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Prestwick3_000036

Prestwick3_000036

Synopsis, 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

A macrolide antibiotic that is similar to ERYTHROMYCIN.

1 2D Structure

Prestwick3_000036

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 Formula	C₄₁H₆₇NO₁₅
Molecular Weight	814.0 g/mol
XLogP3	4.3
Hydrogen Bond Donor Count	0
Hydrogen Bond Acceptor Count	16
Rotatable Bond Count	12
Exact Mass	813.45107043 g/mol
Monoisotopic Mass	813.45107043 g/mol
Topological Polar Surface Area	184 Å²
Heavy Atom Count	57
Formal Charge	0
Complexity	1430
Isotope Atom Count	0
Defined Atom Stereocenter Count	18
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

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.