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    Thiamphenicol

    ACTIVE PHARMA INGREDIENTS

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    2D Structure
    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

    2D Structure

    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 Weight 356.2 g/mol
    Molecular Formula C12H15Cl2NO5S
    XLogP3-0.3
    Hydrogen Bond Donor Count3
    Hydrogen Bond Acceptor Count5
    Rotatable Bond Count6
    Exact Mass355.0047991 g/mol
    Monoisotopic Mass355.0047991 g/mol
    Topological Polar Surface Area112 Ų
    Heavy Atom Count21
    Formal Charge0
    Complexity443
    Isotope Atom Count0
    Defined Atom Stereocenter Count2
    Undefined Atom Stereocenter Count0
    Defined Bond Stereocenter Count0
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count1
    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