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    Tiopronin

    ACTIVE PHARMA INGREDIENTS

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    2D Structure
    Also known as: 1953-02-2, N-(2-mercaptopropionyl)glycine, Acadione, Captimer, Thiopronine, Mucolysin
    Molecular Formula
    C5H9NO3S
    Molecular Weight
    163.20  g/mol
    InChI Key
    YTGJWQPHMWSCST-UHFFFAOYSA-N
    FDA UNII
    C5W04GO61S
    Sulfhydryl acylated derivative of GLYCINE.
    Tiopronin is a Reducing and Complexing Thiol. The mechanism of action of tiopronin is as a Cystine Disulfide Reduction.
    1 2D Structure

    2D Structure

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    2-(2-sulfanylpropanoylamino)acetic acid
    2.1.2 InChI
    InChI=1S/C5H9NO3S/c1-3(10)5(9)6-2-4(7)8/h3,10H,2H2,1H3,(H,6,9)(H,7,8)
    2.1.3 InChI Key
    YTGJWQPHMWSCST-UHFFFAOYSA-N
    2.1.4 Canonical SMILES
    CC(C(=O)NCC(=O)O)S
    2.2 Other Identifiers
    2.2.1 UNII
    C5W04GO61S
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. 2 Mercaptopropionylglycine

    2. 2 Thiol Propionamido Acetic Acid

    3. 2 Thiolpropionamidoacetic Acid

    4. 2-mercaptopropionylglycine

    5. 2-thiol-propionamido-acetic Acid

    6. 2-thiolpropionamidoacetic Acid

    7. Acadione

    8. Acid, 2-thiol-propionamido-acetic

    9. Acid, 2-thiolpropionamidoacetic

    10. Alpha Mercaptopropionylglycine

    11. Alpha-mercaptopropionylglycine

    12. Captimer

    13. Meprin

    14. Mercaptopropionylglycine

    15. Thiola

    16. Thiopronine

    17. Tiopronine

    2.3.2 Depositor-Supplied Synonyms

    1. 1953-02-2

    2. N-(2-mercaptopropionyl)glycine

    3. Acadione

    4. Captimer

    5. Thiopronine

    6. Mucolysin

    7. Capen

    8. Thiola

    9. Tiopronine

    10. Epatiol

    11. 2-(2-sulfanylpropanoylamino)acetic Acid

    12. Thiosol

    13. Glycine, N-(2-mercapto-1-oxopropyl)-

    14. Tiopronin (thiola)

    15. A-mercaptopropionyl Glycine

    16. 2-(2-mercaptopropanamido)acetic Acid

    17. Nsc-760416

    18. Chembl1314

    19. C5w04go61s

    20. N-(2-mercaptopropanoyl)glycine

    21. Thiopronin

    22. Chebi:32229

    23. 2-(2-sulfanylpropanamido)acetic Acid

    24. Ncgc00159422-02

    25. Ncgc00159422-04

    26. Sutilan

    27. Dsstox_cid_3678

    28. Glycine, N-(2-mercapto-1-oxopropyl)- (9ci)

    29. Dsstox_rid_77142

    30. Dsstox_gsid_23678

    31. Thiolpropionamidoacetic Acid

    32. Tioglis

    33. Vincol

    34. Cas-1953-02-2

    35. Meprin (detoxicant)

    36. N-(2-mercapto-1-oxopropyl)glycine

    37. Tiopronine [inn-french]

    38. Tioproninum [inn-latin]

    39. Tiopronino [inn-spanish]

    40. (2-mercaptopropionyl)glycine

    41. Tiopronin [inn:dcf:jan]

    42. Tiopronino

    43. Tioproninum

    44. Ccris 1935

    45. (s)-2-(2-mercaptopropanamido)acetic Acid

    46. Einecs 217-778-4

    47. Thiola (tn)

    48. Brn 1859822

    49. Thiola Ec

    50. Tiopronin (jan/inn)

    51. Tiopronin [inn]

    52. Tiopronin [jan]

    53. Tiopronin [mi]

    54. Glycine, N-(2-mercaptopropionyl)-

    55. Tiopronin [vandf]

    56. 2-mercapto-propionylglycine

    57. Tiopronin [mart.]

    58. Tiopronin [who-dd]

    59. (2-mercaptopropanoyl)glycine

    60. Unii-c5w04go61s

    61. Schembl19989

    62. Mls006010632

    63. Alpha-mercaptopropionyl Glycine

    64. Mercaptopropionylglycine-

    65. N-(2-sulfanylpropanoyl)glycine

    66. Tiopronin [orange Book]

    67. Dtxsid4023678

    68. N-(2-mercaptopropionyl) Glycine

    69. N-(2-mercaptopropanoyl) Glycine

    70. Acadione; Capen; Epatiol; Vincol

    71. Hms3264b11

    72. Hms3655l15

    73. Pharmakon1600-01506190

    74. Amy39003

    75. Bcp13354

    76. Hy-b0373

    77. 2-(2-mercaptopropanamido)aceticacid

    78. Tox21_111654

    79. Bdbm50020805

    80. Mfcd00004861

    81. Mfcd30157366

    82. Nsc760416

    83. S2062

    84. (2-mercaptopropionylamino)acetic Acid

    85. Akos015895408

    86. N-(2-mercaptopropionyl)glycine, 99%

    87. Tox21_111654_1

    88. Ac-2087

    89. Ccg-214007

    90. Db06823

    91. Nsc 760416

    92. (2-mercapto-propionylamino)-acetic Acid

    93. Ncgc00159422-03

    94. As-12522

    95. Smr001550282

    96. Sy262996

    97. Ft-0603530

    98. Ft-0653686

    99. Sw219206-1

    100. T2614

    101. Tiopronin, Vetranal(tm), Analytical Standard

    102. C73708

    103. D01430

    104. Ab00376096_02

    105. 953t022

    106. A813794

    107. Q414456

    108. Sr-01000942263

    109. J-012651

    110. Sr-01000942263-1

    111. Tiopronin, Dextiopronin, Tiopronin (n-2-mercaptopropionyl Glycine)

    2.4 Create Date
    2005-03-25
    3 Chemical and Physical Properties
    Molecular Weight 163.20 g/mol
    Molecular Formula C5H9NO3S
    XLogP3-0.1
    Hydrogen Bond Donor Count3
    Hydrogen Bond Acceptor Count4
    Rotatable Bond Count3
    Exact Mass163.03031432 g/mol
    Monoisotopic Mass163.03031432 g/mol
    Topological Polar Surface Area67.4 Ų
    Heavy Atom Count10
    Formal Charge0
    Complexity148
    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

    Tiopronin is indicated for the prevention of kidney stone formation in patients with severe homozygous cystinuria consisting of a urinary cystine concentration greater than 500 mg/day, and who have failed treatment with non-pharmacological measures of increased fluid intake, decreased sodium and protein intake, and urine alkalinization.

    5 Pharmacology and Biochemistry
    5.1 FDA Pharmacological Classification
    5.1.1 Active Moiety
    TIOPRONIN
    5.1.2 FDA UNII
    C5W04GO61S
    5.1.3 Pharmacological Classes
    N-substituted Glycines [CS]; Reducing and Complexing Thiol [EPC]; Cystine Disulfide Reduction [MoA]
    5.2 ATC Code

    G - Genito urinary system and sex hormones

    G04 - Urologicals

    G04B - Urologicals

    G04BX - Other urologicals

    G04BX16 - Tiopronin

    5.3 Absorption, Distribution and Excretion

    Absorption

    Tiopronin undergoes slow absorption, reaching peak plasma concentration 3-6 hours after ingestion. In a study of healthy subjects, the bioavailability of total and unbound tiopronin was found to be 63% and 40%, respectively.

    Route of Elimination

    Tiopronin is 100% excreted in urine.

    Volume of Distribution

    The volume of distribution of tiopronin is high at 455 L, indicating that a large portion of the drug is bound to tissues outside plasma.

    Clearance

    Total renal clearance for the total and unbound fractions of tiopronin were found to be 3.3 and 13.3 L/h respectively.

    5.4 Metabolism/Metabolites

    The principle metabolite of tiopronin is 2-mercaptopropionic acid (2-MPA). Between 10-15% of the drug is metabolized to 2-MPA via hydrolysis.

    5.5 Biological Half-Life

    Tiopronin has a long terminal half life of 53 hours in healthy subjects. However, the unbound drug fraction of tiopronin is eliminated much more rapidly from plasma with a calculated half life of 1.8 hours.

    5.6 Mechanism of Action

    Kidney stones form when the solubility limit is exceeded and urine becomes supersaturated with endogenous cystine. Tiopronin is an active reducing agent which undergoes a thiol-disulfide exchange with cystine to form a water-soluble mixed disulfide complex. Thus, the amount of sparingly soluble cystine is reduced. By reducing urinary cystine concentrations below the solubility limit, tiopronin helps reduce cystine stone formation.