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Prestwick3_000626

Prestwick3_000626

Synopsis, Chemistry

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Also known as: 81110-73-8, Acetorphan, Benzyl 2-(3-(acetylthio)-2-benzylpropanamido)acetate, Hidrasec, Tiorfan, Racecadotril [inn]

Molecular Formula

C₂₁H₂₃NO₄S

Molecular Weight

385.5 g/mol

InChI Key

ODUOJXZPIYUATO-UHFFFAOYSA-N

FDA UNII

76K53XP4TO

Racecadotril has been investigated for the basic science and treatment of Diarrhea, Acute Diarrhea, and Acute Gastroenteritis.

1 2D Structure

Prestwick3_000626

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

benzyl 2-[[2-(acetylsulfanylmethyl)-3-phenylpropanoyl]amino]acetate

2.1.2 InChI

InChI=1S/C21H23NO4S/c1-16(23)27-15-19(12-17-8-4-2-5-9-17)21(25)22-13-20(24)26-14-18-10-6-3-7-11-18/h2-11,19H,12-15H2,1H3,(H,22,25)

2.1.3 InChI Key

ODUOJXZPIYUATO-UHFFFAOYSA-N

2.1.4 Canonical SMILES

CC(=O)SCC(CC1=CC=CC=C1)C(=O)NCC(=O)OCC2=CC=CC=C2

2.2 Other Identifiers

2.2.1 UNII

76K53XP4TO

2.3 Synonyms

2.3.1 MeSH Synonyms

1. Acetorphan

2. Acetorphan, (r)-isomer

3. Acetorphan, (s)-isomer

4. Ecadotril

5. N-(3-acetylmercapto-2-benzylpropanoyl)glycine Benzyl Ester

6. Retorphan

7. Sinorphan

2.3.2 Depositor-Supplied Synonyms

1. 81110-73-8

2. Acetorphan

3. Benzyl 2-(3-(acetylthio)-2-benzylpropanamido)acetate

4. Hidrasec

5. Tiorfan

6. Racecadotril [inn]

7. Tiorfix

8. S049; Sinorphan

9. Racecadotril (acetorphan)

10. Nsc-759828

11. 76k53xp4to

12. Benzyl 2-[[2-(acetylsulfanylmethyl)-3-phenylpropanoyl]amino]acetate

13. Benzyl (3-(acetylthio)-2-benzylpropanoyl)glycinate

14. Racecadotril (inn)

15. Glycine, N-[2-[(acetylthio)methyl]-1-oxo-3-phenylpropyl]-,phenylmethyl Ester [cas]

16. Glycine, N-[(2r)-2-[(acetylthio)methyl]-1-oxo-3-phenylpropyl]-, Phenylmethyl Ester

17. Smr000449320

18. Sr-01000759384

19. Racecadotril [inn:ban]

20. Unii-76k53xp4to

21. (+/-)-acetorphan

22. Benzyl 2-[[(2s)-2-(acetylsulfanylmethyl)-3-phenylpropanoyl]amino]acetate

23. 2-[[2-[(acetylthio)methyl]-1-oxo-3-phenylpropyl]amino]acetic Acid (phenylmethyl) Ester

24. 2-{[2-[(acetylthio)methyl]-1-oxo-3-phenylpropyl]amino}acetic Acid (phenylmethyl) Ester

25. Hidrasec (tn)

26. Prestwick_926

27. Racecadotril-[d5]

28. Tiorfan (tn)

29. Mfcd00865520

30. Cpd000449320

31. Prestwick0_000626

32. Prestwick1_000626

33. Prestwick2_000626

34. Prestwick3_000626

35. Racecadotril [mi]

36. Acetorphan [vandf]

37. (+-)-n-(2-((acetylthio)methyl)-1-oxo-3-phenylpropyl)glycine Phenylmethyl Ester

38. Glycine, N-(2-((acetylthio)methyl)-1-oxo-3-phenylpropyl)-, Phenylmethyl Ester

39. Glycine, N-(2-((acetylthio)methyl)-1-oxo-3-phenylpropyl)-, Phenylmethyl Ester, (+-)-

40. Bspbio_000592

41. Racecadotril [mart.]

42. Mls000758279

43. Mls001423958

44. Mls006010032

45. Racecadotril [who-dd]

46. Schembl373243

47. Spbio_002811

48. Bpbio1_000652

49. Chembl2103772

50. Dtxsid8045513

51. Chebi:91508

52. Gtpl11654

53. Racecadotril, >=98% (hplc)

54. Hms1569n14

55. Hms2051k05

56. Hms2090l07

57. Hms2096n14

58. Hms2232f17

59. Hms3370b22

60. Hms3393k05

61. Hms3656c10

62. Hms3713n14

63. Hms3744i15

64. Hms3884f04

65. Pharmakon1600-01502331

66. Racecadotril [ep Monograph]

67. Bcp14746

68. Bcp22637

69. Racecadotril For Peak Identification

70. Bdbm50247884

71. Nsc759828

72. S2503

73. Akos015894948

74. Ab07493

75. Ac-1133

76. Ccg-100764

77. Ccg-213824

78. Cs-1127

79. Db11696

80. Hs-0029

81. Nc00014

82. Nsc 759828

83. (+-)-n-(alpha-(mercaptomethyl)hydrocinnamoyl)glycine, Benzyl Ester, Acetate (ester)

84. Ncgc00179511-01

85. Ncgc00179511-04

86. Br164305

87. Hy-17399

88. Sinorphan;bay Y 7432; Bay-y 7432

89. Db-015177

90. Ft-0602523

91. Ft-0700652

92. R0103

93. Sw197043-4

94. D08464

95. 110r738

96. A840045

97. Q416677

98. Sr-01000759384-4

99. Sr-01000759384-5

100. Benzyl N-[3-(acetylthio)-2-benzylpropionyl]glycinate

101. Brd-a08187463-001-03-8

102. N-[3-acetylthio-2-benzylpropanoyl]glycine Benzyl Ester

103. N-[3-(acetylthio)-2-benzylpropionyl]glycine Benzyl Ester

104. Racecadotril, European Pharmacopoeia (ep) Reference Standard

105. N-((r,s)-3-acetylthio-2-benzylpropanoyl)glycine Benzyl Ester

106. (2-acetylsulfanylmethyl-3-phenyl-propionylamino)-acetic Acid Benzyl Ester

107. Benzyl 2-[[2-(acetylsulfanylmethyl)-3-phenyl-propanoyl]amino]acetate;racecadotril

108. Racecadotril For Peak Identification, European Pharmacopoeia (ep) Reference Standard

109. (+/-)-n-(.alpha.-(mercaptomethyl)hydrocinnamoyl)glycine, Benzyl Ester, Acetate (ester)

2.4 Create Date

2005-08-08

3 Chemical and Physical Properties

Molecular Formula	C₂₁H₂₃NO₄S
Molecular Weight	385.5 g/mol
XLogP3	3.3
Hydrogen Bond Donor Count	1
Hydrogen Bond Acceptor Count	5
Rotatable Bond Count	11
Exact Mass	385.13477939 g/mol
Monoisotopic Mass	385.13477939 g/mol
Topological Polar Surface Area	97.8 Å²
Heavy Atom Count	27
Formal Charge	0
Complexity	485
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 Pharmacology and Biochemistry

4.1 MeSH Pharmacological Classification

Antidiarrheals

Miscellaneous agents found useful in the symptomatic treatment of diarrhea. They have no effect on the agent(s) that cause diarrhea, but merely alleviate the condition. (See all compounds classified as Antidiarrheals.)

Protease Inhibitors

Compounds which inhibit or antagonize biosynthesis or actions of proteases (ENDOPEPTIDASES). (See all compounds classified as Protease Inhibitors.)

4.2 ATC Code

A - Alimentary tract and metabolism

A07 - Antidiarrheals, intestinal antiinflammatory/antiinfective agents

A07X - Other antidiarrheals

A07XA - Other antidiarrheals

A07XA04 - Racecadotril