Identification

Name
Acetylcholine
Accession Number
DB03128  (EXPT00412)
Type
Small Molecule
Groups
Approved, Investigational
Description

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.

Structure
Thumb
Synonyms
  • ACh
  • Choline acetate
  • O-Acetylcholine
Product Ingredients
IngredientUNIICASInChI Key
Acetylcholine chlorideAF73293C2R60-31-1JUGOREOARAHOCO-UHFFFAOYSA-N
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Miochol EKit20 mg/2mLNovartis Pharmaceuticals Corporation1993-09-222013-09-30Us
Miochol EPowder, for solution10 mgOphthalmicBausch & Lomb Inc1996-08-14Not applicableCanada
Miochol EKit20 mg/2mLBausch & Lomb Incorporated1993-09-22Not applicableUs
Miochol E Acetylcholine Chloride Oph SolnPowder, for solution10 mgOphthalmicIolab Pharmaceuticals1994-12-311996-09-09Canada
Miogan Pws 20mg/vialPowder, for solution20 mgIntraocularAllergan1990-12-312011-08-04Canada
Categories
UNII
N9YNS0M02X
CAS number
51-84-3
Weight
Average: 146.2074
Monoisotopic: 146.118103761
Chemical Formula
C7H16NO2
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

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.

Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UAcetylcholinesteraseNot AvailableHuman
UMuscarinic acetylcholine receptor M1Not AvailableHuman
UMuscarinic acetylcholine receptor M2Not AvailableHuman
UMuscarinic acetylcholine receptor M3Not AvailableHuman
UMuscarinic acetylcholine receptor M4Not AvailableHuman
UNeuronal acetylcholine receptor subunit alpha-7Not AvailableHuman
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
Toxicity
Not Available
Affected organisms
Not Available
Pathways
PathwayCategory
Lansoprazole Action PathwayDrug action
Lafutidine H2-Antihistamine ActionDrug action
Omeprazole Action PathwayDrug action
Cimetidine Action PathwayDrug action
Esomeprazole Action PathwayDrug action
Pantoprazole Action PathwayDrug action
Roxatidine Acetate Action PathwayDrug action
Phospholipid BiosynthesisMetabolic
Phospholipid BiosynthesisMetabolic
Ranitidine Action PathwayDrug action
Famotidine Action PathwayDrug action
Metiamide Action PathwayDrug action
Rabeprazole Action PathwayDrug action
Nizatidine Action PathwayDrug action
Pirenzepine Action PathwayDrug action
Gastric Acid ProductionPhysiological
Betazole Action PathwayDrug action
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteraction
1,10-PhenanthrolineThe risk or severity of adverse effects can be increased when 1,10-Phenanthroline is combined with Acetylcholine.
AcebutololThe risk or severity of adverse effects can be increased when Acebutolol is combined with Acetylcholine.
AlprenololThe risk or severity of adverse effects can be increased when Alprenolol 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.
AnisodamineThe risk or severity of adverse effects can be increased when Anisodamine is combined with Acetylcholine.
ApramycinThe therapeutic efficacy of Acetylcholine can be decreased when used in combination with Apramycin.
ArbekacinThe therapeutic efficacy of Acetylcholine can be decreased when used in combination with Arbekacin.
ArotinololThe risk or severity of adverse effects can be increased when Arotinolol is combined with Acetylcholine.
AtenololThe risk or severity of adverse effects can be increased when Atenolol is combined with Acetylcholine.
Food Interactions
Not Available

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
ChEBI
15355
ChEMBL
CHEMBL667
PharmGKB
PA448031
IUPHAR
294
Guide to Pharmacology
GtP Drug Page
HET
ACH
Wikipedia
Acetylcholine
ATC Codes
S01EB09 — Acetylcholine
AHFS Codes
  • 52:40.20 — Miotics
PDB Entries
2ace / 2ha4 / 2j0h / 2rin / 2xz5 / 3q5s / 3rqw / 3wip

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
1Active Not RecruitingDiagnosticAntibody Mediated Rejection / Cardiac Allograft Vasculopathy1
1CompletedBasic ScienceHealthy Volunteers1
1CompletedTreatmentHealthy Volunteers1
1CompletedTreatmentIschemic Stress / Transient Non-Lethal Ischemia1
1CompletedTreatmentSickle Cell Disorders1
1RecruitingBasic ScienceMicrovascular coronary artery disease1
1TerminatedTreatmentHuman Immunodeficiency Virus (HIV)1
2CompletedTreatmentDiabetes Mellitus, Non-Insulin Dependent / Non-Insulin Dependent1
2CompletedTreatmentSickle Cell Disorders2
2Not Yet RecruitingTreatmentAnemias1
2TerminatedDiagnosticHyperlipidemias1
3TerminatedPreventionDialysis Catheter Infections1
Not AvailableCompletedNot AvailableCardiovascular Disease (CVD) / Chronic Kidney Disease (CKD)1
Not AvailableCompletedNot AvailableEndothelial Dysfunction / High Blood Pressure (Hypertension) / Malignancies1
Not AvailableCompletedNot AvailableHealthy Volunteers1
Not AvailableCompletedNot AvailableLeiomyomas1
Not AvailableCompletedBasic ScienceHeart Diseases / Heart Failure, Unspecified / Vasodilatation1
Not AvailableCompletedOtherIschemic Preconditioning / Limb Ischemia1
Not AvailableNot Yet RecruitingBasic ScienceIschaemia-reperfusion (IR) Injury1
Not AvailableSuspendedNot AvailableIschemia-Reperfusion Injury1
Not AvailableUnknown StatusDiagnosticAtherosclerosis / Endothelial Dysfunction / Inflammatory Reaction / Myocardial Ischemia1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
  • Novartis AG
  • OMJ Pharmaceuticals
Dosage forms
FormRouteStrength
Kit20 mg/2mL
Powder, for solutionOphthalmic10 mg
Powder, for solutionIntraocular20 mg
Prices
Not Available
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)
US6261546No2001-07-172019-04-29Us

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

Taxonomy

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 / Tetraalkylammonium salt / Carboxylic acid ester / Monocarboxylic acid or derivatives / Carboxylic acid derivative / Organic oxygen compound / Organopnictogen compound / Organic oxide / Hydrocarbon derivative / Organic salt
Molecular Framework
Aliphatic acyclic compounds
External Descriptors
acetate ester, acylcholine (CHEBI:15355) / Acetylcholine (C01996) / a small molecule (ACETYLCHOLINE)

Targets

Kind
Protein
Organism
Human
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. [PubMed:17139284]
  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. [PubMed:17016423]
  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. [PubMed:10592235]
Kind
Protein
Organism
Human
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. [PubMed:10101037]
Kind
Protein
Organism
Human
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. [PubMed:10101037]
Kind
Protein
Organism
Human
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. [PubMed:10101037]
Kind
Protein
Organism
Human
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. [PubMed:10101037]
Kind
Protein
Organism
Human
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. [PubMed:12626641]

Transporters

Kind
Protein
Organism
Human
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. [PubMed:11160873]
Kind
Protein
Organism
Human
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. [PubMed:8898084]

Drug created on June 13, 2005 07:24 / Updated on November 18, 2018 04:51