ACETYLCHOLINE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C7H16NO2
Molecular Weight	146.2074
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	1

SHOW SMILES / InChI

Structure Search

SMILES

CC(=O)OCC[N+](C)(C)C

InChI

InChIKey=OIPILFWXSMYKGL-UHFFFAOYSA-N

InChI=1S/C7H16NO2/c1-7(9)10-6-5-8(2,3)4/h5-6H2,1-4H3/q+1

HIDE SMILES / InChI

Molecular Formula	C7H16NO2
Molecular Weight	146.2074
Charge	1
Count

Stereochemistry	RACEMIC
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description
Sources: https://www.ncbi.nlm.nih.gov/books/NBK11143/ | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4027320/ | https://www.ncbi.nlm.nih.gov/pubmed/23040810 | http://www.bausch.com/Portals/77/-/m/BL/United%20States/Files/Package%20Inserts/Pharma/miochol-e-acetylcholine-chloride-intraocular-solution.pdf

Acetylcholine is the neurotransmitter at neuromuscular junctions, at synapses in the ganglia of the visceral motor system, and at a variety of sites within the central nervous system. Whereas a great deal is known about the function of cholinergic transmission at the neuromuscular junction and at ganglionic synapses, the actions of acetylcholine in the central nervous system are not as well understood. Cholinergic system is an important system and a branch of the autonomic nervous system which plays an important role in memory, digestion, control of heart beat, blood pressure, movement and many other functions. Acetylcholine in the brain alters neuronal excitability, influences synaptic transmission, induces synaptic plasticity, and coordinates firing of groups of neurons. Miochol®-E (acetylcholine chloride intraocular solution) is 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.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Acetylcholinesterase 207 Target ID: CHEMBL220 Sources: https://www.ncbi.nlm.nih.gov/pubmed/28503857	Substrate 656
Muscarinic acetylcholine receptor 160 Target ID: CHEMBL2094109 Sources: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4027320/	Agonist 2662
Muscle-type nicotinic acetylcholine receptor 65 Target ID: CHEMBL2362997 Sources: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4027320/	Agonist 2662
Neuronal acetylcholine receptors; alpha-3/beta-4, alpha-5, beta-2 4 Target ID: CHEMBL2221346 Sources: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4027320/	Agonist 2662

Conditions

Condition	Modality	Targets	Highest Phase	Product
Mydriasis 6 Sources: http://www.bausch.com/Portals/77/-/m/BL/United%20States/Files/Package%20Inserts/Pharma/miochol-e-acetylcholine-chloride-intraocular-solution.pdf	Preventing		Approved 8360	MIOCHOL-E Approved Use 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 Launch Date 7.48656E11

Overview

CYP3A4	CYP2C9	CYP2D6	hERG

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
OCTN2 66	ACHE 10 OCTN1 47

Drug as perpetrator

Target	Modality	Activity	Metabolite	Clinical evidence
OCTN2 71	inhibitor 3240 Sources: https://pubmed.ncbi.nlm.nih.gov/11160873/ Page: 6.0	yes

Drug as victim

Target	Modality	Activity	Metabolite	Clinical evidence
ACHE 10	substrate 3326 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2006/020213s010lbl.pdf#page=1 Page: 1.0	major
OCTN1 47	substrate 3326 Sources: https://pubmed.ncbi.nlm.nih.gov/22206629/ Page: 1.0	yes

Sourcing

Vendor/Aggregator	ID	URL
ChEBI	CHEBI:15355	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:15355
ZINC	ZINC000003079336	http://zinc15.docking.org/substances/ZINC000003079336
eMolecules	1985299	https://www.emolecules.com/cgi-bin/more?vid=1985299

PubMed

Title	Date	PubMed
Diesel exhaust particulate induces airway hyperresponsiveness in a murine model: essential role of GM-CSF.	1999 Nov	10550748
Autocrine interaction between IL-5 and IL-1beta mediates altered responsiveness of atopic asthmatic sensitized airway smooth muscle.	1999 Sep	10487780
Nitric oxide-compromised hypertension: facts and enigmas.	2000	10805402
Gene transfer of endothelial nitric oxide synthase improves relaxation of carotid arteries from diabetic rabbits.	2000 Mar 7	10704171
Influence of nitric oxide donors and of the alpha(2)-agonist UK-14,304 on acetylcholine release in the pig gastric fundus.	2001	11114406
Conversion of the ion selectivity of the 5-HT(3a) receptor from cationic to anionic reveals a conserved feature of the ligand-gated ion channel superfamily.	2001 Apr 6	11139582
Interleukin 10 aggravates experimental autoimmune myasthenia gravis through inducing Th2 and B cell responses to AChR.	2001 Feb 1	11137572
Three-dimensional structure of a complex of galanthamine (Nivalin) with acetylcholinesterase from Torpedo californica: implications for the design of new anti-Alzheimer drugs.	2001 Feb 1	11119642
Interaction kinetics of reversible inhibitors and substrates with acetylcholinesterase and its fasciculin 2 complex.	2001 Feb 16	11036076
Inhibition of a Gi-activated potassium channel (GIRK1/4) by the Gq-coupled m1 muscarinic acetylcholine receptor.	2001 Feb 23	11060307
A pharmacological examination of venoms from three species of death adder (Acanthophis antarcticus, Acanthophis praelongus and Acanthophis pyrrhus).	2001 Feb-Mar	10978738
Rapid eye movement sleep deprivation induces an increase in acetylcholinesterase activity in discrete rat brain regions.	2001 Jan	11151034
Association study of a nicotinic receptor variant with schizophrenic disorders.	2001 Jan	11150893
Nicotinic agonists stimulate acetylcholine release from mouse interpeduncular nucleus: a function mediated by a different nAChR than dopamine release from striatum.	2001 Jan	11145999
Impaired renal vascular endothelial function in vitro in experimental hypercholesterolemia.	2001 Jan	11137100
Anti-oxidative properties of fluvastatin, an HMG-CoA reductase inhibitor, contribute to prevention of atherosclerosis in cholesterol-fed rabbits.	2001 Jan	11137086
Cortical acetylcholine release elicited by stimulation of histamine H1 receptors in the nucleus basalis magnocellularis: a dual-probe microdialysis study in the freely moving rat.	2001 Jan	11135005
Extracellular cyclic ADP-ribose potentiates ACh-induced contraction in bovine tracheal smooth muscle.	2001 Jan	11133499
Adrenal tyrosine hydroxylase activity and gene expression are increased by intraventricular administration of nicotine.	2001 Jan	11123357
Myocardial stunning in exercise-induced ischemia in dogs: lack of late preconditioning.	2001 Jan	11123245
Glutathione attenuates coronary constriction to acetylcholine in patients with coronary spastic angina.	2001 Jan	11123241
Vasoactive intestinal peptide: cardiovascular effects.	2001 Jan	11121793
Role of calcium and calmodulin in ciliary stimulation induced by acetylcholine.	2001 Jan	11121381
The mechanism of resveratrol-induced vasorelaxation differs in the mesenteric resistance arteries of lean and obese rats.	2001 Jan	11115418
Tetanus and botulinum neurotoxins: turning bad guys into good by research.	2001 Jan	10936621
Twenty years of dendrotoxins.	2001 Jan	10936620
Modulation of choline acetyltransferase synthesis by okadaic acid, a phosphatase inhibitor, and KN-62, a CaM kinase inhibitor, in NS-20Y neuroblastoma.	2001 Jan	10913690
Post-ictal analgesia: involvement of opioid, serotoninergic and cholinergic mechanisms.	2001 Jan 12	11150491
Changes in sensitivity of cholinoceptors and adrenoceptors during transhemispheric cortical reorganisation in rat SmI.	2001 Jan 12	11150484
Exercise training in coronary artery disease and coronary vasomotion.	2001 Jan 2	11136704
The M3 muscarinic acetylcholine receptor expressed in HEK-293 cells signals to phospholipase D via G12 but not Gq-type G proteins: regulators of G proteins as tools to dissect pertussis toxin-resistant G proteins in receptor-effector coupling.	2001 Jan 26	11036069
exo-2-(Pyridazin-4-yl)-7-azabicyclo[2.2.1]heptanes: syntheses and nicotinic acetylcholine receptor agonist activity of potent pyridazine analogues of (+/-)-epibatidine.	2001 Jan 4	11141087
Antagonist of nicotinic acetylcholine receptors (nAChR) enhances formalin-induced nociception in rats: tonic role of nAChRs in the control of pain following injury.	2001 Jan 5	11146056
Responder characteristics to a single oral dose of cholinesterase inhibitor: a double-blind placebo-controlled study with tacrine in Alzheimer patients.	2001 Jan-Feb	11125238
Functional reconstitution and characterization of recombinant human alpha 1-glycine receptors.	2001 Jun 15	11145968
The role of nitric oxide on the relaxations of rabbit corpus cavernosum induced by Androctonus australis and Buthotus judaicus scorpion venoms.	2001 May	11072041

Patents

Sample Use Guides

In Vivo Use Guide

Miochol®-E (acetylcholine chloride intraocular solution) is instilled into the anterior chamber before or after securing one or more sutures. Instillation should be gentle and parallel to the iris face and tangential to pupil border. If there are no mechanical hindrances, the pupil starts to constrict in seconds and the peripheral iris is drawn away from the angle of the anterior chamber. Any anatomical hindrance to miosis must be released to permit the desired effect of the drug. In most cases, 0.5 to 2 mL produces satisfactory miosis. Note that the syringe filter supplied with Miochol-E has a priming volume of 0.6 mL (approximately). In cataract surgery, use Miochol-E only after delivery of the lens. Aqueous solutions of acetylcholine chloride are unstable. Prepare solution immediately before use. Do not use solution which is not clear and colorless. Discard any solution that has not been used.

Route of Administration: Other

In Vitro Use Guide

Keratocytes were treated with various concentrations of acetylcholine (0.01-1 uM) for 24 h. Acetylcholine enhances keratocyte proliferation through activation of muscarinic acetylcholine receptors.

Substance Class	Chemical Created by `admin` on `Wed Jul 05 23:08:34 UTC 2023` Edited by `admin` on `Wed Jul 05 23:08:34 UTC 2023`
Record UNII	N9YNS0M02X
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

ACETYLCHOLINE

Systematic Name

English

Acetylcholine [WHO-DD]

Common Name

English

CHOLINE ACETATE (ESTER)

Common Name

English

ACETYLCHOLINE [VANDF]

Common Name

English

ACETYLCHOLINE [USP IMPURITY]

Common Name

English

ACETYLCHOLINE CATION

Common Name

English

ETHANAMINIUM, 2-(ACETYLOXY)-N,N,N-TRIMETHYL-

Systematic Name

English

Classification Tree Code System Code

LOINC

1707-9