bradanicline   Click here for help

GtoPdb Ligand ID: 3969

Synonyms: ATA-101 | ATA101 | compound 7a [PMID 23126648] [4] | TC-5619 | TC5619
Compound class: Synthetic organic
Comment: Bradanicline is an investigational agonist of neuronal α7 subunit-containing nicotinic acetylcholine receptors [4].
Click here for help
2D Structure
Click here for help
Click here for structure editor
Physico-chemical Properties
Click here for help
Hydrogen bond acceptors 4
Hydrogen bond donors 1
Rotatable bonds 5
Topological polar surface area 58.37
Molecular weight 361.18
XLogP 2.55
No. Lipinski's rules broken 0
Click here for help
Canonical SMILES O=C(c1cc2c(o1)cccc2)NC1C2CCN(C1Cc1cccnc1)CC2
Isomeric SMILES O=C(c1cc2c(o1)cccc2)N[C@@H]1C2CCN([C@H]1Cc1cccnc1)CC2
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
1. Canning BJ, Liu Q, Tao M, DeVita R, Perelman M, Hay DW, Dicpinigaitis PV, Liang J. (2022)
Evidence for Alpha7 Nicotinic Receptor Activation During the Cough Suppressing Effects Induced by Nicotine and Identification of ATA-101 as a Potential Novel Therapy for the Treatment of Chronic Cough.
J Pharmacol Exp Ther, 380 (2): 94-103. [PMID:34782407]
2. Hauser TA, Kucinski A, Jordan KG, Gatto GJ, Wersinger SR, Hesse RA, Stachowiak EK, Stachowiak MK, Papke RL, Lippiello PM et al.. (2009)
TC-5619: an alpha7 neuronal nicotinic receptor-selective agonist that demonstrates efficacy in animal models of the positive and negative symptoms and cognitive dysfunction of schizophrenia.
Biochem Pharmacol, 78 (7): 803-12. [PMID:19482012]
3. Lieberman JA, Dunbar G, Segreti AC, Girgis RR, Seoane F, Beaver JS, Duan N, Hosford DA. (2013)
A randomized exploratory trial of an α-7 nicotinic receptor agonist (TC-5619) for cognitive enhancement in schizophrenia.
Neuropsychopharmacology, 38 (6): 968-75. [PMID:23303043]
4. Mazurov AA, Kombo DC, Hauser TA, Miao L, Dull G, Genus JF, Fedorov NB, Benson L, Sidach S, Xiao Y et al.. (2012)
Discovery of (2S,3R)-N-[2-(pyridin-3-ylmethyl)-1-azabicyclo[2.2.2]oct-3-yl]benzo[b]furan-2-carboxamide (TC-5619), a selective α7 nicotinic acetylcholine receptor agonist, for the treatment of cognitive disorders.
J Med Chem, 55 (22): 9793-809. [PMID:23126648]