Moguisteine | CAS#119637-67-1 | cholinergic receptor antagonist

MedKoo Cat#: 530020 | Name: Moguisteine

Description:

WARNING: This product is for research use only, not for human or veterinary use.

Moguisteine is a cholinergic receptor antagonist potentially for the treatment of cough.

Chemical Structure

Moguisteine

CAS#119637-67-1

Theoretical Analysis

MedKoo Cat#: 530020

Name: Moguisteine

CAS#: 119637-67-1

Chemical Formula: C16H21NO5S

Exact Mass: 339.1140

Molecular Weight: 339.41

Elemental Analysis: C, 56.62; H, 6.24; N, 4.13; O, 23.57; S, 9.45

Price and Availability

Size	Price	Availability
200mg	USD 250.00	2 Weeks
500mg	USD 450.00	2 Weeks
1g	USD 750.00	2 Weeks
2g	USD 1,250.00	2 Weeks
5g	USD 2,750.00	2 Weeks
10g	USD 4,650.00	2 Weeks

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Related CAS #

No Data

Synonym

BBR-2173; BBR2173; BBR 2173; Moguisteine

IUPAC/Chemical Name

ethyl 3-(2-((2-methoxyphenoxy)methyl)thiazolidin-3-yl)-3-oxopropanoate

InChi Key

WSYVIAQNTFPTBI-UHFFFAOYSA-N

InChi Code

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

SMILES Code

O=C(OCC)CC(N1C(COC2=CC=CC=C2OC)SCC1)=O

Appearance

Solid powder

Purity

>98% (or refer to the Certificate of Analysis)

Shipping Condition

Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition

Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility

Soluble in DMSO

Shelf Life

>2 years if stored properly

Drug Formulation

This drug may be formulated in DMSO

Stock Solution Storage

0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code

2934.99.9001

More Info

Product Data

Product Data

Instruction

View handling instruction

Biological target:

Moguisteine (BBR-2173) is a novel peripheral non-narcotic antitussive drug.

In vitro activity:

TBD

In vivo activity:

Moguisteine and codeine dose-dependently (respective ED50 values are given in parentheses) inhibited cough induced in guinea-pigs by 7.5% citric acid aerosol (25.2 and 29.2 mg kg-1, p.o.), by 30 microM capsaicin aerosol (19.3 and 15.2 mg kg-1, p.o.), by mechanical stimulation (22.9 and 26.4 mg kg-1, p.o.) and by tracheal electrical stimulation (12.5 and 13.9 mg kg-1, p.o.). Moguisteine was effective against cough induced by tracheal electrical stimulation in dogs (ED50 17.2 mg kg-1, p.o.). Reference: Br J Pharmacol. 1994 Jul;112(3):795-800. https://pubmed.ncbi.nlm.nih.gov/7921605/

	Solvent	mg/mL	mM
Solubility
	DMF	15.0	44.19
	DMF:PBS (pH 7.2) (1:6)	0.1	0.41
	DMSO	59.3	174.82
	Ethanol	68.0	200.35

Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 339.41 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

Formulation protocol:

1. Gallico L, Oggioni N, Dalla Rosa C, Ceserani R, Tognella S. Effects of moguisteine, a peripheral nonnarcotic antitussive agent, on airway inflammation in guinea-pigs in vivo. Eur Respir J. 1996 Mar;9(3):478-85. doi: 10.1183/09031936.96.09030478. PMID: 8730007. 2. Gallico L, Borghi A, Dalla Rosa C, Ceserani R, Tognella S. Moguisteine: a novel peripheral non-narcotic antitussive drug. Br J Pharmacol. 1994 Jul;112(3):795-800. doi: 10.1111/j.1476-5381.1994.tb13149.x. PMID: 7921605; PMCID: PMC1910192.

In vitro protocol:

TBD

In vivo protocol:

1: Teng Y, Song H, Bu F, Wei C, Zhao W, Zhang R, Yuan G, Liu X, Wang B, Guo R. Determination of the active metabolite of moguisteine in human plasma and urine by LC-ESI-MS method and its application in pharmacokinetic study. J Chromatogr B Analyt Technol Biomed Life Sci. 2012 Jun 15;899:31-5. doi: 10.1016/j.jchromb.2012.04.033. PubMed PMID: 22626894. 2: Morita K, Onodera K, Kamei J. Inhaled pinacidil, an ATP-sensitive K+ channel opener, and moguisteine have potent antitussive effects in guinea pigs. Jpn J Pharmacol. 2002 Jun;89(2):171-5. PubMed PMID: 12120760. 3: Ishii R, Furuta M, Hashimoto M, Naruse T, Gallico L, Ceserani R. Effects of moguisteine on the cough reflex induced by afferent electrical stimulation of the superior laryngeal nerve in guinea pigs. Eur J Pharmacol. 1998 Dec 4;362(2-3):207-12. PubMed PMID: 9874172. 4: Morita K, Kamei J. Involvement of ATP-sensitive K(+) channels in the anti-tussive effect of moguisteine. Eur J Pharmacol. 2000 Apr 28;395(2):161-4. PubMed PMID: 10794823. 5: Sant'Ambrogio G, Sant'Ambrogio FB. Action of moguisteine on the activity of tracheobronchial rapidly adapting receptors in the dog. Eur Respir J. 1998 Feb;11(2):339-44. PubMed PMID: 9551735. 6: Kamei J, Morita K. Antitussive effect of moguisteine on the enhanced coughing associated with enalapril in guinea-pig. Eur J Pharmacol. 1996 Sep 26;312(2):235-9. PubMed PMID: 8894601. 7: Morikawa T, Gallico L, Widdicombe J. Actions of moguisteine on cough and pulmonary rapidly adapting receptor activity in the guinea pig. Pharmacol Res. 1997 Feb;35(2):113-8. PubMed PMID: 9175579. 8: Cavalletti E, Montaguti P, Sala F, Ceserani R. Comparative toxicology of two enantiomers of the peripherally acting non-narcotic antitussive drug moguisteine. Arzneimittelforschung. 1996 Dec;46(12):1114-9. PubMed PMID: 9006784. 9: Gallico L, Oggioni N, Dalla Rosa C, Ceserani R, Tognella S. Effects of moguisteine, a peripheral nonnarcotic antitussive agent, on airway inflammation in guinea-pigs in vivo. Eur Respir J. 1996 Mar;9(3):478-85. PubMed PMID: 8730007. 10: Kamei J, Morita K, Kashiwazaki T, Ohsawa M. Antitussive effect of moguisteine on allergic coughs in the guinea pig. Eur J Pharmacol. 1998 Apr 24;347(2-3):253-5. PubMed PMID: 9653890. 11: Bernareggi A, Crema A, Carlesi RM, Castoldi D, Ratti E, Renoldi MI, Ratti D, Ceserani R, Tognella S. Stereoselective pharmacokinetics of moguisteine metabolites in healthy subjects. Eur J Drug Metab Pharmacokinet. 1995 Oct-Dec;20(4):263-70. PubMed PMID: 8983930. 12: Gallico L, Borghi A, Dalla Rosa C, Ceserani R, Tognella S. Moguisteine: a novel peripheral non-narcotic antitussive drug. Br J Pharmacol. 1994 Jul;112(3):795-800. PubMed PMID: 7921605; PubMed Central PMCID: PMC1910192. 13: Gallico L, Borghi A, Cavalletti E, Ceserani R, Tognella S. Antitussive activity of moguisteine enantiomers in guinea-pigs and rats. J Pharm Pharmacol. 1996 Jan;48(1):112-4. PubMed PMID: 8722507. 14: Barnabè R, Berni F, Clini V, Pirrelli M, Pisani Ceretti A, Robuschi M, Rossi M, Sestini P, Tana F, Vaghi A, et al. The efficacy and safety of moguisteine in comparison with codeine phosphate in patients with chronic cough. Monaldi Arch Chest Dis. 1995 Apr;50(2):93-7. PubMed PMID: 7613554. 15: Montaguti P, Ceserani R, Bussi R, Cavalletti E, Tognella S. Reproductive toxicology of the new antitussive moguisteine. Arzneimittelforschung. 1994 Dec;44(12):1347-52. PubMed PMID: 7848355. 16: Cavalletti E, Ceserani R, Sala F, Montaguti P, Tognella S. General toxicology of the new antitussive moguisteine. Arzneimittelforschung. 1994 Nov;44(11):1227-33. PubMed PMID: 7848336. 17: Castoldi D, Oggioni A, Renoldi MI, Ratti E, Di Giovine S, Bernareggi A. Assay of moguisteine metabolites in human plasma and urine: conventional and chiral high-performance liquid chromatographic methods. J Chromatogr B Biomed Appl. 1994 May 13;655(2):243-52. PubMed PMID: 8081470. 18: Luo YL, Li PB, Zhang CC, Zheng YF, Wang S, Nie YC, Zhang KJ, Su WW. Effects of four antitussives on airway neurogenic inflammation in a guinea pig model of chronic cough induced by cigarette smoke exposure. Inflamm Res. 2013 Dec;62(12):1053-61. doi: 10.1007/s00011-013-0664-6. PubMed PMID: 24085318. 19: Aversa C, Cazzola M, Clini V, Dal Negro R, Maiorano V, Tana F, Allegra L. Clinical trial of the efficacy and safety of moguisteine in patients with cough associated with chronic respiratory diseases. Drugs Exp Clin Res. 1993;19(6):273-9. PubMed PMID: 8013271. 20: Oggioni A, Castoldi D, Bernareggi A. Direct HPLC separation of enantiomers of main moguisteine metabolite: comparison of different stationary phases. Farmaco. 1994 Mar;49(3):225-7. PubMed PMID: 8043175.