Identification

Name
Erdosteine
Accession Number
DB05057
Type
Small Molecule
Groups
Investigational
Description

Erdosteine is a mucolytic. Erdosteine is a thiol derivative developed for the treatment of chronic obstructive bronchitis, including acute infective exacerbation of chronic bronchitis. Erdosteine contains 2 blocked sulfhydryl groups which are released following first-pass metabolism. The 3 active metabolites exhibit mucolytic and free radical scavenging activity. Erdosteine modulates mucus production and viscosity and increases mucociliary transport, thereby improving expectoration. It also exhibits inhibitory activity against the effects of free radicals produced by cigarette smoke. Clinical studies in patients with chronic obstructive lung disease have demonstrated the efficacy and tolerability of erdosteine. 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.

Structure
Thumb
Synonyms
Not Available
International/Other Brands
Erdotin
Categories
UNII
76J0853EKA
CAS number
84611-23-4
Weight
Average: 249.307
Monoisotopic: 249.012949225
Chemical Formula
C8H11NO4S2
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

Pharmacology

Indication

Fro the treatment of chronic bronchitis in adults.

Pharmacodynamics
Not Available
Mechanism of action

Erdosteine, an orally mucolytic agent. Erdosteine is a thiol derivative developed for the treatment of chronic obstructive bronchitis, including acute infective exacerbation of chronic bronchitis. Erdosteine contains 2 blocked sulfhydryl groups which are released following first-pass metabolism. The 3 active metabolites exhibit mucolytic and free radical scavenging activity. Erdosteine modulates mucus production and viscosity and increases mucociliary transport, thereby improving expectoration. It also exhibits inhibitory activity against the effects of free radicals produced by cigarette smoke. Clinical studies in patients with chronic obstructive lung disease have demonstrated the efficacy and tolerability of erdosteine. 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
Toxicity
Not Available
Affected organisms
Not Available
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
Not Available
Food Interactions
Not Available

References

General References
Not Available
External Links
PubChem Compound
65632
PubChem Substance
175426937
ChemSpider
59073
ChEBI
135014
ChEMBL
CHEMBL1697744
Wikipedia
Erdosteine
ATC Codes
R05CB15 — Erdosteine

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
1CompletedNot AvailableHealthy Volunteers1
2CompletedTreatmentChronic Bronchitis / Chronic Obstructive Pulmonary Disease (COPD)1
3Unknown StatusTreatmentChronic Obstructive Pulmonary Disease (COPD)1
4WithdrawnTreatmentChronic Obstructive Pulmonary Disease (COPD)1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
Not Available
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/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Taxonomy

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
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
show 17 more
Molecular Framework
Aliphatic heteromonocyclic compounds
External Descriptors
Not Available

Enzymes

Kind
Protein
Organism
Human
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. [PubMed:19039079]

Drug created on October 21, 2007 16:23 / Updated on November 02, 2018 06:08