Explore a selection of our essential drug information below, or:
Identification
- Generic Name
- Pagoclone
- DrugBank Accession Number
- DB04903
- Background
Pagoclone is an anxiolytic drug from the cyclopyrrolone family, which is related to other more well known drugs such as the sleeping medication zopiclone. It is one of a relatively recently developed class of medicines known as the nonbenzodiazepines, which have similar effects to the older benzodiazepine group, but with quite different chemical structures.
- Type
- Small Molecule
- Groups
- Investigational
- Structure
Structure for Pagoclone (DB04903)
- Weight
- Average: 407.893
Monoisotopic: 407.14005467 - Chemical Formula
- C23H22ClN3O2
- Synonyms
- Pagoclone
Pharmacology
- Indication
For the potential treatment of panic and anxiety disorders.
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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.
Target Actions Organism AGamma-aminobutyric acid receptor subunit gamma-3 modulatorHumans UGamma-aminobutyric acid receptor subunit alpha-2 Not Available Humans UGamma-aminobutyric acid receptor subunit alpha-3 Not Available Humans - Absorption
Not Available
- Volume of distribution
Not Available
- Protein binding
Not Available
- Metabolism
- Not Available
- Route of elimination
Not Available
- Half-life
Not Available
- Clearance
Not Available
- Adverse Effects
Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.- Toxicity
Not Available
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs
- Not Available
Interactions
- Drug Interactions
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Drug Interaction Integrate drug-drug
interactions in your software1,2-Benzodiazepine The risk or severity of CNS depression can be increased when Pagoclone is combined with 1,2-Benzodiazepine. Acetazolamide The risk or severity of CNS depression can be increased when Acetazolamide is combined with Pagoclone. Acetophenazine The risk or severity of CNS depression can be increased when Acetophenazine is combined with Pagoclone. Agomelatine The risk or severity of CNS depression can be increased when Pagoclone is combined with Agomelatine. Alfentanil The risk or severity of CNS depression can be increased when Alfentanil is combined with Pagoclone. - Food Interactions
- Not Available
Categories
- Drug Categories
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as naphthyridines. These are compounds containing a naphthyridine moiety, a naphthalene in which a carbon atom has been replaced by a nitrogen in each of the two rings. The naphthyridine skeleton can also be described as an assembly two fused pyridine rings, which do not share their nitrogen atom.
- Kingdom
- Organic compounds
- Super Class
- Organoheterocyclic compounds
- Class
- Diazanaphthalenes
- Sub Class
- Naphthyridines
- Direct Parent
- Naphthyridines
- Alternative Parents
- Isoindolones / Isoindoles / 2-halopyridines / Aryl chlorides / Benzenoids / Imidolactams / Tertiary carboxylic acid amides / Heteroaromatic compounds / Lactams / Ketones show 6 more
- Substituents
- 2-halopyridine / Aromatic heteropolycyclic compound / Aryl chloride / Aryl halide / Azacycle / Benzenoid / Carbonyl group / Carboxamide group / Carboxylic acid derivative / Heteroaromatic compound show 19 more
- Molecular Framework
- Aromatic heteropolycyclic compounds
- External Descriptors
- Not Available
- Affected organisms
- Humans and other mammals
Chemical Identifiers
- UNII
- 38VAG2SA33
- CAS number
- 133737-32-3
- InChI Key
- HIUPRQPBWVEQJJ-UHFFFAOYSA-N
- InChI
- 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
- IUPAC Name
- 2-(7-chloro-1,8-naphthyridin-2-yl)-3-(5-methyl-2-oxohexyl)-2,3-dihydro-1H-isoindol-1-one
- SMILES
- CC(C)CCC(=O)CC1N(C(=O)C2=CC=CC=C12)C1=NC2=C(C=CC(Cl)=N2)C=C1
References
- General References
- de Wit H, Vicini L, Haig GM, Hunt T, Feltner D: Evaluation of the abuse potential of pagoclone, a partial GABAA agonist. J Clin Psychopharmacol. 2006 Jun;26(3):268-73. [Article]
- Atack JR, Pike A, Marshall G, Stanley J, Lincoln R, Cook SM, Lewis RT, Blackaby WP, Goodacre SC, McKernan RM, Dawson GR, Wafford KA, Reynolds DS: The in vivo properties of pagoclone in rat are most likely mediated by 5'-hydroxy pagoclone. Neuropharmacology. 2006 May;50(6):677-89. Epub 2006 Jan 20. [Article]
- Bateson A: Pagoclone Indevus. Curr Opin Investig Drugs. 2003 Jan;4(1):91-5. [Article]
- Sandford JJ, Forshall S, Bell C, Argyropoulos S, Rich A, D'Orlando KJ, Gammans RE, Nutt DJ: Crossover trial of pagoclone and placebo in patients with DSM-IV panic disorder. J Psychopharmacol. 2001 Sep;15(3):205-8. [Article]
- External Links
- PubChem Compound
- 131664
- PubChem Substance
- 175426895
- ChemSpider
- 116335
- ChEMBL
- CHEMBL2104745
- Wikipedia
- Pagoclone
Clinical Trials
- Clinical Trials
Clinical Trial & Rare Diseases Add-on Data Package
Explore 4,000+ rare diseases, orphan drugs & condition pairs, clinical trial why stopped data, & more. Preview package Phase Status Purpose Conditions Count Start Date Why Stopped 100+ additional columns Unlock 175K+ rows when you subscribe.View sample data2 Completed Treatment Persistent Developmental Stuttering 2 somestatus stop reason just information to hide 2 Completed Treatment Premature Ejaculation 1 somestatus stop reason just information to hide 2, 3 Completed Treatment Childhood-Onset Fluency Disorder (Stuttering) 1 somestatus stop reason just information to hide
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
- Not Available
- Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
- Not Available
- Predicted Properties
Property Value Source Water Solubility 0.00655 mg/mL ALOGPS logP 4.6 ALOGPS logP 5.35 Chemaxon logS -4.8 ALOGPS pKa (Strongest Acidic) 12.33 Chemaxon pKa (Strongest Basic) -2.6 Chemaxon Physiological Charge 0 Chemaxon Hydrogen Acceptor Count 4 Chemaxon Hydrogen Donor Count 0 Chemaxon Polar Surface Area 63.16 Å2 Chemaxon Rotatable Bond Count 6 Chemaxon Refractivity 115.16 m3·mol-1 Chemaxon Polarizability 43.42 Å3 Chemaxon Number of Rings 4 Chemaxon Bioavailability 1 Chemaxon Rule of Five No Chemaxon Ghose Filter Yes Chemaxon Veber's Rule No Chemaxon MDDR-like Rule Yes Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 1.0 Blood Brain Barrier + 0.9678 Caco-2 permeable + 0.5426 P-glycoprotein substrate Non-substrate 0.5956 P-glycoprotein inhibitor I Inhibitor 0.8644 P-glycoprotein inhibitor II Inhibitor 0.9725 Renal organic cation transporter Non-inhibitor 0.6472 CYP450 2C9 substrate Non-substrate 0.6975 CYP450 2D6 substrate Non-substrate 0.7898 CYP450 3A4 substrate Substrate 0.7806 CYP450 1A2 substrate Non-inhibitor 0.5159 CYP450 2C9 inhibitor Non-inhibitor 0.5787 CYP450 2D6 inhibitor Non-inhibitor 0.7857 CYP450 2C19 inhibitor Non-inhibitor 0.5737 CYP450 3A4 inhibitor Non-inhibitor 0.8476 CYP450 inhibitory promiscuity High CYP Inhibitory Promiscuity 0.7115 Ames test Non AMES toxic 0.6879 Carcinogenicity Non-carcinogens 0.8244 Biodegradation Not ready biodegradable 0.9922 Rat acute toxicity 2.3601 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9273 hERG inhibition (predictor II) Non-inhibitor 0.5166
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS splash10-0a4i-0001900000-2593a095985974ad87a2 Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS splash10-0a4i-1111900000-4f3db16b2a29eee2da9b Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS splash10-0a4m-5109500000-f4103af74b79f2daa473 Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS splash10-0a4i-2069600000-a76565516f116fbd48fa Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS splash10-0f8a-6469000000-dcd7cce4d8c0c2d4425d Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS splash10-0ul0-7395100000-c28f16eda72bab0ff3aa Predicted 1H NMR Spectrum 1D NMR Not Applicable Predicted 13C NMR Spectrum 1D NMR Not Applicable - Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 197.3823 predictedDeepCCS 1.0 (2019) [M+H]+ 199.77785 predictedDeepCCS 1.0 (2019) [M+Na]+ 205.92183 predictedDeepCCS 1.0 (2019)
Targets
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- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Modulator
- General Function
- Gamma subunit of the heteropentameric ligand-gated chloride channel gated by gamma-aminobutyric acid (GABA), a major inhibitory neurotransmitter in the brain (By similarity). GABA-gated chloride channels, also named GABA(A) receptors (GABAAR), consist of five subunits arranged around a central pore and contain GABA active binding site(s) located at the alpha and beta subunit interface(s) (By similarity). When activated by GABA, GABAARs selectively allow the flow of chloride across the cell membrane down their electrochemical gradient (By similarity)
- Specific Function
- Gaba-a receptor activity
- Gene Name
- GABRG3
- Uniprot ID
- Q99928
- Uniprot Name
- Gamma-aminobutyric acid receptor subunit gamma-3
- Molecular Weight
- 54288.16 Da
References
- Zhou Y, Zhang Y, Zhao D, Yu X, Shen X, Zhou Y, Wang S, Qiu Y, Chen Y, Zhu F: TTD: Therapeutic Target Database describing target druggability information. Nucleic Acids Res. 2024 Jan 5;52(D1):D1465-D1477. doi: 10.1093/nar/gkad751. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Alpha subunit of the heteropentameric ligand-gated chloride channel gated by gamma-aminobutyric acid (GABA), a major inhibitory neurotransmitter in the brain (PubMed:10449790, PubMed:29961870, PubMed:31032849). GABA-gated chloride channels, also named GABA(A) receptors (GABAAR), consist of five subunits arranged around a central pore and contain GABA active binding site(s) located at the alpha and beta subunit interfaces (By similarity). When activated by GABA, GABAARs selectively allow the flow of chloride anions across the cell membrane down their electrochemical gradient (PubMed:10449790). Chloride influx into the postsynaptic neuron following GABAAR opening decreases the neuron ability to generate a new action potential, thereby reducing nerve transmission (By similarity). The alpha-2 subunit exhibits synaptogenic activity together with beta-2 and very little to no activity together with beta-3, the gamma-2 subunit being necessary but not sufficient to induce rapid synaptic contacts formation (By similarity)
- Specific Function
- Benzodiazepine receptor activity
- Gene Name
- GABRA2
- Uniprot ID
- P47869
- Uniprot Name
- Gamma-aminobutyric acid receptor subunit alpha-2
- Molecular Weight
- 51325.85 Da
References
- Atack JR, Pike A, Marshall G, Stanley J, Lincoln R, Cook SM, Lewis RT, Blackaby WP, Goodacre SC, McKernan RM, Dawson GR, Wafford KA, Reynolds DS: The in vivo properties of pagoclone in rat are most likely mediated by 5'-hydroxy pagoclone. Neuropharmacology. 2006 May;50(6):677-89. Epub 2006 Jan 20. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Alpha subunit of the heteropentameric ligand-gated chloride channel gated by gamma-aminobutyric acid (GABA), a major inhibitory neurotransmitter in the brain (PubMed:16412217, PubMed:29053855). GABA-gated chloride channels, also named GABA(A) receptors (GABAAR), consist of five subunits arranged around a central pore and contain GABA active binding site(s) located at the alpha and beta subunit interface(s) (By similarity). When activated by GABA, GABAARs selectively allow the flow of chloride anions across the cell membrane down their electrochemical gradient (PubMed:16412217, PubMed:29053855). Chloride influx into the postsynaptic neuron following GABAAR opening decreases the neuron ability to generate a new action potential, thereby reducing nerve transmission (PubMed:16412217, PubMed:29053855)
- Specific Function
- Benzodiazepine receptor activity
- Gene Name
- GABRA3
- Uniprot ID
- P34903
- Uniprot Name
- Gamma-aminobutyric acid receptor subunit alpha-3
- Molecular Weight
- 55164.055 Da
References
- Atack JR, Pike A, Marshall G, Stanley J, Lincoln R, Cook SM, Lewis RT, Blackaby WP, Goodacre SC, McKernan RM, Dawson GR, Wafford KA, Reynolds DS: The in vivo properties of pagoclone in rat are most likely mediated by 5'-hydroxy pagoclone. Neuropharmacology. 2006 May;50(6):677-89. Epub 2006 Jan 20. [Article]
Drug created at October 21, 2007 22:23 / Updated at August 26, 2024 19:23