Identification

Name
Epibatidine
Accession Number
DB07720
Type
Small Molecule
Groups
Experimental
Description
Not Available
Structure
Thumb
Synonyms
  • (+)-epibatidine
  • (1R,2R,4S)-epibatidine
External IDs
CMI-488
Categories
UNII
M6K314F1XX
CAS number
140111-52-0
Weight
Average: 208.687
Monoisotopic: 208.076726133
Chemical Formula
C11H13ClN2
InChI Key
NLPRAJRHRHZCQQ-IVZWLZJFSA-N
InChI
InChI=1S/C11H13ClN2/c12-11-4-1-7(6-13-11)9-5-8-2-3-10(9)14-8/h1,4,6,8-10,14H,2-3,5H2/t8-,9+,10+/m0/s1
IUPAC Name
(1R,2R,4S)-2-(6-chloropyridin-3-yl)-7-azabicyclo[2.2.1]heptane
SMILES
[H][[email protected]@]12CC[[email protected]@]([H])(N1)[[email protected]]([H])(C2)C1=CC=C(Cl)N=C1

Pharmacology

Indication
Not Available
Structured Indications
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UCHRNA7-FAM7A fusion proteinNot AvailableHuman
UNeuronal acetylcholine receptor subunit alpha-7Not AvailableHuman
UNeuronal acetylcholine receptor subunit beta-2Not AvailableHuman
UNeuronal acetylcholine receptor subunit alpha-2
agonist
Human
UNeuronal acetylcholine receptor subunit alpha-3
agonist
Human
UNeuronal acetylcholine receptor subunit alpha-4
agonist
Human
UNeuronal acetylcholine receptor subunit beta-4
agonist
Human
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
Toxicity
Not Available
Affected organisms
Not Available
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteractionDrug group
1,10-PhenanthrolineThe risk or severity of adverse effects can be increased when 1,10-Phenanthroline is combined with Epibatidine.Experimental
AcebutololThe risk or severity of adverse effects can be increased when Acebutolol is combined with Epibatidine.Approved
AlprenololThe risk or severity of adverse effects can be increased when Alprenolol is combined with Epibatidine.Approved, Withdrawn
AmbenoniumThe risk or severity of adverse effects can be increased when Ambenonium is combined with Epibatidine.Approved
ArotinololThe risk or severity of adverse effects can be increased when Arotinolol is combined with Epibatidine.Approved, Investigational
AtenololThe risk or severity of adverse effects can be increased when Atenolol is combined with Epibatidine.Approved
BefunololThe risk or severity of adverse effects can be increased when Befunolol is combined with Epibatidine.Experimental
BetaxololThe risk or severity of adverse effects can be increased when Betaxolol is combined with Epibatidine.Approved
BevantololThe risk or severity of adverse effects can be increased when Bevantolol is combined with Epibatidine.Approved
BisoprololThe risk or severity of adverse effects can be increased when Bisoprolol is combined with Epibatidine.Approved
BopindololThe risk or severity of adverse effects can be increased when Bopindolol is combined with Epibatidine.Approved
BucindololThe risk or severity of adverse effects can be increased when Bucindolol is combined with Epibatidine.Investigational
BufuralolThe risk or severity of adverse effects can be increased when Bufuralol is combined with Epibatidine.Experimental, Investigational
BupranololThe risk or severity of adverse effects can be increased when Bupranolol is combined with Epibatidine.Approved
CarteololThe risk or severity of adverse effects can be increased when Carteolol is combined with Epibatidine.Approved
CarvedilolThe risk or severity of adverse effects can be increased when Carvedilol is combined with Epibatidine.Approved, Investigational
CeliprololThe risk or severity of adverse effects can be increased when Celiprolol is combined with Epibatidine.Approved, Investigational
CimetropiumEpibatidine may decrease the anticholinergic activities of Cimetropium.Experimental, Investigational
CloranololThe risk or severity of adverse effects can be increased when Cloranolol is combined with Epibatidine.Experimental
CoumaphosThe risk or severity of adverse effects can be increased when Coumaphos is combined with Epibatidine.Vet Approved
DecamethoniumThe risk or severity of adverse effects can be increased when Decamethonium is combined with Epibatidine.Approved
DemecariumThe risk or severity of adverse effects can be increased when Demecarium is combined with Epibatidine.Approved
DichlorvosThe risk or severity of adverse effects can be increased when Dichlorvos is combined with Epibatidine.Vet Approved
DistigmineThe risk or severity of adverse effects can be increased when Distigmine is combined with Epibatidine.Experimental
DonepezilThe risk or severity of adverse effects can be increased when Donepezil is combined with Epibatidine.Approved
EchothiophateThe risk or severity of adverse effects can be increased when Echothiophate is combined with Epibatidine.Approved
EdrophoniumThe risk or severity of adverse effects can be increased when Edrophonium is combined with Epibatidine.Approved
EpanololThe risk or severity of adverse effects can be increased when Epanolol is combined with Epibatidine.Experimental
EsmololThe risk or severity of adverse effects can be increased when Esmolol is combined with Epibatidine.Approved
FenthionThe risk or severity of adverse effects can be increased when Fenthion is combined with Epibatidine.Vet Approved
GalantamineThe risk or severity of adverse effects can be increased when Galantamine is combined with Epibatidine.Approved
Gallamine TriethiodideThe risk or severity of adverse effects can be increased when Gallamine Triethiodide is combined with Epibatidine.Approved
Huperzine AThe risk or severity of adverse effects can be increased when Huperzine A is combined with Epibatidine.Investigational
IndenololThe risk or severity of adverse effects can be increased when Indenolol is combined with Epibatidine.Withdrawn
IpidacrineThe risk or severity of adverse effects can be increased when Ipidacrine is combined with Epibatidine.Experimental
IsoflurophateThe risk or severity of adverse effects can be increased when Isoflurophate is combined with Epibatidine.Approved, Investigational, Withdrawn
LabetalolThe risk or severity of adverse effects can be increased when Labetalol is combined with Epibatidine.Approved
LandiololThe risk or severity of adverse effects can be increased when Landiolol is combined with Epibatidine.Investigational
LevobunololThe risk or severity of adverse effects can be increased when Levobunolol is combined with Epibatidine.Approved
MalathionThe risk or severity of adverse effects can be increased when Malathion is combined with Epibatidine.Approved, Investigational
MefloquineThe risk or severity of adverse effects can be increased when Mefloquine is combined with Epibatidine.Approved
MemantineThe risk or severity of adverse effects can be increased when Memantine is combined with Epibatidine.Approved, Investigational
MepindololThe risk or severity of adverse effects can be increased when Mepindolol is combined with Epibatidine.Experimental
Methanesulfonyl FluorideThe risk or severity of adverse effects can be increased when Methanesulfonyl Fluoride is combined with Epibatidine.Investigational
MetipranololThe risk or severity of adverse effects can be increased when Metipranolol is combined with Epibatidine.Approved
MetoclopramideThe risk or severity of adverse effects can be increased when Metoclopramide is combined with Epibatidine.Approved, Investigational
MetoprololThe risk or severity of adverse effects can be increased when Metoprolol is combined with Epibatidine.Approved, Investigational
MinaprineThe risk or severity of adverse effects can be increased when Minaprine is combined with Epibatidine.Approved
NadololThe risk or severity of adverse effects can be increased when Nadolol is combined with Epibatidine.Approved
NebivololThe risk or severity of adverse effects can be increased when Nebivolol is combined with Epibatidine.Approved, Investigational
NeostigmineThe risk or severity of adverse effects can be increased when Neostigmine is combined with Epibatidine.Approved, Vet Approved
OxprenololThe risk or severity of adverse effects can be increased when Oxprenolol is combined with Epibatidine.Approved
ParaoxonThe risk or severity of adverse effects can be increased when Paraoxon is combined with Epibatidine.Experimental
PenbutololThe risk or severity of adverse effects can be increased when Penbutolol is combined with Epibatidine.Approved, Investigational
PhysostigmineThe risk or severity of adverse effects can be increased when Physostigmine is combined with Epibatidine.Approved
PindololThe risk or severity of adverse effects can be increased when Pindolol is combined with Epibatidine.Approved
Platelet Activating FactorThe risk or severity of adverse effects can be increased when Platelet Activating Factor is combined with Epibatidine.Experimental
PractololThe risk or severity of adverse effects can be increased when Practolol is combined with Epibatidine.Approved
PropranololThe risk or severity of adverse effects can be increased when Propranolol is combined with Epibatidine.Approved, Investigational
PyridostigmineThe risk or severity of adverse effects can be increased when Pyridostigmine is combined with Epibatidine.Approved
RivastigmineThe risk or severity of adverse effects can be increased when Rivastigmine is combined with Epibatidine.Approved, Investigational
SotalolThe risk or severity of adverse effects can be increased when Sotalol is combined with Epibatidine.Approved
TacrineThe risk or severity of adverse effects can be increased when Tacrine is combined with Epibatidine.Investigational, Withdrawn
TalinololThe risk or severity of adverse effects can be increased when Talinolol is combined with Epibatidine.Investigational
TertatololThe risk or severity of adverse effects can be increased when Tertatolol is combined with Epibatidine.Experimental
TimololThe risk or severity of adverse effects can be increased when Timolol is combined with Epibatidine.Approved
TrichlorfonThe risk or severity of adverse effects can be increased when Trichlorfon is combined with Epibatidine.Vet Approved
TubocurarineThe risk or severity of adverse effects can be increased when Tubocurarine is combined with Epibatidine.Approved
Food Interactions
Not Available

References

Synthesis Reference

Csaba Sz antay, Zsuzsanna B. Kardos, Istv an Moldvai, Eszter T. Major, Csaba Sz antay, Jr., Attila M andi, G abor Blask o, Gyula Simig, Gy orgyi Lax, S andor Drabant, Tamas Sz all asi, M arton Fekete, G abor Gigler, "Process for the preparation of epibatidine." U.S. Patent US5545741, issued March, 1994.

US5545741
General References
Not Available
External Links
PubChem Compound
854023
PubChem Substance
99444191
ChemSpider
10399316
BindingDB
50143314
ChEBI
4803
ChEMBL
CHEMBL298826
HET
EPJ
Wikipedia
Epibatidine
PDB Entries
2byq / 3sq6 / 5fjv

Clinical Trials

Clinical Trials
Not Available

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 Solubility0.467 mg/mLALOGPS
logP1.98ALOGPS
logP1.84ChemAxon
logS-2.6ALOGPS
pKa (Strongest Basic)10.54ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area24.92 Å2ChemAxon
Rotatable Bond Count1ChemAxon
Refractivity57.39 m3·mol-1ChemAxon
Polarizability22.07 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+1.0
Blood Brain Barrier+0.9767
Caco-2 permeable-0.5099
P-glycoprotein substrateNon-substrate0.6541
P-glycoprotein inhibitor INon-inhibitor0.7432
P-glycoprotein inhibitor IINon-inhibitor0.8989
Renal organic cation transporterNon-inhibitor0.5127
CYP450 2C9 substrateNon-substrate0.8639
CYP450 2D6 substrateNon-substrate0.7657
CYP450 3A4 substrateNon-substrate0.6359
CYP450 1A2 substrateNon-inhibitor0.7682
CYP450 2C9 inhibitorNon-inhibitor0.9071
CYP450 2D6 inhibitorNon-inhibitor0.9231
CYP450 2C19 inhibitorNon-inhibitor0.9025
CYP450 3A4 inhibitorNon-inhibitor0.8309
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.6843
Ames testNon AMES toxic0.6607
CarcinogenicityNon-carcinogens0.9402
BiodegradationNot ready biodegradable0.992
Rat acute toxicity2.6084 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.8853
hERG inhibition (predictor II)Non-inhibitor0.508
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-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Taxonomy

Description
This compound belongs to the class of organic compounds known as epibatidine analogues. These are compounds containing an epibatidine moiety, with a structure characterized by a 2-chloropyridine moiety connected to an 7-azabicyclo[2.2.1]heptane in exo position.
Kingdom
Organic compounds
Super Class
Alkaloids and derivatives
Class
Epibatidine analogues
Sub Class
Not Available
Direct Parent
Epibatidine analogues
Alternative Parents
Pyrrolidinylpyridines / Aralkylamines / 2-halopyridines / Aryl chlorides / Pyrrolidines / Heteroaromatic compounds / Dialkylamines / Azacyclic compounds / Organopnictogen compounds / Organochlorides
show 1 more
Substituents
Epibatidine-skeleton / Pyrrolidinylpyridine / 2-halopyridine / Aralkylamine / Aryl chloride / Aryl halide / Pyridine / Heteroaromatic compound / Pyrrolidine / Azacycle
show 11 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
alkaloid (CHEBI:4803)

Targets

Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Extracellular ligand-gated ion channel activity
Specific Function
Not Available
Gene Name
CHRFAM7A
Uniprot ID
Q494W8
Uniprot Name
CHRNA7-FAM7A fusion protein
Molecular Weight
46217.335 Da
References
  1. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [PubMed:10592235]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Toxic substance binding
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. The cha...
Gene Name
CHRNA7
Uniprot ID
P36544
Uniprot Name
Neuronal acetylcholine receptor subunit alpha-7
Molecular Weight
56448.925 Da
References
  1. Niessen KV, Tattersall JE, Timperley CM, Bird M, Green C, Seeger T, Thiermann H, Worek F: Interaction of bispyridinium compounds with the orthosteric binding site of human alpha7 and Torpedo californica nicotinic acetylcholine receptors (nAChRs). Toxicol Lett. 2011 Sep 25;206(1):100-4. doi: 10.1016/j.toxlet.2011.06.009. Epub 2011 Jun 16. [PubMed:21703337]
Kind
Protein
Organism
Human
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. Henderson BJ, Carper DJ, Gonzalez-Cestari TF, Yi B, Mahasenan K, Pavlovicz RE, Dalefield ML, Coleman RS, Li C, McKay DB: Structure-activity relationship studies of sulfonylpiperazine analogues as novel negative allosteric modulators of human neuronal nicotinic receptors. J Med Chem. 2011 Dec 22;54(24):8681-92. doi: 10.1021/jm201294r. Epub 2011 Nov 18. [PubMed:22060139]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Agonist
General Function
Drug binding
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.
Gene Name
CHRNA2
Uniprot ID
Q15822
Uniprot Name
Neuronal acetylcholine receptor subunit alpha-2
Molecular Weight
59764.82 Da
References
  1. Stauderman KA, Mahaffy LS, Akong M, Velicelebi G, Chavez-Noriega LE, Crona JH, Johnson EC, Elliott KJ, Gillespie A, Reid RT, Adams P, Harpold MM, Corey-Naeve J: Characterization of human recombinant neuronal nicotinic acetylcholine receptor subunit combinations alpha2beta4, alpha3beta4 and alpha4beta4 stably expressed in HEK293 cells. J Pharmacol Exp Ther. 1998 Feb;284(2):777-89. [PubMed:9454827]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Agonist
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.
Gene Name
CHRNA3
Uniprot ID
P32297
Uniprot Name
Neuronal acetylcholine receptor subunit alpha-3
Molecular Weight
57479.54 Da
References
  1. Stauderman KA, Mahaffy LS, Akong M, Velicelebi G, Chavez-Noriega LE, Crona JH, Johnson EC, Elliott KJ, Gillespie A, Reid RT, Adams P, Harpold MM, Corey-Naeve J: Characterization of human recombinant neuronal nicotinic acetylcholine receptor subunit combinations alpha2beta4, alpha3beta4 and alpha4beta4 stably expressed in HEK293 cells. J Pharmacol Exp Ther. 1998 Feb;284(2):777-89. [PubMed:9454827]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Agonist
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
CHRNA4
Uniprot ID
P43681
Uniprot Name
Neuronal acetylcholine receptor subunit alpha-4
Molecular Weight
69956.47 Da
References
  1. Stauderman KA, Mahaffy LS, Akong M, Velicelebi G, Chavez-Noriega LE, Crona JH, Johnson EC, Elliott KJ, Gillespie A, Reid RT, Adams P, Harpold MM, Corey-Naeve J: Characterization of human recombinant neuronal nicotinic acetylcholine receptor subunit combinations alpha2beta4, alpha3beta4 and alpha4beta4 stably expressed in HEK293 cells. J Pharmacol Exp Ther. 1998 Feb;284(2):777-89. [PubMed:9454827]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Agonist
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.
Gene Name
CHRNB4
Uniprot ID
P30926
Uniprot Name
Neuronal acetylcholine receptor subunit beta-4
Molecular Weight
56378.985 Da
References
  1. Stauderman KA, Mahaffy LS, Akong M, Velicelebi G, Chavez-Noriega LE, Crona JH, Johnson EC, Elliott KJ, Gillespie A, Reid RT, Adams P, Harpold MM, Corey-Naeve J: Characterization of human recombinant neuronal nicotinic acetylcholine receptor subunit combinations alpha2beta4, alpha3beta4 and alpha4beta4 stably expressed in HEK293 cells. J Pharmacol Exp Ther. 1998 Feb;284(2):777-89. [PubMed:9454827]

Drug created on September 15, 2010 15:25 / Updated on December 01, 2017 15:55