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], [2]
Therapeutic Class
Cardiovascular Agents
Drug Type
Small molecular drug
Structure
3D MOL 2D MOL
#Ro5 Violations (Lipinski): 0 Molecular Weight (mw) 146.21
Topological Polar Surface Area (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

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 [3]

Drug Transporter (DTP)
DTP Name DTP ID UniProt ID MOA REF
Choline transporter-like protein 4 (SLC44A4) DT8KXR9 CTL4_HUMAN Substrate [4]
Vesicular acetylcholine transporter (SLC18A3) DT3T2K0 VACHT_HUMAN Substrate [5]
Organic cation transporter 3 (SLC22A3) DT6201N S22A3_HUMAN Substrate [6]
Organic cation transporter 1 (SLC22A1) DTT79CX S22A1_HUMAN Substrate [7]

Drug-Metabolizing Enzyme (DME)
DME Name DME ID UniProt ID MOA REF
Acetylcholinesterase (ACHE)
Main DME
DEQ2BAJ ACES_HUMAN Substrate [8]
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] [38]
Phenyltoloxamine DMKAEQW Moderate Antagonize the effect of Acetylcholine when combined with Phenyltoloxamine. Allergic/hypersensitivity disorder [4A80-4A8Z] [38]
Umeclidinium DM4E8O9 Moderate Antagonize the effect of Acetylcholine when combined with Umeclidinium. Chronic obstructive pulmonary disease [CA22] [38]
Revefenacin DMMP5SI Moderate Antagonize the effect of Acetylcholine when combined with Revefenacin. Chronic obstructive pulmonary disease [CA22] [38]
OPC-34712 DMHG57U Moderate Antagonize the effect of Acetylcholine when combined with OPC-34712. Depression [6A70-6A7Z] [38]
Mepenzolate DM8YU2F Moderate Antagonize the effect of Acetylcholine when combined with Mepenzolate. Digestive system disease [DE2Z] [38]
ITI-007 DMUQ1DO Moderate Antagonize the effect of Acetylcholine when combined with ITI-007. Insomnia [7A00-7A0Z] [38]
Methylscopolamine DM5VWOB Moderate Antagonize the effect of Acetylcholine when combined with Methylscopolamine. Peptic ulcer [DA61] [38]
Acrivastine DMTIGA0 Moderate Antagonize the effect of Acetylcholine when combined with Acrivastine. Vasomotor/allergic rhinitis [CA08] [38]
⏷ 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 Drugs@FDA. U.S. Food and Drug Administration. U.S. Department of Health & Human Services. 2015
3 Thiochrome enhances acetylcholine affinity at muscarinic M4 receptors: receptor subtype selectivity via cooperativity rather than affinity. Mol Pharmacol. 2004 Jan;65(1):257-66.
4 Choline transporter-like protein 4 (CTL4) links to non-neuronal acetylcholine synthesis. J Neurochem. 2013 Aug;126(4):451-61.
5 SLC18: Vesicular neurotransmitter transporters for monoamines and acetylcholine. Mol Aspects Med. 2013 Apr-Jun;34(2-3):360-72.
6 Organic cation transporters: physiology, toxicology and special focus on ethidium as a novel substrate. Curr Drug Metab. 2009 Jul;10(6):617-31.
7 Role of acetylcholine and polyspecific cation transporters in serotonin-induced bronchoconstriction in the mouse. Respir Res. 2006 Apr 12;7:65.
8 How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6.
9 Kinetic characterization of cholinesterases and a therapeutically valuable cocaine hydrolase for their catalytic activities against heroin and its metabolite 6-monoacetylmorphine. Chem Biol Interact. 2018 Sep 25;293:107-114.
10 Influx Transport of Cationic Drug at the Blood-Retinal Barrier: Impact on the Retinal Delivery of Neuroprotectants. Biol Pharm Bull. 2017;40(8):1139-1145.
11 Differential pharmacological in vitro properties of organic cation transporters and regional distribution in rat brain. Neuropharmacology. 2006 Jun;50(8):941-52.
12 Expression of organic cation transporters OCT1 (SLC22A1) and OCT3 (SLC22A3) is affected by genetic factors and cholestasis in human liver. Hepatology. 2009 Oct;50(4):1227-40.
13 Multiple SLC and ABC Transporters Contribute to the Placental Transfer of Entecavir. Drug Metab Dispos. 2017 Mar;45(3):269-278.
14 Interaction of organic cation transporter 3 (SLC22A3) and amphetamine. J Neurochem. 2010 Jul;114(1):142-9.
15 Organic cation transporter 3 (Slc22a3) is implicated in salt-intake regulation. J Neurosci. 2004 Mar 17;24(11):2846-51.
16 Drug specificity and intestinal membrane localization of human organic cation transporters (OCT). Biochem Pharmacol. 2005 Dec 5;70(12):1851-60.
17 Are organic cation transporters capable of transporting prostaglandins? Naunyn Schmiedebergs Arch Pharmacol. 2005 Aug;372(2):125-30.
18 Cisplatin and oxaliplatin, but not carboplatin and nedaplatin, are substrates for human organic cation transporters (SLC22A1-3 and multidrug and toxin extrusion family). J Pharmacol Exp Ther. 2006 Nov;319(2):879-86.
19 Pharmacologic markers and predictors of responses to imatinib therapy in patients with chronic myeloid leukemia. Leuk Lymphoma. 2008 Apr;49(4):639-42.
20 Organic cation transporters are determinants of oxaliplatin cytotoxicity. Cancer Res. 2006 Sep 1;66(17):8847-57.
21 Human intestinal transporter database: QSAR modeling and virtual profiling of drug uptake, efflux and interactions. Pharm Res. 2013 Apr;30(4):996-1007.
22 Implications of genetic polymorphisms in drug transporters for pharmacotherapy. Cancer Lett. 2006 Mar 8;234(1):4-33.
23 Upregulation of histone acetylation reverses organic anion transporter 2 repression and enhances 5-fluorouracil sensitivity in hepatocellular carcinoma
24 Comparison of type I and type II organic cation transport by organic cation transporters and organic anion-transporting polypeptides. J Pharmacol Exp Ther. 2001 Jul;298(1):110-5.
25 Organic cation transporters and their pharmacokinetic and pharmacodynamic consequences. Drug Metab Pharmacokinet. 2008;23(4):243-53.
26 Molecular identification and functional characterization of the human colonic thiamine pyrophosphate transporter. J Biol Chem. 2017 Oct 6;292(40):16526.
27 SLC44A4 mutation causes autosomal dominant hereditary postlingual non-syndromic mid-frequency hearing loss. Hum Mol Genet. 2017 Jan 15;26(2):383-394.
28 Pharmacological characterization of GSK573719 (umeclidinium): a novel, long-acting, inhaled antagonist of the muscarinic cholinergic receptors for treatment of pulmonary diseases. J Pharmacol Exp Ther. 2013 May;345(2):260-70.
29 Characterisation of [3H]-darifenacin as a novel radioligand for the study of muscarinic M3 receptors. J Recept Signal Transduct Res. 1997 Jan-May;17(1-3):177-84.
30 Lithocholylcholine, a bile acid/acetylcholine hybrid, is a muscarinic receptor antagonist. J Pharmacol Exp Ther. 2002 Oct;303(1):29-35.
31 Pharmacological comparison of the cloned human and rat M2 muscarinic receptor genes expressed in the murine fibroblast (B82) cell line. J Pharmacol Exp Ther. 1998 Feb;284(2):500-7.
32 Effects of propiverine hydrochloride (propiverine) on the muscarinic receptor binding affinity in guinea pig tissues and on salivation in conscious dogs. Nihon Yakurigaku Zasshi. 1999 Mar;113(3):157-66.
33 Clinical pipeline report, company report or official report of GlaxoSmithKline.
34 2018 FDA drug approvals.Nat Rev Drug Discov. 2019 Feb;18(2):85-89.
35 The amygdala modulates morphine-induced state-dependent memory retrieval via muscarinic acetylcholine receptors. Neuroscience. 2009 May 5;160(2):255-63.
36 Competitive and non-competitive antagonism exhibited by 'selective' antagonists at atrial and ileal muscarinic receptor subtypes. Br J Pharmacol. 1987 Apr;90(4):701-7.
37 Long-acting bronchodilators in COPD: Where are we now and where are we going Breathe 06/2014; 10(2):110-120.
38 Multum Information Services, Inc. Expert Review Panel.