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    Meclocycline
    Also known as: 73816-42-9, Mecloderm, Meclan, Meclocycline sulfosalicylate salt, Meclutin, Meclan cream
    Molecular Formula
    C29H27ClN2O14S
    Molecular Weight
    695.0  g/mol
    InChI Key
    WVJKUGVVYXCLFV-CCHMMTNSSA-N
    FDA UNII
    46VZA7RX2B
    Meclocycline Sulfosalicylate is the sulfosalicylate salt form of meclocycline, a tetracycline antibiotic with broad-spectrum antibacterial and antiprotozoal activity. Meclocycline sulfosalicylate is bacteriostatic and inhibits bacterial protein synthesis by binding to the 30S ribosomal subunit, thereby preventing the addition of amino acids to the growing peptide chain. This tetracycline is active against a wide range of gram-positive and gram-negative bacteria.
    1 2D Structure

    Meclocycline

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    (4S,4aR,5S,5aR,12aR)-7-chloro-4-(dimethylamino)-1,5,10,11,12a-pentahydroxy-6-methylidene-3,12-dioxo-4,4a,5,5a-tetrahydrotetracene-2-carboxamide;2-hydroxy-5-sulfobenzoic acid
    2.1.2 InChI
    InChI=1S/C22H21ClN2O8.C7H6O6S/c1-6-9-7(23)4-5-8(26)11(9)16(27)12-10(6)17(28)14-15(25(2)3)18(29)13(21(24)32)20(31)22(14,33)19(12)30;8-6-2-1-4(14(11,12)13)3-5(6)7(9)10/h4-5,10,14-15,17,26-28,31,33H,1H2,2-3H3,(H2,24,32);1-3,8H,(H,9,10)(H,11,12,13)/t10-,14-,15+,17+,22+;/m1./s1
    2.1.3 InChI Key
    WVJKUGVVYXCLFV-CCHMMTNSSA-N
    2.1.4 Canonical SMILES
    CN(C)C1C2C(C3C(=C)C4=C(C=CC(=C4C(=C3C(=O)C2(C(=C(C1=O)C(=O)N)O)O)O)O)Cl)O.C1=CC(=C(C=C1S(=O)(=O)O)C(=O)O)O
    2.1.5 Isomeric SMILES
    CN(C)[C@H]1[C@@H]2[C@H]([C@@H]3C(=C)C4=C(C=CC(=C4C(=C3C(=O)[C@@]2(C(=C(C1=O)C(=O)N)O)O)O)O)Cl)O.C1=CC(=C(C=C1S(=O)(=O)O)C(=O)O)O
    2.2 Other Identifiers
    2.2.1 UNII
    46VZA7RX2B
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. 7-chloro-4-(dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,5,10,12,12a-pentahydroxy-6-methylene-1,11-dioxo-2-naphthacene Carboxamide

    2. Gs 2989

    3. Gs-2989

    4. Meclan

    5. Meclocycline

    6. Meclocycline Monohydrochloride, (4s-(4alpha,4aalpha,5alpha,5aalpha,12aalpha))-isomer

    7. Meclosorb

    8. Samil

    2.3.2 Depositor-Supplied Synonyms

    1. 73816-42-9

    2. Mecloderm

    3. Meclan

    4. Meclocycline Sulfosalicylate Salt

    5. Meclutin

    6. Meclan Cream

    7. Meclocycline 5-sulfosalicylate

    8. Meclocyline Sulfosalicylate

    9. Nsc-757831

    10. 46vza7rx2b

    11. Snx-1012

    12. (4s,4ar,5s,5ar,12as)-7-chloro-4-(dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,5,10,12,12a-pentahydroxy-6-methylene-1,11-dioxo-2-naphthacenecarboxamide Mono(5-sulfosalicylate) (salt)

    13. Meclocycline (sulfosalicylate Salt)

    14. (4s,4ar,5s,5ar,12ar)-7-chloro-4-(dimethylamino)-1,5,10,11,12a-pentahydroxy-6-methylidene-3,12-dioxo-4,4a,5,5a-tetrahydrotetracene-2-carboxamide;2-hydroxy-5-sulfobenzoic Acid

    15. Sr-05000001668

    16. Meclocycline Sulfosalicylate [usan]

    17. Einecs 277-614-2

    18. Unii-46vza7rx2b

    19. Ncgc00017134-01

    20. Prestwick_588

    21. Cas-73816-42-9

    22. Meclan (tn)

    23. Meclocycline Sulfosalicylate [usan:usp]

    24. Spectrum_001330

    25. Prestwick0_000456

    26. Prestwick1_000456

    27. Prestwick2_000456

    28. Spectrum2_001405

    29. Spectrum3_000919

    30. Spectrum4_001018

    31. Spectrum5_001522

    32. Dsstox_cid_25596

    33. Dsstox_rid_80989

    34. Dsstox_gsid_45596

    35. Kbiogr_001515

    36. Kbioss_001810

    37. Divk1c_000585

    38. Schembl193563

    39. Spectrum1501118

    40. Spbio_001450

    41. Spbio_002471

    42. Chembl261772

    43. Dtxsid5045596

    44. Schembl23359126

    45. Hms501n07

    46. Kbio1_000585

    47. Kbio2_001810

    48. Kbio2_004378

    49. Kbio2_006946

    50. Kbio3_001898

    51. Ninds_000585

    52. Hms1569k14

    53. Hms1921f17

    54. Hms2092d11

    55. Pharmakon1600-01501118

    56. Meclocycline Sulfosalicylate (usp)

    57. Bcp19781

    58. Hy-b1366

    59. Tox21_110794

    60. Ccg-39023

    61. Nsc757831

    62. Akos026749854

    63. Akos030254832

    64. Nsc 757831

    65. Idi1_000585

    66. (4s,4ar,5s,5ar,12ar)-7-chloro-4-(dimethylamino)-1,5,10,11,12a-pentahydroxy-6-methylidene-3,12-dioxo-4,4a,5,5a-tetrahydrotetracene-2-carboxamide,2-hydroxy-5-sulfobenzoic Acid

    67. 2-naphthacenecarboxamide, 7-chloro-4-(dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,5,10,12,12a-pentahydroxy-6-methylene-1,11-dioxo-, (4s-(4alpha,4aalpha,5alpha,5aalpha,12aalpha))-, Mono(2-hydroxy-5-sulfobenzoate) (salt)

    68. Benzoic Acid, 2-hydroxy-5-sulfo-, Compd. With (4s-(4alpha,4aalpha,5alpha,5aalpha,12aalpha))-7-chloro-4-(dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,5,10,12,12a-pentahydroxy-6-methylene-1,11-dioxo-2-naphthacenecarboxamide (1:1)

    69. Meclocyline Sulfosalicylate [vandf]

    70. Meclocycline 5-sulfosalicylate [mi]

    71. Meclocycline Sulfosalicylate [mart.]

    72. Cs-0013107

    73. Meclocycline Sulfosalicylate [usp-rs]

    74. Meclocycline Sulfosalicylate [who-dd]

    75. D02477

    76. D94875

    77. Meclocycline Sulfosalicylate [orange Book]

    78. Meclocycline Sulfosalicylate [usp Impurity]

    79. Sr-05000001668-1

    80. Sr-05000001668-3

    81. Q27887916

    82. 2-naphthacenecarboxamide, 7-chloro-4-(dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,5,10,12,12a-pentahydroxy-6-methylene-1,11-dioxo-, (4s-(4.alpha.,4a.alpha.,5.alpha.,5a.alpha.,12a.alpha.))-, Mono(2-hydroxy-5-sulfobenzoate) (salt)

    2.4 Create Date
    2011-12-26
    3 Chemical and Physical Properties
    Molecular Weight 695.0 g/mol
    Molecular Formula C29H27ClN2O14S
    Hydrogen Bond Donor Count9
    Hydrogen Bond Acceptor Count15
    Rotatable Bond Count4
    Exact Mass694.0871524 g/mol
    Monoisotopic Mass694.0871524 g/mol
    Topological Polar Surface Area302 Ų
    Heavy Atom Count47
    Formal Charge0
    Complexity1350
    Isotope Atom Count0
    Defined Atom Stereocenter Count5
    Undefined Atom Stereocenter Count0
    Defined Bond Stereocenter Count0
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count2
    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.)

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