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

• ChemBase ID: 73219
• Molecular Formular: C8H11NO4S2
• Molecular Mass: 249.30724
• Monoisotopic Mass: 249.01294984
• SMILES: S1C(=O)C(CC1)NC(=O)CSCC(=O)O
• Canonical SMILES: O=C(NC1CCSC1=O)CSCC(=O)O
• 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)
• InChIKey: QGFORSXNKQLDNO-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-({[(2-oxothiolan-3-yl)carbamoyl]methyl}sulfanyl)acetic acid
• IUPAC Traditional name: erdosteine
• Synonyms: Erdosteine; 2-[[2-Oxo-2-[(tetrahydro-2-oxo-3-thienyl)amino]ethyl]thio]acetic Acid; Dithiosteine; RV 144; Secresolv

Database IDs

• CAS Number: 84611-23-4
• PubChem SID: 162038139
• PubChem CID: 65632

CALCULATED PROPERTIES

• Acid pKa: 3.785577
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): -2.3673952
• LogD (pH = 7.4): -3.9202209
• Log P: -0.65126824
• Molar Refractivity: 57.9153 cm^3
• Polarizability: 22.86089 Å^3
• Polar Surface Area: 83.47 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol
• Apperance: Off-White Solid
• Melting Point: 145-147°C

Safety Information

• Storage Condition: -20°C; Refrigerator

Product Information

• Salt Data: Free Base

DETAILS

Selleck Chemicals - S1825

Research Area: Cancer
Biological Activity:
Erdosteine is a mucolytic which is used in treatment of excessive viscous mucus. Erdosteine belongs to a class of medicines called expectorants. Erdosteine is a homocysteine-derived expectorant which experiences metabolic conversion to produce a thiol containing compound that has free radical scavenging and mucolytic activity. Erdosteine is used for acute episodes of bronchitis where there is a buildup of sticky mucus in the chest. Specifically erdosteine is a thiol derivative developed for the treatment of chronic obstructive bronchitis, including acute infective exacerbation of chronic bronchitis. Erdosteine works by helping to break down mucus secretions. This helps to make mucus runnier and less sticky. This means that it is easier to clear the mucus from the chest. Erdosteine contains two blocked sulfhydryl groups which are released following first-pass metabolism. The three active metabolites exhibit mucolytic and free radical scavenging activity. Erdosteine regulates mucus production and viscosity and increases mucociliary transport, thereby improving expectoration. Erdosteine also reveals inhibitory activity against the effects of free radicals produced by cigarette smoke. Erdosteine significantly inhibited citric acid-induced cough reflexes in guinea-pigs but did not suppress mechanical stimuli-induced cough reflexes. On the other hand, erdosteine is associated with a low incidence of adverse events, most of which are gastrointestinal and generally mild. The LD50 of erdosteine is very high ranging from 3,500 to 5,000 mg/kg. [1] References on Erdosteine[1] Drugs., 1996 Dec, 52(6):875-81

Toronto Research Chemicals - E596050

Erdosteine is a mucolytic. Erdosteine was developed for the treatment of chronic obstructive bronchitis.

REFERENCES

• Dechant KL et al. Drugs. 1996 Dec;52(6):875-81
• Kuvandik, G., et al.: Toxicol. Pathol., 36, 714 (2008)
• Koyu, A., et al.: Mol. Cell. Biochem., 331, 43 (2008)
• Fourches, D., et al.: Chem. Res. Toxicol., 23, 171 (2008)