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    Erdosteine

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    2D Structure
    Also known as: 84611-23-4, Rv 144, Erdosteine [inn], Mucotec, 105426-14-0, Rv-144
    Molecular Formula
    C8H11NO4S2
    Molecular Weight
    249.3  g/mol
    InChI Key
    QGFORSXNKQLDNO-UHFFFAOYSA-N
    FDA UNII
    76J0853EKA
    Erdosteine is a homocysteine-derived thiol derivative with mucolytic and free radical scavenging properties. Erdosteine and its metabolites modulate mucus production and viscosity, by which facilitating mucociliary transport and improving expectoration. This agent also suppresses the chemical-induced cough reflex as well as protects lung tissues from damages caused by cigarette smoking mediated through free radicals scavenging.
    1 2D Structure

    2D Structure

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    2-[2-oxo-2-[(2-oxothiolan-3-yl)amino]ethyl]sulfanylacetic acid
    2.1.2 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)
    2.1.3 InChI Key
    QGFORSXNKQLDNO-UHFFFAOYSA-N
    2.1.4 Canonical SMILES
    C1CSC(=O)C1NC(=O)CSCC(=O)O
    2.2 Other Identifiers
    2.2.1 UNII
    76J0853EKA
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. (+-)-((((tetrahydro-2-oxo-3-thienyl)carbamoyl)methyl)thio)acetic Acid

    2. Dostein

    3. Edirel

    4. Esteclin

    5. Rv 144

    6. Rv-144

    7. S-(2-(n-3-(2-oxo-tetrahydrothienyl)acetamido))thioglycolic Acid

    8. Vectrine

    2.3.2 Depositor-Supplied Synonyms

    1. 84611-23-4

    2. Rv 144

    3. Erdosteine [inn]

    4. Mucotec

    5. 105426-14-0

    6. Rv-144

    7. 2-[2-oxo-2-[(2-oxothiolan-3-yl)amino]ethyl]sulfanylacetic Acid

    8. 2-((2-oxo-2-((2-oxotetrahydrothiophen-3-yl)amino)ethyl)thio)acetic Acid

    9. 76j0853eka

    10. Erdosteine (inn)

    11. Kw-9144

    12. Ncgc00185774-01

    13. 2-({[(2-oxothiolan-3-yl)carbamoyl]methyl}sulfanyl)acetic Acid

    14. Acetic Acid, [[2-oxo-2-[(tetrahydro-2-oxo-3-thienyl)amino]ethyl]thio]-

    15. Dsstox_cid_28661

    16. Dsstox_rid_82931

    17. Dsstox_gsid_48735

    18. Erdosteinum [latin]

    19. Dithiosteine

    20. Erdosteinum

    21. Vectrine

    22. Edirel

    23. ({2-oxo-2-[(2-oxotetrahydro-3-thienyl)amino]ethyl}sulfanyl)acetic Acid

    24. Acetic Acid, ((2-oxo-2-((tetrahydro-2-oxo-3-thienyl)amino)ethyl)thio)-

    25. Cas-84611-23-4

    26. Secresolv

    27. Erdosteine [inn:ban]

    28. Pv 144

    29. Erdostiene

    30. Erdotin

    31. Unii-76j0853eka

    32. 2-(2-oxo-2-(2-oxotetrahydrothiophen-3-ylamino)ethylthio)acetic Acid

    33. Erdosteine,(s)

    34. Mucotec (tn)

    35. Erdosteine [mi]

    36. Dl-s-(2-(n-3-(2-oxotetrahydrotheinyl)acetamido))thioglycolic Acid

    37. ((2-oxo-2-((tetrahydro-2-oxo-3-thienyl)amino)ethyl)thio)acetic Acid

    38. (+-)-((((tetrahydro-2-oxo-3-thienyl)carbamoyl)methyl)thio)acetic Acid

    39. Acide ((2-oxo-3-tetrahydrothienylcarbamoyl)-methylthio)acetique [french]

    40. Erdosteine [mart.]

    41. Erdosteine [who-dd]

    42. Schembl21721

    43. Mls006010056

    44. Chembl1697744

    45. Dtxsid8048735

    46. Erdosteine, >=98% (hplc)

    47. Chebi:135014

    48. Hms3264c11

    49. Hms3655i14

    50. Acide ((2-oxo-3-tetrahydrothienylcarbamoyl)-methylthio)acetique

    51. Hy-b0289

    52. Tox21_113176

    53. Mfcd00867664

    54. S1825

    55. Stl452949

    56. Akos015888361

    57. Tox21_113176_1

    58. Ac-5278

    59. Ccg-213836

    60. Db05057

    61. Ks-1352

    62. Ncgc00185774-02

    63. Ncgc00185774-09

    64. Smr002529560

    65. E1026

    66. Ft-0625684

    67. Ft-0630929

    68. Sw220302-1

    69. D07383

    70. T72990

    71. Ab01274804-01

    72. Ab01274804_02

    73. Ab01274804_03

    74. 611e234

    75. A840878

    76. Sr-01000944253

    77. Q3731252

    78. Sr-01000944253-1

    79. N-(tetrahydro-2-oxo-3-thienyl)-3-thiapentanedioic Acid Monoamide

    80. ({2-oxo-2-[(2-oxotetrahydrothiophen-3-yl)amino]ethyl}sulfanyl)acetic Acid

    81. (+/-)-((((tetrahydro-2-oxo-3-thienyl)carbamoyl)methyl)thio)acetic Acid

    82. 2-[2-oxo-2-[(2-oxotetrahydrothiophen-3-yl)amino]ethyl]sulfanylacetic Acid;erdosteine

    83. Erdosteine; [[2-oxo-2-[(tetrahydro-2-oxo-3-thienyl)amino]ethyl]thio]acetic Acid

    2.4 Create Date
    2005-08-08
    3 Chemical and Physical Properties
    Molecular Weight 249.3 g/mol
    Molecular Formula C8H11NO4S2
    XLogP3-0.1
    Hydrogen Bond Donor Count2
    Hydrogen Bond Acceptor Count6
    Rotatable Bond Count5
    Exact Mass249.01295018 g/mol
    Monoisotopic Mass249.01295018 g/mol
    Topological Polar Surface Area134 Ų
    Heavy Atom Count15
    Formal Charge0
    Complexity282
    Isotope Atom Count0
    Defined Atom Stereocenter Count0
    Undefined Atom Stereocenter Count1
    Defined Bond Stereocenter Count0
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count1
    4 Drug and Medication Information
    4.1 Drug Indication

    Fro the treatment of chronic bronchitis in adults.

    5 Pharmacology and Biochemistry
    5.1 MeSH Pharmacological Classification

    Expectorants

    Agents that increase mucous excretion. Mucolytic agents, that is drugs that liquefy mucous secretions, are also included here. (See all compounds classified as Expectorants.)

    5.2 ATC Code

    R05CB15

    S76 | LUXPHARMA | Pharmaceuticals Marketed in Luxembourg | Pharmaceuticals marketed in Luxembourg, as published by d'Gesondheetskeess (CNS, la caisse nationale de sante, www.cns.lu), mapped by name to structures using CompTox by R. Singh et al. (in prep.). List downloaded from https://cns.public.lu/en/legislations/textes-coordonnes/liste-med-comm.html. Dataset DOI:10.5281/zenodo.4587355

    R - Respiratory system

    R05 - Cough and cold preparations

    R05C - Expectorants, excl. combinations with cough suppressants

    R05CB - Mucolytics

    R05CB15 - Erdosteine

    5.3 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.