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Dirithromycin

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Synopsis

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Chemistry

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Also known as: 62013-04-1, Dynabac, Dirithromycine, Dirithromycinum, Diritromicina, Ly 237216

Molecular Formula

C₄₂H₇₈N₂O₁₄

Molecular Weight

835.1 g/mol

InChI Key

WLOHNSSYAXHWNR-DWIOZXRMSA-N

FDA UNII

1801D76STL

Dirithromycin is a semi-synthetic macrolide antibiotic pro-drug. Dirithromycin is converted by hydrolysis during intestinal absorption into the microbiologically active erythromycylamine. Eryhtromylamine binds to the 50 S subunit of the 70 S ribosome of susceptible organisms, thereby inhibiting bacterial RNA-dependent protein synthesis. This antibiotic is used in the treatment of infections of the respiratory tract, skin and soft tissue caused by gram-positive microorganisms, including S. aureus, S. pneumonia and pyogenes, gram-negative microorganisms, including H. influenzae, L. pneumophila, M. catarrhalis, and M. pneumoniae.

1 2D Structure

Dirithromycin

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

(1R,2R,3R,6R,7S,8S,9R,10R,12R,13S,15R,17S)-9-[(2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy-3-ethyl-2,10-dihydroxy-7-[(2R,4R,5S,6S)-5-hydroxy-4-methoxy-4,6-dimethyloxan-2-yl]oxy-15-(2-methoxyethoxymethyl)-2,6,8,10,12,17-hexamethyl-4,16-dioxa-14-azabicyclo[11.3.1]heptadecan-5-one

2.1.2 InChI

InChI=1S/C42H78N2O14/c1-15-29-42(10,49)37-24(4)32(43-30(56-37)21-52-17-16-50-13)22(2)19-40(8,48)36(58-39-33(45)28(44(11)12)18-23(3)53-39)25(5)34(26(6)38(47)55-29)57-31-20-41(9,51-14)35(46)27(7)54-31/h22-37,39,43,45-46,48-49H,15-21H2,1-14H3/t22-,23-,24+,25+,26-,27+,28+,29-,30-,31+,32+,33-,34+,35+,36-,37-,39+,40-,41-,42-/m1/s1

2.1.3 InChI Key

WLOHNSSYAXHWNR-DWIOZXRMSA-N

2.1.4 Canonical SMILES

CCC1C(C2C(C(C(CC(C(C(C(C(C(=O)O1)C)OC3CC(C(C(O3)C)O)(C)OC)C)OC4C(C(CC(O4)C)N(C)C)O)(C)O)C)NC(O2)COCCOC)C)(C)O

2.1.5 Isomeric SMILES

CC[C@@H]1[C@@]([C@H]2[C@H]([C@H]([C@@H](C[C@@]([C@@H]([C@H]([C@@H]([C@H](C(=O)O1)C)O[C@H]3C[C@@]([C@H]([C@@H](O3)C)O)(C)OC)C)O[C@H]4[C@@H]([C@H](C[C@H](O4)C)N(C)C)O)(C)O)C)N[C@H](O2)COCCOC)C)(C)O

2.2 Other Identifiers

2.2.1 UNII

1801D76STL

2.3 Synonyms

2.3.1 MeSH Synonyms

1. (9s)-9-deoxo-11-deoxy-9,11-(imino((1r)-2-(2-methoxyethoxy)ethylidene)oxy)erythromycin

2. Dynabac

3. Ly 237216

4. Ly-237216

5. Nortron

2.3.2 Depositor-Supplied Synonyms

1. 62013-04-1

2. Dynabac

3. Dirithromycine

4. Dirithromycinum

5. Diritromicina

6. Ly 237216

7. Ly-237216

8. (9s)-9-deoxo-11-deoxy-9,11-(imino((1r)-2-(2-methoxyethoxy)ethylidene)oxy)erythromycin

9. Mls000028564

10. Smr000058954

11. Mls001074061

12. Chebi:474014

13. 1801d76stl

14. Nsc-758672

15. Erythromycin, 9-deoxo-11-deoxy-9,11-(imino(2-(2-methoxyethoxy)ethylidene)oxy)-, (9s(r))-

16. Ly237216

17. (1r,2r,3r,6r,7s,8s,9r,10r,12r,13s,15r,17s)-3-ethyl-2,10-dihydroxy-15-[(2-methoxyethoxy)methyl]-2,6,8,10,12,17-hexamethyl-5-oxo-9-{[3,4,6-trideoxy-3-(dimethylamino)-beta-d-xylo-hexopyranosyl]oxy}-4,16-dioxa-14-azabicyclo[11.3.1]heptadec-7-yl 2,6-dideoxy-3-c-methyl-3-o-methyl-alpha-l-ribo-hexopyranoside

18. (1r,2r,3r,6r,7s,8s,9r,10r,12r,13s,15r,17s)-9-(((2s,3r,4s,6r)-4-(dimethylamino)-3-hydroxy-6-methyltetrahydro-2h-pyran-2-yl)oxy)-3-ethyl-2,10-dihydroxy-7-(((2r,4r,5s,6s)-5-hydroxy-4-methoxy-4,6-dimethyltetrahydro-2h-pyran-2-yl)oxy)-15-((2-methoxyethoxy)methyl)-2,6,8,10,12,17-hexamethyl-4,16-dioxa-14-azabicyclo[11.3.1]heptadecan-5-one

19. Dirithromycine [french]

20. Dirithromycinum [latin]

21. Diritromicina [spanish]

22. Divitross

23. Noriclan

24. Valodin

25. Unii-1801d76stl

26. Ccris 9506

27. Ncgc00178154-03

28. Di0

29. Dynabac (tn)

30. Dirithromycin [usan:usp:inn:ban]

31. Mfcd00865041

32. Spectrum_001476

33. Specplus_000868

34. Opera_id_1686

35. Prestwick3_000557

36. Spectrum2_001655

37. Spectrum3_001630

38. Spectrum4_000597

39. Spectrum5_000715

40. Dirithromycin (usp/inn)

41. Dirithromycin [mi]

42. Dirithromycin [inn]

43. Dirithromycin [usan]

44. Bspbio_000633

45. Bspbio_003299

46. Dirithromycin [vandf]

47. Kbiogr_001094

48. Kbioss_001956

49. Dirithromycin [mart.]

50. Divk1c_006964

51. Spectrum1504144

52. Spbio_001809

53. Dirithromycin [usp-rs]

54. Dirithromycin [who-dd]

55. Bpbio1_000697

56. Chembl1237072

57. Chembl3039471

58. Bdbm59397

59. Cid_6473883

60. Kbio1_001908

61. Kbio2_001956

62. Kbio2_004524

63. Kbio2_007092

64. Kbio3_002519

65. Ase 136

66. Ase-136

67. Hms1922d13

68. Hms2093a06

69. Hms2096p15

70. Hms2233m04

71. Hms3713p15

72. Dirithromycin [ep Impurity]

73. Dirithromycin [orange Book]

74. As-e 136

75. Dirithromycin [ep Monograph]

76. Dirithromycin [usp Impurity]

77. Ccg-39072

78. Zinc96095661

79. Akos025310151

80. Db00954

81. Nsc 758672

82. Ncgc00178154-01

83. Ncgc00178154-02

84. Sbi-0052687.p002

85. Ab00513862

86. D03865

87. T72716

88. Ab00053192_13

89. 013d041

90. A833532

91. Sr-01000721832

92. Sr-05000001888

93. Q1989071

94. Sr-01000721832-3

95. Sr-05000001888-1

96. (9s)-9-deoxo-11-deoxy-9,11-[imino[2-(2-methoxyethoxy)ethylidene]erythromycin

97. (1r,2r,3r,6r,7s,8s,9r,10r,12r,13s,15r,17s)-3-ethyl-2,10-dihydroxy-15-[(2-methoxyethoxy)methyl]-2,6,8,10,12,17-hexamethyl-5-oxo-9-{[3,4,6-trideoxy-3-(dimethylamino)-beta-d-xylo-hexopyranosyl]oxy}-4,16-dioxa-14-azabicyclo[11.3.1]heptadecan-7-yl 2,6-dideoxy-3-c-methyl-3-o-methyl-alpha-l-ribo-hexopyranoside

98. (1r,2r,3r,6r,7s,8s,9r,10r,12r,13s,15r,17s)-9-[(2s,3r,4s,6r)-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy-3-ethyl-2,10-dihydroxy-7-[(2r,4r,5s,6s)-5-hydroxy-4-methoxy-4,6-dimethyloxan-2-yl]oxy-15-(2-methoxyethoxymethyl)-2,6,8,10,12,17-hexamethyl-4,16-dioxa-14-azabicyclo[11.3.1]heptadecan-5-one

99. (1s,2r,3r,6r,7s,8s,9r,10r,12r,13s,15r,17s)-9-[(2s,3r,4s,6r)-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy-3-ethyl-2,10-dihydroxy-7-[(2r,4r,5s,6s)-5-hydroxy-4-methoxy-4,6-dimethyloxan-2-yl]oxy-15-(2-methoxyethoxymethyl)-2,6,8,10,12,17-hexamethyl-4,16-dioxa-14-azabicyclo[11.3.1]heptadecan-5-one

100. (1s,2r,4r,5r,6s,7s,8r,11r,12r,13r,15r,17s)-5-[(2s,3r,4s,6r)-4-(dimethylamino)-3-hydroxy-6-methyl-tetrahydropyran-2-yl]oxy-11-ethyl-4,12-dihydroxy-7-[(2r,4r,5s,6s)-5-hydroxy-4-methoxy-4,6-dimethyl-tetrahydropyran-2-yl]oxy-15-(2-methoxyethoxymethyl)-2,4,6,8,12,17-hexamethyl-10,14-dioxa-16-azabicyclo[11.3.1]heptadecan-9-one

101. (1s,2r,4r,5r,6s,7s,8r,11r,12r,13r,15r,17s)-5-[(2s,3r,4s,6r)-4-(dimethylamino)-6-methyl-3-oxidanyl-oxan-2-yl]oxy-11-ethyl-7-[(2r,4r,5s,6s)-4-methoxy-4,6-dimethyl-5-oxidanyl-oxan-2-yl]oxy-15-(2-methoxyethoxymethyl)-2,4,6,8,12,17-hexamethyl-4,12-bis(oxidanyl

102. (1s,2r,4r,5r,6s,7s,8r,11r,12r,13r,15r,17s)-5-[[(2s,3r,4s,6r)-4-(dimethylamino)-3-hydroxy-6-methyl-2-oxanyl]oxy]-11-ethyl-4,12-dihydroxy-7-[[(2r,4r,5s,6s)-5-hydroxy-4-methoxy-4,6-dimethyl-2-oxanyl]oxy]-15-(2-methoxyethoxymethyl)-2,4,6,8,12,17-hexamethyl-10

2.4 Create Date

2006-04-29

3 Chemical and Physical Properties

Molecular Formula	C₄₂H₇₈N₂O₁₄
Molecular Weight	835.1 g/mol
XLogP3	4.2
Hydrogen Bond Donor Count	5
Hydrogen Bond Acceptor Count	16
Rotatable Bond Count	12
Exact Mass	834.54530517 g/mol
Monoisotopic Mass	834.54530517 g/mol
Topological Polar Surface Area	196 Å²
Heavy Atom Count	58
Formal Charge	0
Complexity	1300
Isotope Atom Count	0
Defined Atom Stereocenter Count	20
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 the following mild-to-moderate infections caused by susceptible strains of microorganisms: acute bacterial exacerbations of chronic bronchitis, secondary bacterial infection of acute bronchitis, community-acquired pneumonia, pharyngitis/tonsilitis, and uncomplicated skin and skin structure infections.

5 Pharmacology and Biochemistry

5.1 Pharmacology

Dirithromycin is a pro-drug which is converted non-enzymatically during intestinal absorption into the microbiologically active moiety erythromycylamine. Erythromycylamine exerts its activity by binding to the 50S ribosomal subunits of susceptible mircoorganisms resulting in inhibition of protein synthesis. Dirithromycin/erythromycylamine has been shown to be active against most strains of the following microorganisms both in vitro and in clinical infections: Staphylococcus aureus (methicillin-susceptible strains only), Streptococcus pneumoniae, Streptococcus pyogenes, Haemophilus influenzae, Legionella pneumophila, Moraxella catarrhalis, and Mycoplasma pneumoniae.

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

J01FA13 - Dirithromycin

5.4 Absorption, Distribution and Excretion

Absorption

Oral dirithromycin is rapidly absorbed, with an absolute bioavailability of approximately 10%. Dietary fat has little or no effect on the bioavailability of dirithromycin.

5.5 Metabolism/Metabolites

Dirithromycin is converted by nonenzymatic hydrolysis during absorption to the active compound, erythromycylamine. Sixty to 90% of a dose is hydrolyzed to erythromycylamine within 35 minutes after dosing, and conversion is nearly complete after 1.5 hours. Erythromycylamine undergoes little or no hepatic biotransformation. No other metabolites of dirithromycin have been detected in the serum.

5.6 Biological Half-Life

The mean plasma half-life of erythromycylamine was estimated to be about 8 h (2 to 36 h), with a mean urinary terminal elimination half-life of about 44 h (16 to 65 h) in patients with normal renal function.

5.7 Mechanism of Action

Dirithromycin prevents bacteria from growing, by interfering with their protein synthesis. Dirithromycin binds to the 50S subunit of the 70S bacterial ribosome, and thus inhibits the translocation of peptides. Dirithromycin has over 10 times higher affinity to the subunit 50S than erythromycin. In addition, dirithromycin binds simultaneously in to two domains of 23S RNA of the ribosomal subunit 50S, where older macrolides bind only in one. Dirithromycin can also inhibit the formation of ribosomal subunits 50S and 30S.

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