BRADANICLINE TOSYLATE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C22H23N3O2.C7H8O3S
Molecular Weight	533.639
Optical Activity	UNSPECIFIED
Defined Stereocenters	2 / 2
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CC1=CC=C(C=C1)S(O)(=O)=O.O=C(N[C@@H]2C3CCN(CC3)[C@H]2CC4=CN=CC=C4)C5=CC6=CC=CC=C6O5

InChI

InChIKey=YDJXUVIIXSFVOJ-OZYANKIXSA-N

InChI=1S/C22H23N3O2.C7H8O3S/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;1-6-2-4-7(5-3-6)11(8,9)10/h1-6,9,13-14,16,18,21H,7-8,10-12H2,(H,24,26);2-5H,1H3,(H,8,9,10)/t18-,21+;/m0./s1

HIDE SMILES / InChI

Molecular Formula	C7H8O3S
Molecular Weight	172.202
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Molecular Formula	C22H23N3O2
Molecular Weight	361.4369
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	2 / 2
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://clinicaltrials.gov/ct2/show/NCT03622216 | https://www.ncbi.nlm.nih.gov/pubmed/26071208 | https://www.bloomberg.com/research/stocks/private/snapshot.asp?privcapId=378739964

Bradanicline (formerly known as ATA-101 or TC-5619), a selective full agonist for the alpha7 neuronal nicotinic receptor (NNR) subtype was developed for the treatment of central nervous system diseases and disorders. Bradanicline participated in phase II clinical trials for patients with negative and cognitive symptoms of schizophrenia; however, results did not support a benefit of the drug. The development was also discontinued for Alzheimer's disease and attention-deficit hyperactivity disorder. In addition, it was announced that the first patient had been treated in Phase 2 clinical trial in chronic cough with bradanicline. Phase 2 will test the efficacy and safety of bradanicline in up to 49 patients with refractory chronic cough. Refractory chronic cough is defined as a cough that persists for eight weeks or more. In the plans will conduct additional clinical trials to test the safety and efficacy of bradanicline.

Originator

Approval Year

PubMed

Title	Date	PubMed
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.	2009 Oct 1	19482012
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.	2012 Nov 26	23126648
A randomized exploratory trial of an α-7 nicotinic receptor agonist (TC-5619) for cognitive enhancement in schizophrenia.	2013 May	23303043

Patents

Sample Use Guides

In Vivo Use Guide

Randomized crossover design of 3 different doses of bradanicline (film-coated tablets) to be administered orally QD

Route of Administration: Oral

Substance Class	Chemical Created by `admin` on `Fri Dec 15 19:50:57 GMT 2023` Edited by `admin` on `Fri Dec 15 19:50:57 GMT 2023`
Record UNII	3821HT7KCR
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

BRADANICLINE TOSYLATE

Common Name

English

TC-5619 TOSYLATE

Common Name

English

TC 5619 TOSYLATE

Code

English

2-BENZOFURANCARBOXAMIDE, N-((2S,3R)-2-(3-PYRIDINYLMETHYL)-1-AZABICYCLO(2.2.2)OCT-3-YL)-, 4-METHYLBENZENESULFONATE (1:1)

Systematic Name

English

Code System Code Type Description

DRUG BANK

DBSALT001881