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
Thumb
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.

Pharmacology
Accelerate your drug discovery research with the industry’s only fully connected ADMET dataset, ideal for:
Machine Learning
Data Science
Drug Discovery
Accelerate your drug discovery research with our fully connected ADMET dataset
Learn more
Contraindications & Blackbox Warnings
Contraindications
Contraindications & Blackbox Warnings
With our commercial data, access important information on dangerous risks, contraindications, and adverse effects.
Learn more
Our Blackbox Warnings cover Risks, Contraindications, and Adverse Effects
Learn more
Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
UAcetylcholinesteraseNot AvailableHumans
UMuscarinic acetylcholine receptor M1Not AvailableHumans
UMuscarinic acetylcholine receptor M2Not AvailableHumans
UMuscarinic acetylcholine receptor M3Not AvailableHumans
UMuscarinic acetylcholine receptor M4Not AvailableHumans
UNeuronal acetylcholine receptor subunit alpha-7Not AvailableHumans
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
Medicalerrors
Reduce medical errors
and improve treatment outcomes with our comprehensive & structured data on drug adverse effects.
Learn more
Reduce medical errors & improve treatment outcomes with our adverse effects data
Learn more
Toxicity

Not Available

Pathways
PathwayCategory
Cimetidine Action PathwayDrug action
Gastric Acid ProductionPhysiological
Betazole Action PathwayDrug action
Phospholipid BiosynthesisMetabolic
Nizatidine Action PathwayDrug action
Lafutidine H2-Antihistamine ActionDrug action
Esomeprazole Action PathwayDrug action
Omeprazole Action PathwayDrug action
Lansoprazole Action PathwayDrug action
Pantoprazole Action PathwayDrug action
Rabeprazole Action PathwayDrug action
Ranitidine Action PathwayDrug action
Famotidine Action PathwayDrug action
Pirenzepine Action PathwayDrug action
Roxatidine Acetate Action PathwayDrug action
Metiamide Action PathwayDrug 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.
DrugInteraction
AcebutololThe risk or severity of adverse effects can be increased when Acebutolol is combined with Acetylcholine.
AcyclovirThe risk or severity of adverse effects can be increased when Acyclovir is combined with Acetylcholine.
AmantadineThe risk or severity of adverse effects can be increased when Amantadine is combined with Acetylcholine.
AmbenoniumThe risk or severity of adverse effects can be increased when Ambenonium is combined with Acetylcholine.
AmikacinThe therapeutic efficacy of Acetylcholine can be decreased when used in combination with Amikacin.
AprotininThe risk or severity of adverse effects can be increased when Aprotinin is combined with Acetylcholine.
AtenololThe risk or severity of adverse effects can be increased when Atenolol is combined with Acetylcholine.
BetaineThe risk or severity of adverse effects can be increased when Betaine is combined with Acetylcholine.
BetaxololThe risk or severity of adverse effects can be increased when Betaxolol is combined with Acetylcholine.
BisoprololThe risk or severity of adverse effects can be increased when Bisoprolol is combined with Acetylcholine.
Interactions
Improve patient outcomes
Build effective decision support tools with the industry’s most comprehensive drug-drug interaction checker.
Learn more
Food Interactions
No interactions found.

Products

Products
Comprehensive & structured drug product info
From application numbers to product codes, connect different identifiers through our commercial datasets.
Learn more
Easily connect various identifiers back to our datasets
Learn more
Product Ingredients
IngredientUNIICASInChI Key
Acetylcholine chlorideAF73293C2R60-31-1JUGOREOARAHOCO-UHFFFAOYSA-N
Brand Name Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
Miochol EKit20 mg/2mLIntraocularNovartis Pharmaceuticals Corporation1993-09-222013-09-30US flag
Miochol EPowder, for solution20 mg / vialOphthalmicBausch & Lomb Inc1996-08-14Not applicableCanada flag
Miochol EKit20 mg/2mLIntraocularBausch & Lomb Incorporated1993-09-22Not applicableUS flag
Miochol E Acetylcholine Chloride Oph SolnPowder, for solution10 mg / mLOphthalmicIolab Pharmaceuticals1994-12-311996-09-09Canada flag
Miogan Pws 20mg/vialPowder, for solution20 mg / vialIntraocularAllergan1990-12-312011-08-04Canada flag

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
Human Metabolome Database
HMDB0000895
KEGG Compound
C01996
PubChem Compound
187
PubChem Substance
46504484
ChemSpider
182
BindingDB
10759
RxNav
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
PhaseStatusPurposeConditionsCount
2CompletedTreatmentDiabetes Mellitus, Noninsulin Dependent / Non-Insulin Dependent1
2CompletedTreatmentMemory Disorders, Age Related1
2CompletedTreatmentSchizophrenia1
2CompletedTreatmentSickle Cell Anemia1
2CompletedTreatmentSickle Cell Disease (SCD)1
2TerminatedDiagnosticHyperlipidemias1
2TerminatedTreatmentAnemia1
1CompletedNot AvailableInflammation1
1CompletedBasic ScienceHealthy Volunteers1
1CompletedBasic ScienceMicrovascular coronary artery disease1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
  • Novartis AG
  • OMJ Pharmaceuticals
Dosage Forms
FormRouteStrength
KitIntraocular20 mg/2mL
Powder, for solutionOphthalmic20 mg / vial
SolutionIntraocular
Powder, for solutionOphthalmic10 mg / mL
Powder, for solutionIntraocular20 mg / vial
Injection, powder, for solutionIntraocular
Prices
Not Available
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)Region
US6261546No2001-07-172019-04-29US flag

Properties

State
Solid
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.136 mg/mLALOGPS
logP-2.9ALOGPS
logP-4.2ChemAxon
logS-3.1ALOGPS
pKa (Strongest Basic)-7ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area26.3 Å2ChemAxon
Rotatable Bond Count4ChemAxon
Refractivity51.35 m3·mol-1ChemAxon
Polarizability16.69 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption-0.974
Blood Brain Barrier+0.9506
Caco-2 permeable+0.7245
P-glycoprotein substrateNon-substrate0.5678
P-glycoprotein inhibitor INon-inhibitor0.9815
P-glycoprotein inhibitor IINon-inhibitor0.9436
Renal organic cation transporterNon-inhibitor0.7024
CYP450 2C9 substrateNon-substrate0.8287
CYP450 2D6 substrateNon-substrate0.7531
CYP450 3A4 substrateSubstrate0.5447
CYP450 1A2 substrateNon-inhibitor0.8913
CYP450 2C9 inhibitorNon-inhibitor0.9611
CYP450 2D6 inhibitorNon-inhibitor0.8953
CYP450 2C19 inhibitorNon-inhibitor0.9565
CYP450 3A4 inhibitorNon-inhibitor0.9689
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9839
Ames testNon AMES toxic0.8702
CarcinogenicityCarcinogens 0.6303
BiodegradationReady biodegradable0.8804
Rat acute toxicity2.4062 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9083
hERG inhibition (predictor II)Non-inhibitor0.8171
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
MS/MS Spectrum - Quattro_QQQ 10V, PositiveLC-MS/MSsplash10-000j-9600000000-ec60451904fda7dde556
MS/MS Spectrum - Quattro_QQQ 25V, PositiveLC-MS/MSsplash10-000l-9000000000-2ea4c086c3ab458a1d7c
MS/MS Spectrum - Quattro_QQQ 40V, PositiveLC-MS/MSsplash10-0006-9000000000-98d5a70eed75a0945da4
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, PositiveLC-MS/MSsplash10-0002-1900000000-2da10e016ac539b6e981
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, PositiveLC-MS/MSsplash10-000i-9000000000-7efaaa08a6c43d816358
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, PositiveLC-MS/MSsplash10-000i-9000000000-eb7d66198d7674cbbd2a
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, PositiveLC-MS/MSsplash10-000l-9000000000-41b87d773c58129802e9
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, PositiveLC-MS/MSsplash10-0006-9000000000-9e8e66250f2cf34a2046
LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , PositiveLC-MS/MSsplash10-0002-0900000000-f7fe18f2371596dc7333
LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 30V, PositiveLC-MS/MSsplash10-000j-9800000000-b0f987ebcb0179a2c5ab
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-000i-9000000000-1be58612df9c1eef1282
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-0002-1900000000-2da10e016ac539b6e981
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-000i-9000000000-7efaaa08a6c43d816358
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-000i-9000000000-eb7d66198d7674cbbd2a
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-000l-9000000000-41b87d773c58129802e9
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-0006-9000000000-9ac44e29bdfbddf1b90d
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-0002-0900000000-f7fe18f2371596dc7333
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-000j-9800000000-b0f987ebcb0179a2c5ab
MS/MS Spectrum - , positiveLC-MS/MSsplash10-000j-9400000000-8a3a0b77e93715b85ed4
1H NMR Spectrum1D NMRNot Applicable
[1H,1H] 2D NMR Spectrum2D NMRNot Applicable
[1H,13C] 2D NMR Spectrum2D NMRNot Applicable

Targets

Drugtargets
Accelerate your drug discovery research
with our fully connected ADMET & drug target dataset.
Learn more
Accelerate your drug discovery research with our ADMET & drug target dataset
Learn more
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
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
  2. 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]
  3. 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
  1. 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
  1. 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
  1. 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
  1. 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
  1. 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
  1. 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
  1. 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]
  2. 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