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Chemistry

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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

Troleandomycin
A macrolide antibiotic that is similar to ERYTHROMYCIN.
1 2D Structure

Troleandomycin

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.


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