Basic information
- CAS
133737-32-3- Standard SMILES
CC(C)CCC(=O)CC1c2ccccc2C(=O)N1c1ccc2ccc(Cl)nc2n1- InChIKey
HIUPRQPBWVEQJJ-UHFFFAOYSA-N- Molecular formula
- C23H22ClN3O2
- Average molar mass
- 407.9 g/mol
- Monoisotopic mass
- 407.1400546
Names & identifiers
- Preferred name
- Pagoclone
- IUPAC
- 2-(7-chloro-1,8-naphthyridin-2-yl)-3-(5-methyl-2-oxohexyl)-3H-isoindol-1-one
- English name
- Pagoclone
- Molecular formula
- C23H22ClN3O2
- Molecular weight
- 407.89
Names & synonyms
Pagoclone133737-32-3IP 456PagoclonaRP 62955RP-62955IP-456CI-10432-(7-chloro-1,8-naphthyridin-2-yl)-3-(5-methyl-2-oxohexyl)-2,3-dihydro-1H-isoindol-1-one38VAG2SA33DTXSID40869830IP456
Show more names
Pagoclone Labeled d42-(7-Chloro-2-naphthyridin-1,8-yl)-3-(5-methyl-2-oxohexyl)isoindolin-1-one2-(7-chloro-1,8-naphthyridine-2-yl)-3-(5-methyl-2-oxo-hexyl)-1-isoindolinone1H-Isoindol-1-one, 2-(7-chloro-1,8-naphthyridin-2-yl)-2,3-dihydro-3-(5-methyl-2-oxohexyl)-
RP62955pagoclonumRefChem:858293DTXCID908177402-(7-chloro-1.8-naphthyridin-2-yl)-2,3-dihydro-3-(5-methyl-2-oxohexyl)-1H-isoindol-1-one133737-48-1rac-Pagoclone2-(7-chloro-1,8-naphthyridin-2-yl)-3-(5-methyl-2-oxohexyl)isoindolin-1-one
Database identifiers
- CAS
133737-32-3、133737-48-1- PubChem CID
- 131664
- DTXSID
DTXSID40869830- ChEMBL
CHEMBL2104745- Nikkaji
- J481.630G
Properties
Computed structural properties
- XLogP
- 4.6
- Topological polar surface area
- 63.2 Ų
- Hydrogen bond donors
- 0
- Hydrogen bond acceptors
- 4
- Rotatable bonds
- 6
- Heavy atoms
- 29
- Formal charge
- 0
- Complexity
- 613
Physicochemical properties
- Melting point
- 173 · 173-179°C
- storage temp.
- -20 °C · -20°C Freezer
- solubility
- DMSO (Slightly), Methanol (Slightly)
- form
- Solid
- color
- Pale Orange to Pale Red
- FDA UNII
- 38 VAG2SA33 · 38VAG2SA33
Chemistry & industry
Pharmacology
Pharmacodynamics
Pagoclone was originally developed as an anti-anxiety drug, but never commercialised. It is a partial agonist acting at GABAA receptors in the brain. In contrast to zopiclone, pagoclone produces anxiolytic effects with little or no sedative or amnestic actions at low doses.
Mechanism of Action
Pagoclone is a subtype-selective drug which binds primarily to the alpha2/alpha3 subtypes of the GABAA receptor which are responsible for the anti-anxiety effects of these kind of drugs, but has relatively little efficacy at the alpha1 subtype which produces the sedative and memory loss effects.
Applications
DescriptionPagoclone is a new cyclopyrrolone partial agonist. In animal models of antianxiety activity, pagoclone is more potent than benzodiazepines, is less sedating, and has a high therapeutic index (Table 29–1). In clinical studies, pagoclone is well tolerated and does not appear to cause sedation or affect psychomotor or cognitive performance. In studies of volunteers, it has been shown that it does not cause withdrawal symptoms on abrupt discontinuation after 14 days. These factors all suggest that pagoclone may be an important drug for the future. It is currently entering dose-ranging and comparative studies involving patients with anxiety disorders, and in a pilot crossover study, it reduced panic attacks; adverse effects were not different from or more numerous than those reported with placebo (Sandford et al. 1998).
UsesAnti-anxiety agent.
UsesPagoclone is a partial GABAA agonist, used to reduce panic attacks and appear to decrease symptoms of generalized anxiety.
Upstream & downstream products
Upstream raw materials
Related reactions
10 records
Compound notes
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