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Alpharma Brand Of Roxithromycin

Alpharma Brand of Roxithromycin

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Also known as: Roxithromycin, 80214-83-1, Roxithromycine, Roxithromycinum, Roxitromicina, Ru 965

Molecular Formula

C₄₁H₇₆N₂O₁₅

Molecular Weight

837.0 g/mol

InChI Key

RXZBMPWDPOLZGW-XMRMVWPWSA-N

FDA UNII

21KOF230FA

Semisynthetic derivative of erythromycin. It is concentrated by human phagocytes and is bioactive intracellularly. While the drug is active against a wide spectrum of pathogens, it is particularly effective in the treatment of respiratory and genital tract infections.

1 2D Structure

Alpharma Brand of Roxithromycin

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

(3R,4S,5S,6R,7R,9R,10E,11S,12R,13S,14R)-6-[(2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy-14-ethyl-7,12,13-trihydroxy-4-[(2R,4R,5S,6S)-5-hydroxy-4-methoxy-4,6-dimethyloxan-2-yl]oxy-10-(2-methoxyethoxymethoxyimino)-3,5,7,9,11,13-hexamethyl-oxacyclotetradecan-2-one

2.1.2 InChI

InChI=1S/C41H76N2O15/c1-15-29-41(10,49)34(45)24(4)31(42-53-21-52-17-16-50-13)22(2)19-39(8,48)36(58-38-32(44)28(43(11)12)18-23(3)54-38)25(5)33(26(6)37(47)56-29)57-30-20-40(9,51-14)35(46)27(7)55-30/h22-30,32-36,38,44-46,48-49H,15-21H2,1-14H3/b42-31+/t22-,23-,24+,25+,26-,27+,28+,29-,30+,32-,33+,34-,35+,36-,38+,39-,40-,41-/m1/s1

2.1.3 InChI Key

RXZBMPWDPOLZGW-XMRMVWPWSA-N

2.1.4 Canonical SMILES

CCC1C(C(C(C(=NOCOCCOC)C(CC(C(C(C(C(C(=O)O1)C)OC2CC(C(C(O2)C)O)(C)OC)C)OC3C(C(CC(O3)C)N(C)C)O)(C)O)C)C)O)(C)O

2.1.5 Isomeric SMILES

CC[C@@H]1[C@@]([C@@H]([C@H](/C(=N/OCOCCOC)/[C@@H](C[C@@]([C@@H]([C@H]([C@@H]([C@H](C(=O)O1)C)O[C@H]2C[C@@]([C@H]([C@@H](O2)C)O)(C)OC)C)O[C@H]3[C@@H]([C@H](C[C@H](O3)C)N(C)C)O)(C)O)C)C)O)(C)O

2.2 Other Identifiers

2.2.1 UNII

21KOF230FA

2.3 Synonyms

2.3.1 MeSH Synonyms

1. Biaxsig

2. Claramid

3. Infectoroxit

4. Macrosil

5. Mtw-roxithromycin

6. Rotesan

7. Rotramin

8. Roxi 1a Pharma

9. Roxi Basics

10. Roxi Tad

11. Roxi Von Ct

12. Roxi-paed 1a Pharma

13. Roxi-puren

14. Roxi-q

15. Roxi-saar

16. Roxi-wolff

17. Roxibeta

18. Roxidura

19. Roxigamma

20. Roxigrn

21. Roxihexal

22. Roxithro-lich

23. Roxithromycin

24. Ru 28965

25. Ru 965

26. Ru-28965

27. Ru-965

28. Ru28965

29. Ru965

30. Rulid

2.3.2 Depositor-Supplied Synonyms

1. Roxithromycin

2. 80214-83-1

3. Roxithromycine

4. Roxithromycinum

5. Roxitromicina

6. Ru 965

7. Ru 28965

8. Ru-965

9. Rulid

10. Chebi:48935

11. Nsc-758443

12. Erythromycin 9-(o-((2-methoxyethoxy)methyl)oxime)

13. 21kof230fa

14. Ru-28965

15. 9-(o-((2-methoxyethoxy)methyl)oxime)erythromycin

16. (9e)-erythromycin 9-(o-((2-methoxyethoxy)methyl)oxime)

17. (e)-roxithromycin

18. Roxithromycine [french]

19. Roxithromycinum [latin]

20. Roxitromicina [spanish]

21. (3r,4s,5s,6r,7r,9r,11s,12r,13s,14r,e)-6-(((2s,3r,4s,6r)-4-(dimethylamino)-3-hydroxy-6-methyltetrahydro-2h-pyran-2-yl)oxy)-14-ethyl-7,12,13-trihydroxy-4-(((2r,4r,5s,6s)-5-hydroxy-4-methoxy-4,6-dimethyltetrahydro-2h-pyran-2-yl)oxy)-10-(((2-methoxyethoxy)methoxy)imino)-3,5,7,9,11,13-hexamethyloxacyclotetradecan-2-one

22. Rulide (tn)

23. 9-[o-[(2-methoxyethoxy)methyl]oxime]erythromycin

24. Sr-05000001850

25. Chebi:48844

26. Unii-21kof230fa

27. Erythromycin, 9-(o-((2-methoxyethoxy)methyl)oxime), (9e)-

28. Ccris 3461

29. Roxithromycin,(s)

30. (3r,4s,5s,6r,7r,9r,10e,11s,12r,13s,14r)-6-[(2s,3r,4s,6r)-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy-14-ethyl-7,12,13-trihydroxy-4-[(2r,4r,5s,6s)-5-hydroxy-4-methoxy-4,6-dimethyloxan-2-yl]oxy-10

31. Roxithromycin [usan:inn:ban:jan]

32. Rc2952

33. Brn 4286925

34. Spectrum5_001058

35. Roxithromycin [mi]

36. Roxithromycin [inn]

37. Roxithromycin [jan]

38. Roxithromycin [usan]

39. Schembl65985

40. Bspbio_002717

41. Roxithromycin [mart.]

42. Spectrum1503276

43. 9-[o-(2-methoxyethoxymethyl)-oxime] Of Erythromycin

44. Erythromycin, 9-(o-((2-methoxyethoxy)methyl)oxime)

45. Roxithromycin [who-dd]

46. Chembl1214185

47. Hms501d04

48. Hms1922o19

49. Hms2093c11

50. Hms3714l09

51. Pharmakon1600-01503276

52. Roxithromycin (jp17/usan/inn)

53. Roxithromycin [ep Impurity]

54. Hy-b0435

55. Roxithromycin [ep Monograph]

56. Bdbm50248154

57. Ccg-39329

58. Mfcd00214389

59. Nsc758443

60. Zinc96061888

61. Akos015969730

62. Db00778

63. Nsc 758443

64. Idi1_000382

65. Ncgc00178510-01

66. Roxithromycin 100 Microg/ml In Methanol

67. (3r,4s,5s,6r,7r,9r,10e,11s,12r,13s,14r)-6-[(2s,3r,4s,6r)-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy-14-ethyl-7,12,13-trihydroxy-4-[(2r,4r,5s,6s)-5-hydroxy-4-methoxy-4,6-dimethyloxan-2-yl]oxy-10-(2-methoxyethoxymethoxyimino)-3,5,7,9,11,13-hexamethyl-oxacyclotetradecan-2-one

68. Roxithromycin 1000 Microg/ml In Methanol

69. Sbi-0051809.p002

70. Roxithromycin 100 Microg/ml In Acetonitrile

71. D01710

72. Ab00052342_02

73. Sr-05000001850-1

74. Sr-05000001850-2

75. Brd-k38684403-001-03-9

76. Brd-k38684403-001-05-4

77. Q27895851

78. 9-[o-[(2-methoxyethoxy)methyl]oxime]erythromycin, (9e)-

79. (e)-erythromycin-9-(o-((2-methoxyethoxy)methyl)oxime)

80. Erythromycin 9-(e)-(o-((2-methoxyethoxy)methyl)oxime)

81. Erythromycin A, 9-(o-(2-methoxyethoxymethyl)-oxime)

82. (3r,4s,5s,6r,7r,9r,10e,11s,12r,13s,14r)-4-(2,6-dideoxy-3-c-methyl-3-o-methyl-alpha-l-ribo-hexopyranosyloxy)-14-ethyl-7,12,13-trihydroxy-10-{[(2-methoxyethoxy)methoxy]imino}-6-[3,4,6-trideoxy-3-(dimethylamino)-beta-d-xylo-hexopyranosyloxy]-3,5,7,9,11,13-hexamethyloxacyclotetradecan-2-one

83. (3r,4s,5s,6r,7r,9r,10e,11s,12r,13s,14r)-6-[(2s,3r,4s,6r)-4-(dimethylamino)-3-hydroxy-6-methyl-tetrahydropyran-2-yl]oxy-14-ethyl-7,12,13-trihydroxy-4-[(2r,4r,5s,6s)-5-hydroxy-4-methoxy-4,6-dimethyl-tetrahydropyran-2-yl]oxy-10-(2-methoxyethoxymethoxyimino)-3,5,7,9,11,13-hexamethyl-oxacyclotetradecan-2-one

84. (3r,4s,5s,6r,7r,9r,10e,11s,12r,13s,14r)-6-{[(2s,3r,4s,6r)-4-(dimethylamino)-3-hydroxy-6-methyltetrahydro-2h-pyran-2-yl]oxy}-14-ethyl-7,12,13-trihydroxy-4-{[(2r,4r,5s,6s)-5-hydroxy-4-methoxy-4,6-dimethyltetrahydro-2h-pyran-2-yl]oxy}-10-{[(2-methoxyethoxy)m

85. (3r,4s,5s,6r,7r,9r,10e,11s,12r,13s,14r)-6-{[(2s,3r,4s,6r)-4-(dimethylamino)-3-hydroxy-6-methyltetrahydro-2h-pyran-2-yl]oxy}-14-ethyl-7,12,13-trihydroxy-4-{[(2r,4r,5s,6s)-5-hydroxy-4-methoxy-4,6-dimethyltetrahydro-2h-pyran-2-yl]oxy}-10-{[(2-methoxyethoxy)methoxy]imino}-3,5,7,9,11,13-hexamethyloxacyclotetradecan-2-one

86. (3r,4s,5s,6r,7r,9r,10e,11s,12r,13s,14r)-6-{[(2s,3r,4s,6r)-4-(dimethylamino)-3-hydroxy-6-methyltetrahydro-2h-pyran-2-yl]oxy}-14-ethyl-7,12,13-trihydroxy-4-{[(2r,4r,5s,6s)-5-hydroxy-4-methoxy-4,6-dimethyltetrahydro-2h-pyran-2-yl]oxy}-3,5,7,9,11,13-hexamethyloxacyclotetradecane-2,10-dione 10-{o-[(2-methoxyethoxy)methyl]oxime} (non-preferred Name)

87. (3r,4s,5s,6r,7r,9r,11s,12r,13s,14r)-4-((2,6dideoxy-3-c-methyl-3-o-methyl-.alpha.-l-ribo-hexopyranosyl)oxy)-14-ethyl-7,12,13-trihydroxy-10-((e)((2-methoxyethoxy)methoxy)imino)-3,5,7,9,11,13hexamethyl-6-((3,4,6-trideoxy-3-(dimethylamino)-.beta.-d-xylohexopyranosyl)oxy)oxacyclotetradecan-2-one

88. (3r,4s,5s,6r,7r,9r,11s,12r,13s,14r)-4-(2,6-dideoxy-3-c-methyl-3-o-methyl-alpha-l-ribo-hexopyranosyloxy)-14-ethyl-7,12,13-trihydroxy-10-{[(2-methoxyethoxy)methoxy]imino}-6-[3,4,6-trideoxy-3-(dimethylamino)-beta-d-xylo-hexopyranosyloxy]-3,5,7,9,11,13-hexamethyloxacyclotetradecan-2-one

89. (3r,4s,5s,6r,7r,9r,11s,12r,13s,14r)-6-{[(2s,3r,4s,6r)-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy}-14-ethyl-7,12,13-trihydroxy-4-{[(2r,4r,5s,6s)-5-hydroxy-4-methoxy-4,6-dimethyloxan-2-yl]oxy}-3,5,7,9,11,13-hexamethyl-10-(2,4,7-trioxa-1-azaoctan-1-ylidene)-1-oxacyclotetradecan-2-one

90. (3r,4s,5s,6r,7r,9r,11s,12r,13s,14r,e)-6-(((2s,3r,6r)-4-(dimethylamino)-3-hydroxy-6-methyltetrahydro-2h-pyran-2-yl)oxy)-14-ethyl-7,12,13-trihydroxy-4-(((2r,4r,5s,6s)-5-hydroxy-4-methoxy-4,6-dimethyltetrahydro-2h-pyran-2-yl)oxy)-10-(((2-methoxyethoxy)methoxy)imino)-3,5,7,9,11,13-hexamethyloxacyclotetradecan-2-one

2.4 Create Date

2006-07-15

3 Chemical and Physical Properties

Molecular Formula	C₄₁H₇₆N₂O₁₅
Molecular Weight	837.0 g/mol
XLogP3	3.1
Hydrogen Bond Donor Count	5
Hydrogen Bond Acceptor Count	17
Rotatable Bond Count	13
Exact Mass	836.52456972 g/mol
Monoisotopic Mass	836.52456972 g/mol
Topological Polar Surface Area	217 Å²
Heavy Atom Count	58
Formal Charge	0
Complexity	1310
Isotope Atom Count	0
Defined Atom Stereocenter Count	18
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	1
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

4 Drug and Medication Information

4.1 Drug Indication

Used to treat respiratory tract, urinary and soft tissue infections.

5 Pharmacology and Biochemistry

5.1 Pharmacology

Roxithromycin has the following antibacterial spectrum in vitro: Streptococcus agalactiae, Streptococcus pneumoniae (Pneumococcus), Neisseria meningitides (Meningococcus), Listeria monocytogenes, Mycoplasma pneumoniae, Chlamydia trachomatis, Ureaplasma urealyticum, Legionella pneumophila, Helicobacter (Campylobacter), Gardnerella vaginalis, Bordetella pertussis, Moraxella catarrhalis (Branhamella Catarrhalis), and Haemophilus ducreyi. Roxithromycin is highly concentrated in polymorphonuclear leukocytes and macrophages, achieving intracellular concentrations greater than those outside the cell. Roxithromycin enhances the adhesive and chemotactic functions of these cells which in the presence of infection produce phagocytosis and bacterial lysis. Roxithromycin also possesses intracellular bactericidal activity.

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

J01FA06 - Roxithromycin

5.4 Absorption, Distribution and Excretion

Absorption

Very rapidly absorbed and diffused into most tissues and phagocytes.

5.5 Metabolism/Metabolites

Hepatic. Roxithromycin is only partially metabolised, more than half the parent compound being excreted unchanged. Three metabolites have been identified in urine and faeces: the major metabolite is descladinose roxithromycin, with N-mono and N-di-demethyl roxithromycin as minor metabolites. The respective percentage of roxithromycin and these three metabolites is similar in urine and faeces.

5.6 Biological Half-Life

12 hours

5.7 Mechanism of Action

Roxithromycin prevents bacterial growth by interfering with their protein synthesis. It binds to the 50S subunit of bacterial ribosomes and inhibits the translocation of peptides.