aceclidine

{{Drugbox

| Verifiedfields = changed

| Watchedfields = changed

| verifiedrevid = 477237849

| IUPAC_name = 1-Azabicyclo[2.2.2]oct-3-yl acetate; 3-Quinuclidinyl Acetate

| image = Aceclidine.svg

| alt = Skeletal formula of aceclidine

| width = 140

| image2 = Aceclidine 3D ball.png

| width2 = 175

| alt2 = Ball-and-stick model of the aceclidine molecule

| tradename =

| Drugs.com = {{drugs.com|international|aceclidine}}

| pregnancy_category =

| legal_status = Rx-only

| routes_of_administration = Topical (ophthalmic solution)

| bioavailability =

| metabolism = deacetylation?

| excretion =

| CAS_number_Ref = {{cascite|changed|??}}

| CAS_number = 827-61-2

| CAS_supplemental =
6109-70-2 (HCl)

| ATC_prefix = S01

| ATC_suffix = EB08

| PubChem = 1979

| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

| ChemSpiderID = 1902

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = 0578K3ELIO

| KEGG_Ref = {{keggcite|correct|kegg}}

| KEGG = D02750

| ChEMBL_Ref = {{ebicite|correct|EBI}}

| ChEMBL = 20835

| C=9 | H=15 | N=1 | O=2

| smiles = O=C(OC2C1CCN(CC1)C2)C

| StdInChI_Ref = {{stdinchicite|correct|chemspider}}

| StdInChI = 1S/C9H15NO2/c1-7(11)12-9-6-10-4-2-8(9)3-5-10/h8-9H,2-6H2,1H3

| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}

| StdInChIKey = WRJPSSPFHGNBMG-UHFFFAOYSA-N

}}

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.{{cite journal | vauthors = Shannon HE, Hart JC, Bymaster FP, Calligaro DO, DeLapp NW, Mitch CH, Ward JS, Fink-Jensen A, Sauerberg P, Jeppesen L, Sheardown MJ, Swedberg MD | display-authors = 6 | title = Muscarinic receptor agonists, like dopamine receptor antagonist antipsychotics, inhibit conditioned avoidance response in rats | journal = The Journal of Pharmacology and Experimental Therapeutics | volume = 290 | issue = 2 | pages = 901–907 | date = August 1999 | pmid = 10411607 | url = http://jpet.aspetjournals.org/cgi/pmidlookup?view=long&pmid=10411607 }}

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.{{cite journal | vauthors = Aggarwal VK, Emme I, Fulford SY | title = 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 | journal = The Journal of Organic Chemistry | volume = 68 | issue = 3 | pages = 692–700 | date = February 2003 | pmid = 12558387 | doi = 10.1021/jo026671s }}