Epibatidine
Identification
- Generic Name
- Epibatidine
- DrugBank Accession Number
- DB07720
- Background
Not Available
- Type
- Small Molecule
- Groups
- Experimental
- Structure
Structure for Epibatidine (DB07720)
- Weight
- Average: 208.687
Monoisotopic: 208.076726133 - Chemical Formula
- C11H13ClN2
- Synonyms
- (+)-epibatidine
- (1R,2R,4S)-epibatidine
- External IDs
- CMI-488
Pharmacology
- Indication
Not Available
Reduce drug development failure ratesBuild, train, & validate machine-learning modelswith evidence-based and structured datasets.Build, train, & validate predictive machine-learning models with structured datasets.- Contraindications & Blackbox Warnings
Avoid life-threatening adverse drug eventsImprove clinical decision support with information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events & improve clinical decision support.- Pharmacodynamics
Not Available
- Mechanism of action
Target Actions Organism UCHRNA7-FAM7A fusion protein Not Available Humans UNeuronal acetylcholine receptor subunit alpha-7 Not Available Humans UNeuronal acetylcholine receptor subunit beta-2 Not Available Humans UNeuronal acetylcholine receptor subunit alpha-2 agonistHumans UNeuronal acetylcholine receptor subunit alpha-3 agonistHumans UNeuronal acetylcholine receptor subunit alpha-4 agonistHumans UNeuronal acetylcholine receptor subunit beta-4 agonistHumans - 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
Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates.Improve decision support & research outcomes with our structured adverse effects data.- 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.
Drug Interaction Integrate drug-drug
interactions in your softwareAcebutolol The risk or severity of adverse effects can be increased when Acebutolol is combined with Epibatidine. Ambenonium The risk or severity of adverse effects can be increased when Ambenonium is combined with Epibatidine. Amikacin The therapeutic efficacy of Epibatidine can be decreased when used in combination with Amikacin. Aprotinin The risk or severity of adverse effects can be increased when Aprotinin is combined with Epibatidine. Atenolol The risk or severity of adverse effects can be increased when Atenolol is combined with Epibatidine. Betaine The risk or severity of adverse effects can be increased when Betaine is combined with Epibatidine. Betaxolol The risk or severity of adverse effects can be increased when Betaxolol is combined with Epibatidine. Bisoprolol The risk or severity of adverse effects can be increased when Bisoprolol is combined with Epibatidine. Capreomycin The therapeutic efficacy of Epibatidine can be decreased when used in combination with Capreomycin. Capsaicin The risk or severity of adverse effects can be increased when Capsaicin is combined with Epibatidine. 
Identify potential medication risksEasily compare up to 40 drugs with our drug interaction checker.Get severity rating, description, and management advice.Learn more - 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
- External Links
- 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
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
Property Value Source Water Solubility 0.467 mg/mL ALOGPS logP 1.98 ALOGPS logP 1.84 ChemAxon logS -2.6 ALOGPS pKa (Strongest Basic) 10.54 ChemAxon Physiological Charge 1 ChemAxon Hydrogen Acceptor Count 2 ChemAxon Hydrogen Donor Count 1 ChemAxon Polar Surface Area 24.92 Å2 ChemAxon Rotatable Bond Count 1 ChemAxon Refractivity 57.39 m3·mol-1 ChemAxon Polarizability 22.07 Å3 ChemAxon Number of Rings 3 ChemAxon Bioavailability 1 ChemAxon Rule of Five Yes ChemAxon Ghose Filter Yes ChemAxon Veber's Rule Yes ChemAxon MDDR-like Rule No ChemAxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 1.0 Blood Brain Barrier + 0.9767 Caco-2 permeable - 0.5099 P-glycoprotein substrate Non-substrate 0.6541 P-glycoprotein inhibitor I Non-inhibitor 0.7432 P-glycoprotein inhibitor II Non-inhibitor 0.8989 Renal organic cation transporter Non-inhibitor 0.5127 CYP450 2C9 substrate Non-substrate 0.8639 CYP450 2D6 substrate Non-substrate 0.7657 CYP450 3A4 substrate Non-substrate 0.6359 CYP450 1A2 substrate Non-inhibitor 0.7682 CYP450 2C9 inhibitor Non-inhibitor 0.9071 CYP450 2D6 inhibitor Non-inhibitor 0.9231 CYP450 2C19 inhibitor Non-inhibitor 0.9025 CYP450 3A4 inhibitor Non-inhibitor 0.8309 CYP450 inhibitory promiscuity High CYP Inhibitory Promiscuity 0.6843 Ames test Non AMES toxic 0.6607 Carcinogenicity Non-carcinogens 0.9402 Biodegradation Not ready biodegradable 0.992 Rat acute toxicity 2.6084 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.8853 hERG inhibition (predictor II) Non-inhibitor 0.508
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted GC-MS Spectrum - GC-MS Predicted GC-MS Not Available Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS Not Available
Targets
Build, predict & validate machine-learning models
Use our structured and evidence-based datasets to unlock newinsights and accelerate drug research.
Use our structured and evidence-based datasets to unlock new insights and accelerate drug research.
- 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
- 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]
- 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
- 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]
- 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
- 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]
- 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
- 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]
- 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
- 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]
- 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
- 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]
- 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
- 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 on September 15, 2010 21:25 / Updated on June 12, 2020 16:52