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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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Prevent Adverse Drug Events TodayTap into our Clinical API for life-saving information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events with our Clinical API- Pharmacodynamics
Not Available
- Mechanism of action
Target Actions Organism 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
Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured 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. - Food Interactions
- No interactions found.
Products
Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.- 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 Kit; Solution 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 
Miochol-E Powder, for solution 20 mg / vial Ophthalmic Bausch & Lomb Inc 1996-08-14 Not applicable Canada Miogan Pws 20mg/vial Powder, for solution 20 mg / vial Intraocular Allergan 1990-12-31 2011-08-04 Canada - Over the Counter Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image MIOCHOL-E INTRAOCULAR SOLUTION Injection 20 mg/2ml Intraocular BAUSCH & LOMB (SINGAPORE) PRIVATE LIMITED 1997-03-18 Not applicable Singapore 
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 / 7prr … show 14 more
Clinical Trials
- Clinical Trials
Clinical Trial & Rare Diseases Add-on Data Package
Explore 4,000+ rare diseases, orphan drugs & condition pairs, clinical trial why stopped data, & more. Preview package Phase Status Purpose Conditions Count Start Date Why Stopped 100+ additional columns Unlock 175K+ rows when you subscribe.View sample dataNot Available Active Not Recruiting Basic Science Oral Soft Tissue Conditions / Vasodilation 1 somestatus stop reason just information to hide Not Available Completed Not Available Cancer / Endothelial Dysfunction / Hypertension 1 somestatus stop reason just information to hide Not Available Completed Not Available Cardiovascular Disease (CVD) / Chronic Kidney Disease (CKD) 1 somestatus stop reason just information to hide Not Available Completed Not Available Healthy Volunteers (HV) 1 somestatus stop reason just information to hide Not Available Completed Not Available Type 1 Diabetes Mellitus 1 somestatus stop reason just information to hide
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Novartis AG
- OMJ Pharmaceuticals
- Dosage Forms
Form Route Strength Kit Intraocular 20 mg/2mL Kit; solution Intraocular 20 mg/2mL Solution Intraocular Powder, for solution Ophthalmic 10 mg / mL Powder, for solution Ophthalmic 20 mg / vial Injection Intraocular 20 mg/2ml 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
- Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 125.69508 predictedDeepCCS 1.0 (2019) [M+H]+ 128.36234 predictedDeepCCS 1.0 (2019) [M+Na]+ 136.54405 predictedDeepCCS 1.0 (2019)
Targets
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- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- The muscarinic acetylcholine receptor mediates various cellular responses, including inhibition of adenylate cyclase, breakdown of phosphoinositides and modulation of potassium channels through the action of G proteins. Primary transducing effect is Pi turnover
- Specific Function
- G protein-coupled acetylcholine receptor activity
- 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
- The muscarinic acetylcholine receptor mediates various cellular responses, including inhibition of adenylate cyclase, breakdown of phosphoinositides and modulation of potassium channels through the action of G proteins. Primary transducing effect is adenylate cyclase inhibition. Signaling promotes phospholipase C activity, leading to the release of inositol trisphosphate (IP3); this then triggers calcium ion release into the cytosol
- Specific Function
- Arrestin family protein binding
- 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
- The muscarinic acetylcholine receptor mediates various cellular responses, including inhibition of adenylate cyclase, breakdown of phosphoinositides and modulation of potassium channels through the action of G proteins. Primary transducing effect is Pi turnover
- Specific Function
- Acetylcholine binding
- 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
- The muscarinic acetylcholine receptor mediates various cellular responses, including inhibition of adenylate cyclase, breakdown of phosphoinositides and modulation of potassium channels through the action of G proteins. Primary transducing effect is inhibition of adenylate cyclase
- Specific Function
- G protein-coupled acetylcholine receptor activity
- 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
- 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
- Specific Function
- Acetylcholine binding
- 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]
Enzymes
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- No
- Actions
- Substrate
- General Function
- Hydrolyzes rapidly the acetylcholine neurotransmitter released into the synaptic cleft allowing to terminate the signal transduction at the neuromuscular junction. Role in neuronal apoptosis
- Specific Function
- Acetylcholine binding
- Gene Name
- ACHE
- Uniprot ID
- P22303
- Uniprot Name
- Acetylcholinesterase
- Molecular Weight
- 67795.525 Da
References
- Li S, Li AJ, Travers J, Xu T, Sakamuru S, Klumpp-Thomas C, Huang R, Xia M: Identification of Compounds for Butyrylcholinesterase Inhibition. SLAS Discov. 2021 Dec;26(10):1355-1364. doi: 10.1177/24725552211030897. Epub 2021 Jul 16. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- No
- Actions
- Substrate
- General Function
- Esterase with broad substrate specificity. Contributes to the inactivation of the neurotransmitter acetylcholine. Can degrade neurotoxic organophosphate esters
- Specific Function
- Acetylcholinesterase activity
- Gene Name
- BCHE
- Uniprot ID
- P06276
- Uniprot Name
- Cholinesterase
- Molecular Weight
- 68417.575 Da
References
- Li S, Li AJ, Travers J, Xu T, Sakamuru S, Klumpp-Thomas C, Huang R, Xia M: Identification of Compounds for Butyrylcholinesterase Inhibition. SLAS Discov. 2021 Dec;26(10):1355-1364. doi: 10.1177/24725552211030897. Epub 2021 Jul 16. [Article]
Transporters
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General 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 (PubMed:10454528, PubMed:10525100, PubMed:10966938, PubMed:17509700, PubMed:20722056, PubMed:33124720). Also transports organic cations such as tetraethylammonium (TEA) without the involvement of sodium. Relative uptake activity ratio of carnitine to TEA is 11.3 (PubMed:10454528, PubMed:10525100, PubMed:10966938). In intestinal epithelia, transports the quorum-sensing pentapeptide CSF (competence and sporulation factor) from Bacillus Subtilis wich induces cytoprotective heat shock proteins contributing to intestinal homeostasis (PubMed:18005709). May also contribute to regulate the transport of organic compounds in testis across the blood-testis-barrier (Probable)
- Specific Function
- (r)-carnitine transmembrane transporter activity
- Gene Name
- SLC22A5
- Uniprot ID
- O76082
- Uniprot Name
- Organic cation/carnitine transporter 2
- 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
- Electrogenic voltage-dependent transporter that mediates the transport of a variety of organic cations such as endogenous bioactive amines, cationic drugs and xenobiotics (PubMed:11388889, PubMed:11408531, PubMed:12439218, PubMed:12719534, PubMed:15389554, PubMed:16263091, PubMed:16272756, PubMed:16581093, PubMed:19536068, PubMed:21128598, PubMed:23680637, PubMed:24961373, PubMed:34040533, PubMed:9187257, PubMed:9260930, PubMed:9655880). Functions as a pH- and Na(+)-independent, bidirectional transporter (By similarity). Cation cellular uptake or release is driven by the electrochemical potential (i.e. membrane potential and concentration gradient) and substrate selectivity (By similarity). Hydrophobicity is a major requirement for recognition in polyvalent substrates and inhibitors (By similarity). Primarily expressed at the basolateral membrane of hepatocytes and proximal tubules and involved in the uptake and disposition of cationic compounds by hepatic and renal clearance from the blood flow (By similarity). Most likely functions as an uptake carrier in enterocytes contributing to the intestinal elimination of organic cations from the systemic circulation (PubMed:16263091). Transports endogenous monoamines such as N-1-methylnicotinamide (NMN), guanidine, histamine, neurotransmitters dopamine, serotonin and adrenaline (PubMed:12439218, PubMed:24961373, PubMed:35469921, PubMed:9260930). Also transports natural polyamines such as spermidine, agmatine and putrescine at low affinity, but relatively high turnover (PubMed:21128598). Involved in the hepatic uptake of vitamin B1/thiamine, hence regulating hepatic lipid and energy metabolism (PubMed:24961373). Mediates the bidirectional transport of acetylcholine (ACh) at the apical membrane of ciliated cell in airway epithelium, thereby playing a role in luminal release of ACh from bronchial epithelium (PubMed:15817714). Transports dopaminergic neuromodulators cyclo(his-pro) and salsolinol with lower efficency (PubMed:17460754). Also capable of transporting non-amine endogenous compounds such as prostaglandin E2 (PGE2) and prostaglandin F2-alpha (PGF2-alpha) (PubMed:11907186). May contribute to the transport of cationic compounds in testes across the blood-testis-barrier (Probable). Also involved in the uptake of xenobiotics tributylmethylammonium (TBuMA), quinidine, N-methyl-quinine (NMQ), N-methyl-quinidine (NMQD) N-(4,4-azo-n-pentyl)-quinuclidine (APQ), azidoprocainamide methoiodide (AMP), N-(4,4-azo-n-pentyl)-21-deoxyajmalinium (APDA) and 4-(4-(dimethylamino)styryl)-N-methylpyridinium (ASP) (PubMed:11408531, PubMed:15389554, PubMed:35469921, PubMed:9260930)
- Specific Function
- (r)-carnitine transmembrane transporter activity
- 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 at June 13, 2005 13:24 / Updated at September 17, 2024 22:26