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Details

Stereochemistry RACEMIC
Molecular Formula C8H11NO4S2
Molecular Weight 249.307
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of ERDOSTEINE

SMILES

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

InChI

InChIKey=QGFORSXNKQLDNO-UHFFFAOYSA-N
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)

HIDE SMILES / InChI

Molecular Formula C8H11NO4S2
Molecular Weight 249.307
Charge 0
Count
Stereochemistry RACEMIC
Additional Stereochemistry No
Defined Stereocenters 0 / 1
E/Z Centers 0
Optical Activity ( + / - )

Description
Curator's Comment: description was created based on several sources, including, http://www.ncbi.nlm.nih.gov/pubmed/18046899, https://www.old.health.gov.il/units/pharmacy/trufot/alonim/ERDOTIN_dr_1322978767512.pdf

Erdosteine is an antioxidant compound developed by Edmond Pharma and approved in Europe for the treatment of chronic bronchitis and COPD. Erdosteine has two thiol groups and is believed to act as a free radicals scavenger (through the formation of the active metabolite I, N-thiodiglycolylhomocysteine). Also the drug effect may be due to the inhibition of the activity of elastase enzyme and its interaction with mucosa. The drug got Orphan Drug designation by FDA for the treatment of bronchiectasis.

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
ERDOTIN

Approved Use

Mucolytic agent in acute and chronic respiratory diseases.
Primary
ERDOTIN

Approved Use

Mucolytic agent in acute and chronic respiratory diseases.
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
1.419 μg/mL
600 mg single, oral
dose: 600 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
ERDOSTEINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
1.594 μg/mL
600 mg single, oral
dose: 600 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
ERDOSTEINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
1.34 μg/mL
900 mg single, oral
dose: 900 mg
route of administration: Oral
experiment type: SINGLE
co-administered: THEOPHYLLINE
ERDOSTEINE plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: MALE
food status: FASTED
1.15 μg/mL
300 mg 3 times / day multiple, oral
dose: 300 mg
route of administration: Oral
experiment type: MULTIPLE
co-administered: THEOPHYLLINE
ERDOSTEINE plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: MALE
food status: FASTED
3.45 μg/mL
900 mg single, oral
dose: 900 mg
route of administration: Oral
experiment type: SINGLE
co-administered: THEOPHYLLINE
HOMOCYSTEINE,N-[[(CARBOXYMETHYL)THIO]ACETYL]- plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: MALE
food status: FASTED
3.17 μg/mL
300 mg 3 times / day multiple, oral
dose: 300 mg
route of administration: Oral
experiment type: MULTIPLE
co-administered: THEOPHYLLINE
HOMOCYSTEINE,N-[[(CARBOXYMETHYL)THIO]ACETYL]- plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: MALE
food status: FASTED
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
3.492 μg × h/mL
600 mg single, oral
dose: 600 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
ERDOSTEINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
3.523 μg × h/mL
600 mg single, oral
dose: 600 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
ERDOSTEINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
3.71 μg × h/mL
900 mg single, oral
dose: 900 mg
route of administration: Oral
experiment type: SINGLE
co-administered: THEOPHYLLINE
ERDOSTEINE plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: MALE
food status: FASTED
3.55 μg × h/mL
300 mg 3 times / day multiple, oral
dose: 300 mg
route of administration: Oral
experiment type: MULTIPLE
co-administered: THEOPHYLLINE
ERDOSTEINE plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: MALE
food status: FASTED
12.32 μg × h/mL
900 mg single, oral
dose: 900 mg
route of administration: Oral
experiment type: SINGLE
co-administered: THEOPHYLLINE
HOMOCYSTEINE,N-[[(CARBOXYMETHYL)THIO]ACETYL]- plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: MALE
food status: FASTED
12.23 μg × h/mL
300 mg 3 times / day multiple, oral
dose: 300 mg
route of administration: Oral
experiment type: MULTIPLE
co-administered: THEOPHYLLINE
HOMOCYSTEINE,N-[[(CARBOXYMETHYL)THIO]ACETYL]- plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: MALE
food status: FASTED
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
2.478 h
600 mg single, oral
dose: 600 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
ERDOSTEINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
2.603 h
600 mg single, oral
dose: 600 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
ERDOSTEINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
1.29 h
900 mg single, oral
dose: 900 mg
route of administration: Oral
experiment type: SINGLE
co-administered: THEOPHYLLINE
ERDOSTEINE plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: MALE
food status: FASTED
1.36 h
300 mg 3 times / day multiple, oral
dose: 300 mg
route of administration: Oral
experiment type: MULTIPLE
co-administered: THEOPHYLLINE
ERDOSTEINE plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: MALE
food status: FASTED
1.68 h
900 mg single, oral
dose: 900 mg
route of administration: Oral
experiment type: SINGLE
co-administered: THEOPHYLLINE
HOMOCYSTEINE,N-[[(CARBOXYMETHYL)THIO]ACETYL]- plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: MALE
food status: FASTED
1.49 h
300 mg 3 times / day multiple, oral
dose: 300 mg
route of administration: Oral
experiment type: MULTIPLE
co-administered: THEOPHYLLINE
HOMOCYSTEINE,N-[[(CARBOXYMETHYL)THIO]ACETYL]- plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: MALE
food status: FASTED
Doses

Doses

DosePopulationAdverse events​
300 mg 3 times / day multiple, oral
Recommended
Dose: 300 mg, 3 times / day
Route: oral
Route: multiple
Dose: 300 mg, 3 times / day
Sources:
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: M+F
Food Status: UNKNOWN
Sources:
PubMed

PubMed

TitleDatePubMed
The SH-metabolite I of erdosteine, a mucolytic drug, enhances the inhibitory effect of salbutamol on the respiratory burst of neutrophils.
2002
The combination of the SH metabolite of erdosteine (a mucoactive drug) and ciprofloxacin increases the inhibition of bacterial adhesiveness achieved by ciprofloxacin alone.
2002
Effects of erdosteine treatment against doxorubicin-induced toxicity through erythrocyte and plasma oxidant/antioxidant status in rats.
2003 Apr
Oral erdosteine administration attenuates cisplatin-induced renal tubular damage in rats.
2003 Feb
Erdosteine prevents doxorubicin-induced cardiotoxicity in rats.
2003 Oct
Sensitive determination of erdosteine in human plasma by use of automated 96-well solid-phase extraction and LC-MS/MS.
2004 Feb 18
Inhibitory effects of metabolite I of erdosteine on the generation of nitric oxide and peroxynitrite chemiluminescence by human neutrophils.
2004 Jul
Erdosteine improves oxidative damage in a rat model of renal ischemia-reperfusion injury.
2004 Jul-Aug
A combination of budesonide and the SH-metabolite I of erdosteine acts synergistically in reducing chemiluminescence during human neutrophil respiratory burst.
2005 Jun
Role of mucolytics in the management of COPD.
2006
Pharmacological treatment of chronic obstructive pulmonary disease.
2006
Regulation of sepsis-induced apoptosis of pulmonary cells by posttreatment of erdosteine and N-aceylcysteine.
2006 Dec 7
Comparison of the effects of erdosteine and N-acetylcysteine on apoptosis regulation in endotoxin-induced acute lung injury.
2006 Jul-Aug
Pharmacology and clinical efficacy of erdosteine in chronic obstructive pulmonary disease.
2007 Dec
Erdosteine treatment attenuates oxidative stress and fibrosis in experimental biliary obstruction.
2007 Mar
The effects of erdosteine, N-acetylcysteine and vitamin E on nicotine-induced apoptosis of cardiac cells.
2007 May-Jun
Effectiveness of erdosteine in elderly patients with bronchiectasis and hypersecretion: a 15-day, prospective, parallel, open-label, pilot study.
2007 Sep
Changes in blood ROS, e-NO, and some pro-inflammatory mediators in bronchial secretions following erdosteine or placebo: a controlled study in current smokers with mild COPD.
2008
Antioxidant effect of sulphurous thermal water on human neutrophil bursts: chemiluminescence evaluation.
2008
The effects of erdosteine on lung injury induced by the ischemia-reperfusion of the hind-limbs in rats.
2008 Apr
Antioxidant therapeutic advances in COPD.
2008 Dec
Renoprotective effect of erdosteine in rats against gentamicin nephrotoxicity: a comparison of 99mTc-DMSA uptake with biochemical studies.
2008 Jan
Erdosteine enhances airway response to salbutamol in patients with mild-to-moderate COPD.
2008 Oct
Erdosteine modulates radiocontrast-induced hepatotoxicity in rat.
2009 Apr
Raft of results energizes researchers.
2009 Sep-Oct
Free radical scavenging activity of erdosteine metabolite I investigated by electron paramagnetic resonance spectroscopy.
2010
Ambroxol - Resurgence of an old molecule as an anti-inflammatory agent in chronic obstructive airway diseases.
2010 Apr
Beneficial effect of erdosteine on methotrexate-induced testicular toxicity in mice.
2010 Aug
Effects of sulphurous water on human neutrophil elastase release.
2010 Dec
Association between lung function and exacerbation frequency in patients with COPD.
2010 Dec 9
Modulation of cytokine and nitric oxide by mesenchymal stem cell transfer in lung injury/fibrosis.
2010 Feb 8
Exaggerated liver injury induced by renal ischemia reperfusion in diabetes: effect of exenatide.
2010 Jul-Sep
Effect of the mucolytic erdosteine on the success rate of PPI-based first-line triple therapy for Helicobacter pylori eradication: a prospective, double-blind, randomized, placebo-controlled study.
2010 Jun
Patents

Sample Use Guides

1 capsule (300 mg) 2-3 times a day
Route of Administration: Oral
In Vitro Use Guide
Unknown
Substance Class Chemical
Created
by admin
on Mon Mar 31 18:20:17 GMT 2025
Edited
by admin
on Mon Mar 31 18:20:17 GMT 2025
Record UNII
76J0853EKA
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
ERDOSTEINE
INN   MART.   MI   WHO-DD  
INN  
Official Name English
MUCOTEC
Preferred Name English
RV144
Code English
RV-144
Code English
Erdosteine [WHO-DD]
Common Name English
ERDOSTEINE [MART.]
Common Name English
erdosteine [INN]
Common Name English
ERDOSTEINE [MI]
Common Name English
(±)-((((TETRAHYDRO-2-OXO-3-THIENYL)CARBAMOYL)METHYL)THIO)ACETIC ACID
Systematic Name English
Classification Tree Code System Code
FDA ORPHAN DRUG 417413
Created by admin on Mon Mar 31 18:20:17 GMT 2025 , Edited by admin on Mon Mar 31 18:20:17 GMT 2025
WHO-ATC R05CB15
Created by admin on Mon Mar 31 18:20:17 GMT 2025 , Edited by admin on Mon Mar 31 18:20:17 GMT 2025
WHO-VATC QR05CB15
Created by admin on Mon Mar 31 18:20:17 GMT 2025 , Edited by admin on Mon Mar 31 18:20:17 GMT 2025
NCI_THESAURUS C74536
Created by admin on Mon Mar 31 18:20:17 GMT 2025 , Edited by admin on Mon Mar 31 18:20:17 GMT 2025
EU-Orphan Drug EU/3/12/1084
Created by admin on Mon Mar 31 18:20:17 GMT 2025 , Edited by admin on Mon Mar 31 18:20:17 GMT 2025
Code System Code Type Description
NCI_THESAURUS
C61750
Created by admin on Mon Mar 31 18:20:17 GMT 2025 , Edited by admin on Mon Mar 31 18:20:17 GMT 2025
PRIMARY
MESH
C048498
Created by admin on Mon Mar 31 18:20:17 GMT 2025 , Edited by admin on Mon Mar 31 18:20:17 GMT 2025
PRIMARY
EVMPD
SUB06595MIG
Created by admin on Mon Mar 31 18:20:17 GMT 2025 , Edited by admin on Mon Mar 31 18:20:17 GMT 2025
PRIMARY
ChEMBL
CHEMBL1697744
Created by admin on Mon Mar 31 18:20:17 GMT 2025 , Edited by admin on Mon Mar 31 18:20:17 GMT 2025
PRIMARY
RXCUI
24305
Created by admin on Mon Mar 31 18:20:17 GMT 2025 , Edited by admin on Mon Mar 31 18:20:17 GMT 2025
PRIMARY RxNorm
DRUG CENTRAL
1041
Created by admin on Mon Mar 31 18:20:17 GMT 2025 , Edited by admin on Mon Mar 31 18:20:17 GMT 2025
PRIMARY
EPA CompTox
DTXSID8048735
Created by admin on Mon Mar 31 18:20:17 GMT 2025 , Edited by admin on Mon Mar 31 18:20:17 GMT 2025
PRIMARY
PUBCHEM
65632
Created by admin on Mon Mar 31 18:20:17 GMT 2025 , Edited by admin on Mon Mar 31 18:20:17 GMT 2025
PRIMARY
MERCK INDEX
m4974
Created by admin on Mon Mar 31 18:20:17 GMT 2025 , Edited by admin on Mon Mar 31 18:20:17 GMT 2025
PRIMARY Merck Index
CAS
84611-23-4
Created by admin on Mon Mar 31 18:20:17 GMT 2025 , Edited by admin on Mon Mar 31 18:20:17 GMT 2025
PRIMARY
WIKIPEDIA
ERDOSTEINE
Created by admin on Mon Mar 31 18:20:17 GMT 2025 , Edited by admin on Mon Mar 31 18:20:17 GMT 2025
PRIMARY
DRUG BANK
DB05057
Created by admin on Mon Mar 31 18:20:17 GMT 2025 , Edited by admin on Mon Mar 31 18:20:17 GMT 2025
PRIMARY
SMS_ID
100000084578
Created by admin on Mon Mar 31 18:20:17 GMT 2025 , Edited by admin on Mon Mar 31 18:20:17 GMT 2025
PRIMARY
FDA UNII
76J0853EKA
Created by admin on Mon Mar 31 18:20:17 GMT 2025 , Edited by admin on Mon Mar 31 18:20:17 GMT 2025
PRIMARY
INN
6032
Created by admin on Mon Mar 31 18:20:17 GMT 2025 , Edited by admin on Mon Mar 31 18:20:17 GMT 2025
PRIMARY
Related Record Type Details
METABOLITE ACTIVE -> PRODRUG
METABOLITE -> PARENT
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ACTIVE MOIETY