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Erdosteine

HCID 65632
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Basic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
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Basic information

CAS
105426-14-0
Standard SMILES
O=C(O)CSCC(=O)NC1CCSC1=O
InChIKey
QGFORSXNKQLDNO-UHFFFAOYSA-N
Molecular formula
C8H11NO4S2
Average molar mass
249.3 g/mol
Monoisotopic mass
249.01295018

Overview

Erdosteine is a N-acyl-amino acid.

Names & identifiers

Preferred name
Erdosteine
IUPAC
2-[2-oxo-2-[(2-oxothiolan-3-yl)amino]ethyl]sulfanylacetic acid
English name
Erdosteine
Molecular formula
C8H11NO4S2
Molecular weight
249.31

Names & synonyms

Erdosteine84611-23-4RV-144ErdosteinumMucotecDTXSID8048735erdosteinaErdotin76J0853EKARV144DTXCID50286612-({[(2-oxothiolan-3-yl)carbamoyl]methyl}sulfanyl)acetic acid
Show more names
pv144KW-9144ErdostenErdostieneErdosteine1Erdosteine>
(+-)-((((Tetrahydro-2-oxo-3-thienyl)carbamoyl)methyl)thio)acetic acid2-((((2-oxothiolan-3-yl)carbamoyl)methyl)sulfanyl)acetic acidRefChem:137478R05CB15DithiosteineRV 1442-[2-oxo-2-[(2-oxothiolan-3-yl)amino]ethyl]sulfanylacetic acid105426-14-0

Database identifiers

CAS
105426-14-0、84611-23-4
PubChem CID
65632
DTXSID
DTXSID8048735
ChEMBL
CHEMBL1697744
ChEBI
CHEBI:135014
UNII
76J0853EKA
EC Number
642-172-5
Nikkaji
J325.880G

Properties

Computed structural properties

XLogP
-0.1
Topological polar surface area
134 Ų
Hydrogen bond donors
2
Hydrogen bond acceptors
6
Rotatable bonds
5
Heavy atoms
15
Formal charge
0
Complexity
282

Experimental & physicochemical properties

DrugsPharmaceuticals -> Used in Switzerland

Physicochemical properties

Melting point
156 · 156-160°C
Boiling point
590.4 · 590.4±50.0 °C(Predicted)
Density
1.48 · 1.48±0.1 g/cm3(Predicted)
storage temp.
2 · Sealed in dry,2-8°C
solubility
Acetonitrile (Slightly), DMSO (Slightly), Methanol (Slightly)
pka
3.71 · 3.71(at 25℃)
form
Solid
color
White to Off-White
λmax
236 nm · 236nm(H2O)(lit.)
Merck
14 · 14,3647
InChI
1S/C8H11NO4S2/c10-6(3-14-4-7(11)12)9-5-1-2-15-8(5)13/h5H,1-4H2,(H,9,10)(H,11,12)
InChIKey
QGFORSXNKQLDNO-UHFFFAOYSA-N
SMILES
S1CCC(C1=O)NC(=O)CSCC(=O)O

Safety & regulation

Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.

GHS classification

GHS Classification · 5 items

This chemical does not meet GHS hazard criteria for 12.5% (1 of 8) of reports.

Warning

H302 (75%): Harmful if swallowed [Warning Acute toxicity, oral]

P264, P264+P265, P270, P280, P301+P317, P302+P352, P305+P351+P338, P317, P321, P330, P337+P317, P362+P364, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 8 reports by companies from 5 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Hazard information

Hazard Classes and CategoriesAcute Tox. 4 (75%)

Safety data

wgk
WGK 3
rtecs
AJ1476200
hs_code
2934.99.9001
Toxicity
LD50 in mice and rats (g/kg): >10 orally; >3.5 i.v. (Gonella)
Signal word
Warning
Symbol(GHS)
GHS07
Storage Class
11 - Combustible Solids
Hazard statements
H302-H315-H320-H335
Hazard Classifications
Acute Tox. 4 Oral
Precautionary statements
P261-P280-P301+P312-P302+P352-P305+P351+P338

Chemistry & industry

Pharmacology

ATC Code · 3 items

R05CB15

R - Respiratory system

QR - Respiratory system

Mechanism of Action · 1 item

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 Pharmacological ClassificationAgents that increase mucous excretion. Mucolytic agents, that is drugs that liquefy mucous secretions, are also included here.
Applications · 4 items

DescriptionErdosteine is a new expectorant introduced in France for the treatment of chronic bronchitis. Erdosteine possesses mucomodulator, mucolytic, mucokinetic and free radical scavenging properties. Its therapeutic efficacy has been demonstrated in patients affected by congestion and viscous mucus in higher and lower respiratory tracts as in acute and chronic bronchitis, sinusitis, otitis, tracheopharyngitis and coryza. Erdosteine acts through its active metabolites containing free sulfhydryl groups which are able to depolymerize the mucopolysaccharides of the excreatum by breaking the disulfide linkages (thereby lowing its viscosity). The prodrug approach provides unique characteristics to erdosteine by offering stable therapeutic efficacy and prevention of the gastric mucus from lythic phenomena. The agent was also reported to have local antiinflammatory and antielastase properties and enhances penetration of antibiotics into bronchial mucus.

Related reactions

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Compound notes

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On this pageBasic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
CAS DataBase Reference
84611 · 84611-23-4(CAS DataBase Reference)
FDA UNII
76 J0853EKA · 76J0853EKA
ATC code
5 CB15 · R05CB15
UNSPSC Code
12352200 · 12352200
NACRES
77 · NA.77
Symbol(GHS)
7 · GHS07
Signal word
Warning
Hazard statements
302 · H302-H315-H320-H335
Precautionary statements
261 · P261-P280-P301+P312-P302+P352-P305+P351+P338
WGK Germany
3 · WGK 3
RTECS
1476200 · AJ1476200
HS Code
2934.99 · 2934.99.9001
Storage Class
11 · 11 - Combustible Solids
Hazard Classifications
4 Oral · Acute Tox. 4 Oral
Toxicity
50 in · LD50 in mice and rats (g/kg): >10 orally; >3.5 i.v. (Gonella)

DescriptionErdosteine is a mucolytic agent and an antioxidant. It inhibits LPS-induced IκB kinase (IKK) activity, NF-κB-mediated transcription, and production of IL-6 and IL-1β in RAW 264.7 cells. Erdosteine (7.5 mg/kg) prevents depletion of renal catalase and glutathione peroxidase (GPX) and increases in renal malondialdehyde (MDA) and nitric oxide (NO) levels in a rat model of nephrotoxicity induced by cisplatin . It reduces spinal cord lipid peroxidation and destruction of spinal motor neurons in a rabbit model of spinal cord ischemia and reperfusion injury induced by thoracoabdominal aortic clamping. Erdosteine (150 mg/kg) reduces lung weight, MDA and protein carbonyl levels, and macrophage and neutrophil accumulation in a mouse model of acute lung injury induced by oleic acid (Item Nos. 90260 | 24659). Formulations containing erdosteine have been used in the treatment of chronic obstructive pulmonary disease (COPD).

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

UsesErdosteine is a mucolytic. Erdosteine was developed for the treatment of chronic obstructive bronchitis.

Upstream & downstream products

Upstream raw materials

N-CHLOROACETYL-DL-HOMOCYSTEINE THIOLACTONEThiodiglycolic AnhydrideHOMOCYSTEINE THIOLACTONEThioglycolic acid

Suppliers1 total

Hefei TNJ Chemical Industry Co.,Ltd.+86-0551-65418684 +86-18949823763 · [email protected]

Additional notes

DefinitionChEBI: Erdosteine is a N-acyl-amino acid.