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

Details

Stereochemistry ACHIRAL
Molecular Formula C10H14N2
Molecular Weight 162.2316
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 1
Charge 0

SHOW SMILES / InChI
Structure of RIVANICLINE

SMILES

CNCC\C=C\C1=CN=CC=C1

InChI

InChIKey=JUOSGGQXEBBCJB-GORDUTHDSA-N
InChI=1S/C10H14N2/c1-11-7-3-2-5-10-6-4-8-12-9-10/h2,4-6,8-9,11H,3,7H2,1H3/b5-2+

HIDE SMILES / InChI

Molecular Formula C10H14N2
Molecular Weight 162.2316
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 1
Optical Activity NONE

Rivanicline (also known as RJR-2403 or TC-2403) is a partial neuronal nicotinic acetylcholine receptor agonist. This compound binds primarily to the α4β2 receptor subtype. Rivanicline was originally developed for Alzheimer’s disease and shows pronounced anti-amnesic and increased recognition memory in rats. Because rivanicline also inhibits Interleukin-8 production, it has been further developed as a potential anti-inflammatory treatment for ulcerative colitis (in which nicotine is of therapeutic value but has adverse events). Rivanicline effectively inhibited TNF- and LPS-induced IL-8 production in different cell types, without toxic effects. Rivanicline was also evaluated as a potential compound for the development of nicotinic therapeutics to treat neurological diseases in cases of compromised cholinergic neurotransmission.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
25.0 nM [Ki]
46.0 µM [EC50]
PubMed

PubMed

TitleDatePubMed
RJR-2403: a nicotinic agonist with CNS selectivity II. In vivo characterization.
1996 Dec
RJR-2403: a nicotinic agonist with CNS selectivity I. In vitro characterization.
1996 Dec
Sex differences in cholinergic analgesia II: differing mechanisms in two models of allodynia.
1999 Nov
Synthesis of (+/-)-methyl-(1-aryl-4-pyridin-3-yl-but-3-enyl)-amines.
2001 Dec
Nicotinic acetylcholine receptor regulation of spinal norepinephrine release.
2002 Jun
3-(4-Aminobutyn-1-yl)pyridines: binding at alpha 4 beta 2 nicotinic cholinergic receptors.
2004 Jan 19
Antiamnestic effect of alpha7-nicotinic receptor agonist RJR-2403 in middle-aged ovariectomized rats with Alzheimer type dementia.
2006 Dec
(E)-metanicotine hemigalactarate (TC-2403-12) inhibits IL-8 production in cells of the inflamed mucosa.
2007 Mar
Patents
Substance Class Chemical
Created
by admin
on Fri Dec 15 15:25:57 UTC 2023
Edited
by admin
on Fri Dec 15 15:25:57 UTC 2023
Record UNII
6H35LF645A
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
RIVANICLINE
INN  
INN  
Official Name English
(E)-METANICOTINE
Common Name English
N-METHYL-4-(3-PYRIDINYL)-(3E)-3-BUTEN-1-AMINE
Systematic Name English
(3E)-N-METHYL-4-(PYRIDIN-3-YL)BUT-3-EN-1-AMINE
Systematic Name English
TRANS-METANICOTINE
Common Name English
rivanicline [INN]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C73579
Created by admin on Fri Dec 15 15:25:57 UTC 2023 , Edited by admin on Fri Dec 15 15:25:57 UTC 2023
Code System Code Type Description
INN
8628
Created by admin on Fri Dec 15 15:25:57 UTC 2023 , Edited by admin on Fri Dec 15 15:25:57 UTC 2023
PRIMARY
CAS
15585-43-0
Created by admin on Fri Dec 15 15:25:57 UTC 2023 , Edited by admin on Fri Dec 15 15:25:57 UTC 2023
PRIMARY
MESH
C012419
Created by admin on Fri Dec 15 15:25:57 UTC 2023 , Edited by admin on Fri Dec 15 15:25:57 UTC 2023
PRIMARY
EPA CompTox
DTXSID101017740
Created by admin on Fri Dec 15 15:25:57 UTC 2023 , Edited by admin on Fri Dec 15 15:25:57 UTC 2023
PRIMARY
NCI_THESAURUS
C66518
Created by admin on Fri Dec 15 15:25:57 UTC 2023 , Edited by admin on Fri Dec 15 15:25:57 UTC 2023
PRIMARY
ChEMBL
CHEMBL132966
Created by admin on Fri Dec 15 15:25:57 UTC 2023 , Edited by admin on Fri Dec 15 15:25:57 UTC 2023
PRIMARY
WIKIPEDIA
RIVANICLINE
Created by admin on Fri Dec 15 15:25:57 UTC 2023 , Edited by admin on Fri Dec 15 15:25:57 UTC 2023
PRIMARY
SMS_ID
300000036936
Created by admin on Fri Dec 15 15:25:57 UTC 2023 , Edited by admin on Fri Dec 15 15:25:57 UTC 2023
PRIMARY
FDA UNII
6H35LF645A
Created by admin on Fri Dec 15 15:25:57 UTC 2023 , Edited by admin on Fri Dec 15 15:25:57 UTC 2023
PRIMARY
DRUG BANK
DB05855
Created by admin on Fri Dec 15 15:25:57 UTC 2023 , Edited by admin on Fri Dec 15 15:25:57 UTC 2023
PRIMARY
PUBCHEM
5310967
Created by admin on Fri Dec 15 15:25:57 UTC 2023 , Edited by admin on Fri Dec 15 15:25:57 UTC 2023
PRIMARY
Related Record Type Details
TARGET->PARTIAL AGONIST
SALT/SOLVATE -> PARENT
Related Record Type Details
ACTIVE MOIETY