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Details

Stereochemistry ACHIRAL
Molecular Formula 2C10H14N2.C6H10O8
Molecular Weight 534.6019
Optical Activity UNSPECIFIED
Defined Stereocenters 4 / 4
E/Z Centers 2
Charge 0

SHOW SMILES / InChI
Structure of RIVANICLINE GALACTARATE

SMILES

CNCC\C=C\C1=CN=CC=C1.CNCC\C=C\C2=CN=CC=C2.O[C@@H]([C@@H](O)[C@H](O)C(O)=O)[C@@H](O)C(O)=O

InChI

InChIKey=CIMKLHOSRSGWFB-MWCLJRRUSA-N
InChI=1S/2C10H14N2.C6H10O8/c2*1-11-7-3-2-5-10-6-4-8-12-9-10;7-1(3(9)5(11)12)2(8)4(10)6(13)14/h2*2,4-6,8-9,11H,3,7H2,1H3;1-4,7-10H,(H,11,12)(H,13,14)/b2*5-2+;/t;;1-,2+,3+,4-

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

Molecular Formula C6H10O8
Molecular Weight 210.1388
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 4 / 4
E/Z Centers 0
Optical Activity UNSPECIFIED

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
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
Patents
Substance Class Chemical
Created
by admin
on Fri Dec 15 16:32:32 GMT 2023
Edited
by admin
on Fri Dec 15 16:32:32 GMT 2023
Record UNII
VAS2V13A9H
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
RIVANICLINE GALACTARATE
USAN  
USAN  
Official Name English
Bis[(3E)-N-methyl-4-(pyridin-3-yl)but-3-en-1-amine] galactarate
Common Name English
(E)-METANICOTINE GALACTARATE
Common Name English
GALACTARIC ACID, COMPOUND WITH N-METHYL-4-(3-PYRIDINYL)-(3E)-3-BUTEN-1-AMINE (1:2)
Common Name English
RIVANICLINE GALACTARATE [USAN]
Common Name English
TRANS-METANICOTINE GALACTARATE
Common Name English
TC-02403-12
Code English
GALACTARIC ACID, COMPD. WITH N-METHYL-4-(3-PYRIDINYL)-(3E)-3-BUTEN-1-AMINE (1:2)
Systematic Name English
Classification Tree Code System Code
NCI_THESAURUS C73579
Created by admin on Fri Dec 15 16:32:32 GMT 2023 , Edited by admin on Fri Dec 15 16:32:32 GMT 2023
Code System Code Type Description
CAS
675132-86-2
Created by admin on Fri Dec 15 16:32:32 GMT 2023 , Edited by admin on Fri Dec 15 16:32:32 GMT 2023
PRIMARY
SMS_ID
300000044442
Created by admin on Fri Dec 15 16:32:32 GMT 2023 , Edited by admin on Fri Dec 15 16:32:32 GMT 2023
PRIMARY
FDA UNII
VAS2V13A9H
Created by admin on Fri Dec 15 16:32:32 GMT 2023 , Edited by admin on Fri Dec 15 16:32:32 GMT 2023
PRIMARY
PUBCHEM
46174135
Created by admin on Fri Dec 15 16:32:32 GMT 2023 , Edited by admin on Fri Dec 15 16:32:32 GMT 2023
PRIMARY
USAN
QQ-103
Created by admin on Fri Dec 15 16:32:32 GMT 2023 , Edited by admin on Fri Dec 15 16:32:32 GMT 2023
PRIMARY
NCI_THESAURUS
C72425
Created by admin on Fri Dec 15 16:32:32 GMT 2023 , Edited by admin on Fri Dec 15 16:32:32 GMT 2023
PRIMARY
ChEMBL
CHEMBL132966
Created by admin on Fri Dec 15 16:32:32 GMT 2023 , Edited by admin on Fri Dec 15 16:32:32 GMT 2023
PRIMARY
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