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Details

Stereochemistry RACEMIC
Molecular Formula C16H21NO5S
Molecular Weight 339.407
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of MOGUISTEINE

SMILES

CCOC(=O)CC(=O)N1CCSC1COC2=C(OC)C=CC=C2

InChI

InChIKey=WSYVIAQNTFPTBI-UHFFFAOYSA-N
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

HIDE SMILES / InChI

Molecular Formula C16H21NO5S
Molecular Weight 339.407
Charge 0
Count
Stereochemistry RACEMIC
Additional Stereochemistry No
Defined Stereocenters 0 / 1
E/Z Centers 0
Optical Activity ( + / - )

Moguisteine is a non-narcotic antitussive compound. Moguisteine demonstrated inhibitory effect on rapidly adapting irritant receptors that could account for the antitussigenic effect of this compound. Furthermore, it is possible that ATP-sensitive K(+) channels may be involved in the anti-tussive effect of peripherally acting non-narcotic moguisteine. The drug did not show any toxic effect on the dams and their fetuses, nor did it have any teratogenic effect in either of the tested species. Finally, moguisteine had no adverse effects, either on parturition or on peri-and postnatal survival and/or development of the offspring. It was reported that moguisteine to be effective in reducing cough frequency in chronic cough of bronchitis and COPD. It was recommended for the short-term symptomatic relief of coughing. Preregistration of moguisteine in Italy is discontinued.

CNS Activity

Curator's Comment: poor penetration - 0.01% of the administered dose (guinea-pigs data)

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
3570.47 ng/mL
400 mg single, oral
dose: 400 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
MOGUISTEINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
1397.87 ng/mL
200 mg 3 times / day multiple, oral
dose: 200 mg
route of administration: Oral
experiment type: MULTIPLE
co-administered:
MOGUISTEINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
11637.72 ng × h/mL
400 mg single, oral
dose: 400 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
MOGUISTEINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
5547.88 ng × h/mL
200 mg 3 times / day multiple, oral
dose: 200 mg
route of administration: Oral
experiment type: MULTIPLE
co-administered:
MOGUISTEINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
1.54 h
400 mg single, oral
dose: 400 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
MOGUISTEINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
1.57 h
200 mg 3 times / day multiple, oral
dose: 200 mg
route of administration: Oral
experiment type: MULTIPLE
co-administered:
MOGUISTEINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
Doses

Doses

DosePopulationAdverse events​
400 mg single, oral
Highest studied dose
Dose: 400 mg
Route: oral
Route: single
Dose: 400 mg
Sources: Page: p.169
healthy, ADULT
n = 4
Health Status: healthy
Age Group: ADULT
Sex: M+F
Food Status: FASTED
Population Size: 4
Sources: Page: p.169
200 mg 3 times / day multiple, oral
Studied dose
Dose: 200 mg, 3 times / day
Route: oral
Route: multiple
Dose: 200 mg, 3 times / day
Sources: Page: p.169
healthy, ADULT
n = 4
Health Status: healthy
Age Group: ADULT
Sex: M+F
Food Status: FASTED
Population Size: 4
Sources: Page: p.169
Sourcing

Sourcing

Vendor/AggregatorIDURL
PubMed

PubMed

TitleDatePubMed
Clinical trial of the efficacy and safety of moguisteine in patients with cough associated with chronic respiratory diseases.
1993
Reproductive toxicology of the new antitussive moguisteine.
1994 Dec
Moguisteine: a novel peripheral non-narcotic antitussive drug.
1994 Jul
Assay of moguisteine metabolites in human plasma and urine: conventional and chiral high-performance liquid chromatographic methods.
1994 May 13
General toxicology of the new antitussive moguisteine.
1994 Nov
The efficacy and safety of moguisteine in comparison with codeine phosphate in patients with chronic cough.
1995 Apr
Effects of four antitussives on airway neurogenic inflammation in a guinea pig model of chronic cough induced by cigarette smoke exposure.
2013 Dec
Patents

Sample Use Guides

100 mg three times a day
Route of Administration: Oral
In Vitro Use Guide
Unknown
Substance Class Chemical
Created
by admin
on Fri Dec 15 16:20:26 GMT 2023
Edited
by admin
on Fri Dec 15 16:20:26 GMT 2023
Record UNII
6Y556547YY
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
MOGUISTEINE
INN   MART.  
INN  
Official Name English
moguisteine [INN]
Common Name English
MOGUISTEINE [MART.]
Common Name English
BBR2173
Code English
ETHYL (±)-2-((O-METHOXYPHENOXY)METHYL)-.BETA.-OXO-3-THIAZOLIDINEPROPIONATE
Common Name English
NSC-759829
Code English
BBR-2173
Code English
Classification Tree Code System Code
NCI_THESAURUS C74536
Created by admin on Fri Dec 15 16:20:26 GMT 2023 , Edited by admin on Fri Dec 15 16:20:26 GMT 2023
Code System Code Type Description
FDA UNII
6Y556547YY
Created by admin on Fri Dec 15 16:20:26 GMT 2023 , Edited by admin on Fri Dec 15 16:20:26 GMT 2023
PRIMARY
NSC
759829
Created by admin on Fri Dec 15 16:20:26 GMT 2023 , Edited by admin on Fri Dec 15 16:20:26 GMT 2023
PRIMARY
WIKIPEDIA
Moguisteine
Created by admin on Fri Dec 15 16:20:26 GMT 2023 , Edited by admin on Fri Dec 15 16:20:26 GMT 2023
PRIMARY
ChEMBL
CHEMBL146980
Created by admin on Fri Dec 15 16:20:26 GMT 2023 , Edited by admin on Fri Dec 15 16:20:26 GMT 2023
PRIMARY
NCI_THESAURUS
C66178
Created by admin on Fri Dec 15 16:20:26 GMT 2023 , Edited by admin on Fri Dec 15 16:20:26 GMT 2023
PRIMARY
EPA CompTox
DTXSID00869634
Created by admin on Fri Dec 15 16:20:26 GMT 2023 , Edited by admin on Fri Dec 15 16:20:26 GMT 2023
PRIMARY
INN
6464
Created by admin on Fri Dec 15 16:20:26 GMT 2023 , Edited by admin on Fri Dec 15 16:20:26 GMT 2023
PRIMARY
CAS
119637-67-1
Created by admin on Fri Dec 15 16:20:26 GMT 2023 , Edited by admin on Fri Dec 15 16:20:26 GMT 2023
PRIMARY
MESH
C087933
Created by admin on Fri Dec 15 16:20:26 GMT 2023 , Edited by admin on Fri Dec 15 16:20:26 GMT 2023
PRIMARY
PUBCHEM
65935
Created by admin on Fri Dec 15 16:20:26 GMT 2023 , Edited by admin on Fri Dec 15 16:20:26 GMT 2023
PRIMARY
SMS_ID
100000080355
Created by admin on Fri Dec 15 16:20:26 GMT 2023 , Edited by admin on Fri Dec 15 16:20:26 GMT 2023
PRIMARY
EVMPD
SUB09038MIG
Created by admin on Fri Dec 15 16:20:26 GMT 2023 , Edited by admin on Fri Dec 15 16:20:26 GMT 2023
PRIMARY
Related Record Type Details
ACTIVE MOIETY