Moguisteine

Moguisteine
Identifiers
	IUPAC name Ethyl 3-{2-[(2-methoxyphenoxy)methyl]-1,3-thiazolidin-3-yl}-3-oxopropanoate;
CAS Number	119637-67-1;
PubChemCID	65935;
ChemSpider	59340;
UNII	6Y556547YY;
ChEMBL	ChEMBL146980;
CompTox Dashboard(EPA)	DTXSID00869634;
Chemical and physical data
Formula	C16H21NO5S
Molar mass	339.41g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CCOC(=O)CC(=O)N1CCSC1COC2=CC=CC=C2OC;
	InChI 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;

Moguisteineis a non-narcotic, peripherally actingantitussive.^[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 withCOPD,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]

It was discovered by searching forexpectorantsof thethiazolidineclass, 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 ofATP-sensitive potassium channels.^[7]

References

^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.PMC1910192.PMID 7921605.
^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.
^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.
^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.
^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.PMC3127247.PMID 16428717.
^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.
^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.

[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.PMC1910192.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.PMC3127247.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.

[1]

[2]

[3]

[4]

[5]

[6]

[7]