Erdosteine

Identification

Summary

Erdosteine is a mucolytic agent used to treat conditions characterized by pathological mucus such as respiratory tract infections and chronic obstructive pulmonary disease (COPD).

Generic Name
Erdosteine
DrugBank Accession Number
DB05057
Background

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.

Type
Small Molecule
Groups
Approved, Investigational
Structure
Weight
Average: 249.307
Monoisotopic: 249.012949225
Chemical Formula
C8H11NO4S2
Synonyms
  • Erdosteine

Pharmacology

Indication

Fro the treatment of chronic bronchitis in adults.

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Associated Conditions
Indication TypeIndicationCombined Product DetailsApproval LevelAge GroupPatient CharacteristicsDose Form
Symptomatic treatment ofExcess mucus or phlegm•••••••••••••••••••• •••••••• ••••••••••• •••••
Symptomatic treatment ofExcess mucus or phlegm•••••••••••••••••••• •••••••• ••••••••••• •••••
Symptomatic treatment ofExcess mucus or phlegm•••••••••••••••••••• •••••••• ••••••••••• •••••
Associated Therapies
Contraindications & Blackbox Warnings
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Pharmacodynamics

Not Available

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.

Absorption

Not Available

Volume of distribution

Not Available

Protein binding

Not Available

Metabolism
Not Available
Route of elimination

Not Available

Half-life

Not Available

Clearance

Not Available

Adverse Effects
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Toxicity

Not Available

Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Not Available
Food Interactions
Not Available

Products

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International/Other Brands
Erdotin

Categories

ATC Codes
R05CB15 — Erdosteine
Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as n-acyl-alpha amino acids and derivatives. These 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
Heterocyclic fatty acids / Thiolanes / Carbothioic S-lactones / Thiolactones / Thioesters / Secondary carboxylic acid amides / Sulfenyl compounds / Monocarboxylic acids and derivatives / Dialkylthioethers / Carboxylic acids
show 5 more
Substituents
Aliphatic heteromonocyclic compound / Carbonyl group / Carbothioic s-lactone / Carboxamide group / Carboxylic acid / Dialkylthioether / Fatty acid / Fatty acyl / Heterocyclic fatty acid / Hydrocarbon derivative
show 17 more
Molecular Framework
Aliphatic heteromonocyclic compounds
External Descriptors
Not Available
Affected organisms
Not Available

Chemical Identifiers

UNII
76J0853EKA
CAS number
84611-23-4
InChI Key
QGFORSXNKQLDNO-UHFFFAOYSA-N
InChI
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)
IUPAC Name
2-({[(2-oxothiolan-3-yl)carbamoyl]methyl}sulfanyl)acetic acid
SMILES
OC(=O)CSCC(=O)NC1CCSC1=O

References

General References
Not Available
PubChem Compound
65632
PubChem Substance
175426937
ChemSpider
59073
RxNav
24305
ChEBI
135014
ChEMBL
CHEMBL1697744
Wikipedia
Erdosteine

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
4WithdrawnTreatmentChronic Obstructive Pulmonary Disease (COPD)1
3Unknown StatusTreatmentChronic Obstructive Pulmonary Disease (COPD)1
2CompletedTreatmentChronic Bronchitis / Chronic Obstructive Pulmonary Disease (COPD)1
1CompletedNot AvailableHealthy Volunteers (HV)1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
FormRouteStrength
SuspensionOral
Capsule, coatedOral300 mg
Powder, for suspensionOral3.5 g
Tablet, for solutionOral300 mg
PowderOral
SuspensionOral100 ml
SuspensionOral200 ml
GranuleOral225 mg
CapsuleOral150 MG
CapsuleOral300 MG
Granule, for suspensionOral175 MG/5ML
Granule, for suspensionOral225 MG
Powder, for solution225 MG/3ML
SuspensionOral3.5 %
Tablet, for suspensionOral300 MG
CapsuleOral300.000 mg
Granule, for suspensionOral
Powder, for suspensionOral
SuspensionOral3.150 g
Tablet, for suspensionOral
Syrup
SuspensionOral175 mg/5ml
Syrup175 mg/5ml
CapsuleOral
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility4.85 mg/mLALOGPS
logP-0.43ALOGPS
logP-0.65Chemaxon
logS-1.7ALOGPS
pKa (Strongest Acidic)3.79Chemaxon
pKa (Strongest Basic)-3.7Chemaxon
Physiological Charge-1Chemaxon
Hydrogen Acceptor Count4Chemaxon
Hydrogen Donor Count2Chemaxon
Polar Surface Area83.47 Å2Chemaxon
Rotatable Bond Count5Chemaxon
Refractivity57.92 m3·mol-1Chemaxon
Polarizability23.92 Å3Chemaxon
Number of Rings1Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterNoChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.6471
Blood Brain Barrier+0.6902
Caco-2 permeable-0.7045
P-glycoprotein substrateNon-substrate0.6432
P-glycoprotein inhibitor INon-inhibitor0.9302
P-glycoprotein inhibitor IINon-inhibitor0.9466
Renal organic cation transporterNon-inhibitor0.8739
CYP450 2C9 substrateNon-substrate0.6811
CYP450 2D6 substrateNon-substrate0.8182
CYP450 3A4 substrateNon-substrate0.5736
CYP450 1A2 substrateNon-inhibitor0.8874
CYP450 2C9 inhibitorNon-inhibitor0.9498
CYP450 2D6 inhibitorNon-inhibitor0.9574
CYP450 2C19 inhibitorNon-inhibitor0.9019
CYP450 3A4 inhibitorNon-inhibitor0.9838
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9839
Ames testNon AMES toxic0.8554
CarcinogenicityNon-carcinogens0.9708
BiodegradationReady biodegradable0.9168
Rat acute toxicity1.4281 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9779
hERG inhibition (predictor II)Non-inhibitor0.9479
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-014i-1920000000-1192ac6a028c8b831ee2
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-014r-9700000000-0b3d8fdbccb066972636
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0h0c-4920000000-f91f5067273dfa470086
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0006-9400000000-18418c0b6f6656d6514e
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0ly2-6910000000-58ce8ce0a5fe849008f6
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-03dv-9200000000-2f3c9a0d83e1b77b55da
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-146.62257
predicted
DeepCCS 1.0 (2019)
[M+H]+149.53368
predicted
DeepCCS 1.0 (2019)
[M+Na]+158.46408
predicted
DeepCCS 1.0 (2019)

Enzymes

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Zinc ion binding
Specific Function
Catalyzes the hydrolytic deamination of adenosine and 2-deoxyadenosine. Plays an important role in purine metabolism and in adenosine homeostasis. Modulates signaling by extracellular adenosine, an...
Gene Name
ADA
Uniprot ID
P00813
Uniprot Name
Adenosine deaminase
Molecular Weight
40764.13 Da
References
  1. Yilmaz HR, Uz E, Gokalp O, Ozcelik N, Cicek E, Ozer MK: Protective role of caffeic acid phenethyl ester and erdosteine on activities of purine-catabolizing enzymes and level of nitric oxide in red blood cells of isoniazid-administered rats. Toxicol Ind Health. 2008 Sep;24(8):519-24. doi: 10.1177/0748233708098128. [Article]

Drug created at October 21, 2007 22:23 / Updated at June 12, 2021 10:53