NAV

Rivanicline

Identification

Generic Name
Rivanicline
DrugBank Accession Number
DB05855
Background

Rivanicline (TC-2403, RJR-2403, (E)-metanicotine) is a partial agonist at neuronal nicotinic acetylcholine receptors, binding primarily to the α4β2 subtype. It was originally developed as a potential treatment for Alzheimer's disease for its nootropic effects but has also been found to inhibit the production of Interleukin-8. It has subsequently been developed as a potential anti-inflammatory treatment for ulcerative colitis. Rivanicline also has stimulant and analgesic actions which are thought due to increased noradrenaline release.

Type
Small Molecule
Groups
Investigational
Structure
3D
Similar Structures
Weight
Average: 162.2316
Monoisotopic: 162.115698458
Chemical Formula
C10H14N2
Synonyms
  • (3E)-N-methyl-4-(pyridin-3-yl)but-3-en-1-amine
  • (E)-metanicotine
  • (E)-N-Methyl-4-(3-pyridinyl)-3-butene-1-amine
  • N-methyl-4-(3-pyridinyl)-(3E)-3-buten-1-amine
  • Rivanicline
  • trans-metanicotine
External IDs
  • RJR-2403
  • TC-2403
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Pharmacology

Indication

Investigated for use/treatment in ulcerative colitis.

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Contraindications & Blackbox Warnings
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Pharmacodynamics

Not Available

Mechanism of action

Rivanicline is a (E)-metanicotine hemigalactarate. It effectively inhibits TNF- and LPS-induced IL-8 production in different cell types.

TargetActionsOrganism
UNeuronal acetylcholine receptor subunit beta-2Not AvailableHumans
UInterleukin-8
antagonist
Humans
Absorption

Not Available

Volume of distribution

Not Available

Protein binding

Not Available

Metabolism
Not Available
Route of elimination

Not Available

Half-life

Not Available

Clearance

Not Available

Adverse Effects
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Toxicity

Not Available

Pathways
Not Available
Pharmacogenomic Effects/ADRs Browse all" title="About SNP Mediated Effects/ADRs" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">
Not Available

Interactions

Drug Interactions Learn More" title="About Drug Interactions" id="structured-interactions-info" class="drug-info-popup" href="javascript:void(0);">
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Not Available
Food Interactions
Not Available

Categories

Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as pyridines and derivatives. These are compounds containing a pyridine ring, which is a six-member aromatic heterocycle which consists of one nitrogen atom and five carbon atoms.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Pyridines and derivatives
Sub Class
Not Available
Direct Parent
Pyridines and derivatives
Alternative Parents
Heteroaromatic compounds / Dialkylamines / Azacyclic compounds / Organopnictogen compounds / Hydrocarbon derivatives
Substituents
Amine / Aromatic heteromonocyclic compound / Azacycle / Heteroaromatic compound / Hydrocarbon derivative / Organic nitrogen compound / Organonitrogen compound / Organopnictogen compound / Pyridine / Secondary aliphatic amine
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
Not Available
Affected organisms
Not Available

Chemical Identifiers

UNII
6H35LF645A
CAS number
15585-43-0
InChI Key
JUOSGGQXEBBCJB-GORDUTHDSA-N
InChI
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+
IUPAC Name
methyl[(3E)-4-(pyridin-3-yl)but-3-en-1-yl]amine
SMILES
CNCC\C=C\C1=CN=CC=C1

References

General References
  1. Spoettl T, Paetzel C, Herfarth H, Bencherif M, Schoelmerich J, Greinwald R, Gatto GJ, Rogler G: (E)-metanicotine hemigalactarate (TC-2403-12) inhibits IL-8 production in cells of the inflamed mucosa. Int J Colorectal Dis. 2007 Mar;22(3):303-12. Epub 2006 May 20. [Article]
  2. Jang J, Sin KS, Park H: Synthesis of (+/-)-methyl-(1-aryl-4-pyridin-3-yl-but-3-enyl)-amines. Arch Pharm Res. 2001 Dec;24(6):503-7. [Article]
  3. Sapronov NS, Fedotova YO, Kuznetsova NN: Antiamnestic effect of alpha7-nicotinic receptor agonist RJR-2403 in middle-aged ovariectomized rats with Alzheimer type dementia. Bull Exp Biol Med. 2006 Dec;142(6):700-2. [Article]
  4. Li X, Eisenach JC: Nicotinic acetylcholine receptor regulation of spinal norepinephrine release. Anesthesiology. 2002 Jun;96(6):1450-6. [Article]
PubChem Compound
5310967
PubChem Substance
175427044
ChemSpider
4470511
BindingDB
50061561
ChEMBL
CHEMBL132966
ZINC
ZINC000001543478
Wikipedia
Rivanicline

Clinical Trials

Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">
PhaseStatusPurposeConditionsCount

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility4.74 mg/mLALOGPS
logP1.33ALOGPS
logP1.21Chemaxon
logS-1.5ALOGPS
pKa (Strongest Basic)10.47Chemaxon
Physiological Charge1Chemaxon
Hydrogen Acceptor Count2Chemaxon
Hydrogen Donor Count1Chemaxon
Polar Surface Area24.92 Å2Chemaxon
Rotatable Bond Count4Chemaxon
Refractivity52.22 m3·mol-1Chemaxon
Polarizability19.24 Å3Chemaxon
Number of Rings1Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleYesChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.9951
Blood Brain Barrier+0.9705
Caco-2 permeable+0.7877
P-glycoprotein substrateSubstrate0.6532
P-glycoprotein inhibitor INon-inhibitor0.9388
P-glycoprotein inhibitor IINon-inhibitor0.9564
Renal organic cation transporterInhibitor0.5555
CYP450 2C9 substrateNon-substrate0.7962
CYP450 2D6 substrateSubstrate0.7056
CYP450 3A4 substrateNon-substrate0.7158
CYP450 1A2 substrateNon-inhibitor0.9046
CYP450 2C9 inhibitorNon-inhibitor0.8863
CYP450 2D6 inhibitorNon-inhibitor0.8652
CYP450 2C19 inhibitorNon-inhibitor0.8969
CYP450 3A4 inhibitorNon-inhibitor0.8308
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9327
Ames testNon AMES toxic0.7565
CarcinogenicityNon-carcinogens0.9354
BiodegradationNot ready biodegradable0.8191
Rat acute toxicity1.8142 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.6043
hERG inhibition (predictor II)Non-inhibitor0.8207
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSsplash10-0006-9500000000-26be2a9230e472b1a316
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-01q9-0900000000-638e1a594674429ecfc8
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-03di-0900000000-c5fa25c602163fb79b85
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0f89-2900000000-60627402177fd3d1bbea
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-03di-1900000000-f4c1a2f7bd71c606b35b
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0f6x-9600000000-f73f5a6006e140c9fd7d
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0f96-9400000000-4b69ac80470d668e8ac6
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-145.7185359
predicted
DarkChem Lite v0.1.0
[M-H]-135.78816
predicted
DeepCCS 1.0 (2019)
[M+H]+146.4422359
predicted
DarkChem Lite v0.1.0
[M+H]+139.16011
predicted
DeepCCS 1.0 (2019)
[M+Na]+146.1018359
predicted
DarkChem Lite v0.1.0
[M+Na]+148.52534
predicted
DeepCCS 1.0 (2019)

Targets

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Details1. Neuronal acetylcholine receptor subunit beta-2
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Ligand-gated ion channel activity
Specific Function
After binding acetylcholine, the AChR responds by an extensive change in conformation that affects all subunits and leads to opening of an ion-conducting channel across the plasma membrane permeabl...
Gene Name
CHRNB2
Uniprot ID
P17787
Uniprot Name
Neuronal acetylcholine receptor subunit beta-2
Molecular Weight
57018.575 Da
References
  1. Li X, Eisenach JC: Nicotinic acetylcholine receptor regulation of spinal norepinephrine release. Anesthesiology. 2002 Jun;96(6):1450-6. [Article]
Details2. Interleukin-8
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Antagonist
General Function
Interleukin-8 receptor binding
Specific Function
IL-8 is a chemotactic factor that attracts neutrophils, basophils, and T-cells, but not monocytes. It is also involved in neutrophil activation. It is released from several cell types in response t...
Gene Name
CXCL8
Uniprot ID
P10145
Uniprot Name
Interleukin-8
Molecular Weight
11097.98 Da
References
  1. Spoettl T, Paetzel C, Herfarth H, Bencherif M, Schoelmerich J, Greinwald R, Gatto GJ, Rogler G: (E)-metanicotine hemigalactarate (TC-2403-12) inhibits IL-8 production in cells of the inflamed mucosa. Int J Colorectal Dis. 2007 Mar;22(3):303-12. Epub 2006 May 20. [Article]

Drug created at November 18, 2007 18:28 / Updated at February 21, 2021 18:51