Identification
NameEpibatidine
Accession NumberDB07720
TypeSmall Molecule
GroupsExperimental
DescriptionNot Available
Structure
Thumb
Synonyms
(+)-epibatidine
(1R,2R,4S)-epibatidine
External IDs CMI-488
Product Ingredients Not Available
Approved Prescription ProductsNot Available
Approved Generic Prescription ProductsNot Available
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International BrandsNot Available
Brand mixturesNot Available
Categories
UNIIM6K314F1XX
CAS number140111-52-0
WeightAverage: 208.687
Monoisotopic: 208.076726133
Chemical FormulaC11H13ClN2
InChI KeyNLPRAJRHRHZCQQ-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
IndicationNot Available
Structured Indications Not Available
PharmacodynamicsNot Available
Mechanism of action
TargetKindPharmacological actionActionsOrganismUniProt ID
CHRNA7-FAM7A fusion proteinProteinunknownNot AvailableHumanQ494W8 details
Neuronal acetylcholine receptor subunit alpha-7ProteinunknownNot AvailableHumanP36544 details
Neuronal acetylcholine receptor subunit beta-2ProteinunknownNot AvailableHumanP17787 details
Neuronal acetylcholine receptor subunit alpha-2Proteinunknown
agonist
HumanQ15822 details
Neuronal acetylcholine receptor subunit alpha-3Proteinunknown
agonist
HumanP32297 details
Neuronal acetylcholine receptor subunit alpha-4Proteinunknown
agonist
HumanP43681 details
Neuronal acetylcholine receptor subunit beta-4Proteinunknown
agonist
HumanP30926 details
Related Articles
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
MetabolismNot Available
Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicityNot Available
Affected organismsNot Available
PathwaysNot 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risk or severity of adverse effects can be increased when Alprenolol is combined with EPIBATIDINE.Approved, Withdrawn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
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
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
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
EsmololThe risk or severity of adverse effects can be increased when Esmolol is combined with EPIBATIDINE.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
Ginkgo bilobaThe risk or severity of adverse effects can be increased when Ginkgo biloba is combined with EPIBATIDINE.Approved, Nutraceutical
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
IsoflurophateThe risk or severity of adverse effects can be increased when Isoflurophate is combined with EPIBATIDINE.Approved, 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 Aop200704 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
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
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
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
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
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.Withdrawn
TimololThe risk or severity of adverse effects can be increased when Timolol is combined with EPIBATIDINE.Approved
TubocurarineThe risk or severity of adverse effects can be increased when Tubocurarine is combined with EPIBATIDINE.Approved
Food InteractionsNot 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 ReferencesNot Available
External Links
ATC CodesNot Available
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelNot Available
MSDSNot Available
Clinical Trials
Clinical Trials Not Available
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
StateSolid
Experimental PropertiesNot 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
SpectraNot Available
Taxonomy
DescriptionThis compound belongs to the class of chemical entities 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.
KingdomChemical entities
Super ClassOrganic compounds
ClassAlkaloids and derivatives
Sub ClassEpibatidine analogues
Direct ParentEpibatidine analogues
Alternative ParentsPyrrolidinylpyridines / Aralkylamines / 2-halopyridines / Aryl chlorides / Pyrrolidines / Heteroaromatic compounds / Dialkylamines / Azacyclic compounds / Organopnictogen compounds / Organochlorides
SubstituentsEpibatidine-skeleton / Pyrrolidinylpyridine / 2-halopyridine / Aralkylamine / Aryl chloride / Aryl halide / Pyridine / Heteroaromatic compound / Pyrrolidine / Azacycle
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptorsalkaloid (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
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 channel is blocked by alpha-bungarotoxin.
Gene Name:
CHRNA7
Uniprot ID:
P36544
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 permeable to sodiun ions.
Gene Name:
CHRNB2
Uniprot ID:
P17787
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
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
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 permeable to sodium ions.
Gene Name:
CHRNA4
Uniprot ID:
P43681
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
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 July 07, 2017 03:06