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Details

Stereochemistry RACEMIC
Molecular Formula C9H15NO2
Molecular Weight 169.2209
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of ACECLIDINE

SMILES

CC(=O)OC1CN2CCC1CC2

InChI

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

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 ( + / - )

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

CNS Penetrant
2554
Curator's Comment: Known to be CNS penetrant in mouse; rats. Human data not available

Originator

Rubitsov, M.V.|Muklina, E.
3
Curator's Comment: Aceclidine was first prepared in 1960

Approval Year

Unknown
139594
Targets

Targets

Primary TargetPharmacologyConditionPotency
Agonist
2678
 17.0 µM [EC50]
Agonist
2678
Agonist
2678
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Approved
8429
Glaunorm

Approved Use

Glaucoma, in its different clinical forms

Launch Date

-3.1968E9
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

Patents

US2016008278
3
US2016058825
3
US3997543
10

Sample Use Guides

In Vivo Use Guide
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
In Vitro Use Guide
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 16:35:08 UTC 2023
Edited
by admin
on Fri Dec 15 16:35:08 UTC 2023
Record UNII
0578K3ELIO
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
ACECLIDINE
INN   MART.   USAN   WHO-DD  
INN   USAN  
Official Name English
Aceclidine [WHO-DD]
Common Name English
NSC-657843
Code English
3-Quinuclidinol acetate (ester)
Common Name English
ACECLIDINE [USAN]
Common Name English
3-QUINUCLIDINOL DL-FORM ACETATE (ESTER) [MI]
Common Name English
3-ACETOXYQUINUCLIDINE
Systematic Name English
NSC-758239
Code English
1-AZABICYCLO(2.2.2)OCTAN-3-OL, ACETATE (ESTER)
Common Name English
ACECLIDINE [MART.]
Common Name English
aceclidine [INN]
Common Name English
Classification Tree Code System Code
WHO-ATC S01EB08
Created by admin on Fri Dec 15 16:35:08 UTC 2023 , Edited by admin on Fri Dec 15 16:35:08 UTC 2023
NCI_THESAURUS C47796
Created by admin on Fri Dec 15 16:35:08 UTC 2023 , Edited by admin on Fri Dec 15 16:35:08 UTC 2023
WHO-ATC S01EB58
Created by admin on Fri Dec 15 16:35:08 UTC 2023 , Edited by admin on Fri Dec 15 16:35:08 UTC 2023
WHO-VATC QS01EB08
Created by admin on Fri Dec 15 16:35:08 UTC 2023 , Edited by admin on Fri Dec 15 16:35:08 UTC 2023
WHO-VATC QS01EB58
Created by admin on Fri Dec 15 16:35:08 UTC 2023 , Edited by admin on Fri Dec 15 16:35:08 UTC 2023
Code System Code Type Description
CAS
827-61-2
Created by admin on Fri Dec 15 16:35:08 UTC 2023 , Edited by admin on Fri Dec 15 16:35:08 UTC 2023
PRIMARY
PUBCHEM
1979
Created by admin on Fri Dec 15 16:35:08 UTC 2023 , Edited by admin on Fri Dec 15 16:35:08 UTC 2023
PRIMARY
EVMPD
SUB05199MIG
Created by admin on Fri Dec 15 16:35:08 UTC 2023 , Edited by admin on Fri Dec 15 16:35:08 UTC 2023
PRIMARY
EPA CompTox
DTXSID2045658
Created by admin on Fri Dec 15 16:35:08 UTC 2023 , Edited by admin on Fri Dec 15 16:35:08 UTC 2023
PRIMARY
MESH
C084650
Created by admin on Fri Dec 15 16:35:08 UTC 2023 , Edited by admin on Fri Dec 15 16:35:08 UTC 2023
PRIMARY
FDA UNII
0578K3ELIO
Created by admin on Fri Dec 15 16:35:08 UTC 2023 , Edited by admin on Fri Dec 15 16:35:08 UTC 2023
PRIMARY
NSC
657843
Created by admin on Fri Dec 15 16:35:08 UTC 2023 , Edited by admin on Fri Dec 15 16:35:08 UTC 2023
PRIMARY
MERCK INDEX
m9469
Created by admin on Fri Dec 15 16:35:08 UTC 2023 , Edited by admin on Fri Dec 15 16:35:08 UTC 2023
PRIMARY Merck Index
NCI_THESAURUS
C81044
Created by admin on Fri Dec 15 16:35:08 UTC 2023 , Edited by admin on Fri Dec 15 16:35:08 UTC 2023
PRIMARY
DRUG BANK
DB13262
Created by admin on Fri Dec 15 16:35:08 UTC 2023 , Edited by admin on Fri Dec 15 16:35:08 UTC 2023
PRIMARY
NSC
758239
Created by admin on Fri Dec 15 16:35:08 UTC 2023 , Edited by admin on Fri Dec 15 16:35:08 UTC 2023
PRIMARY
WIKIPEDIA
Aceclidine
Created by admin on Fri Dec 15 16:35:08 UTC 2023 , Edited by admin on Fri Dec 15 16:35:08 UTC 2023
PRIMARY
ChEMBL
CHEMBL20835
Created by admin on Fri Dec 15 16:35:08 UTC 2023 , Edited by admin on Fri Dec 15 16:35:08 UTC 2023
PRIMARY
ECHA (EC/EINECS)
212-574-1
Created by admin on Fri Dec 15 16:35:08 UTC 2023 , Edited by admin on Fri Dec 15 16:35:08 UTC 2023
PRIMARY
DRUG CENTRAL
4314
Created by admin on Fri Dec 15 16:35:08 UTC 2023 , Edited by admin on Fri Dec 15 16:35:08 UTC 2023
PRIMARY
INN
1367
Created by admin on Fri Dec 15 16:35:08 UTC 2023 , Edited by admin on Fri Dec 15 16:35:08 UTC 2023
PRIMARY
SMS_ID
100000087890
Created by admin on Fri Dec 15 16:35:08 UTC 2023 , Edited by admin on Fri Dec 15 16:35:08 UTC 2023
PRIMARY
Related Record Type Details
Structure of ACECLIDINE SALICYLATE
SALT/SOLVATE -> PARENT
Structure of ACECLIDINE HYDROCHLORIDE
SALT/SOLVATE -> PARENT
Structure of ACECLIDINE, (R)-
ENANTIOMER -> RACEMATE
Structure of ACECLIDINE, (S)-
ENANTIOMER -> RACEMATE
Related Record Type Details
Structure of ACECLIDINE
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