLOPROPYL-1,2,4-OXADIAZOL-3-YL)-5-(1-METHYLETHYL)-

Systematic Name

English

FG-10571

Code

English

panadiplon [INN]

Common Name

English

U-78875

Code

English

PANADIPLON [USAN]

Common Name

English

3-(5-CYCLOPROPYL-1,2,4-OXADIAZOL-3-YL)-5-(1-METHYLETHYL)-IMIDAZO(1,5-A)QUINOXALIN-4(5H)-ONE

Systematic Name

English

Classification Tree Code System Code

NCI_THESAURUS

C28197