Roxithromycin is a semisynthetic macrolide antibiotic and is sparingly soluble in aqueous solution ( 0.019 mg/mL).
| Mechanism of Action | Macrolide antibiotics inhibit bacterial growth by targeting the 50S ribosomal subunit preventing peptide bond formation and translocation during protein synthesis. Resistance to roxithromycin is commonly attributed to mutations in 50S rRNA preventing roxithromycin binding allowing the cell to synthesize proteins free of error. |
| Spectrum | Roxithromycin is a broad spectrum antibiotic targeting a wide range of gram positive and gram negative bacteria especially those which cause respiratory and urinary tract infections. |
| Impurity Profile | Impurity A| (3R,4S,5S,6R,7R,9R,11R,12R,13S,14R)-4-[(2,6-dideoxy-3-C-methyl-3-O-methyl-汐-l-ribo-hexopyranosyl)oxy]-14-ethyl-7,12,13-trihydroxy-3,5,7,9,11,13-hexamethyl-6-[[3,4,6-trideoxy-3-(dimethylamino)-汕-d-xylo-hexopyranosyl]oxy]oxacyclotetradecane-2,10-dione (erythromycin A)|7540-22-9|C37H67NO13|733.93| Impurity B| 3-O-de(2,6-dideoxy-3-C-methyl-3-O-methyl-汐-l-ribo-hexopyranosyl)erythromycin 9-(E)-[O-[(2-methoxyethoxy)methyl]oxime]|214902-82-6|C33H62N2O12|678.85| Impurity C| erythromycin 9-(E)-oxime|13127-18-9|C37H68N2O13|748.94| Impurity D| erythromycin 9-(Z)-[O-[(2-methoxyethoxy)methyl]oxime]||C41H76N2O15|837| Impurity E| 3∩∩-O-demethylerythromycin 9-(E)-[O-[(2-methoxyethoxy)methyl]oxime]||C40H74N2O15|823.02| Impurity F| 3∩-N-demethylerythromycin 9-(E)-[O-[(2-methoxyethoxy)methyl]oxime]|118267-18-8|C40H74N2O15|823.02| Impurity G| erythromycin 9-(E)-[O-[[(2-methoxyethoxy)methoxy]methyl]oxime]|425365-64-6|C42H78N2O16|867.07| Impurity H| 12-deoxyerythromycin 9-(E)-[O-[(2-methoxyethoxy)methyl]oxime]|107749-06-4|C41H76N2O14|821| Impurity I| 2∩-O-[(2-methoxyethoxy)methyl]erythromycin 9-(E)-[O-[(2-methoxyethoxy)methyl]oxime]||C45H85N2O17|926| Impurity J| erythromycin 9-(E)-[O-[(2-chloroethoxy)methyl]oxime]|134834-12-1|C40H73ClN2O14|841.5| Impurity K| erythromycin 9-(E)-[O-[[2-(hydroxymethoxy)ethoxy]methyl]oxime]||C41H76N2O16|837.03| |
| Microbiology Applications | Roxithromycin is commonly used in clinical in vitro microbiological antimicrobial susceptibility tests (panels, discs, and MIC strips) against gram positive and gram negative microbial isolates. Medical microbiologists use AST results to recommend antibiotic treatment options for infected patients. Representative MIC values include:
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| Molecular Formula | C41H76N2O15 |
| References | Lovmar, Martin, and Tanel Tenson. "The Mechanism of Action of Macrolides, Lincosamides and Streptogramin B Reveals the Nascent Peptide Exit Path in the Ribosome."Journal of Molecular Microbiology 330.5 (2003): 1005-014. |
| MIC | Actinomyces israelii| 0.03 - 0.06|| Actinomyces odontolyticus| 0.03 - 0.06|| Anaerobiospirillum succiniciproducens | 4 - >32|| Anaerobiospirillum thomasii | 4 - >32|| Arcanobacterium haemolyticum| ≤0.015 - 0.03|| Arcanobacterium pyogenes| ≤0.015 - 0.03|| Bacteroides fragilis| 0.12 - 16|| Bacteroides gracilis| 0.25 - 4|| Bacteroides tectum | 0.5 - 1|| Bacteroides ureolyticus| 0.125 - 4|| Bilophila wadsworthia| 16 - >32|| Borrelia afzelii| 0.0039 - 0.0625|| Borrelia bissettii | 0.0312|| Borrelia burgdorferi| 0.0019 - 0.0156|| Borrelia burgdorferi S.L.| 0.015 - 0.125|| Borrelia garinii| 0.0039 - 0.0625|| Borrelia valaisiana| 0.0078|| Brevibacterium spp.| ≤0.03 - >128|| Burkholderia mallei| 32|| Chlamydia pneumonia| 0.025 - 2|| Clostridium clostridioforme| 0.5 - >32|| Clostridium difficile| 0.5 - >32|| Clostridium innocuum| 1 - >32|| Clostridium ramosum| 1 - >32|| Corynebacterium afermentans| 0.03 - >128|| Corynebacterium amycolatum| 0.5 - >128|| Corynebacterium jeikeium| 0.25 - >128|| Corynebacterium minutissimum| ≤0.03 - >64|| Corynebacterium pseudodiphtheriticum| ≤0.015 - 16|| Corynebacterium striatum| ≤0.015 - >128|| Corynebacterium urealyticum| ≤0.015 - 128|| Coryneform| 0.03 - >128|| Edwardsiella hoshinae | 32 - ≥128|| Edwardsiella ictaluri | 8 - ≥128|| Edwardsiella tarda| 32 - ≥128|| Enterococcus| 0.03 - ≥512|| Enterococcus faecalis| 0.5|| Enterococcus faecium| 8 - 16|| Erysipelothrix rhusiopathiae| 0.06 - 0.12|| Fusobacterium gonidiaformans | 2 - >32|| Fusobacterium mortiferum| 8 - >32|| Fusobacterium naviforme| 2 - >32|| Fusobacterium necrogenes | 8 - >32|| Fusobacterium necrophorum| 2 - >32|| Fusobacterium nucleatum| 2 - >32|| Fusobacterium nucleatum subsp. animalis | 2 - >32|| Fusobacterium russii | ≤0.015 - >32|| Fusobacterium ulcerans | 8 - >32|| Fusobacterium varium| >32|| Haemolytic streptococci| 0.015 - 16|| Haemophilus influenzae| 0.25 - 64|| Haemophilus spp.| 2 - 32|| Legionella spp.| 0.03 - 0.25|| Listeria monocytogenes| 0.25 - 0.5|| Listeria spp.| 0.25 - 0.5|| Moraxella catarrhalis| ≤0.03 - 4|| Mycobacterium abscessus| 0.25 - >64|| Mycobacterium chelonae| 0.12 - 16|| Mycobacterium fortuitum| 0.12 - >64|| Mycobacterium mucogenicum| ≤0.03 - 0.5|| Mycobacterium peregrinum| 0.12 - 1|| Mycoplasma fermentans| 32 - 64|| Mycoplasma genitalium| ≤0.015|| Mycoplasma hominis| >64|| Mycoplasma penetrans| 0.5|| Mycoplasma pneumonia| 0.0019 - 0.03|| Neisseria cinerea| 2 - 8|| Neisseria lactamica| 4 - 8|| Neisseria meningitidis| 0.06 - 4|| Neisseria mucosa| 0.25 - 16|| Neisseria perflava/sicca| 1 - 16|| Neisseria polysaccharea| 0.06 - 2|| Neisseria spp.| 0.015 - 2|| Oerskovia spp.| 0.03 - >128|| Peptostreptococcus asaccharolyticus| 4 - >32|| Peptostreptococcus magnus| 4 - >32|| Peptostreptococcus micros| 1|| Peptostreptococcus prevotii| 0.03 - >32|| Pneumococci| 0.03 - 128|| Porphyromonas asaccharolytica| 0.03 - 4|| Porphyromonas cangingivalis | 0.03 - 0.25|| Porphyromonas canoris | 0.06 - 0.25|| Porphyromonas cansulci | 0.03 - 0.25|| Porphyromonas circumdentaria | 0.03 - 0.25|| Porphyromonas gingivalis| 0.06 - 0.25|| Porphyromonas levii | 0.03 - 0.25|| Porphyromonas macacae | 0.06 - 0.25|| Prevotella bivia| 0.125 - >32|| Prevotella buccae| 0.25 - 8|| Prevotella denticola| 0.125 - 16|| Prevotella heparinolytica | 0.25 - 0.5|| Prevotella intermedia| 0.03 - 1|| Prevotella loescheii| 0.125 - 16|| Prevotella melaninogenica| 0.125 - 16|| Prevotella oris| 0.25 - 8 || Pseudomonas aeruginosa| 32|| Rhodococcus equi| ≤0.015 - 0.25|| Staphylococci| 0.03 - 128|| Staphylococcus aureus| 0.25 - >128|| Streptococcus agalactiae| 0.06 - >64|| Streptococcus pneumonia| 0.12 - >64|| Streptococcus pyogenes| 0.015 - >64|| Turicella otitidis| 0.03 - >128|| Ureaplasma urealyticum| 0.06 - 0.5|| Veillonella spp.| 0.5 - >32|| |