Moguisteine

Moguisteine is a non-narcotic, peripherally acting antitussive.[1] In a small double-blind, randomized controlled trial, 200 mg of moguisteine suspension taken 3 times daily significantly reduced the frequency of coughing in patients with COPD, compared to placebo.[2] It has also been studied in small trials in comparison to codeine[3] and dextromethorphan,[4] and has similar efficacy to both. It has not been approved for use in the United States.[5]

Moguisteine
Identifiers
  • Ethyl 3-{2-[(2-methoxyphenoxy)methyl]-1,3-thiazolidin-3-yl}-3-oxopropanoate
CAS Number
PubChem CID
ChemSpider
UNII
ChEMBL
Chemical and physical data
FormulaC16H21NO5S
Molar mass339.41 g·mol−1
3D model (JSmol)
  • CCOC(=O)CC(=O)N1CCSC1COC2=CC=CC=C2OC
  • InChI=1S/C16H21NO5S/c1-3-21-16(19)10-14(18)17-8-9-23-15(17)11-22-13-7-5-4-6-12(13)20-2/h4-7,15H,3,8-11H2,1-2H3
  • Key:WSYVIAQNTFPTBI-UHFFFAOYSA-N

It was discovered by searching for expectorants of the thiazolidine class, when compounds with a cough suppressant effect were accidentally found and moguisteine was selected as the most effective and safest representative of the class.[6] Its mechanism of action may be the activation of ATP-sensitive potassium channels.[7]

References
  1. Gallico L, Borghi A, Dalla Rosa C, Ceserani R, Tognella S (July 1994). "Moguisteine: a novel peripheral non-narcotic antitussive drug". British Journal of Pharmacology. 112 (3): 795–800. doi:10.1111/j.1476-5381.1994.tb13149.x. PMC 1910192. PMID 7921605.
  2. Aversa C, Cazzola M, Clini V, Dal Negro R, Maiorano V, Tana F, Allegra L (1993). "Clinical trial of the efficacy and safety of moguisteine in patients with cough associated with chronic respiratory diseases". Drugs Under Experimental and Clinical Research. 19 (6): 273–9. PMID 8013271.
  3. Barnabè R, Berni F, Clini V, Pirrelli M, Pisani Ceretti A, Robuschi M, et al. (April 1995). "The efficacy and safety of moguisteine in comparison with codeine phosphate in patients with chronic cough". Monaldi Archives for Chest Disease = Archivio Monaldi per le Malattie del Torace. 50 (2): 93–7. PMID 7613554.
  4. Del Donno M, Aversa C, Corsico R, Foresi A, Grassi V, Malerba M, et al. (1994). "Efficacy and Safety of Moguisteine in Comparison with Dextromethorphan in Patients with Persistent Cough". Drug Investigation. 7 (2): 93–100. doi:10.1007/BF03257404. S2CID 72285850.
  5. Bolser DC (January 2006). "Cough suppressant and pharmacologic protussive therapy: ACCP evidence-based clinical practice guidelines". Chest. 129 (1 Suppl): 238S–249S. doi:10.1378/chest.129.1_suppl.238S. PMC 3127247. PMID 16428717.
  6. Gandolfi CA, Di Domenico R, Spinelli S, Gallico L, Fiocchi L, Lotto A, et al. (February 1995). "N-acyl-2-substituted-1,3-thiazolidines, a new class of non-narcotic antitussive agents: studies leading to the discovery of ethyl 2-[(2-methoxyphenoxy)methyl]-beta-oxothiazolidine-3-propanoate". Journal of Medicinal Chemistry. 38 (3): 508–25. doi:10.1021/jm00003a014. PMID 7853344.
  7. Morita K, Kamei J (April 2000). "Involvement of ATP-sensitive K(+) channels in the anti-tussive effect of moguisteine". European Journal of Pharmacology. 395 (2): 161–4. doi:10.1016/s0014-2999(00)00197-7. PMID 10794823.
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