Thiamphenicol

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Also known as: 15318-45-3, Thiophenicol, Raceophenidol, (+)-thiamphenicol, Dextrosulphenidol, Thiocymetin

Molecular Formula

C₁₂H₁₅Cl₂NO₅S

Molecular Weight

356.2 g/mol

InChI Key

OTVAEFIXJLOWRX-NXEZZACHSA-N

FDA UNII

283383NO13

A methylsulfonyl analog of CHLORAMPHENICOL. It is an antibiotic and immunosuppressive agent.

1 2D Structure

Thiamphenicol

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

2,2-dichloro-N-[(1R,2R)-1,3-dihydroxy-1-(4-methylsulfonylphenyl)propan-2-yl]acetamide

2.1.2 InChI

InChI=1S/C12H15Cl2NO5S/c1-21(19,20)8-4-2-7(3-5-8)10(17)9(6-16)15-12(18)11(13)14/h2-5,9-11,16-17H,6H2,1H3,(H,15,18)/t9-,10-/m1/s1

2.1.3 InChI Key

OTVAEFIXJLOWRX-NXEZZACHSA-N

2.1.4 Canonical SMILES

CS(=O)(=O)C1=CC=C(C=C1)C(C(CO)NC(=O)C(Cl)Cl)O

2.1.5 Isomeric SMILES

CS(=O)(=O)C1=CC=C(C=C1)[C@H]([C@@H](CO)NC(=O)C(Cl)Cl)O

2.2 Other Identifiers

2.2.1 UNII

283383NO13

2.3 Synonyms

2.3.1 MeSH Synonyms

1. Dextrosulfenidol

2. Raceophenidol

3. Thiamcol

4. Thiomycetin

5. Thiophenicol

6. Urfamycin

7. Vicemycetin

2.3.2 Depositor-Supplied Synonyms

1. 15318-45-3

2. Thiophenicol

3. Raceophenidol

4. (+)-thiamphenicol

5. Dextrosulphenidol

6. Thiocymetin

7. Thiocymetin (tn)

8. Armai (tn)

9. Racefenicol

10. Urfamycine

11. Dexawin

12. Igralin

13. Racephenicol [usan]

14. Racephenicol

15. Armai

16. Win-5063-2

17. 847-25-6

18. Thiamphenicol (thiophenicol)

19. Racefenicol [inn]

20. 2,2-dichloro-n-[(1r,2r)-1,3-dihydroxy-1-(4-methylsulfonylphenyl)propan-2-yl]acetamide

21. Flq7571npm

22. 2,2-dichloro-n-{(1r,2r)-2-hydroxy-1-(hydroxymethyl)-2-[4-(methylsulfonyl)phenyl]ethyl}acetamide

23. Mls001332640

24. D-(+)-threo-2,2-dichloro-n-(beta-hydroxy-alpha-(hydroxymethyl)-p-(methylsulfonyl)phenethyl)acetamide

25. Chebi:32215

26. 2,2-dichloro-n-((1r,2r)-1,3-dihydroxy-1-(4-(methylsulfonyl)phenyl)propan-2-yl)acetamide

27. Nsc-522822

28. Thiamphenicolum

29. Smr000857096

30. D-thiocymetin

31. D-thiophenicol

32. 283383no13

33. Dsstox_cid_1338

34. Dsstox_rid_76092

35. Dsstox_gsid_21338

36. Acetamide, 2,2-dichloro-n-((1r,2r)-2-hydroxy-1-(hydroxymethyl)-2-(4-(methylsulfonyl)phenyl)ethyl)-

37. Tiamfenicolo [dcit]

38. Racefenicolo

39. Racefenicolum

40. Tiamfenicol

41. Tiamfenicolo

42. Thiamphenicol Dl-form

43. Win 5063-2

44. Acetamide, 2,2-dichloro-n-(2-hydroxy-1-(hydroxymethyl)-2-(4-(methylsulfonyl)phenyl)ethyl)-, (r-(r*,r*))-

45. Tiamfenicol [inn-spanish]

46. 2,2-dichloro-n-[(1r,2r)-1,3-dihydroxy-1-(4-methanesulfonylphenyl)propan-2-yl]acetamide

47. Thiamphenicolum [inn-latin]

48. 8065 C.b.

49. Racefenicolo [dcit]

50. (+/-)-thiamphenicol

51. Sr-05000001829

52. Einecs 239-355-3

53. Thiamphenicol [usan:inn:ban:jan]

54. Unii-flq7571npm

55. Nsc 522822

56. Racefenicolum [inn-latin]

57. Win-5063

58. Ccris 8588

59. Thiamphenicol Dl-

60. Unii-283383no13

61. Ncgc00016714-01

62. 2,2-dichloro-n-((1r,2r)-2-hydroxy-1-(hydroxymethyl)-2-(4-(methylsulfonyl)phenyl)ethyl)acetamide

63. Prestwick_885

64. Cas-15318-45-3

65. Mfcd00467983

66. Spectrum_001428

67. Prestwick0_000025

68. Prestwick1_000025

69. Prestwick2_000025

70. Prestwick3_000025

71. Spectrum2_000856

72. Spectrum3_001562

73. Spectrum4_000733

74. Spectrum5_001617

75. Thiamphenicol [mi]

76. D-d-threo-2-dichloroacetamido-1-(4-methylsulfonylphenyl)-1,3-propanediol

77. D-threo-(1r,2r)-1-(p-methylsulfonylphenyl)-2-dichloroacetamido-1,3-propanediol

78. Thiamphenicol [inn]

79. Thiamphenicol [jan]

80. Thiamphenicol [usan]

81. Schembl34635

82. Bspbio_000089

83. Bspbio_003064

84. Kbiogr_001026

85. Kbioss_001908

86. Cid_27200

87. Mls001332639

88. Mls002154177

89. Divk1c_000842

90. Spectrum1503136

91. Thiamphenicol [mart.]

92. Spbio_000871

93. Spbio_002010

94. Thiamphenicol [who-dd]

95. Bpbio1_000099

96. Chembl1236282

97. Dtxsid5021338

98. Thiamphenicol (jan/usan/inn)

99. Bdbm58925

100. Hms502k04

101. Kbio1_000842

102. Kbio2_001908

103. Kbio2_004476

104. Kbio2_007044

105. Kbio3_002564

106. Ninds_000842

107. Thiamphenicol, Analytical Standard

108. Hms1568e11

109. Hms1922g19

110. Hms2092l18

111. Hms2095e11

112. Hms2232e21

113. Hms3712e11

114. Pharmakon1600-01503136

115. Zinc538440

116. Thiamphenicol Dl-form [mi]

117. Bcp32746

118. Hy-b0479

119. Thiamphenicol [ep Monograph]

120. Tox21_110577

121. Tox21_200816

122. Ccg-40309

123. Nsc758396

124. S2583

125. Akos015951269

126. Dl-threo-2-dichloroacetamido-1-(4-methylsulfonyl-phenyl)-1,3-propanediol

127. Tox21_110577_1

128. Db08621

129. Nsc-758396

130. Idi1_000842

131. Smp2_000125

132. Ncgc00178319-01

133. Ncgc00178319-02

134. Ncgc00178319-03

135. Ncgc00178319-06

136. Ncgc00178319-07

137. Ncgc00258370-01

138. (+-)-threo-2,2-dichloro-n-(beta-hydroxy-alpha-(hydroxymethyl)-p-(methylsulfonyl)phenethyl)acetamide

139. Acetamide, 2,2-dichloro-n-(beta-hydroxy-alpha-(hydroxymethyl)-p-(methylsulfonyl)phenethyl)-, D-threo-(+)

140. Acetamide, 2,2-dichloro-n-(beta-hydroxy-alpha-(hydroxymethyl)-p-(methylsulfonyl)phenethyl)-, Threo-(+-)-

141. As-12501

142. Sbi-0051779.p002

143. Sw197006-3

144. T2802

145. Thiamphenicol 100 Microg/ml In Acetonitrile

146. Thiamphenicol 1000 Microg/ml In Acetonitrile

147. D01407

148. Ab00052321_10

149. Ab00052321_11

150. 318t453

151. A809401

152. Q425015

153. Sr-05000001829-1

154. Sr-05000001829-3

155. Brd-k79711234-001-06-8

156. Brd-k79711234-001-11-8

157. Thiamphenicol, European Pharmacopoeia (ep) Reference Standard

158. Thiophenicol; Dextrosulphenidol; Descocin; Hyrazin; Masatirin; Urfamycine

159. 2,2-dichloro-n-[(1r,2r)-1,3-dihydroxy-1-[4-(methylsulfonyl)phenyl]-2-propyl]acetamide

160. 2,2-dichloro-n-[(1r,2r)-2-hydroxy-2-(4-mesylphenyl)-1-methylol-ethyl]acetamide

161. 2,2-bis(chloranyl)-n-[(1r,2r)-1-(4-methylsulfonylphenyl)-1,3-bis(oxidanyl)propan-2-yl]ethanamide

162. Acetamide, 2,2-dichloro-n-((1r,2r)-2-hydroxy-1-(hydroxymethyl)-2-(4-(methylsulfonyl)phenyl)ethyl)-, Rel-

163. Acetamide, 2,2-dichloro-n-(.beta.-hydroxy-.alpha.-(hydroxymethyl)-p-(methylsulfonyl)phenethyl)-, Threo-(+/-)-

164. Acetamide, 2,2-dichloro-n-(2-hydroxy-1-(hydroxymethyl)-2-(4-(methylsulfonyl)phenyl)ethyl)-, (r*,r*)-(+-)-

165. Acetamide, 2,2-dichloro-n-(2-hydroxy-1-(hydroxymethyl)-2-(4-(methylsulfonyl)phenyl)ethyl)-, (r*,r*)-(+/-)-

166. Acetamide,2,2-dichloro-n-[(1r,2r)-2-hydroxy-1-(hydroxymethyl)-2-[4-(methylsulfonyl)phenyl]ethyl]-

167. Th8

2.4 Create Date

2005-06-24

3 Chemical and Physical Properties

Molecular Formula	C₁₂H₁₅Cl₂NO₅S
Molecular Weight	356.2 g/mol
XLogP3	-0.3
Hydrogen Bond Donor Count	3
Hydrogen Bond Acceptor Count	5
Rotatable Bond Count	6
Exact Mass	355.0047991 g/mol
Monoisotopic Mass	355.0047991 g/mol
Topological Polar Surface Area	112 Å²
Heavy Atom Count	21
Formal Charge	0
Complexity	443
Isotope Atom Count	0
Defined Atom Stereocenter Count	2
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

4 Pharmacology and Biochemistry

4.1 MeSH Pharmacological Classification

Anti-Bacterial Agents

Substances that inhibit the growth or reproduction of BACTERIA. (See all compounds classified as Anti-Bacterial Agents.)

4.2 ATC Code

J01BA02

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

J - Antiinfectives for systemic use

J01 - Antibacterials for systemic use

J01B - Amphenicols

J01BA - Amphenicols

J01BA02 - Thiamphenicol