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Identification
NameAcetylcholine
Accession NumberDB03128  (EXPT00412)
TypeSmall Molecule
GroupsApproved
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. [PubChem]

Structure
Thumb
Synonyms
Acetylcholine Chloride
External Identifiers Not Available
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Miochol EkitBausch & Lomb Incorporated1993-09-22Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Miochol Epowder for solution10 mgophthalmicBausch & Lomb Inc1996-08-14Not applicableCanada 5f16b84899037e23705f146ff57e3794121879cb055f0954756d94bc690476b4
Miochol E Acetylcholine Chloride Oph Solnpowder for solution10 mgophthalmicIolab Pharmaceuticals1994-12-311996-09-09Canada 5f16b84899037e23705f146ff57e3794121879cb055f0954756d94bc690476b4
Miogan Pws 20mg/vialpowder for solution20 mgintraocularAllergan Inc1990-12-312011-08-04Canada 5f16b84899037e23705f146ff57e3794121879cb055f0954756d94bc690476b4
Generic Prescription ProductsNot Available
Over the Counter ProductsNot Available
International BrandsNot Available
Brand mixturesNot Available
SaltsNot Available
Categories
UNIIN9YNS0M02X
CAS number51-84-3
WeightAverage: 146.2074
Monoisotopic: 146.118103761
Chemical FormulaC7H16NO2
InChI KeyInChIKey=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
Taxonomy
DescriptionThis 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.
KingdomOrganic compounds
Super ClassOrganonitrogen compounds
ClassQuaternary ammonium salts
Sub ClassCholines
Direct ParentAcyl cholines
Alternative Parents
Substituents
  • Acyl choline
  • Acetate salt
  • Carboxylic acid ester
  • Monocarboxylic acid or derivatives
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Amine
  • Organic cation
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Pharmacology
IndicationUsed 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.
PharmacodynamicsNot Available
Mechanism of actionNot Available
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
MetabolismNot Available
Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicityNot Available
Affected organismsNot Available
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
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 )
Pharmacoeconomics
ManufacturersNot Available
Packagers
Dosage forms
FormRouteStrength
Kit
Powder for solutionophthalmic10 mg
Powder for solutionintraocular20 mg
PricesNot Available
Patents
CountryPatent NumberApprovedExpires (estimated)
United States62615461999-04-292019-04-29
Properties
StateSolid
Experimental PropertiesNot 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 FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
Spectra
Spectrum TypeDescriptionSplash Key
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-zn00000000-ec60451904fda7dde556View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-z100000000-2ea4c086c3ab458a1d7cView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-z200000000-98d5a70eed75a0945da4View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positivesplash10-4z00000000-2da10e016ac539b6e981View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positivesplash10-z300000000-7efaaa08a6c43d816358View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positivesplash10-z000000000-eb7d66198d7674cbbd2aView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positivesplash10-z000000000-41b87d773c58129802e9View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positivesplash10-z000000000-9e8e66250f2cf34a2046View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positivesplash10-3z00000000-f7fe18f2371596dc7333View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 30V, Positivesplash10-zx00000000-b0f987ebcb0179a2c5abView in MoNA
1D NMR1H NMR SpectrumNot Available
2D NMR[1H,1H] 2D NMR SpectrumNot Available
2D NMR[1H,13C] 2D NMR SpectrumNot 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 ReferencesNot Available
External Links
ATC CodesS01EB09
AHFS CodesNot Available
PDB Entries
FDA labelNot Available
MSDSNot Available
Interactions
Drug Interactions
Drug
AcebutololThe risk or severity of adverse effects can be increased when Acebutolol is combined with Acetylcholine.
AtenololThe risk or severity of adverse effects can be increased when Atenolol is combined with Acetylcholine.
BendroflumethiazideThe risk or severity of adverse effects can be increased when Bendroflumethiazide 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.
CarteololThe risk or severity of adverse effects can be increased when Carteolol is combined with Acetylcholine.
CarvedilolThe risk or severity of adverse effects can be increased when Carvedilol is combined with Acetylcholine.
DonepezilThe risk or severity of adverse effects can be increased when Donepezil is combined with Acetylcholine.
EdrophoniumThe risk or severity of adverse effects can be increased when Edrophonium is combined with Acetylcholine.
EsmololThe risk or severity of adverse effects can be increased when Esmolol is combined with Acetylcholine.
GalantamineThe risk or severity of adverse effects can be increased when Galantamine is combined with Acetylcholine.
LabetalolThe risk or severity of adverse effects can be increased when Labetalol is combined with Acetylcholine.
LevobunololThe risk or severity of adverse effects can be increased when Levobunolol is combined with Acetylcholine.
MetipranololThe risk or severity of adverse effects can be increased when Metipranolol is combined with Acetylcholine.
MetoprololThe risk or severity of adverse effects can be increased when Metoprolol is combined with Acetylcholine.
NadololThe risk or severity of adverse effects can be increased when Nadolol is combined with Acetylcholine.
NebivololThe risk or severity of adverse effects can be increased when Nebivolol is combined with Acetylcholine.
NeostigmineThe risk or severity of adverse effects can be increased when Neostigmine is combined with Acetylcholine.
PenbutololThe risk or severity of adverse effects can be increased when Penbutolol is combined with Acetylcholine.
PhysostigmineThe risk or severity of adverse effects can be increased when Physostigmine is combined with Acetylcholine.
PindololThe risk or severity of adverse effects can be increased when Pindolol is combined with Acetylcholine.
PropranololThe risk or severity of adverse effects can be increased when Propranolol is combined with Acetylcholine.
PyridostigmineThe risk or severity of adverse effects can be increased when Pyridostigmine is combined with Acetylcholine.
RivastigmineThe risk or severity of adverse effects can be increased when Rivastigmine is combined with Acetylcholine.
SotalolThe risk or severity of adverse effects can be increased when Sotalol is combined with Acetylcholine.
TimololThe risk or severity of adverse effects can be increased when Timolol is combined with Acetylcholine.
Food InteractionsNot Available

Targets

1. Acetylcholinesterase

Kind: Protein

Organism: Human

Pharmacological action: unknown

Components

Name UniProt ID Details
Acetylcholinesterase P22303 Details

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
  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
  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

Enzymes

1. Cytochrome P450 2D6

Kind: Protein

Organism: Human

Pharmacological action: unknown

Actions: substrate

Components

Name UniProt ID Details
Cytochrome P450 2D6 P10635 Details

References:

  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. Epub 2009 Nov 24. Pubmed

Transporters

1. Solute carrier family 22 member 5

Kind: Protein

Organism: Human

Pharmacological action: unknown

Actions: inhibitor

Components

Name UniProt ID Details
Solute carrier family 22 member 5 O76082 Details

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

2. Solute carrier family 22 member 1

Kind: Protein

Organism: Human

Pharmacological action: unknown

Actions: substrate

Components

Name UniProt ID Details
Solute carrier family 22 member 1 O15245 Details

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

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Drug created on June 13, 2005 07:24 / Updated on January 12, 2016 14:13