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Erdosteine

Erdosteine structure

CAS No:
84611-23-4
Formula:
C8H11NO4S2
Chemical Name:
Erdosteine
Synonyms:
Acetic acid,2-[[2-oxo-2-[(tetrahydro-2-oxo-3-thienyl)amino]ethyl]thio]-;Acetic acid,[[2-oxo-2-[(tetrahydro-2-oxo-3-thienyl)amino]ethyl]thio]-;2-[[2-Oxo-2-[(tetrahydro-2-oxo-3-thienyl)amino]ethyl]thio]acetic acid;Erdosteine;RV 144;Dithiosteine;Secresolv;Erdostin;Mucotec;2-[2-Oxo-2-[(2-oxothiolan-3-yl)amino]ethyl]sulfanylacetic acid;2-([[(2-Oxothiolan-3-yl)carbamoyl]methyl]sulfanyl)acetic acid;105426-14-0
Categories:
Active Pharmaceutical Ingredients > Respiratory Drugs

Description

Erdosteine inhibits lipopolysaccharide (LPS)-induced NF-κB activation.

Erdosteine is a N-acyl-amino acid.|Erdosteine is a drug that causes a breakdown of mucus, also known as a mucolytic agent. It is a thiol derivative produced for the clinical management of chronic obstructive bronchitis, in addition to infective exacerbations of chronic bronchitis. This drug contains sulfhydryl groups which are released after erdosteine undergoes hepatic first pass metabolism. Three active metabolites result and possess mucolytic activity in addition to free radical scavenging activity. Erdosteine acts to control mucus production and control its viscosity while increasing mucociliary transport. It also combats the effects of free radicals resulting from cigarette smoke. Erdosteine has been shown to be safe and well tolerated in clinical trials. Erdosteine 300mg twice daily reduced cough (both frequency and severity) and sputum viscosity more quickly and more effectively than placebo and reduced the adhesivity of sputum more effectively than ambroxol 30mg twice daily. Co-administration of erdosteine and amoxicillin in patients with acute infective exacerbation of chronic bronchitis resulted in higher concentrations of the antibiotic in the sputum, leading to earlier and more pronounced amelioration of clinical symptoms compared with placebo. Erdosteine is associated with a low incidence of adverse events, most of which are gastrointestinal and generally mild.

Erdosteine Basic Attributes

Molecular Weight：

249.31

Exact Mass：

249.31

EC Number：

1312995-182-4

DSSTox ID：

DTXSID8048735

ATC Code：

R05CB15|R - Respiratory system

HScode：

2934999090

Characteristics

PSA：

134

XLogP3：

-0.1

Density：

1.5±0.1 g/cm3

Melting Point：

156-158 °C

Boiling Point：

590.4°C at 760 mmHg

Flash Point：

310.8±30.1 °C

Refractive Index：

1.615

Storage Conditions：

Refrigerator

Toxicity：

LD50 in mice and rats (g/kg): >10 orally; >3.5 i.v. (Gonella)

Safety Information

Transport codes：

NONH for all modes of transport

wgk germany：

hazard class code：

R36/37/38:Irritating to eyes, respiratory system and skin .

safety instructions：

S26-S36/37/39

RTECS Number：

AJ1476200

Precautionary statement(s)：

P301 + P312 + P330

Hazard Statements：

H302

GHS Classification：

|Warning|H302 (50%): Harmful if swallowed [Warning Acute toxicity, oral]|P264, P270, P280, P301+P312, P305+P351+P338, P330, P337+P313, and P501|Aggregated GHS information provided by 3 companies from 3 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Drug Information

Drug Indication：

Fro the treatment of chronic bronchitis in adults.

MeSH：

Agents that increase mucous excretion. Mucolytic agents, that is drugs that liquefy mucous secretions, are also included here. (See all compounds classified as Expectorants.)

Mechanism of Action：

Erdosteine, is an orally administered mucolytic agent. It is classified as a thiol derivative and produced for the management of symptoms caused by chronic obstructive bronchitis. Erdosteine contains sulfhydryl groups which are released after hepatic first-pass metabolism in the liver. Its active metabolites (3 in number) exert both mucolytic activity and scavenging activity against free radicals. Erdosteine acts to regulate the production of mucus in the airway and regulates its viscosity while enhancing mucociliary transport. This leads to an increase in expectoration. Erdosteine shows inhibition against the effects of free radicals from cigarette smoke. Clinical studies in patients with chronic obstructive lung disease (COPD) have shown that this drug is generally safe and well tolerated. Erdosteine 300mg twice daily reduced cough (both frequency and severity) and sputum viscosity more quickly and more effectively than placebo and reduced the adhesivity of sputum more effectively than ambroxol 30mg twice daily. Co-administration of erdosteine and amoxicillin in patients with acute infective exacerbation of chronic bronchitis resulted in higher concentrations of the antibiotic in the sputum, leading to earlier and more pronounced amelioration of clinical symptoms compared with placebo. Erdosteine is associated with a low incidence of adverse events, most of which are gastrointestinal and generally mild.

MeSH Entry Terms：

Dostein

Erdosteine Use and Manufacturing

Uses

A mucolytic, developed for the treatment of chronic obstructive bronchitis.

Use Classification：

Human drugs -> Rare disease (orphan)

Computed Properties

Molecular Weight:249.3
XLogP3:-0.1
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:6
Rotatable Bond Count:5
Exact Mass:249.01295018
Monoisotopic Mass:249.01295018
Topological Polar Surface Area:134
Heavy Atom Count:15
Complexity:282
Undefined Atom Stereocenter Count:1
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

Drug Function and Efficacy

This product is a mucolytic agent and a prodrug. It is transformed into active metabolites containing free sulfhydryl groups by the liver to dissolve mucosmetic phlegm. Its mechanism of action may be mainly to break the disulfide bonds of mucin in bronchial secretions through metabolites containing free sulfhydryl groups, change its composition and rheological properties (reduce sputum viscosity), and thus facilitate sputum discharge. In addition, this product also has the effect of enhancing the function of mucociliary function.

This ingredient has been used in drugs with the following functions (note: it does not mean that the ingredient itself has the following health functions)

Related Drugs

Erdosteine Capsules
Ingredients	(±)-N-[2-[(Carboxymethylthio)-acetyl]-homocysteine thiolactone
Indication	Not yet clear.
Specifications	0.15g
Manufacturer	XI'AN HAIXIN Pharmaceutical Co., Ltd.

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