NAV

Epibatidine

Identification

Generic Name
Epibatidine
DrugBank Accession Number
DB07720
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
3D
Similar Structures
Weight
Average: 208.687
Monoisotopic: 208.076726133
Chemical Formula
C11H13ClN2
Synonyms
  • (+)-epibatidine
  • (1R,2R,4S)-epibatidine
External IDs
  • CMI-488

Pharmacology

Indication

Not Available

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Contraindications & Blackbox Warnings
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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
UCHRNA7-FAM7A fusion proteinNot AvailableHumans
UNeuronal acetylcholine receptor subunit alpha-7Not AvailableHumans
UNeuronal acetylcholine receptor subunit beta-2Not AvailableHumans
UNeuronal acetylcholine receptor subunit alpha-2
agonist
Humans
UNeuronal acetylcholine receptor subunit alpha-3
agonist
Humans
UNeuronal acetylcholine receptor subunit alpha-4
agonist
Humans
UNeuronal acetylcholine receptor subunit beta-4
agonist
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
Not Available

Interactions

Drug Interactions
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.
DrugInteraction
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AcebutololThe risk or severity of adverse effects can be increased when Acebutolol 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.
AprotininThe risk or severity of adverse effects can be increased when Aprotinin is combined with Epibatidine.
AtenololThe risk or severity of adverse effects can be increased when Atenolol is combined with Epibatidine.
BetaineThe risk or severity of adverse effects can be increased when Betaine is combined with Epibatidine.
BetaxololThe risk or severity of adverse effects can be increased when Betaxolol is combined with Epibatidine.
BisoprololThe risk or severity of adverse effects can be increased when Bisoprolol is combined with Epibatidine.
CapreomycinThe therapeutic efficacy of Epibatidine can be decreased when used in combination with Capreomycin.
CapsaicinThe risk or severity of adverse effects can be increased when Capsaicin is combined with Epibatidine.
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Food Interactions
Not Available

Categories

Drug Categories
Chemical TaxonomyProvided by Classyfire
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
2-halopyridine / Amine / Aralkylamine / Aromatic heteropolycyclic compound / Aryl chloride / Aryl halide / Azacycle / Epibatidine-skeleton / Heteroaromatic compound / Hydrocarbon derivative
show 11 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
alkaloid (CHEBI:4803)
Affected organisms
Not Available

Chemical Identifiers

UNII
M6K314F1XX
CAS number
140111-52-0
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

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
PubChem Compound
854023
PubChem Substance
99444191
ChemSpider
10399316
BindingDB
50143314
ChEBI
4803
ChEMBL
CHEMBL298826
ZINC
ZINC000000402872
PDBe Ligand
EPJ
Wikipedia
Epibatidine
PDB Entries
2byq / 3sq6 / 5fjv / 7koq / 7kox

Clinical Trials

Clinical Trials
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 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

Targets

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Details1. CHRNA7-FAM7A fusion protein
Kind
Protein
Organism
Humans
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. [Article]
Details2. Neuronal acetylcholine receptor subunit alpha-7
Kind
Protein
Organism
Humans
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. [Article]
Details3. 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. 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. [Article]
Details4. Neuronal acetylcholine receptor subunit alpha-2
Kind
Protein
Organism
Humans
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. [Article]
Details5. Neuronal acetylcholine receptor subunit alpha-3
Kind
Protein
Organism
Humans
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. [Article]
Details6. Neuronal acetylcholine receptor subunit alpha-4
Kind
Protein
Organism
Humans
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. [Article]
Details7. Neuronal acetylcholine receptor subunit beta-4
Kind
Protein
Organism
Humans
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. [Article]

Drug created at September 15, 2010 21:25 / Updated at June 12, 2020 16:52