ContaminantDB: Erdosteine

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-05-22 06:39:27 UTC

Update Date

2016-11-09 01:16:06 UTC

Accession Number

CHEM019960

Identification

Common Name

Erdosteine

Class

Small Molecule

Description

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.

Contaminant Sources

STOFF IDENT Compounds
ToxCast & Tox21 Chemicals

Contaminant Type

Not Available

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
Mucotec	Kegg
Dostein	MeSH
Esteclin	MeSH
Edirel	MeSH
S-(2-(N-3-(2-oxo-Tetrahydrothienyl)acetamido))thioglycolic acid	MeSH
Vectrine	MeSH
2-({[(2-oxothiolan-3-yl)-C-hydroxycarbonimidoyl]methyl}sulfanyl)acetate	Generator
2-({[(2-oxothiolan-3-yl)-C-hydroxycarbonimidoyl]methyl}sulphanyl)acetate	Generator
2-({[(2-oxothiolan-3-yl)-C-hydroxycarbonimidoyl]methyl}sulphanyl)acetic acid	Generator

Chemical Formula

C₈H₁₁NO₄S₂

Average Molecular Mass

249.307 g/mol

Monoisotopic Mass

249.013 g/mol

CAS Registry Number

84611-23-4

IUPAC Name

2-({[(2-oxothiolan-3-yl)carbamoyl]methyl}sulfanyl)acetic acid

Traditional Name

erdosteine

SMILES

OC(=O)CSCC(=O)NC1CCSC1=O

InChI Identifier

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)

InChI Key

QGFORSXNKQLDNO-UHFFFAOYSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as n-acyl-alpha amino acids and derivatives. N-acyl-alpha amino acids and derivatives are compounds containing an alpha amino acid (or a derivative thereof) which bears an acyl group at its terminal nitrogen atom.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

N-acyl-alpha amino acids and derivatives

Alternative Parents

Substituents

N-acyl-alpha amino acid or derivatives
Heterocyclic fatty acid
Fatty acyl
Fatty acid
Carbothioic s-lactone
Thiolane
Carboxamide group
Secondary carboxylic acid amide
Thiocarboxylic acid ester
Thiolactone
Carboxylic acid
Monocarboxylic acid or derivatives
Thiocarboxylic acid or derivatives
Thioether
Organoheterocyclic compound
Dialkylthioether
Sulfenyl compound
Organosulfur compound
Organooxygen compound
Organonitrogen compound
Organic oxide
Organic nitrogen compound
Hydrocarbon derivative
Organic oxygen compound
Carbonyl group
Organopnictogen compound
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

Not Available

Biological Properties

Status

Detected and Not Quantified

Origin

Not Available

Cellular Locations

Not Available

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Physical Properties

State

Not Available

Appearance

Not Available

Experimental Properties

Property	Value
Melting Point	Not Available
Boiling Point	Not Available
Solubility	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	4.85 g/L	ALOGPS
logP	-0.43	ALOGPS
logP	-0.65	ChemAxon
logS	-1.7	ALOGPS
pKa (Strongest Acidic)	3.79	ChemAxon
pKa (Strongest Basic)	-3.7	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	83.47 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	57.92 m³·mol⁻¹	ChemAxon
Polarizability	23.92 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-6920000000-327bda33a46fd6535fa4	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0udi-1690000000-07ff72f262f96058571c	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0159-5920000000-9b6774a3340de914fd70	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-01b9-9600000000-627d0e96978f0b93f243	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0005-4490000000-3da2677013ff98714340	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0006-9510000000-af80b10116d37bb5e6fd	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-056v-9100000000-ad701484a699f7668023	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-014i-0940000000-aa544a13afca0f897261	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0670-8900000000-10f057a815e8fdc28e87	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0077-9200000000-72a360f78859358b2136	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-002b-1290000000-5136480b27602dbba174	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0pvm-7940000000-83973701a813ee0b4c43	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-000e-9300000000-1f5014efd3970f0bd9b3	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum

Toxicity Profile

Route of Exposure

Not Available

Mechanism of Toxicity

Not Available

Metabolism

Not Available

Toxicity Values

Not Available

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

Not Available

Uses/Sources

Not Available

Minimum Risk Level

Not Available

Health Effects

Not Available

Symptoms

Not Available

Treatment

Not Available

Concentrations

Not Available

External Links

DrugBank ID

DB05057

HMDB ID

Not Available

FooDB ID

Not Available

Phenol Explorer ID

Not Available

KNApSAcK ID

Not Available

BiGG ID

Not Available

BioCyc ID

Not Available

METLIN ID

Not Available

PDB ID

Not Available

Wikipedia Link

Erdosteine

Chemspider ID

Not Available

ChEBI ID

Not Available

PubChem Compound ID

Not Available

Kegg Compound ID

Not Available

YMDB ID

Not Available

ECMDB ID

Not Available

References

Synthesis Reference

Not Available

MSDS

Not Available

General References

Not Available

Erdosteine (CHEM019960)

Structure for CHEM019960: Erdosteine