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Identification
NameAcetylcholine
Accession NumberDB03128  (EXPT00412)
Typesmall molecule
Groupsexperimental
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
SynonymLanguageCode
Acetylcholine ChlorideNot AvailableNot Available
SaltsNot Available
Brand namesNot Available
Brand mixturesNot Available
Categories
CAS number51-84-3
WeightAverage: 146.2074
Monoisotopic: 146.118103761
Chemical FormulaC7H16NO2
InChI KeyOIPILFWXSMYKGL-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
Mass SpecNot Available
Taxonomy
KingdomOrganic Compounds
SuperclassOrganonitrogen Compounds
ClassQuaternary Ammonium Salts
SubclassCholines
Direct parentCholines
Alternative parentsCarboxylic Acid Esters; Ethers; Enolates; Polyamines
Substituentscarboxylic acid ester; polyamine; carboxylic acid derivative; enolate; ether; amine
Classification descriptionThis compound belongs to the cholines. These are organic compounds containing a N,N,N-trimethylethanolammonium cation.
Pharmacology
IndicationNot Available
PharmacodynamicsNot Available
Mechanism of actionNot Available
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
Metabolism
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
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 substrate Non-inhibitor 0.9611
CYP450 2D6 substrate Non-inhibitor 0.8953
CYP450 2C19 substrate Non-inhibitor 0.9565
CYP450 3A4 substrate 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
Pharmacoeconomics
Manufacturers
  • Novartis pharmaceuticals corp
Packagers
Dosage formsNot Available
PricesNot Available
Patents
CountryPatent NumberApprovedExpires (estimated)
United States62615461999-04-292019-04-29
Properties
Statesolid
Experimental PropertiesNot Available
Predicted Properties
PropertyValueSource
water solubility1.36e-01 g/lALOGPS
logP-2.9ALOGPS
logP-4.2ChemAxon
logS-3.1ALOGPS
pKa (strongest basic)-7ChemAxon
physiological charge1ChemAxon
hydrogen acceptor count1ChemAxon
hydrogen donor count0ChemAxon
polar surface area26.3ChemAxon
rotatable bond count4ChemAxon
refractivity51.35ChemAxon
polarizability16.69ChemAxon
number of rings0ChemAxon
bioavailability1ChemAxon
rule of fiveYesChemAxon
Ghose filterNoChemAxon
Veber's ruleYesChemAxon
MDDR-like ruleNoChemAxon
Spectra
SpectraMS/MSLC-MS1D NMR2D NMR
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 ReferenceNot Available
External Links
ResourceLink
KEGG CompoundC01996
PubChem Compound187
PubChem Substance46504484
ChEBI15355
ChEMBL
PharmGKBPA448031
IUPHAR294
Guide to Pharmacology294
HETACH
ATC CodesNot Available
AHFS CodesNot Available
PDB Entries
FDA labelNot Available
MSDSNot Available
Interactions
Drug Interactions
Drug
TacrineThe acetylcholinesterase inhibitor, Tacrine, may increase the adverse/toxic effects of Acetylcholine, a cholinergic agonist. Monitor for increased cholinergic effects and toxicity.
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 September 16, 2013 17:20