Bradanicline

Identification

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Name
Bradanicline
Accession Number
DB06090
Type
Small Molecule
Groups
Investigational
Description

Bradanicline, a novel small molecule that modulates the activity of the neuronal nicotinic receptor (NNR) subtype known as alpha7(α7). Bradanicline belongs to a new class of drugs for the treatment of central nervous system diseases and disorders.

Structure
Thumb
Synonyms
Not Available
External IDs
TC 5619 / TC-5619
Product Ingredients
IngredientUNIICASInChI Key
Bradanicline hydrochlorideD266D7TY9B1111941-90-2ISPRRZDPZDVHLE-OZYANKIXSA-N
Bradanicline tosylate3821HT7KCR1111942-11-0YDJXUVIIXSFVOJ-OZYANKIXSA-N
Categories
UNII
UM3821998K
CAS number
639489-84-2
Weight
Average: 361.445
Monoisotopic: 361.179026993
Chemical Formula
C22H23N3O2
InChI Key
OXKRFEWMSWPKKV-GHTZIAJQSA-N
InChI
InChI=1S/C22H23N3O2/c26-22(20-13-17-5-1-2-6-19(17)27-20)24-21-16-7-10-25(11-8-16)18(21)12-15-4-3-9-23-14-15/h1-6,9,13-14,16,18,21H,7-8,10-12H2,(H,24,26)/t18-,21+/m0/s1
IUPAC Name
N-[(2S,3R)-2-[(pyridin-3-yl)methyl]-1-azabicyclo[2.2.2]octan-3-yl]-1-benzofuran-2-carboxamide
SMILES
[H][C@@]1(CC2=CC=CN=C2)N2CCC(CC2)[C@@]1([H])NC(=O)C1=CC2=C(O1)C=CC=C2

Pharmacology

Indication

Investigated for use/treatment in neurologic disorders.

Pharmacodynamics
Not Available
Mechanism of action

Bradanicline, a novel small molecule that modulates the activity of the neuronal nicotinic receptor (NNR) subtype known as alpha7(α7). The α7 NNR is associated with a variety of biological functions. In particular, the α7 NNR has been shown in animal studies to be an essential regulator of both inflammation arising from injury or infection and cognitive functions. α7 NNR plays a role in protecting neuronal cells from deterioration and death, a process known as neuroprotection.

TargetActionsOrganism
UAlpha-7 nicotinic cholinergic receptor subunitNot AvailableHumans
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
Not Available
Food Interactions
Not Available

References

General References
Not Available
External Links
PubChem Compound
25147644
PubChem Substance
175427053
ChemSpider
26366935
BindingDB
50393247
ChEMBL
CHEMBL1258006
Wikipedia
Bradanicline

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
1CompletedDiagnosticAlzheimer's Disease (AD)1
2CompletedTreatmentAttention Deficit Disorder With Hyperactivity (ADHD)1
2CompletedTreatmentCognitive Dysfunctions / Negative Symptoms / Schizophrenic Disorders1
2CompletedTreatmentCognitive Dysfunctions / Schizophrenic Disorders1
2RecruitingTreatmentChronic Cough (CC)1

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 Solubility0.0559 mg/mLALOGPS
logP2.74ALOGPS
logP2.36ChemAxon
logS-3.8ALOGPS
pKa (Strongest Acidic)14.57ChemAxon
pKa (Strongest Basic)7.44ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area58.37 Å2ChemAxon
Rotatable Bond Count4ChemAxon
Refractivity103.6 m3·mol-1ChemAxon
Polarizability40.05 Å3ChemAxon
Number of Rings5ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9929
Blood Brain Barrier+0.9384
Caco-2 permeable-0.5681
P-glycoprotein substrateSubstrate0.6162
P-glycoprotein inhibitor IInhibitor0.7817
P-glycoprotein inhibitor IIInhibitor0.87
Renal organic cation transporterInhibitor0.5813
CYP450 2C9 substrateNon-substrate0.8777
CYP450 2D6 substrateNon-substrate0.5
CYP450 3A4 substrateSubstrate0.6271
CYP450 1A2 substrateInhibitor0.5739
CYP450 2C9 inhibitorInhibitor0.5
CYP450 2D6 inhibitorInhibitor0.7462
CYP450 2C19 inhibitorInhibitor0.7294
CYP450 3A4 inhibitorNon-inhibitor0.6073
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.9138
Ames testNon AMES toxic0.6482
CarcinogenicityNon-carcinogens0.9429
BiodegradationNot ready biodegradable0.9964
Rat acute toxicity2.5836 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.7514
hERG inhibition (predictor II)Inhibitor0.6864
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

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 benzofurans. These are organic compounds containing a benzene ring fused to a furan. Furan is a five-membered aromatic ring with four carbon atoms and one oxygen atom.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Benzofurans
Sub Class
Not Available
Direct Parent
Benzofurans
Alternative Parents
2-heteroaryl carboxamides / Quinuclidines / Furoic acid and derivatives / Aralkylamines / Benzenoids / Pyridines and derivatives / Piperidines / Heteroaromatic compounds / Amino acids and derivatives / Trialkylamines
show 7 more
Substituents
Benzofuran / 2-heteroaryl carboxamide / Furoic acid or derivatives / Quinuclidine / Aralkylamine / Piperidine / Pyridine / Benzenoid / Furan / Heteroaromatic compound
show 17 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
Not Available

Targets

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Not Available
Specific Function
Not Available
Gene Name
CHRNA7
Uniprot ID
Q693P7
Uniprot Name
Alpha-7 nicotinic cholinergic receptor subunit
Molecular Weight
2987.635 Da

Drug created on November 18, 2007 11:29 / Updated on June 04, 2019 06:21