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
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-
| 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 |
| 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
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
Target ID: CHEMBL1907589 Sources: https://www.ncbi.nlm.nih.gov/pubmed/14698195 |
25.0 nM [Ki] | ||
Target ID: CHEMBL1907594 Sources: https://www.ncbi.nlm.nih.gov/pubmed/9435889 |
46.0 µM [EC50] |
PubMed
| Title | Date | PubMed |
|---|---|---|
| (E)-metanicotine hemigalactarate (TC-2403-12) inhibits IL-8 production in cells of the inflamed mucosa. | 2007-03 |
|
| Antiamnestic effect of alpha7-nicotinic receptor agonist RJR-2403 in middle-aged ovariectomized rats with Alzheimer type dementia. | 2006-12 |
|
| 3-(4-Aminobutyn-1-yl)pyridines: binding at alpha 4 beta 2 nicotinic cholinergic receptors. | 2004-01-19 |
|
| Nicotinic acetylcholine receptor regulation of spinal norepinephrine release. | 2002-06 |
|
| Synthesis of (+/-)-methyl-(1-aryl-4-pyridin-3-yl-but-3-enyl)-amines. | 2001-12 |
|
| Sex differences in cholinergic analgesia II: differing mechanisms in two models of allodynia. | 1999-11 |
|
| RJR-2403: a nicotinic agonist with CNS selectivity II. In vivo characterization. | 1996-12 |
|
| RJR-2403: a nicotinic agonist with CNS selectivity I. In vitro characterization. | 1996-12 |
Patents
| Substance Class |
Chemical
Created
by
admin
on
Edited
Mon Mar 31 18:30:50 GMT 2025
by
admin
on
Mon Mar 31 18:30:50 GMT 2025
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| Record UNII |
VAS2V13A9H
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| Record Status |
Validated (UNII)
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| Record Version |
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Official Name | English | ||
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NCI_THESAURUS |
C73579
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675132-86-2
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300000044442
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VAS2V13A9H
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46174135
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QQ-103
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C72425
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CHEMBL132966
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PARENT -> SALT/SOLVATE |
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ACTIVE MOIETY |