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Chemistry

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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

Tiopronin

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 Formula	C₅H₉NO₃S
Molecular Weight	163.20 g/mol
XLogP3	-0.1
Hydrogen Bond Donor Count	3
Hydrogen Bond Acceptor Count	4
Rotatable Bond Count	3
Exact Mass	163.03031432 g/mol
Monoisotopic Mass	163.03031432 g/mol
Topological Polar Surface Area	67.4 Å²
Heavy Atom Count	10
Formal Charge	0
Complexity	148
Isotope Atom Count	0
Defined Atom Stereocenter Count	0
Undefined Atom Stereocenter Count	1
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

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.

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