Erdosteine

Title: Erdosteine
CAS Registry Number: 84611-23-4
CAS Name: [[2-Oxo-2-[(tetrahydro-2-oxo-3-thienyl)amino]ethyl]thio]acetic acid
Additional Names: (±)-[[[(tetrahydro-2-oxo-3-thienyl)carbamoyl]methyl]thio]acetic acid; DL-S-[2-[N-3-(2-oxotetrahydrothienyl)acetamido]]thioglycolic acid; N-(carboxymethylthioacetyl)homocysteine thiolactone; dithiosteine
Manufacturers' Codes: RV-144
Trademarks: Secresolv (Refarmed)
Molecular Formula: C8H11NO4S2
Molecular Weight: 249.31
Percent Composition: C 38.54%, H 4.45%, N 5.62%, O 25.67%, S 25.72%
Literature References: Homocysteine thiolactone derivative with mucomodulating activity. Prepn: J. Gonella, EP 61386; idem, US 4411909 (1982, 1983 both to Refarmed); M. Gobetti et al., Farmaco Ed. Sci. 41, 69 (1986). Clinical trial in bronchitis: G. Ricevuti et al., Thorax 43, 585 (1988). Clinical effect on a1-antitrypsin levels in cigarette smokers: M. Vagliasindi, G. B. Fregnan, Int. J. Clin. Pharmacol. Ther. Toxicol. 27, 238 (1989).
Properties: Crystals from ethanol, mp 156-158°. pKa 3.71. LD50 in mice and rats (g/kg): >10 orally; >3.5 i.v. (Gonella).
Melting point: mp 156-158°
pKa: pKa 3.71
Toxicity data: LD50 in mice and rats (g/kg): >10 orally; >3.5 i.v. (Gonella)
Therap-Cat: Mucolytic.
Keywords: Mucolytic.
Ergocornine Ergocristine Ergocryptine Ergocryptinine Ergoflavin

Erdosteine
Erdosteine.png
Systematic (IUPAC) name
2-[(2-oxothiolan-3-yl)carbamoylmethylsulfanyl]acetic acid
Clinical data
AHFS/Drugs.com International Drug Names
Legal status  ?
Routes oral, inhalation
Pharmacokinetic data
Protein binding 65%
Metabolism hepatic
Half-life 1-3 hours
Identifiers
CAS number 84611-23-4 YesY
ATC code R05CB15
PubChem CID 65632
ChemSpider 59073 YesY
UNII 76J0853EKA YesY
KEGG D07383 YesY
Chemical data
Formula C8H11NO4S2 
Mol. mass 249.309 g/mol
 YesY (what is this?)  (verify)

Erdosteine is a mucolytic. Specifically it is a thiol derivative developed for the treatment of chronic obstructive bronchitis, including acute infective exacerbation of chronic bronchitis. 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 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.Template:Drugs Exp Clin Res. 2004;30(4):143-52.The effect of long-term treatment with erdosteine on chronic obstructive pulmonary disease: the EQUALIFE Study. Erdosteine 300 mg 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 bromhexine 30 mg twice daily.[citation needed]

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.[citation needed]

Erdosteine is associated with a low incidence of adverse events, most of which are gastrointestinal and generally mild. The LD50 is very high, 3,500-5,000 mg/kg.

Tradenames used in Europe: Erdomed Erdopect Erdostin Erdotin Evosten Mucodox Mucofor Theovix Tusselin Vectrine

Apart from the Tradenames listed above, in other regions of the world the product is also marketed under: Asdigan Biopulmin Dostein Dostin Dostol Ectrin Edotin Erdos Esteclin Fluidasa Mucoflux Mucotec Mukial Zertin