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    Roxithromycin

    ACTIVE PHARMA INGREDIENTS

    INTERMEDIATES

    FINISHED DOSAGE FORMULATIONS

    DIGITAL CONTENT

    GLOBAL SALES INFORMATION

    MARKET PLACE

    REF. STANDARDS & IMPURITIES

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    2D Structure
    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

    2D Structure

    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 Weight 837.0 g/mol
    Molecular Formula C41H76N2O15
    XLogP33.1
    Hydrogen Bond Donor Count5
    Hydrogen Bond Acceptor Count17
    Rotatable Bond Count13
    Exact Mass836.52456972 g/mol
    Monoisotopic Mass836.52456972 g/mol
    Topological Polar Surface Area217 Ų
    Heavy Atom Count58
    Formal Charge0
    Complexity1310
    Isotope Atom Count0
    Defined Atom Stereocenter Count18
    Undefined Atom Stereocenter Count0
    Defined Bond Stereocenter Count1
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count1
    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.