Bradanicline

Identification

Generic Name
Bradanicline
DrugBank Accession Number
DB06090
Background

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.

Type
Small Molecule
Groups
Investigational
Structure
Weight
Average: 361.445
Monoisotopic: 361.179026993
Chemical Formula
C22H23N3O2
Synonyms
  • Bradanicline
External IDs
  • TC 5619
  • TC-5619

Pharmacology

Indication

Investigated for use/treatment in neurologic disorders.

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Contraindications & Blackbox Warnings
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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
UNeuronal acetylcholine receptor subunit alpha-7Not 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

Adverse Effects
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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.
Not Available
Food Interactions
Not Available

Products

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Product Ingredients
IngredientUNIICASInChI Key
Bradanicline hydrochlorideD266D7TY9B1111941-90-2ISPRRZDPZDVHLE-OZYANKIXSA-N
Bradanicline tosylate3821HT7KCR1111942-11-0YDJXUVIIXSFVOJ-OZYANKIXSA-N

Categories

Drug Categories
Chemical TaxonomyProvided by Classyfire
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
2-heteroaryl carboxamide / Amine / Amino acid or derivatives / Aralkylamine / Aromatic heteropolycyclic compound / Azacycle / Benzenoid / Benzofuran / Carboxamide group / Carboxylic acid derivative
show 17 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
Not Available
Affected organisms
Not Available

Chemical Identifiers

UNII
UM3821998K
CAS number
639489-84-2
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

References

General References
Not Available
PubChem Compound
25147644
PubChem Substance
175427053
ChemSpider
26366935
BindingDB
50393247
ChEMBL
CHEMBL1258006
ZINC
ZINC000064540331
Wikipedia
Bradanicline

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
2CompletedTreatmentAttention Deficit Hyperactivity Disorder (ADHD)2
2CompletedTreatmentChronic Cough (CC)1
2CompletedTreatmentCognitive Dysfunctions / Negative Symptoms / Schizophrenia1
2CompletedTreatmentCognitive Dysfunctions / Schizophrenia1
1CompletedDiagnosticAlzheimer's Disease (AD)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/MSsplash10-03di-0009000000-4663a1c76238165e5dd5
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-03di-0109000000-21626bdaa806bd415ce9
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-03di-0029000000-485cb9cef5ef425b6b42
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-03dl-2539000000-c36877c6c298b00e58b6
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-00kg-5911000000-e26eca8e3836b054781f
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-014l-3913000000-9d7fa0ad7e62bcc6bd30
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-197.2872334
predicted
DarkChem Lite v0.1.0
[M-H]-180.40456
predicted
DeepCCS 1.0 (2019)
[M+H]+198.3178334
predicted
DarkChem Lite v0.1.0
[M+H]+182.80013
predicted
DeepCCS 1.0 (2019)
[M+Na]+198.4652334
predicted
DarkChem Lite v0.1.0
[M+Na]+188.71265
predicted
DeepCCS 1.0 (2019)

Targets

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Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Toxic substance binding
Specific Function
After binding acetylcholine, the AChR responds by an extensive change in conformation that affects all subunits and leads to opening of an ion-conducting channel across the plasma membrane. The cha...
Gene Name
CHRNA7
Uniprot ID
P36544
Uniprot Name
Neuronal acetylcholine receptor subunit alpha-7
Molecular Weight
56448.925 Da

Drug created at November 18, 2007 18:29 / Updated at February 13, 2024 02:57