Aceclidine

Last updated
Aceclidine
Aceclidine.svg
Aceclidine 3D ball.png
Clinical data
AHFS/Drugs.com International Drug Names
Routes of
administration
Topical (ophthalmic solution)
ATC code
Legal status
Legal status
  • In general: ℞ (Prescription only)
Pharmacokinetic data
Metabolism deacetylation?
Identifiers
  • 1-Azabicyclo[2.2.2]oct-3-yl acetate; 3-Quinuclidinyl Acetate
CAS Number
PubChem CID
ChemSpider
UNII
KEGG
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard 100.011.431 OOjs UI icon edit-ltr-progressive.svg
Chemical and physical data
Formula C9H15NO2
Molar mass 169.224 g·mol−1
3D model (JSmol)
  • O=C(OC2C1CCN(CC1)C2)C
  • InChI=1S/C9H15NO2/c1-7(11)12-9-6-10-4-2-8(9)3-5-10/h8-9H,2-6H2,1H3 Yes check.svgY
  • Key:WRJPSSPFHGNBMG-UHFFFAOYSA-N Yes check.svgY
 X mark.svgNYes check.svgY  (what is this?)    (verify)

Aceclidine (Glaucostat, Glaunorm, Glaudin) is a parasympathomimetic miotic agent used in the treatment of narrow angle glaucoma.

Contents

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]

See also

Related Research Articles

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Acetylcholine (ACh) is an organic compound that functions in the brain and body of many types of animals as a neurotransmitter. Its name is derived from its chemical structure: it is an ester of acetic acid and choline. Parts in the body that use or are affected by acetylcholine are referred to as cholinergic.

<span class="mw-page-title-main">Muscarine</span> Chemical compound

Muscarine, L-(+)-muscarine, or muscarin is a natural product found in certain mushrooms, particularly in Inocybe and Clitocybe species, such as the deadly C. dealbata. Mushrooms in the genera Entoloma and Mycena have also been found to contain levels of muscarine which can be dangerous if ingested. Muscarine has been found in harmless trace amounts in Boletus, Hygrocybe, Lactarius and Russula. Trace concentrations of muscarine are also found in Amanita muscaria, though the pharmacologically more relevant compound from this mushroom is the Z-drug-like alkaloid muscimol. A. muscaria fruitbodies contain a variable dose of muscarine, usually around 0.0003% fresh weight. This is very low and toxicity symptoms occur very rarely. Inocybe and Clitocybe contain muscarine concentrations up to 1.6%.

<span class="mw-page-title-main">Agonist</span> Chemical which binds to and activates a biochemical receptor

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<span class="mw-page-title-main">Muscarinic acetylcholine receptor</span> Acetylcholine receptors named for their selective binding of muscarine

Muscarinic acetylcholine receptors, or mAChRs, are acetylcholine receptors that form G protein-coupled receptor complexes in the cell membranes of certain neurons and other cells. They play several roles, including acting as the main end-receptor stimulated by acetylcholine released from postganglionic fibers. They are mainly found in the parasympathetic nervous system, but also have a role in the sympathetic nervous system in the control of sweat glands.

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Muscarinic acetylcholine receptor M<sub>1</sub> Protein-coding gene in the species Homo sapiens

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Muscarinic acetylcholine receptor M<sub>2</sub> Protein-coding gene in the species Homo sapiens

The muscarinic acetylcholine receptor M2, also known as the cholinergic receptor, muscarinic 2, is a muscarinic acetylcholine receptor that in humans is encoded by the CHRM2 gene. Multiple alternatively spliced transcript variants have been described for this gene. It is Gi-coupled, reducing intracellular levels of cAMP.

Muscarinic acetylcholine receptor M<sub>3</sub> Protein and coding gene in humans

The muscarinic acetylcholine receptor, also known as cholinergic/acetylcholine receptor M3, or the muscarinic 3, is a muscarinic acetylcholine receptor encoded by the human gene CHRM3.

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Vedaclidine (INN, codenamed LY-297,802, NNC 11-1053) is an experimental analgesic drug which acts as a mixed agonist–antagonist at muscarinic acetylcholine receptors, being a potent and selective agonist for the M1 and M4 subtypes, yet an antagonist at the M2, M3 and M5 subtypes. It is orally active and an effective analgesic over 3× the potency of morphine, with side effects such as salivation and tremor only occurring at many times the effective analgesic dose. Human trials showed little potential for development of dependence or abuse, and research is continuing into possible clinical application in the treatment of neuropathic pain and cancer pain relief.

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<span class="mw-page-title-main">AC-42</span> Chemical compound

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References

  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.