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Details

Stereochemistry RACEMIC
Molecular Formula C9H15NO2.ClH
Molecular Weight 205.682
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of ACECLIDINE HYDROCHLORIDE

SMILES

Cl.CC(=O)OC1CN2CCC1CC2

InChI

InChIKey=LWWSARSTZGNKGV-UHFFFAOYSA-N
InChI=1S/C9H15NO2.ClH/c1-7(11)12-9-6-10-4-2-8(9)3-5-10;/h8-9H,2-6H2,1H3;1H

HIDE SMILES / InChI

Molecular Formula C9H15NO2
Molecular Weight 169.2209
Charge 0
Count
Stereochemistry RACEMIC
Additional Stereochemistry No
Defined Stereocenters 0 / 1
E/Z Centers 0
Optical Activity ( + / - )

Molecular Formula ClH
Molecular Weight 36.461
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description
Curator's Comment: Description was created using several sources including: https://www.ncbi.nlm.nih.gov/pubmed/16229863 | https://www.ncbi.nlm.nih.gov/pubmed/12579779 | https://www.ncbi.nlm.nih.gov/pubmed/10845594

Aceclidine is a parasympathomimetic agent used in the treatment of open-angle glaucoma as topical eye drop solution. It is as a muscarinic acetylcholine receptor agonist with weak anticholinesterase activity. Acting directly on the motor end-plate (cholinergic nerve endings) it decreases intraocular pressure and mediates the contraction of iris muscle. Aceclidine increased outflow facility in human eyes in vitro by a direct stimulation of the outflow tissues in the absence of an intact ciliary muscle. This effect was biphasic, occurring at concentrations of 10 uM and lower with no effect at higher concentrations. Passed numerous clinical trials in Russia, France, Italy and other countries and was widely used in Europe but never been in clinical use in USA.

CNS Activity

Curator's Comment: Known to be CNS penetrant in mouse; rats. Human data not available

Originator

Curator's Comment: Aceclidine was first prepared in 1960

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Glaunorm

Approved Use

Glaucoma, in its different clinical forms

Launch Date

1969
PubMed

PubMed

TitleDatePubMed
[The selectivity of the action of muscarinic agonists in vivo].
1994 Mar-Apr
Correlation between pK(a) and reactivity of quinuclidine-based catalysts in the Baylis-Hillman reaction: discovery of quinuclidine as optimum catalyst leading to substantial enhancement of scope.
2003 Feb 7
Pharmacological management of night vision disturbances after refractive surgery Results of a randomized clinical trial.
2005 Sep
Aceclidine and pilocarpine interact differently with muscarinic receptor in isolated rabbit iris muscle.
2006 Feb 28
[The role of M-cholinoreceptors in the regulation of Th1 and Th2 lymphocyte functions].
2008 Mar-Apr
Aceclidine, brimonidine tartrate, and dapiprazole: comparison of miotic effect and tolerability under different lighting conditions.
2009 Jan
Effectiveness of daily use of brimonidine as antimydriatic agent.
2009 Oct
Role of cholinergic and cytokine regulation of T cell function in stimulation and inhibition of immune reactions in intoxication by organophosphorus compounds in different doses.
2009 Sep
Patents

Sample Use Guides

Instill 2 drops of Glaunorm (2% aceclidine hydrochloride solution) into the conjunctival sac every 8 hours following the doctor's prescription
Route of Administration: Topical
Human eyes were dissected and perfused. A steady state baseline facility was established for 90 minutes, after which up to four sequential concentrations ranging from 1 nM to 10 mM of aceclidine, were added to the perfusion medium. Outflow facility increased from baseline facility in eyes treated with aceclidine at lower concentrations (1 nM to 1 uM) but remained unchanged at higher concentrations.
Substance Class Chemical
Created
by admin
on Fri Dec 15 15:34:53 GMT 2023
Edited
by admin
on Fri Dec 15 15:34:53 GMT 2023
Record UNII
3B22O325Q6
Record Status Validated (UNII)
Record Version
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Name Type Language
ACECLIDINE HYDROCHLORIDE
MART.   WHO-DD  
Common Name English
ACECLIDINE HYDROCHLORIDE [MART.]
Common Name English
GLAUCOSTAT
Common Name English
QUINUCLIDIN-3-YL ACETATE HYDROCHLORIDE
Systematic Name English
ACECLIDINE HCL
Common Name English
3-QUINUCLIDINOL DL-FORM ACETATE HYDROCHLORIDE [MI]
Common Name English
3-QUINUCLIDINOL DL-FORM ACETATE HYDROCHLORIDE
MI  
Common Name English
Aceclidine hydrochloride [WHO-DD]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C47796
Created by admin on Fri Dec 15 15:34:53 GMT 2023 , Edited by admin on Fri Dec 15 15:34:53 GMT 2023
Code System Code Type Description
SMS_ID
100000078824
Created by admin on Fri Dec 15 15:34:53 GMT 2023 , Edited by admin on Fri Dec 15 15:34:53 GMT 2023
PRIMARY
MERCK INDEX
m9469
Created by admin on Fri Dec 15 15:34:53 GMT 2023 , Edited by admin on Fri Dec 15 15:34:53 GMT 2023
PRIMARY Merck Index
NCI_THESAURUS
C96880
Created by admin on Fri Dec 15 15:34:53 GMT 2023 , Edited by admin on Fri Dec 15 15:34:53 GMT 2023
PRIMARY
ECHA (EC/EINECS)
228-071-5
Created by admin on Fri Dec 15 15:34:53 GMT 2023 , Edited by admin on Fri Dec 15 15:34:53 GMT 2023
PRIMARY
EVMPD
SUB00241MIG
Created by admin on Fri Dec 15 15:34:53 GMT 2023 , Edited by admin on Fri Dec 15 15:34:53 GMT 2023
PRIMARY
EPA CompTox
DTXSID30976587
Created by admin on Fri Dec 15 15:34:53 GMT 2023 , Edited by admin on Fri Dec 15 15:34:53 GMT 2023
PRIMARY
CAS
6109-70-2
Created by admin on Fri Dec 15 15:34:53 GMT 2023 , Edited by admin on Fri Dec 15 15:34:53 GMT 2023
PRIMARY
FDA UNII
3B22O325Q6
Created by admin on Fri Dec 15 15:34:53 GMT 2023 , Edited by admin on Fri Dec 15 15:34:53 GMT 2023
PRIMARY
PUBCHEM
170367
Created by admin on Fri Dec 15 15:34:53 GMT 2023 , Edited by admin on Fri Dec 15 15:34:53 GMT 2023
PRIMARY
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