Dirithromycin

개요Dirithromycin, an orally active oxazine derivative of erythromycin, is a secondgeneration macrolide antibiotic. It was first introduced in Spain for the treatment of respiratory tract, skin and soft tissue infections. It is safe and effective in treating acute bronchitis, acute bacterial exacerbation of chronic bronchitis, pneumonia, pharyngitis, and tonsillitis. Dirithromycin has been reported to have a similar antimicrobial spectrum and potency to erythromycin. However, compared to other macrolide antibiotics, dirithromycin has improved oral bioavailability, higher tissue permeability and longer duration of action. The once-daily therapy regiment is advantageous in terms of patient compliance and is a good alternative for patients who are unable to take penicillin.

용도Dirithromycin is a macrolide antibiotic pro-drug of 9S-erythromycylamine, a close analogue of erythromycin in which the 9-keto group is replaced with an amino group in the S-configuration. Although erythromycylamine overcomes the acid instability of erythromycin, it is poorly absorbed following oral administration. Dirithromycin is formed by reacting erythromycylamine with an aldehyde to form a Schiff base which undergoes cyclisation to an oxazine with the C11-alcohol. Dirithromycin provides higher tissue levels and prolonged in vivo half-life by slowly releasing erythromycylamine.

일반 설명The incidence and severity of GI adverse effects associatedwith dirithromycin are similar to those seen with oralerythromycin. Preliminary studies indicate that dirithromycinand erythromycyclamine do not interact significantly with cytochromeP450 oxygenases. Thus, the likelihood of interferencein the oxidative metabolism of drugs such as phenytoin,theophylline, and cyclosporine by these enzymes may be lesswith dirithromycin than with erythromycin. Dirithromycin isrecommended as an alternative to erythromycin for the treatmentof bacterial infections of the upper and lower respiratorytracts, such as pharyngitis, tonsillitis, bronchitis, and pneumonia,and for bacterial infections of other soft tissues and theskin. The once-daily dosing schedule for dirithromycin is advantageousin terms of better patient compliance. Its place intherapy remains to be fully assessed.

정의ChEBI: The hemi-aminal resulting from the condensation of the erythromycin derivative (9S)-erythromycyclamine with 2-(2-methoxyethoxy)acetaldehyde. As the oxazine ring containing the hemi-aminal group is unstable under both acidic and alkaline co ditions, dirithromycin functions as a more lipid-soluble prodrug for (9S)-erythromycyclamine. Administered as enteric coated tablets to protect it from acid catalysed hydrolysis in the stomach, it is used to treat respiratory tract, skin, nd soft tissue infections caused by susceptible organisms.