CAS 639489-84-2 Bradanicline (HCID 25147644)

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Basic information

CAS: 639489-84-2
Standard SMILES: O=C(N[C@@H]1C2CCN(CC2)[C@H]1Cc1cccnc1)c1cc2ccccc2o1
InChIKey: OXKRFEWMSWPKKV-GHTZIAJQSA-N
Molecular formula: C22H23N3O2
Average molar mass: 361.4 g/mol
Monoisotopic mass: 361.17902698

Overview

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.

Names & identifiers

Preferred name: Bradanicline
IUPAC: N-[(2S,3R)-2-(pyridin-3-ylmethyl)-1-azabicyclo[2.2.2]octan-3-yl]-1-benzofuran-2-carboxamide
English name: TC 5619
Molecular formula: C22H23N3O2
Molecular weight: 361.44

Names & synonyms

Bradanicline639489-84-2TC-5619BradaniclinaTC 5619ATA-101Bradanicline [USAN:INN]N-[(2S,3R)-2-(pyridin-3-ylmethyl)-1-azabicyclo[2.2.2]octan-3-yl]-1-benzofuran-2-carboxamideBRADANICLINE [INN]BRADANICLINE [USAN]UM3821998KBRADANICLINE [WHO-DD]

Show more names

Bradanicline (TC-5619)N-((2S,3R)-2-(pyridin-3-ylmethyl)quinuclidin-3-yl)benzofuran-2-carboxamide

ATA101DTXSID402137782-Benzofurancarboxamide, N-((2S,3R)-2-(3-pyridinylmethyl)-1-azabicyclo(2.2.2)oct-3-yl)-compound 7a [PMID 23126648]compound 7a (PMID 23126648)N-[(2S,3R)-2-[(pyridin-3-yl)methyl]-1-azabicyclo[2.2.2]octan-3-yl]-1-benzofuran-2-carboxamidebradaniclinum2-Benzofurancarboxamide, N-[(2S,3R)-2-(3-pyridinylmethyl)-1-azabicyclo[2.2.2]oct-3-yl]-

Database identifiers

CAS: 639489-84-2
PubChem CID: 25147644
DTXSID: DTXSID40213778
ChEMBL: CHEMBL1258006
UNII: UM3821998K

Properties

Computed structural properties

XLogP: 3.5
Topological polar surface area: 58.4 Å²
Hydrogen bond donors: 1
Hydrogen bond acceptors: 4
Rotatable bonds: 4
Heavy atoms: 27
Formal charge: 0
Complexity: 534

Experimental & physicochemical properties

DrugsPharmaceuticals -> Listed in ZINC15

Physicochemical properties

Boiling point: 592.3 · 592.3±35.0 °C(Predicted)
Density: 1.28 · 1.28±0.1 g/cm3(Predicted)
storage temp.: -20 °C · Store at -20°C
solubility: 25 mg/mL · DMSO : 25 mg/mL (69.17 mM; ultrasonic and warming and heat to 60°C)
form: Solid
pka: 13.37 · 13.37±0.40(Predicted)
color: White to off-white
FDA UNII: 3821998 K · UM3821998K

Chemistry & industry

Pharmacology

Mechanism of Action · 1 item

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.

Applications

UsesBradanicline is a highly selective α7 nicotinic acetylcholine receptor (nAChR) agonist (humanα7 nAChR: EC50=17 nM; Ki= 1.4 nM). Bradanicline is used for the research of cognitive disorders[1][2].