Aceclidine

Aceclidine
Clinical data
AHFS/Drugs.com	International Drug Names
Routes of; administration	Topical (ophthalmic solution)
ATC code	S01EB08 (WHO) ;
Legal status
Legal status	In general: ℞ (Prescription only);
Pharmacokinetic data
Metabolism	deacetylation?
Identifiers
	IUPAC name 1-Azabicyclo[2.2.2]oct-3-yl acetate; 3-Quinuclidinyl Acetate;
CAS Number	827-61-2 ; 6109-70-2 (HCl);
PubChem CID	1979;
ChemSpider	1902 ;
UNII	0578K3ELIO;
KEGG	D02750 ;
ChEMBL	ChEMBL20835 ;
CompTox Dashboard (EPA)	DTXSID2045658 ;
ECHA InfoCard	100.011.431
Chemical and physical data
Formula	C9H15NO2
Molar mass	169.224 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES O=C(OC2C1CCN(CC1)C2)C;
	InChI InChI=1S/C9H15NO2/c1-7(11)12-9-6-10-4-2-8(9)3-5-10/h8-9H,2-6H2,1H3 ; Key:WRJPSSPFHGNBMG-UHFFFAOYSA-N ;
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Aceclidine (Glaucostat, Glaunorm, Glaudin) is a parasympathomimetic miotic agent used in the treatment of narrow angle glaucoma.

Medicinal properties

Aceclidine decreases intraocular pressure. It acts as a muscarinic acetylcholine receptor agonist.^[1]

Side effects of aceclidine include increased salivation and bradycardia (in excessive doses).

Chemistry

Aceclidine is an organic compound that is structurally related to quinuclidine. As such its alternative name is 3-acetoxyquinuclidine. Its protonated derivative has a pKa of 9.3.^[2]

References

^ Shannon HE, Hart JC, Bymaster FP, Calligaro DO, DeLapp NW, Mitch CH, et al. (August 1999). "Muscarinic receptor agonists, like dopamine receptor antagonist antipsychotics, inhibit conditioned avoidance response in rats". The Journal of Pharmacology and Experimental Therapeutics. 290 (2): 901–907. PMID 10411607.
^ Aggarwal VK, Emme I, Fulford SY (February 2003). "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". The Journal of Organic Chemistry. 68 (3): 692–700. doi:10.1021/jo026671s. PMID 12558387.

[pmid10411607-1] Shannon HE, Hart JC, Bymaster FP, Calligaro DO, DeLapp NW, Mitch CH, et al. (August 1999). "Muscarinic receptor agonists, like dopamine receptor antagonist antipsychotics, inhibit conditioned avoidance response in rats". The Journal of Pharmacology and Experimental Therapeutics. 290 (2): 901–907. PMID 10411607.

[2] Aggarwal VK, Emme I, Fulford SY (February 2003). "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". The Journal of Organic Chemistry. 68 (3): 692–700. doi:10.1021/jo026671s. PMID 12558387.

[1]

[2]

Medicinal properties

Chemistry

See also

References