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][C@@]12CC[C@@]([H])(N1)[C@]([H])(C2)C1=CC=C(Cl)N=C1

Pharmacology

Indication
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
DrugInteraction
1,10-PhenanthrolineThe risk or severity of adverse effects can be increased when 1,10-Phenanthroline is combined with Epibatidine.
AcebutololThe risk or severity of adverse effects can be increased when Acebutolol is combined with Epibatidine.
AlprenololThe risk or severity of adverse effects can be increased when Alprenolol is combined with Epibatidine.
AmbenoniumThe risk or severity of adverse effects can be increased when Ambenonium is combined with Epibatidine.
AmikacinThe therapeutic efficacy of Epibatidine can be decreased when used in combination with Amikacin.
AnisodamineThe risk or severity of adverse effects can be increased when Anisodamine is combined with Epibatidine.
ApramycinThe therapeutic efficacy of Epibatidine can be decreased when used in combination with Apramycin.
ArbekacinThe therapeutic efficacy of Epibatidine can be decreased when used in combination with Arbekacin.
ArotinololThe risk or severity of adverse effects can be increased when Arotinolol is combined with Epibatidine.
AtenololThe risk or severity of adverse effects can be increased when Atenolol is combined with Epibatidine.
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 November 02, 2018 06:37