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
Structure for Erdosteine (DB05057)
- 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 Therapies
- Contraindications & Blackbox Warnings
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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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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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- 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
- External Links
- PubChem Compound
- 65632
- PubChem Substance
- 175426937
- ChemSpider
- 59073
- 24305
- ChEBI
- 135014
- ChEMBL
- CHEMBL1697744
- Wikipedia
- Erdosteine
Clinical Trials
- Clinical Trials
Phase Status Purpose Conditions Count 4 Withdrawn Treatment Chronic Obstructive Pulmonary Disease (COPD) 1 3 Unknown Status Treatment Chronic Obstructive Pulmonary Disease (COPD) 1 2 Completed Treatment Chronic Bronchitis / Chronic Obstructive Pulmonary Disease (COPD) 1 1 Completed Not Available Healthy Subjects (HS) 1
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
Form Route Strength Suspension Oral Capsule, coated Oral 300 mg Powder, for suspension Oral 3.5 g Tablet, for solution Oral 300 mg Powder Oral Suspension Oral 100 ml Suspension Oral 200 ml Granule Oral 225 mg Capsule Oral 150 MG Capsule Oral 300 MG Granule, for suspension Oral 175 MG/5ML Granule, for suspension Oral 225 MG Powder, for solution 225 MG/3ML Suspension Oral 3.5 % Tablet, for suspension Oral 300 MG Granule, for suspension Oral Powder, for suspension Oral Tablet, for suspension Oral Syrup Syrup 175 mg/5ml Capsule Oral - Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
- Not Available
- Predicted Properties
Property Value Source Water Solubility 4.85 mg/mL 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 - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.6471 Blood Brain Barrier + 0.6902 Caco-2 permeable - 0.7045 P-glycoprotein substrate Non-substrate 0.6432 P-glycoprotein inhibitor I Non-inhibitor 0.9302 P-glycoprotein inhibitor II Non-inhibitor 0.9466 Renal organic cation transporter Non-inhibitor 0.8739 CYP450 2C9 substrate Non-substrate 0.6811 CYP450 2D6 substrate Non-substrate 0.8182 CYP450 3A4 substrate Non-substrate 0.5736 CYP450 1A2 substrate Non-inhibitor 0.8874 CYP450 2C9 inhibitor Non-inhibitor 0.9498 CYP450 2D6 inhibitor Non-inhibitor 0.9574 CYP450 2C19 inhibitor Non-inhibitor 0.9019 CYP450 3A4 inhibitor Non-inhibitor 0.9838 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.9839 Ames test Non AMES toxic 0.8554 Carcinogenicity Non-carcinogens 0.9708 Biodegradation Ready biodegradable 0.9168 Rat acute toxicity 1.4281 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9779 hERG inhibition (predictor II) Non-inhibitor 0.9479
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS Not Available
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
- 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