Erythromycin azalide

Azalides azithromycin Azoles fluconazole, itraconazole, ketoconazole, and voriconazole Macrolides erythromycin, clarithromycin Protease inhibitors amprenavir, indinavir, lopinavir/ritonavir, nelfinavir, ritonavir, and saquinavir Quinolones ciprofloxacin, gatifloxacin, levofloxacin, moxifloxacin. 

See section on treatment of bacterial pneumonia. Macrolide/azalide erythromycin, clarithromycin, azithromycin. cTetracydine tetracycline hydrochloride, doxycydine. Cephalosporin cefuroxime, ceftriaxone, cefotaxime. eCarbapenem imipenem-cilastatin, meropenem. Fluoroquinolone ciprofloxacin, gatifloxacin, or levofloxacin. 

Macrolide/azalide erythromycin, clarithromydn-azithromycin. femisynthetic penicillin nafcillin, oxacillin. 

Azithromycin is an azalide antibiotic, a sub-class of the macrolides. Azithromycin differs chemically from erythromycin in that a methyl substituted nitrogen atom is incorporated into the lactone ring. 

Amacher DE, Schomaker SJ, Retsema JA. Comparison of the effects of the new azalide antibiotic, azithromycin, and erythromycin estolate on rat liver cytochrome P-450. Antimicrob Agents Chemother 1991 35(6) 1186-90. 

Azithromycin, an azalide antibiotic and derivative of erythromycin, is a safe and effective alternate treatment of moderate to severe inflammatory acne. With a half-life of 68 hours, it may be intermittently dosed three times a week. One study using pulse therapy, 500 mg daily for 3 to 4 consecutive days every week for 4 weeks, demonstrated efficacy similar to other systemic antibacterial agents. Adherence is high with this regimen, and phototoxicity and resistance have not been reported. ... 

Azalides azithromycin azoies fiuconazoie, itraconazoie, ketoconazoie, and voriconazoie macroiides erythromycin, ciarithromycin protease inhibitors aprenavir, indinavir, iopinavir/ritonavir, neifinavir, ritonavir, and saquinavir quinoiones ciprofioxacin, gatifioxacin, ievofioxacin, moxifioxacin. 

See section on treatment of bacterial pneumonia. Macrolide/azalide erythromycin, clarithromycin-azithromycin. Tetracycline tetracycline HCI, doxycycline. 

Several structural modifications of the C-9 ketone of erythromycin have been explored oximes and hydrazones are less prone to intramolecular cydization, but they often have less antibiotic activity than erythromycin (140). Synthesis of more complex oxime derivatives resulted in the development of roxithromycin, the 9-[0-(2-methoxyethoxy)methyl]oxime (33) (141). Reduction of the oximes and hydrazones produced 9(S)-erythromycylamine (34) as the principal product, with minor amounts of the 9(R)-isomer (140) however, clinical studies showed that 9(5)-erythromycyclamine and its N-benzylidene derivative were poody absorbed in humans (142). Evaluation of more complex oxazine derivatives of erythromycylamine led to dirithromycin, the 2-(2-methoxyethoxy)ethylidene oxazine derivative (35) (143). A third route to modification of the ketone utilized a Beckmann rearrangement of the 9-oxime to expand the 14-membered ring to a 15-membered intermediate, which was subsequently reduced and AT-methylated to yield azithromycin (36) (144,145). The term azalide was proposed to denote these 15-membered azalactones (10,145). 

Azithromycin, called an azalide, has been formed by semisynthetic conversion of erythromycin to a ring-expanded analogue in which an N-methyl group has been inserted between carbons 9 and 10, and the carbonyl moiety thus is absent (Fig. 38.28). Azithromycin has a 15-membered lactone ring. 

Drugs in this class include erythromycin, tylosin, spiramycin, tylvalosin, carbomycin, oleandomycin, tilmi-cosin (all macrolides), azithromycin (an azalide), and... 

Erythromycin, from the actinomycete Saccharo-polyspora (formerly Streptomyces) erythraea, is the first member of this family of antibiotics to be marketed and successfully used clinically to treat infections in humans. It has an antimicrobial spectrum at least as wide as the penicillins, and interestingly, from our perspective, it is often used as a replacement for patients allergic to that group of drags. Besides erythromycin, other members of the macrolide family of antibiotics that are clinically useful include azithromycin, clarithromycin, dirithromycin, roxithromycin, telithromycin (these six are approved by the FDA), oleandomycin, and spiramycin. Clarithromycin, dirithromycin, and roxithromycin and the azalide azithromycin are more recent members of the group and can be regarded as newer generation macrolide antibiotics. 

Fig. 6.1 Structure of the macrolide antibiotic erythromycin (a) which contains a 14-membeied lactone ring. The azalide, azithromycin (b), derived from erythromycin, has an iV-methyl group incorporated into the lactone ring, making it a 15-membered ring (compare highlighted sections)...

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