ACETYLCHOLINE CHLORIDE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C7H16NO2.Cl
Molecular Weight	181.66
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

[Cl-].CC(=O)OCC[N+](C)(C)C

InChI

InChIKey=JUGOREOARAHOCO-UHFFFAOYSA-M

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

HIDE SMILES / InChI

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 661
Muscarinic acetylcholine receptor 160 Target ID: CHEMBL2094109 Sources: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4027320/	Agonist 2678
Muscle-type nicotinic acetylcholine receptor 65 Target ID: CHEMBL2362997 Sources: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4027320/	Agonist 2678
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 2678

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 8429	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 1993

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 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/11160873/ Page: 6.0	yes

Drug as victim

Target	Modality	Activity	Metabolite	Clinical evidence
ACHE 10	substrate 3367 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2006/020213s010lbl.pdf#page=1 Page: 1.0	major
OCTN1 47	substrate 3367 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
Nitric oxide-compromised hypertension: facts and enigmas.	2000	10805402
Differential modulation of frontal cortex acetylcholine by injection of substance P into the nucleus basalis magnocellularis region in the freely-moving vs. the anesthetized preparation.	2000 Dec 1	11020227
Allosteric interactions of staurosporine and other indolocarbazoles with N-[methyl-(3)H]scopolamine and acetylcholine at muscarinic receptor subtypes: identification of a second allosteric site.	2000 Jul	10860942
Allergen-induced airway inflammation and bronchial responsiveness in interleukin-5 receptor alpha chain-deficient mice.	2000 Jun	10848907
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
A conformational intermediate between the resting and desensitized states of the nicotinic acetylcholine receptor.	2001 Feb 16	11083863
Depletion of phosphatidylinositol 4,5-bisphosphate by activation of phospholipase C-coupled receptors causes slow inhibition but not desensitization of G protein-gated inward rectifier K+ current in atrial myocytes.	2001 Feb 23	11104770
Projections and pathways of VIP- and nNOS-containing airway neurons in ferret trachea.	2001 Jan	11152648
Arterial remodeling in chronic sinoaortic-denervated rats.	2001 Jan	11152375
Effects of LY117018 and the estrogen analogue, 17alpha-ethinylestradiol, on vascular reactivity, platelet aggregation, and lipid metabolism in the insulin-resistant JCR:LA-cp male rat: role of nitric oxide.	2001 Jan	11152369
Rapid eye movement sleep deprivation induces an increase in acetylcholinesterase activity in discrete rat brain regions.	2001 Jan	11151034
Coronary endothelial dysfunction after ischemia and reperfusion: a new therapeutic target?	2001 Jan	11151023
Dynamic restoration of dystrophin to dystrophin-deficient myotubes.	2001 Jan	11150969
Mechanical efficiency of isolated in situ perfused hearts of the eel Anguilla australis.	2001 Jan	11137449
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
Exercise and the endothelium.	2001 Jan	11136508
Ischemic preconditioning with opening of mitochondrial adenosine triphosphate-sensitive potassium channels or Na/H exchange inhibition: which is the best protective strategy for heart transplants?	2001 Jan	11135172
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
A new hypoglycemic agent, JTT-608, evokes protein kinase A-mediated Ca(2+) signaling in rat islet beta-cells: strict regulation by glucose, link to insulin release, and cooperation with glucagon-like peptide-1(7-36)amide and pituitary adenylate cyclase-activating polypeptide.	2001 Jan	11123358
Glutathione attenuates coronary constriction to acetylcholine in patients with coronary spastic angina.	2001 Jan	11123241
Vagosympathetic interactions in ischemia-induced myocardial norepinephrine and acetylcholine release.	2001 Jan	11123236
Increased inactivation of nitric oxide is involved in coronary endothelial dysfunction in heart failure.	2001 Jan	11123219
Stress and gastrointestinal tract. II. Stress and intestinal barrier function.	2001 Jan	11123192
Capillary recruitment is impaired in essential hypertension and relates to insulin's metabolic and vascular actions.	2001 Jan	11121808
Contractile properties of the elasmobranch rectal gland.	2001 Jan	11104711
CHRNB2 is the second acetylcholine receptor subunit associated with autosomal dominant nocturnal frontal lobe epilepsy.	2001 Jan	11104662
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
A noninvasive measurement of reactive hyperemia that can be used to assess resistance artery endothelial function in humans.	2001 Jan 1	11137850
Post-ictal analgesia: involvement of opioid, serotoninergic and cholinergic mechanisms.	2001 Jan 12	11150491
Impairment of maze learning in rats by restricting environmental space.	2001 Jan 12	11121873
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
Aversive hypothalamic stimulation releases acetylcholine in the nucleus accumbens, and stimulation-escape decreases it.	2001 Jan 5	11146052
Site of resting state inhibition of the nicotinic acetylcholine receptor by a hydrophobic inhibitor.	2001 Jan 9	11141083
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
Gyroxin fails to modify in vitro release of labelled dopamine and acetylcholine from rat and mouse striatal tissue.	2001 Jun	11137545
Location of the polyamine binding site in the vestibule of the nicotinic acetylcholine receptor ion channel.	2001 Mar 2	11104766
Constitutive signaling by Kaposi's sarcoma-associated herpesvirus G-protein-coupled receptor desensitizes calcium mobilization by other receptors.	2001 Mar 9	11116138
Role of rapsyn tetratricopeptide repeat and coiled-coil domains in self-association and nicotinic acetylcholine receptor clustering.	2001 Mar 9	11087759

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.

Name

Type

Language

ACETYLCHOLINE CHLORIDE

Official Name

English

Choline acetate (ester) chloride

Common Name

English

ACETYLCHOLINE CHLORIDE [ORANGE BOOK]

Common Name

English

ACETYLCHOLINE CHLORIDE [EP MONOGRAPH]

Common Name

English

ACETYLCHOLINE CHLORIDE FOR INJECTION [JAN]

Common Name

English

2-(ACETYLOXY)-N,N,N-TRIMETHYLETHANAMINIUM CHLORIDE (1:1)

Systematic Name

English

acetylcholine chloride [INN]

Common Name

English

ACETYLCHOLINE CHLORIDE [MI]

Common Name

English

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

Systematic Name

English

ACETYLCHOLINE CHLORIDE [MART.]

Common Name

English

ACETYLCHOLINE CHLORIDE [USP IMPURITY]

Common Name

English

ACETYLCHOLINE CHLORIDE [USP-RS]

Common Name

English

ACETYLCHOLINE CHLORIDE [VANDF]

Common Name

English

ACETYLCHOLINE CHLORIDE [USP MONOGRAPH]

Common Name

English

Acetylcholine chloride [WHO-DD]

Common Name

English

MIOCHOL

Brand Name

English

NSC-755845

Code

English

Classification Tree Code System Code

NCI_THESAURUS

C47796

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Code System Code Type Description

INN

438

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MERCK INDEX

m1352

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Merck Index

RS_ITEM_NUM

1008501

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FDA UNII

AF73293C2R

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NSC

755845

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DAILYMED

AF73293C2R

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RXCUI

20814

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RxNorm

NCI_THESAURUS

C47382

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SMS_ID

100000084619

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ChEMBL

CHEMBL667

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CHEBI

2417

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CAS

60-31-1

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EPA CompTox

DTXSID5048978

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EVMPD

SUB05228MIG

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PUBCHEM

6060

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ECHA (EC/EINECS)

200-468-8

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DRUG BANK

DBSALT002814

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ACTIVE MOIETY


					N9YNS0M02X

ACETYLCHOLINE

SUBSTANCE RECORD


					AF73293C2R

ACETYLCHOLINE CHLORIDE

Details

SMILES

InChI

CNS Activity

Originator

Approval Year

Targets

Conditions

Approved Use

Launch Date

Overview

OverviewOther

Drug as perpetrator​

Drug as victim

Sourcing

PubMed

Patents

Sample Use Guides

Drug as perpetrator