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    Troleandomycin

    ACTIVE PHARMA INGREDIENTS

    FINISHED DOSAGE FORMULATIONS

    PharmaCompass
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    2D Structure
    Also known as: Triacetyloleandomycin, Oleandomycin triacetate, Oleandocetine, Cyclamycin, Tribiocillina, Oleandomycin triacetyl ester
    Molecular Formula
    C41H67NO15
    Molecular Weight
    814.0  g/mol
    InChI Key
    LQCLVBQBTUVCEQ-QTFUVMRISA-N
    FDA UNII
    C4DZ64560D
    A macrolide antibiotic that is similar to ERYTHROMYCIN.
    1 2D Structure

    2D Structure

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    [(3R,5S,6S,7R,8S,9R,12R,13S,14S,15R)-6-[(2S,3R,4S,6R)-3-acetyloxy-4-(dimethylamino)-6-methyloxan-2-yl]oxy-8-[(2R,4S,5S,6S)-5-acetyloxy-4-methoxy-6-methyloxan-2-yl]oxy-5,7,9,12,13,15-hexamethyl-10,16-dioxo-1,11-dioxaspiro[2.13]hexadecan-14-yl] acetate
    2.1.2 InChI
    InChI=1S/C41H67NO15/c1-19-17-41(18-49-41)38(46)23(5)34(53-27(9)43)21(3)25(7)52-39(47)24(6)35(56-32-16-31(48-14)36(26(8)51-32)54-28(10)44)22(4)33(19)57-40-37(55-29(11)45)30(42(12)13)15-20(2)50-40/h19-26,30-37,40H,15-18H2,1-14H3/t19-,20+,21-,22+,23+,24+,25+,26-,30-,31-,32-,33-,34-,35-,36-,37+,40-,41+/m0/s1
    2.1.3 InChI Key
    LQCLVBQBTUVCEQ-QTFUVMRISA-N
    2.1.4 Canonical SMILES
    CC1CC(C(C(O1)OC2C(CC3(CO3)C(=O)C(C(C(C(OC(=O)C(C(C2C)OC4CC(C(C(O4)C)OC(=O)C)OC)C)C)C)OC(=O)C)C)C)OC(=O)C)N(C)C
    2.1.5 Isomeric SMILES
    C[C@@H]1C[C@@H]([C@H]([C@@H](O1)O[C@H]2[C@H](C[C@@]3(CO3)C(=O)[C@@H]([C@H]([C@H]([C@H](OC(=O)[C@@H]([C@H]([C@@H]2C)O[C@H]4C[C@@H]([C@H]([C@@H](O4)C)OC(=O)C)OC)C)C)C)OC(=O)C)C)C)OC(=O)C)N(C)C
    2.2 Other Identifiers
    2.2.1 UNII
    C4DZ64560D
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. Oleandocetin

    2. Tao

    3. Triacetyloleandomycin

    2.3.2 Depositor-Supplied Synonyms

    1. Triacetyloleandomycin

    2. Oleandomycin Triacetate

    3. Oleandocetine

    4. Cyclamycin

    5. Tribiocillina

    6. Oleandomycin Triacetyl Ester

    7. 2751-09-9

    8. Evramicina

    9. Troleandomicina

    10. Troleandomycine

    11. Triocetin

    12. Aovine

    13. Troleandomycinum

    14. Oleandomycin, Triacetate (ester)

    15. Matromycin T

    16. Oleandomycin Triacetate Ester

    17. Triacetyloleandomycinum

    18. Matromicina

    19. Treolmicina

    20. Oleandomycin (as Troleandomycin)

    21. Chebi:45735

    22. C4dz64560d

    23. Nsc-108166

    24. Ai3-50166

    25. Tao

    26. Triacetyloleandomycin (jan)

    27. Triacetyloleandomycin [jan]

    28. Oleandomycin, Triacetyl-

    29. Triolan

    30. Viamicina

    31. Wytrion

    32. Treis-micina

    33. Wy 651

    34. Acetyloleandomycin

    35. Tao (van)

    36. Tao (tn)

    37. Prestwick3_000036

    38. Troleandomycin [mi]

    39. Troleandomycin (usan/inn)

    40. Troleandomycin [inn]

    41. Bspbio_000131

    42. Troleandomycin [usan]

    43. Troleandomycine [inn-french]

    44. Troleandomycinum [inn-latin]

    45. Schembl125071

    46. Troleandomycin [vandf]

    47. Unii-c4dz64560d

    48. Troleandomicina [inn-spanish]

    49. Triacetyl Ester Of Oleandomycin

    50. Troleandomycin [mart.]

    51. Bpbio1_000145

    52. Chembl564085

    53. T.a.o.

    54. Troleandomycin [who-dd]

    55. Dtxsid2023721

    56. Hms2089b10

    57. Hms2095g13

    58. Hms3712g13

    59. Fmoc-(r)-3-amino-5-hexenoicacid

    60. Einecs 220-392-9

    61. Troleandomycin [orange Book]

    62. Bdbm50370258

    63. Lmpk04000042

    64. Troleandomycin [usp Impurity]

    65. Troleandomycin [usan:usp:inn:ban]

    66. Zinc169307271

    67. Ccg-220036

    68. Db13179

    69. Nsc 108166

    70. Ncgc00179654-01

    71. Hy-108881

    72. Ab00513798

    73. Cs-0031241

    74. D01322

    75. Ab00513798-02

    76. Oleandomycin (as Troleandomycin) [vandf]

    77. Q1087499

    78. Brd-k38310698-001-01-9

    79. (3r,5r,6s,7r,8r,11r,12s,13r,14s,15s)-12-[(4-o-acetyl-2,6-dideoxy-3-o-methyl-alpha-l-arabino-hexopyranosyl)oxy]-14-{[2-o-acetyl-3,4,6-trideoxy-3-(dimethylamino)-beta-d-xylo-hexopyranosyl]oxy}-5,7,8,11,13,15-hexamethyl-4,10-dioxo-1,9-dioxaspiro[2.13]hexadecan-6-yl Acetate

    80. [(3r,5s,6s,7r,8s,9r,12r,13s,14s,15r)-6-[(2s,3r,4s,6r)-3-acetyloxy-4-(dimethylamino)-6-methyloxan-2-yl]oxy-8-[(2r,4s,5s,6s)-5-acetyloxy-4-methoxy-6-methyloxan-2-yl]oxy-5,7,9,12,13,15-hexamethyl-10,16-dioxo-1,11-dioxaspiro[2.13]hexadecan-14-yl] Acetate

    2.4 Create Date
    2005-06-24
    3 Chemical and Physical Properties
    Molecular Weight 814.0 g/mol
    Molecular Formula C41H67NO15
    XLogP34.3
    Hydrogen Bond Donor Count0
    Hydrogen Bond Acceptor Count16
    Rotatable Bond Count12
    Exact Mass813.45107043 g/mol
    Monoisotopic Mass813.45107043 g/mol
    Topological Polar Surface Area184 Ų
    Heavy Atom Count57
    Formal Charge0
    Complexity1430
    Isotope Atom Count0
    Defined Atom Stereocenter Count18
    Undefined Atom Stereocenter Count0
    Defined Bond Stereocenter Count0
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count1
    4 Drug and Medication Information
    4.1 Drug Indication

    For the treatment of bacterial infection.

    5 Pharmacology and Biochemistry
    5.1 Pharmacology

    Troleandomycin, like other macrolide antibiotics, inhibits bacterial protein synthesis to prevent growth.

    5.2 MeSH Pharmacological Classification

    Anti-Bacterial Agents

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

    5.3 ATC Code

    J - Antiinfectives for systemic use

    J01 - Antibacterials for systemic use

    J01F - Macrolides, lincosamides and streptogramins

    J01FA - Macrolides

    J01FA08 - Troleandomycin

    5.4 Metabolism/Metabolites

    Troleandomycin has known human metabolites that include [(3R,5S,6S,7R,8S,9R,12R,13S,14S,15R)-8-[(2R,4S,5S,6S)-5-acetyloxy-4-methoxy-6-methyloxan-2-yl]oxy-6-[(2S,3R,4S,6R)-3-acetyloxy-6-methyl-4-(methylamino)oxan-2-yl]oxy-5,7,9,12,13,15-hexamethyl-10,16-dioxo-1,11-dioxaspiro[2.13]hexadecan-14-yl] acetate.

    S73 | METXBIODB | Metabolite Reaction Database from BioTransformer | DOI:10.5281/zenodo.4056560

    5.5 Mechanism of Action

    As a macrolide, troleandomycin binds to the 50S subunit of the bacterial ribosome. This binding inhibits translocation of tRNA along the A, P, and E sites of the ribosome. With tRNA unable to move from site to site, amino acids cannot be deposited onto the polypeptide chain leading to failure of protein synthesis. Bacterial cell growth and duplication is inhibited without the ability to generate the necessary proteins.