Acetylcholine
Identification
- Summary
Acetylcholine is a parasympathomimetic neurotransmitter used to induce miosis of the iris in seconds after delivery of the lens in cataract surgery, in penetrating keratoplasty, iridectomy and other anterior segment surgery where rapid miosis may be required.
- Brand Names
- Miochol
- Generic Name
- Acetylcholine
- DrugBank Accession Number
- DB03128
- Background
A neurotransmitter. Acetylcholine in vertebrates is the major transmitter at neuromuscular junctions, autonomic ganglia, parasympathetic effector junctions, a subset of sympathetic effector junctions, and at many sites in the central nervous system. It is generally not used as an administered drug because it is broken down very rapidly by cholinesterases, but it is useful in some ophthalmological applications.
- Type
- Small Molecule
- Groups
- Approved, Investigational
- Structure
Structure for Acetylcholine (DB03128)
- Weight
- Average: 146.2074
Monoisotopic: 146.118103761 - Chemical Formula
- C7H16NO2
- Synonyms
- Acetylcholine
- ACh
- Choline acetate
- O-Acetylcholine
Pharmacology
- Indication
Used to obtain miosis of the iris in seconds after delivery of the lens in cataract surgery, in penetrating keratoplasty, iridectomy and other anterior segment surgery where rapid miosis may be required.
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Contraindications & Blackbox WarningsWith our commercial data, access important information on dangerous risks, contraindications, and adverse effects.Our Blackbox Warnings cover Risks, Contraindications, and Adverse Effects- Pharmacodynamics
Not Available
- Mechanism of action
Target Actions Organism UAcetylcholinesterase Not Available Humans UMuscarinic acetylcholine receptor M1 Not Available Humans UMuscarinic acetylcholine receptor M2 Not Available Humans UMuscarinic acetylcholine receptor M3 Not Available Humans UMuscarinic acetylcholine receptor M4 Not Available Humans UNeuronal acetylcholine receptor subunit alpha-7 Not Available 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
Reduce medical errorsand improve treatment outcomes with our comprehensive & structured data on drug adverse effects.Reduce medical errors & improve treatment outcomes with our adverse effects data- Toxicity
Not Available
- Pathways
Pathway Category Cimetidine Action Pathway Drug action Gastric Acid Production Physiological Betazole Action Pathway Drug action Phospholipid Biosynthesis Metabolic Nizatidine Action Pathway Drug action Lafutidine H2-Antihistamine Action Drug action Esomeprazole Action Pathway Drug action Omeprazole Action Pathway Drug action Lansoprazole Action Pathway Drug action Pantoprazole Action Pathway Drug action Rabeprazole Action Pathway Drug action Ranitidine Action Pathway Drug action Famotidine Action Pathway Drug action Pirenzepine Action Pathway Drug action Roxatidine Acetate Action Pathway Drug action Metiamide Action Pathway Drug action - 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 Acetylcholine. Acyclovir The risk or severity of adverse effects can be increased when Acyclovir is combined with Acetylcholine. Amantadine The risk or severity of adverse effects can be increased when Amantadine is combined with Acetylcholine. Ambenonium The risk or severity of adverse effects can be increased when Ambenonium is combined with Acetylcholine. Amikacin The therapeutic efficacy of Acetylcholine 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 Acetylcholine. Atenolol The risk or severity of adverse effects can be increased when Atenolol is combined with Acetylcholine. Betaine The risk or severity of adverse effects can be increased when Betaine is combined with Acetylcholine. Betaxolol The risk or severity of adverse effects can be increased when Betaxolol is combined with Acetylcholine. Bisoprolol The risk or severity of adverse effects can be increased when Bisoprolol is combined with Acetylcholine. 
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- No interactions found.
Products
Comprehensive & structured drug product infoFrom application numbers to product codes, connect different identifiers through our commercial datasets.Easily connect various identifiers back to our datasets- Product Ingredients
Ingredient UNII CAS InChI Key Acetylcholine chloride AF73293C2R 60-31-1 JUGOREOARAHOCO-UHFFFAOYSA-N - Brand Name Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Miochol E Kit 20 mg/2mL Intraocular Novartis Pharmaceuticals Corporation 1993-09-22 2013-09-30 US 
Miochol E Powder, for solution 20 mg / vial Ophthalmic Bausch & Lomb Inc 1996-08-14 Not applicable Canada 
Miochol E Kit 20 mg/2mL Intraocular Bausch & Lomb Incorporated 1993-09-22 Not applicable US Miochol E Acetylcholine Chloride Oph Soln Powder, for solution 10 mg / mL Ophthalmic Iolab Pharmaceuticals 1994-12-31 1996-09-09 Canada Miogan Pws 20mg/vial Powder, for solution 20 mg / vial Intraocular Allergan 1990-12-31 2011-08-04 Canada
Categories
- ATC Codes
- S01EB09 — Acetylcholine
- Drug Categories
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as acyl cholines. These are acylated derivatives of choline. Choline or 2-Hydroxy-N,N,N-trimethylethanaminium is a quaternary ammonium salt with the chemical formula (CH3)3N+(CH2)2OH.
- Kingdom
- Organic compounds
- Super Class
- Organic nitrogen compounds
- Class
- Organonitrogen compounds
- Sub Class
- Quaternary ammonium salts
- Direct Parent
- Acyl cholines
- Alternative Parents
- Tetraalkylammonium salts / Carboxylic acid esters / Monocarboxylic acids and derivatives / Organopnictogen compounds / Organic salts / Organic oxides / Hydrocarbon derivatives / Carbonyl compounds / Amines / Organic cations
- Substituents
- Acyl choline / Aliphatic acyclic compound / Amine / Carbonyl group / Carboxylic acid derivative / Carboxylic acid ester / Hydrocarbon derivative / Monocarboxylic acid or derivatives / Organic cation / Organic oxide
- Molecular Framework
- Aliphatic acyclic compounds
- External Descriptors
- acetate ester, acylcholine (CHEBI:15355) / Acetylcholine (C01996) / a small molecule (ACETYLCHOLINE)
- Affected organisms
- Not Available
Chemical Identifiers
- UNII
- N9YNS0M02X
- CAS number
- 51-84-3
- InChI Key
- OIPILFWXSMYKGL-UHFFFAOYSA-N
- InChI
- InChI=1S/C7H16NO2/c1-7(9)10-6-5-8(2,3)4/h5-6H2,1-4H3/q+1
- IUPAC Name
- [2-(acetyloxy)ethyl]trimethylazanium
- SMILES
- CC(=O)OCC[N+](C)(C)C
References
- Synthesis Reference
Masao Tanihara, Hideaki Yamada, Toshihide Nakashima, Yoshiaki Omura, Koichi Takakura, "Human IgG.sub.1 monoclonal antibody specific for the nicotinic acetylcholine receptor and hybridoma producing the antibody." U.S. Patent US5192684, issued December, 1984.
US5192684- General References
- Not Available
- External Links
- Human Metabolome Database
- HMDB0000895
- KEGG Compound
- C01996
- PubChem Compound
- 187
- PubChem Substance
- 46504484
- ChemSpider
- 182
- BindingDB
- 10759
- 194
- ChEBI
- 15355
- ChEMBL
- CHEMBL667
- ZINC
- ZINC000003079336
- PharmGKB
- PA448031
- Guide to Pharmacology
- GtP Drug Page
- PDBe Ligand
- ACH
- Wikipedia
- Acetylcholine
- PDB Entries
- 2ace / 2ha4 / 2j0h / 2rin / 2xz5 / 3q5s / 3rqw / 3wip / 6v1r
Clinical Trials
- Clinical Trials
Phase Status Purpose Conditions Count 2 Completed Treatment Diabetes Mellitus, Noninsulin Dependent / Non-Insulin Dependent 1 2 Completed Treatment Memory Disorders, Age Related 1 2 Completed Treatment Schizophrenia 1 2 Completed Treatment Sickle Cell Anemia 1 2 Completed Treatment Sickle Cell Disease (SCD) 1 2 Terminated Diagnostic Hyperlipidemias 1 2 Terminated Treatment Anemia 1 1 Completed Not Available Inflammation 1 1 Completed Basic Science Healthy Volunteers 1 1 Completed Basic Science Microvascular coronary artery disease 1
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Novartis AG
- OMJ Pharmaceuticals
- Dosage Forms
Form Route Strength Kit Intraocular 20 mg/2mL Powder, for solution Ophthalmic 20 mg / vial Solution Intraocular Powder, for solution Ophthalmic 10 mg / mL Powder, for solution Intraocular 20 mg / vial Injection, powder, for solution Intraocular - Prices
- Not Available
- Patents
Patent Number Pediatric Extension Approved Expires (estimated) Region US6261546 No 2001-07-17 2019-04-29 US
Properties
- State
- Solid
- Experimental Properties
- Not Available
- Predicted Properties
Property Value Source Water Solubility 0.136 mg/mL ALOGPS logP -2.9 ALOGPS logP -4.2 ChemAxon logS -3.1 ALOGPS pKa (Strongest Basic) -7 ChemAxon Physiological Charge 1 ChemAxon Hydrogen Acceptor Count 1 ChemAxon Hydrogen Donor Count 0 ChemAxon Polar Surface Area 26.3 Å2 ChemAxon Rotatable Bond Count 4 ChemAxon Refractivity 51.35 m3·mol-1 ChemAxon Polarizability 16.69 Å3 ChemAxon Number of Rings 0 ChemAxon Bioavailability 1 ChemAxon Rule of Five Yes ChemAxon Ghose Filter No ChemAxon Veber's Rule Yes ChemAxon MDDR-like Rule No ChemAxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption - 0.974 Blood Brain Barrier + 0.9506 Caco-2 permeable + 0.7245 P-glycoprotein substrate Non-substrate 0.5678 P-glycoprotein inhibitor I Non-inhibitor 0.9815 P-glycoprotein inhibitor II Non-inhibitor 0.9436 Renal organic cation transporter Non-inhibitor 0.7024 CYP450 2C9 substrate Non-substrate 0.8287 CYP450 2D6 substrate Non-substrate 0.7531 CYP450 3A4 substrate Substrate 0.5447 CYP450 1A2 substrate Non-inhibitor 0.8913 CYP450 2C9 inhibitor Non-inhibitor 0.9611 CYP450 2D6 inhibitor Non-inhibitor 0.8953 CYP450 2C19 inhibitor Non-inhibitor 0.9565 CYP450 3A4 inhibitor Non-inhibitor 0.9689 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.9839 Ames test Non AMES toxic 0.8702 Carcinogenicity Carcinogens 0.6303 Biodegradation Ready biodegradable 0.8804 Rat acute toxicity 2.4062 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9083 hERG inhibition (predictor II) Non-inhibitor 0.8171
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Targets
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- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Serine hydrolase activity
- Specific Function
- Terminates signal transduction at the neuromuscular junction by rapid hydrolysis of the acetylcholine released into the synaptic cleft. Role in neuronal apoptosis.
- Gene Name
- ACHE
- Uniprot ID
- P22303
- Uniprot Name
- Acetylcholinesterase
- Molecular Weight
- 67795.525 Da
References
- Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
- Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [Article]
- 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
- Phosphatidylinositol phospholipase c activity
- Specific Function
- The muscarinic acetylcholine receptor mediates various cellular responses, including inhibition of adenylate cyclase, breakdown of phosphoinositides and modulation of potassium channels through the...
- Gene Name
- CHRM1
- Uniprot ID
- P11229
- Uniprot Name
- Muscarinic acetylcholine receptor M1
- Molecular Weight
- 51420.375 Da
References
- Birdsall NJ, Farries T, Gharagozloo P, Kobayashi S, Lazareno S, Sugimoto M: Subtype-selective positive cooperative interactions between brucine analogs and acetylcholine at muscarinic receptors: functional studies. Mol Pharmacol. 1999 Apr;55(4):778-86. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- G-protein coupled acetylcholine receptor activity
- Specific Function
- The muscarinic acetylcholine receptor mediates various cellular responses, including inhibition of adenylate cyclase, breakdown of phosphoinositides and modulation of potassium channels through the...
- Gene Name
- CHRM2
- Uniprot ID
- P08172
- Uniprot Name
- Muscarinic acetylcholine receptor M2
- Molecular Weight
- 51714.605 Da
References
- Birdsall NJ, Farries T, Gharagozloo P, Kobayashi S, Lazareno S, Sugimoto M: Subtype-selective positive cooperative interactions between brucine analogs and acetylcholine at muscarinic receptors: functional studies. Mol Pharmacol. 1999 Apr;55(4):778-86. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Receptor activity
- Specific Function
- The muscarinic acetylcholine receptor mediates various cellular responses, including inhibition of adenylate cyclase, breakdown of phosphoinositides and modulation of potassium channels through the...
- Gene Name
- CHRM3
- Uniprot ID
- P20309
- Uniprot Name
- Muscarinic acetylcholine receptor M3
- Molecular Weight
- 66127.445 Da
References
- Birdsall NJ, Farries T, Gharagozloo P, Kobayashi S, Lazareno S, Sugimoto M: Subtype-selective positive cooperative interactions between brucine analogs and acetylcholine at muscarinic receptors: functional studies. Mol Pharmacol. 1999 Apr;55(4):778-86. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Guanyl-nucleotide exchange factor activity
- Specific Function
- The muscarinic acetylcholine receptor mediates various cellular responses, including inhibition of adenylate cyclase, breakdown of phosphoinositides and modulation of potassium channels through the...
- Gene Name
- CHRM4
- Uniprot ID
- P08173
- Uniprot Name
- Muscarinic acetylcholine receptor M4
- Molecular Weight
- 53048.65 Da
References
- Birdsall NJ, Farries T, Gharagozloo P, Kobayashi S, Lazareno S, Sugimoto M: Subtype-selective positive cooperative interactions between brucine analogs and acetylcholine at muscarinic receptors: functional studies. Mol Pharmacol. 1999 Apr;55(4):778-86. [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
- Zhao L, Kuo YP, George AA, Peng JH, Purandare MS, Schroeder KM, Lukas RJ, Wu J: Functional properties of homomeric, human alpha 7-nicotinic acetylcholine receptors heterologously expressed in the SH-EP1 human epithelial cell line. J Pharmacol Exp Ther. 2003 Jun;305(3):1132-41. Epub 2003 Mar 6. [Article]
Transporters
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- Symporter activity
- Specific Function
- Sodium-ion dependent, high affinity carnitine transporter. Involved in the active cellular uptake of carnitine. Transports one sodium ion with one molecule of carnitine. Also transports organic cat...
- Gene Name
- SLC22A5
- Uniprot ID
- O76082
- Uniprot Name
- Solute carrier family 22 member 5
- Molecular Weight
- 62751.08 Da
References
- Ohashi R, Tamai I, Nezu Ji J, Nikaido H, Hashimoto N, Oku A, Sai Y, Shimane M, Tsuji A: Molecular and physiological evidence for multifunctionality of carnitine/organic cation transporter OCTN2. Mol Pharmacol. 2001 Feb;59(2):358-66. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- Secondary active organic cation transmembrane transporter activity
- Specific Function
- Translocates a broad array of organic cations with various structures and molecular weights including the model compounds 1-methyl-4-phenylpyridinium (MPP), tetraethylammonium (TEA), N-1-methylnico...
- Gene Name
- SLC22A1
- Uniprot ID
- O15245
- Uniprot Name
- Solute carrier family 22 member 1
- Molecular Weight
- 61153.345 Da
References
- Busch AE, Quester S, Ulzheimer JC, Gorboulev V, Akhoundova A, Waldegger S, Lang F, Koepsell H: Monoamine neurotransmitter transport mediated by the polyspecific cation transporter rOCT1. FEBS Lett. 1996 Oct 21;395(2-3):153-6. [Article]
- Kummer W, Wiegand S, Akinci S, Wessler I, Schinkel AH, Wess J, Koepsell H, Haberberger RV, Lips KS: Role of acetylcholine and polyspecific cation transporters in serotonin-induced bronchoconstriction in the mouse. Respir Res. 2006 Apr 12;7:65. doi: 10.1186/1465-9921-7-65. [Article]
Drug created on June 13, 2005 13:24 / Updated on July 29, 2021 06:27