U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ABSOLUTE
Molecular Formula C22H23N3O2
Molecular Weight 361.4369
Optical Activity UNSPECIFIED
Defined Stereocenters 2 / 2
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of BRADANICLINE

SMILES

O=C(N[C@@H]1C2CCN(CC2)[C@H]1CC3=CN=CC=C3)C4=CC5=CC=CC=C5O4

InChI

InChIKey=OXKRFEWMSWPKKV-GHTZIAJQSA-N
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

HIDE SMILES / InChI

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

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.

Approval Year

PubMed

PubMed

TitleDatePubMed
A randomized exploratory trial of an α-7 nicotinic receptor agonist (TC-5619) for cognitive enhancement in schizophrenia.
2013 May
Patents

Sample Use Guides

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 19:43:16 GMT 2023
Edited
by admin
on Fri Dec 15 19:43:16 GMT 2023
Record UNII
UM3821998K
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
BRADANICLINE
INN   USAN   WHO-DD  
USAN   INN  
Official Name English
TC-5619
Code English
BRADANICLINE [USAN]
Common Name English
ATA-101
Code English
bradanicline [INN]
Common Name English
TC 5619
Code English
Bradanicline [WHO-DD]
Common Name English
2-BENZOFURANCARBOXAMIDE, N-((2S,3R)-2-(3-PYRIDINYLMETHYL)-1-AZABICYCLO(2.2.2)OCT-3-YL)-
Systematic Name English
N-[(2S,3R)-2-(Pyridin-3-ylmethyl)-1-azabicyclo[2.2.2]oct-3-yl]-1-benzofuran-2-carboxamide
Systematic Name English
Code System Code Type Description
SMS_ID
300000034086
Created by admin on Fri Dec 15 19:43:16 GMT 2023 , Edited by admin on Fri Dec 15 19:43:16 GMT 2023
PRIMARY
NCI_THESAURUS
C169814
Created by admin on Fri Dec 15 19:43:16 GMT 2023 , Edited by admin on Fri Dec 15 19:43:16 GMT 2023
PRIMARY
USAN
ZZ-160
Created by admin on Fri Dec 15 19:43:16 GMT 2023 , Edited by admin on Fri Dec 15 19:43:16 GMT 2023
PRIMARY
ChEMBL
CHEMBL1258006
Created by admin on Fri Dec 15 19:43:16 GMT 2023 , Edited by admin on Fri Dec 15 19:43:16 GMT 2023
PRIMARY
CAS
639489-84-2
Created by admin on Fri Dec 15 19:43:16 GMT 2023 , Edited by admin on Fri Dec 15 19:43:16 GMT 2023
PRIMARY
INN
9893
Created by admin on Fri Dec 15 19:43:16 GMT 2023 , Edited by admin on Fri Dec 15 19:43:16 GMT 2023
PRIMARY
DRUG BANK
DB06090
Created by admin on Fri Dec 15 19:43:16 GMT 2023 , Edited by admin on Fri Dec 15 19:43:16 GMT 2023
PRIMARY
WIKIPEDIA
TC-5619
Created by admin on Fri Dec 15 19:43:16 GMT 2023 , Edited by admin on Fri Dec 15 19:43:16 GMT 2023
PRIMARY
FDA UNII
UM3821998K
Created by admin on Fri Dec 15 19:43:16 GMT 2023 , Edited by admin on Fri Dec 15 19:43:16 GMT 2023
PRIMARY
PUBCHEM
25147644
Created by admin on Fri Dec 15 19:43:16 GMT 2023 , Edited by admin on Fri Dec 15 19:43:16 GMT 2023
PRIMARY
EPA CompTox
DTXSID40213778
Created by admin on Fri Dec 15 19:43:16 GMT 2023 , Edited by admin on Fri Dec 15 19:43:16 GMT 2023
PRIMARY
Related Record Type Details
TARGET -> AGONIST
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
Related Record Type Details
ACTIVE MOIETY