General
Preferred name
RIVANICLINE
Synonyms
Rivanicline oxalate ()
RJR-2403 (oxalate) ()
(E)-Metanicotine (oxalate) ()
Rivanicline 2HCl(15585-43-0 Free base) ()
RJR 2403 oxalate ()
RJR-2403 ()
RJR 2403 ()
METANICOTINE ()
Rivanicline hemioxalate ()
RJR-2403 (hemioxalate) ()
(E)-Metanicotine (hemioxalate) ()
RJR-2403 oxalate ()
Rivanicline 2HCl ()
RIVANICLINE GALACTARATE ()
(E)-Metanicotine ()
TC-2403 ()
Trans-metanicotine ()
Rivaniclina ()
TC-02403-12 ()
(e)-metanicotine galactarate ()
Trans-metanicotine galactarate ()
Rivanicline (hydrochloride) ()
P&D ID
PD008934
CAS
220662-95-3
538-79-4
15585-43-0
1129-68-6
Tags
available
drug candidate
Drug indication
Cognitive impairment
Drug Status
investigational
Max Phase
2.0
Structure
Probe scores
P&D probe-likeness score
[[ v.score ]]%
Structure formats
[[ format ]]
[[ compound[format === 'MOL' ? 'molblock' : format.toLowerCase()] ]]
Description
(extracted from source data)
DESCRIPTION Rivanicline is an agonist at neural nicotinic acetylcholine receptors, binding primarily to the α4β2 subtype . Potential clinical use of rivanicline is discussed in patent US5616707 . (GtoPdb)
DESCRIPTION Rivanicline hemioxalate (RJR-2403 hemioxalate; (E)-Metanicotine hemioxalate) is a neuronal nicotinic receptor agonist, showing high selectivity for the ¦Á4¦Â2 subtype (Ki=26 nM); > 1,000 fold selectivity than ¦Á7 receptors(Ki= 3.6 ¦ÌM).;IC50 value: 26 nM [1];Target: ¦Á4¦Â2 nAChR;in vitro: At concentrations up to 1 mM, Rivanicline does not significantly activate nAChRs in PC12 cells, muscle type nAChRs or muscarinic receptors. Dose-response curves for agonist-induced ileum contraction indicate that Rivanicline is less than one-tenth as potent as nicotine with greatly reduced efficacy. Rivanicline does not antagonize nicotine-stimulated muscle or ganglionic nAChR function (IC50 > 1 mM). Chronic exposure of M10 cells to Rivanicline (10 microM) results in an up-regulation of high-affinity nAChRs phenomenologically similar to that seen with nicotine [1].;in vivo: Rivanicline significantly improved passive avoidance retention after scopolamine-induced amnesia and enhanced both working and reference memory in rats with ibotenic acid lesions of the forebrain cholinergic projection system in an 8-arm radial maze paradigm. By comparison, Rivanicline was 15 to 30-fold less potent than nicotine in decreasing body temperature, respiration, Y-maze rears and crosses and acoustic startle response [2]. Metanicotine was about 5-fold less potent than nicotine in the tail-flick test after s.c administration, but slightly more potent after central administration [3].
PRICE 65
DESCRIPTION Rivanicline 2HCl is a selective neuronal nicotinic receptor inhibitor with a high affinity for the ??4??2 subtype.
DESCRIPTION At concentrations up to 1 mM, RJR-2403 does not significantly activate nAChRs in PC12 cells, muscle type nAChRs or muscarinic receptors. Dose-response curves for agonist-induced ileum contraction indicate that RJR-2403 is less than one-tenth as potent as nicotine with greatly reduced efficacy. RJR-2403 does not antagonize nicotine-stimulated muscle or ganglionic nAChR function (IC50 > 1 mM). Chronic exposure of M10 cells to RJR-2403 (10 microM) results in an up-regulation of high-affinity nAChRs phenomenologically similar to that seen with nicotine.
RJR-2403 significantly improved passive avoidance retention after scopolamine-induced amnesia and enhanced both working and reference memory in rats with ibotenic acid lesions of the forebrain cholinergic projection system in an 8-arm radial maze paradigm. By comparison, RJR-2403 was 15 to 30-fold less potent than nicotine in decreasing body temperature, respiration, Y-maze rears and crosses and acoustic startle response. Metanicotine was about 5-fold less potent than nicotine in the tail-flick test after s.c administration, but slightly more potent after central administration. (BOC Sciences Bioactive Compounds)
DESCRIPTION Selective AMPA agonist; more water soluble form of (RS)-AMPA (Cat. No. 0169) (Tocris Bioactive Compound Library)
DESCRIPTION A neuronal nicotinic receptor agonist, showing high selectivity for the α4β2 subtype (Ki values are 26 and 36000 nM for α4β2 and α7 receptors respectively). Active in vivo. (BOC Sciences Bioactive Compounds)
DESCRIPTION Rivanicline 2HCl is a selective neuronal nicotinic receptor inhibitor with a high affinity for the α4β2 subtype. (TargetMol Bioactive Compound Library)
Cell lines
0
Organisms
1
Compound Sets
17
BOC Sciences Bioactive Compounds
rjr-2403-cas-15585-43-0-item-84-262892
rjr-2403-oxalate-cas-220662-95-3-item-84-463592
Cayman Chemical Bioactives
42184
ChEMBL Drugs
CHEMBL132966
CHEMBL2107367
Concise Guide to Pharmacology 2017/18
3994
Concise Guide to Pharmacology 2019/20
3994
Concise Guide to Pharmacology 2021/22
3994
Concise Guide to Pharmacology 2023/24
3994
Drug Repurposing Hub
DrugBank
DB05855
DrugMAP
DMOZEN6
EU-OPENSCREEN Bioactive Compound Library
EOS100825
Guide to Pharmacology
3994
MedChem Express Bioactive Compound Library
HY-13225B
Novartis Chemogenetic Library (NIBR MoA Box)
ReFrame library
TargetMol Bioactive Compound Library
T12738L1
Tocris Bioactive Compound Library
1053
External IDs
38
Properties
(calculated by RDKit )
Molecular Weight
162.12
Hydrogen Bond Acceptors
2
Hydrogen Bond Donors
1
Rotatable Bonds
4
Ring Count
1
Aromatic Ring Count
1
cLogP
1.7
TPSA
24.92
Fraction CSP3
0.3
Chiral centers
0.0
Largest ring
6.0
QED
0.68
Structural alerts
0
No structural alerts detected
Related compounds
Custom attributes
(extracted from source data)
Target
nAChR
α4β2 nAChR
CHRNA4, CHRNB2, CXCL8
Pathway
Neuronal Signaling
Membrane Transporter/Ion Channel
Neuroscience
Primary Target
Nicotinic (?4?2) Receptors
MOA
Agonist
Nicotinic Receptor Agonists
Nicotinic alpha4beta2 Agonists
acetylcholine receptor agonist
Member status
member
Source data