Details of the Drug

General Information of Drug (ID: DMDF79Z)

Drug Name
Acetylcholine
Synonyms
acetylcholine; Choline acetate; O-Acetylcholine; Acetyl choline ion; Acetylcholinum; 51-84-3; (2-Acetoxyethyl)trimethylammonium; Acetyl choline cation; Choline acetate (ester); 2-(Acetyloxy)-N,N,N-trimethylethanaminium; Ach; Azetylcholin; ethanaminium, 2-(acetyloxy)-N,N,N-trimethyl-; UNII-N9YNS0M02X; BRN 1764436; CHEBI:15355; Bromoacetylcholine; EINECS 200-128-9; CHEMBL667; N9YNS0M02X; [2-(acetyloxy)ethyl]trimethylazanium; Ethanaminium, 2-(acetyloxy)-N,N,N-trimethyl- (9CI); 2-acetyloxyethyl-trimethylazanium; [3H]acetylcholine; Miochol; Miochol-e
Indication
Disease Entry ICD 11 Status REF
Cataract 9B10 Approved [1]
Therapeutic Class
Cardiovascular Agents
Drug Type
Small molecular drug
Structure
3D MOL 2D MOL
#Ro5 Violations (Lipinski): 0 Molecular Weight (mw) 146.21
Logarithm of the Partition Coefficient (xlogp) 0.2
Rotatable Bond Count (rotbonds) 4
Hydrogen Bond Donor Count (hbonddonor) 0
Hydrogen Bond Acceptor Count (hbondacc) 2
Chemical Identifiers
Formula
C7H16NO2+
IUPAC Name
2-acetyloxyethyl(trimethyl)azanium
Canonical SMILES
CC(=O)OCC[N+](C)(C)C
InChI
InChI=1S/C7H16NO2/c1-7(9)10-6-5-8(2,3)4/h5-6H2,1-4H3/q+1
InChIKey
OIPILFWXSMYKGL-UHFFFAOYSA-N
Cross-matching ID
PubChem CID
187
ChEBI ID
CHEBI:15355
CAS Number
51-84-3
DrugBank ID
DB03128
TTD ID
D0Q9HF
VARIDT ID
DR00070
INTEDE ID
DR0041
Combinatorial Drugs (CBD) Click to Jump to the Detailed CBD Information of This Drug

Molecular Interaction Atlas of This Drug


Drug Therapeutic Target (DTT)
DTT Name DTT ID UniProt ID MOA REF
Muscarinic acetylcholine receptor (CHRM) TTOXS3C NOUNIPROTAC Agonist [2]

Drug Transporter (DTP)
DTP Name DTP ID UniProt ID MOA REF
Choline transporter-like protein 4 (SLC44A4) DT8KXR9 CTL4_HUMAN Substrate [3]
Vesicular acetylcholine transporter (SLC18A3) DT3T2K0 VACHT_HUMAN Substrate [4]
Organic cation transporter 3 (SLC22A3) DT6201N S22A3_HUMAN Substrate [5]
Organic cation transporter 1 (SLC22A1) DTT79CX S22A1_HUMAN Substrate [6]

Drug-Metabolizing Enzyme (DME)
DME Name DME ID UniProt ID MOA REF
Acetylcholinesterase (ACHE)
Main DME 		DEQ2BAJ ACES_HUMAN Substrate [7]

Drug Off-Target (DOT)
DOT Name DOT ID UniProt ID Interaction REF
Acetylcholinesterase (ACHE) OT2H8HG6 ACES_HUMAN Biotransformations [8]
Cholinesterase (BCHE) OTOH3WQ9 CHLE_HUMAN Regulation of Drug Effects [9]
Glutamate--cysteine ligase catalytic subunit (GCLC) OTESDI4D GSH1_HUMAN Drug Response [10]
Glutamate--cysteine ligase regulatory subunit (GCLM) OT6CP234 GSH0_HUMAN Drug Response [11]
Granulocyte-macrophage colony-stimulating factor (CSF2) OT1M7D28 CSF2_HUMAN Protein Interaction/Cellular Processes [12]
Interleukin-1 receptor antagonist protein (IL1RN) OT308CBE IL1RA_HUMAN Drug Response [13]
Interleukin-5 (IL5) OTAFPSCO IL5_HUMAN Drug Response [14]
Interleukin-5 receptor subunit alpha (IL5RA) OTMSLUG9 IL5RA_HUMAN Drug Response [14]
Lipoprotein lipase (LPL) OTTW0267 LIPL_HUMAN Drug Response [15]
Muscarinic acetylcholine receptor M1 (CHRM1) OTKW3E6B ACM1_HUMAN Gene/Protein Processing [16]
Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction Atlas of This Drug

Drug-Drug Interaction (DDI) Information of This Drug

Coadministration of a Drug Treating the Disease Different from Acetylcholine (Comorbidity)
DDI Drug Name DDI Drug ID Severity Mechanism Comorbidity REF
Mepyramine DMB4SFH Moderate Antagonize the effect of Acetylcholine when combined with Mepyramine. Allergic/hypersensitivity disorder [4A80-4A8Z] [17]
Phenyltoloxamine DMKAEQW Moderate Antagonize the effect of Acetylcholine when combined with Phenyltoloxamine. Allergic/hypersensitivity disorder [4A80-4A8Z] [17]
Umeclidinium DM4E8O9 Moderate Antagonize the effect of Acetylcholine when combined with Umeclidinium. Chronic obstructive pulmonary disease [CA22] [17]
Revefenacin DMMP5SI Moderate Antagonize the effect of Acetylcholine when combined with Revefenacin. Chronic obstructive pulmonary disease [CA22] [17]
OPC-34712 DMHG57U Moderate Antagonize the effect of Acetylcholine when combined with OPC-34712. Depression [6A70-6A7Z] [17]
Mepenzolate DM8YU2F Moderate Antagonize the effect of Acetylcholine when combined with Mepenzolate. Digestive system disease [DE2Z] [17]
ITI-007 DMUQ1DO Moderate Antagonize the effect of Acetylcholine when combined with ITI-007. Insomnia [7A00-7A0Z] [17]
Methylscopolamine DM5VWOB Moderate Antagonize the effect of Acetylcholine when combined with Methylscopolamine. Peptic ulcer [DA61] [17]
Acrivastine DMTIGA0 Moderate Antagonize the effect of Acetylcholine when combined with Acrivastine. Vasomotor/allergic rhinitis [CA08] [17]
⏷ Show the Full List of 9 DDI Information of This Drug

References

1 URL: http://www.guidetopharmacology.org Nucleic Acids Res. 2015 Oct 12. pii: gkv1037. The IUPHAR/BPS Guide to PHARMACOLOGY in 2016: towards curated quantitative interactions between 1300 protein targets and 6000 ligands. (Ligand id: 294).
2 Thiochrome enhances acetylcholine affinity at muscarinic M4 receptors: receptor subtype selectivity via cooperativity rather than affinity. Mol Pharmacol. 2004 Jan;65(1):257-66.
3 Choline transporter-like protein 4 (CTL4) links to non-neuronal acetylcholine synthesis. J Neurochem. 2013 Aug;126(4):451-61.
4 SLC18: Vesicular neurotransmitter transporters for monoamines and acetylcholine. Mol Aspects Med. 2013 Apr-Jun;34(2-3):360-72.
5 Organic cation transporters: physiology, toxicology and special focus on ethidium as a novel substrate. Curr Drug Metab. 2009 Jul;10(6):617-31.
6 Role of acetylcholine and polyspecific cation transporters in serotonin-induced bronchoconstriction in the mouse. Respir Res. 2006 Apr 12;7:65.
7 How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6.
8 Monitoring the reaction of carbachol with acetylcholinesterase by thioflavin T fluorescence and acetylthiocholine hydrolysis. Chem Biol Interact. 2008 Sep 25;175(1-3):235-41. doi: 10.1016/j.cbi.2008.06.002. Epub 2008 Jun 17.
9 Interaction between CYP19 aromatase and butyrylcholinesterase genes increases Alzheimer's disease risk. Dement Geriatr Cogn Disord. 2005;20(2-3):153-7. doi: 10.1159/000087065. Epub 2005 Jul 13.
10 Association of polymorphism in glutamate-cysteine ligase catalytic subunit gene with coronary vasomotor dysfunction and myocardial infarction. J Am Coll Cardiol. 2003 Feb 19;41(4):539-45. doi: 10.1016/s0735-1097(02)02866-8.
11 Polymorphism in glutamate-cysteine ligase modifier subunit gene is associated with impairment of nitric oxide-mediated coronary vasomotor function. Circulation. 2003 Sep 23;108(12):1425-7. doi: 10.1161/01.CIR.0000091255.63645.98. Epub 2003 Sep 15.
12 Acetylcholine and nicotine stimulate the release of granulocyte-macrophage colony stimulating factor from cultured human bronchial epithelial cells. Naunyn Schmiedebergs Arch Pharmacol. 1998 Apr;357(4):472-5. doi: 10.1007/pl00005195.
13 Autocrine interaction between IL-5 and IL-1beta mediates altered responsiveness of atopic asthmatic sensitized airway smooth muscle. J Clin Invest. 1999 Sep;104(5):657-67. doi: 10.1172/JCI7137.
14 The IL-5 receptor on human bronchus selectively primes for hyperresponsiveness. J Allergy Clin Immunol. 2002 Mar;109(3):404-9. doi: 10.1067/mai.2002.122459.
15 Tissue-specific expression of human lipoprotein lipase in the vascular system affects vascular reactivity in transgenic mice. Br J Pharmacol. 2002 Jan;135(1):143-54. doi: 10.1038/sj.bjp.0704440.
16 Regional differences in functional receptor distribution and calcium mobilization in the intact human lens. Invest Ophthalmol Vis Sci. 2001 Sep;42(10):2355-63.
17 Multum Information Services, Inc. Expert Review Panel.