Identification

Name
Adipiplon
Accession Number
DB06579
Type
Small Molecule
Groups
Investigational
Description

Adipiplon (NG2-73) is an anxiolytic drug developed by Neurogen Corporation. It has similar effects to benzodiazepine drugs, but is structurally distinct and so is classed as a nonbenzodiazepine anxiolytic.

Structure
Thumb
Synonyms
Not Available
External IDs
NG2-73
Categories
UNII
OPL214POJ1
CAS number
840486-93-3
Weight
Average: 351.389
Monoisotopic: 351.160771771
Chemical Formula
C18H18FN7
InChI Key
UAMAIHOEGLEXSV-UHFFFAOYSA-N
InChI
InChI=1S/C18H18FN7/c1-3-5-13-15(22-11-26-17(13)23-12(2)24-26)10-25-9-8-21-18(25)16-14(19)6-4-7-20-16/h4,6-9,11H,3,5,10H2,1-2H3
IUPAC Name
3-fluoro-2-[1-({2-methyl-8-propyl-[1,2,4]triazolo[1,5-c]pyrimidin-7-yl}methyl)-1H-imidazol-2-yl]pyridine
SMILES
CCCC1=C(CN2C=CN=C2C2=C(F)C=CC=N2)N=CN2N=C(C)N=C12

Pharmacology

Indication

Investigated for use/treatment in insomnia and sleep disorders.

Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
AGABA-A receptor (benzodiazepine site)
partial agonist
Human
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
Toxicity
Not Available
Affected organisms
Not Available
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteraction
2,5-Dimethoxy-4-ethylthioamphetamineThe risk or severity of adverse effects can be increased when Adipiplon is combined with 2,5-Dimethoxy-4-ethylthioamphetamine.
3,4-MethylenedioxyamphetamineThe risk or severity of adverse effects can be increased when 3,4-Methylenedioxyamphetamine is combined with Adipiplon.
4-Bromo-2,5-dimethoxyamphetamineThe risk or severity of adverse effects can be increased when 4-Bromo-2,5-dimethoxyamphetamine is combined with Adipiplon.
4-MethoxyamphetamineThe risk or severity of adverse effects can be increased when 4-Methoxyamphetamine is combined with Adipiplon.
5-methoxy-N,N-dimethyltryptamineThe risk or severity of adverse effects can be increased when Adipiplon is combined with 5-methoxy-N,N-dimethyltryptamine.
7-NitroindazoleThe risk or severity of adverse effects can be increased when 7-Nitroindazole is combined with Adipiplon.
AcepromazineThe risk or severity of adverse effects can be increased when Acepromazine is combined with Adipiplon.
AceprometazineThe risk or severity of adverse effects can be increased when Aceprometazine is combined with Adipiplon.
AcetazolamideThe risk or severity of adverse effects can be increased when Acetazolamide is combined with Adipiplon.
AcetophenazineThe risk or severity of adverse effects can be increased when Acetophenazine is combined with Adipiplon.
Food Interactions
Not Available

References

General References
Not Available
External Links
PubChem Compound
11198924
PubChem Substance
347827777
ChemSpider
9373993
ChEMBL
CHEMBL2103791
Wikipedia
Adipiplon

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
2TerminatedTreatmentPrimary Insomnia1

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
PropertyValueSource
Water Solubility0.031 mg/mLALOGPS
logP2.53ALOGPS
logP3.24ChemAxon
logS-4ALOGPS
pKa (Strongest Basic)2.96ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area73.79 Å2ChemAxon
Rotatable Bond Count5ChemAxon
Refractivity116.55 m3·mol-1ChemAxon
Polarizability35.5 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Taxonomy

Description
This compound belongs to the class of organic compounds known as triazolopyrimidines. These are polycyclic aromatic compounds containing triazole ring fused to a pyrimidine ring. Triazole is a five-membered ring consisting of two carbon atoms and three nitrogen atoms. Pyrimidine is a 6-membered ring consisting of four carbon atoms and two nitrogen centers at the 1- and 3- ring positions.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Triazolopyrimidines
Sub Class
Not Available
Direct Parent
Triazolopyrimidines
Alternative Parents
Pyrimidines and pyrimidine derivatives / Pyridines and derivatives / N-substituted imidazoles / Aryl fluorides / Triazoles / Heteroaromatic compounds / Azacyclic compounds / Organonitrogen compounds / Organofluorides / Hydrocarbon derivatives
Substituents
Triazolopyrimidine / Aryl fluoride / Aryl halide / N-substituted imidazole / Pyridine / Pyrimidine / Triazole / Imidazole / Azole / 1,2,4-triazole
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
Not Available

Targets

Kind
Protein group
Organism
Human
Pharmacological action
Yes
Actions
Partial agonist
General Function
Inhibitory extracellular ligand-gated ion channel activity
Specific Function
Component of the heteropentameric receptor for GABA, the major inhibitory neurotransmitter in the vertebrate brain. Functions also as histamine receptor and mediates cellular responses to histamine...

Components:
References
  1. Development of Subtype-Selective GABAA Receptor Compounds for the Treatment of Anxiety, Sleep Disorders and Epilepsy [Link]

Drug created on March 19, 2008 10:37 / Updated on November 02, 2018 06:17