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The New Macrolides Azithromycin and Clarithromycin MEGANNE S

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The New Macrolides Azithromycin and Clarithromycin MEGANNE S 31 Articles The New Macrolides Azithromycin and Clarithromycin MEGANNE S. KANATANI, PharmD, Sepulveda, and B. JOSEPH GUGLIELMO, PharmD, San Francisco, California Clarithromycin and azithromycin are among the new generation of macrolides that have recently been approved for use. Compared with currently available antibiotics, these agents may be given less frequently and, in the case of azithromycin, for a shorter duration. In vitro data suggest an antimicro- bial advantage of both clarithromycin and azithromycin against atypical mycobacterial and toxoplas- mal species and possibly Haemophilus influenzae. The cost of both these agents is substantially higher than that of erythromycin and doxycycline, although the convenience of single-dose azithromycin is appealing compared with a 7-day course of doxycycline for chlamydial urethritis and cervicitis. These agents appear to offer advantages over erythromycin in the treatment of Mycobacterium avium-intra- cellulare. Additional data are needed to establish their role in other bacterial infections. (Kanatani MS, Guglielmo BJ: The new macrolides-Azithromycin and clarithromycin. West J Med 1994; 160:31-37) Erythromycin has been widely used in the treatment to erythromycin, whereas azithromycin is a 15-membered of pneumonias, including those caused by atypical compound referred to as an azalide. Structural modifica- organisms such as Legionella pneumophila and Myco- tions prevent their degrading in an acid medium, so both plasma pneumoniae.' Many of these pathogens multiply have a more predictable oral bioavailability. intracellularly and are resistant to standard j-lactam ther- apy. Erythromycin has limitations, a requirement for fre- TABLE 1.-Comparative Pharmacokinetic Variables of quent doses, distressing gastrointestinal side effects, and Erythromycin, Azithromycin, and Clarithromycin* reduced effectiveness after exposure to gastric acid. To improve the spectrum of activity and decrease dis- Drug ond Dose advantages, a new generation of macrolide compounds Erythromycin, Azithromycin, Clorithromycin, has been developed. These include azithromycin, clarith- Variable 500 mg 500 mg 500 mg romycin, roxithromycin, dirithromycin, micocamycin, Oral bioavailability, %t .. 35 ± 25t 37 55 to 68 Taken with food ......... No No Yes and rokitamycin. Azithromycin and clarithromycin have Serum half-life, hr§ ...... 1.5 to 3 11 to 14 4.9 recently been approved by the Food and Drug Admin- Frequency of dosing, istration. Both appear to have more activity against M x/day ............. 4 1 2 pneumoniae, Haemophilus influenzae, and Chlamydia Alter dose in moderate trachomatis, among others, in addition to increased tissue renal failure ........... Yes No Yes or cellular penetration. They require less frequent dosing *From Gilman et aI2; Wilson and van Boxtel3; Neu4; Davey'; Ball"; and Lode.12 tOral bioavailability refers to the fraction of the parent compound that reaches the sys- and may have fewer severe gastrointestinal side effects temic circulation. tEnterc-coated erythromycin base; absorption is dependent on the salt form and tempo- than erythromycin. In this review we summarize the phar- ral relation to meals. macology, spectrum of activity, and clinical use of azith- §The half-life is the time required for the plasma concentration in the body to decline by romycin and clarithromycin. half. Pharmacokinetics Clarithromycin is rapidly absorbed from the gastroin- Azithromycin and clarithromycin are different from testinal tract regardless of when taken and achieves peak the prototypic macrolide, erythromycin (Table 1). Eryth- serum concentrations in two hours. It has a predictable romycin is acid labile. In the stomach, it rapidly decom- rate of absorption, and 55% to 68% is available in the poses to two inactive metabolites, one of which may serum. Food does not influence its bioavailability but contribute to the gastrointestinal side effects. As a result slightly delays the time to peak concentration."35 Cla- of this instability and depending on the salt form, the rate rithromycin is metabolized by the liver. One metabolite, of absorption may be unpredictable (35% ± 25%).23 14-hydroxy-clarithromycin, has at least comparable and Clarithromycin is a 14-membered macrolide similar possibly better antimicrobial activity than the parent com- From the Division of Clinical Pharmacy, University of Califomia, San Francisco, School of Pharmacy. Dr Kanatani is now with the Department of Pharmacy, Depart- ment of Veterans Affairs Medical Center, Sepulveda, Califomia. Reprint requests to B. Joseph Guglielmo, PharmD, Division of Clinical Pharmacy, UCSF School of Pharmacy, Rm C-I152, Box 0622, San Francisco, CA 94143-0622. 32 WJM, January 1994-Vol 160, No. 1 The New Macrolides-Kanatani et al ABBREVIATIONS USED IN TEXT TABLE 2.-In Vitro 90% Minimal Inhibitory Concentrations AIDS = acquired immunodeficiency syndrome (MICd0) of Erythromycin, Azithromycin, and Clarithromycin* CFU = colony-forming units mg/liter MICwo = 90% minimal inhibitory concentration MIC,w Bacteria Erythromycin Azithromycin Clarithromycin Borrelia burgdorferi ....... 0.06 0.015 0.015-0.06 pound.5 The prolonged half-life of both clarithromycin Campylobacterjejuni ..... 1.0 0.12 2.0 and its 14-hydroxy metabolite allows for twice-a-day Chiamydia pneumoniae ... 0.06 0.5 0.007 dosing. The renal clearance of clarithromycin and 14- Chlamydia trachomatis.... 2.0 0.25 0.125 hydroxy-clarithromycin approximates glomerular filtra- Hoemophilus influenzae ... 2.0-8.0 0.25-2.0 2.0-8.0t tion.5 Moderate to severe renal failure alters the clearance Helicobacter pylori........ 0.25 0.25 0.03 Legionella pneumophila ... 2.0 2.0 0.25 of both clarithromycin and its 14-hydroxy metabolite so Moraxella catarrhalis ..... 0.25 0.06 0.12-0.25 that patients with a creatinine clearance of less than 0.50 Mycobacterium avium- ml per second ml per (30 minute) should have doses de- intracellulare....... ....>64 32->64 4-16 creased by half.6 Mycoplasma pneumoniae < 0.01 <0.01 0.5 Azithromycin, like clarithromycin, is readily absorbed Neisseria gonorrhoeae .... 0.25-0.5 0.03-0.06 0.25-0.5 from the gastrointestinal tract and achieves peak serum Staphylococcus aureus .... 0.25 1.0 0.12 levels within two hours. The bioavailability of azithro- Streptococcus mycin is substantially less than that of clarithromycin, pneumoniae ........... 0.015-0.25 0.015-0.25 0.015-0.06 about 37% to 40%. Food will decrease the bioavailability *From Williams16; Brown et al21; Preac-Mursic et a123; Mursic et a124; and Ridgway et al.25 tThe MIC,, of clanthromycin alone; 14-hydroxy, the metabolite, may contrbute to antimi- of azithromycin as much as 50%, so each dose should be crobial activity. taken at least an hour before or two hours after a meal.7-9 It is metabolized by the liver, but unlike clarithromycin, Erythromycin is inactive against most gram-negative its metabolites do not show notable antimicrobial activity. organisms (including Escherichia coli and Salmonella, Azithromycin has an unusually long half-life so that Shigella, and Pseudomonas species). Similarly, both once-a-day dosing is possible. High concentrations are azithromycin and clarithromycin are ineffective against achieved in tissue (skin, lungs, sputum, tonsils, and cer- Pseudomonas species and most aerobic gram-negative vix). The extensive intracellular uptake of azithromycin bacilli, but azithromycin exhibits enhanced activity results in a tissue half-life between two and four days.' In against H influenzae when compared with erythromycin. addition, azithromycin concentrates in polymorphonu- It is unclear whether this increased activity results in a clear leukocytes and phagocytes, suggesting that phago- reliable drug against H influenzae."1 In one study, the per- cytes may play a role in the transport of the drug to the sistence of H influenzae was shown in 5 of 21 patients site(s) of infection.'" The intestinal tract is the major route treated for an exacerbation of acute bronchitis; all 5 of elimination for azithromycin; only 6% to 20% is elim- patients required alternative antibiotic therapy.'7 Clarith- inated renally."",2 Therefore, in patients with mild renal romycin and its 14-hydroxy metabolite also appear to be dysfunction, dose adjustment is not warranted. In patients moderately active against H influenzae.'8 with severe renal dysfunction, however, a decrease in Both azithromycin and clarithromycin show promise dose or frequency of dosing intervals may be indicated. in the treatment of atypical pathogens such as Mycobac- terium avium-intracellulare, Mycobacterium chelonei, Antimicrobial Spectrum Mycobacteriumfortuitum, Borrelia burgdorferi, and Tox- As a class, the macrolide antibiotics, specifically eryth- oplasma gondii. Clarithromycin has been shown to in- romycin, clarithromycin, and azithromycin, exert their hibit M avium-intracellulare at concentrations achieved in antimicrobial activity by binding to the 50S subunit of the both lung tissue and macrophages (90% of minimal in- 70S ribosome, which interferes with protein biosynthesis hibitory concentration [MICj1] = 4 to 16 mg per liter), of susceptible organisms."4"3 Resistance is chromosome with enhanced activity when used in combination with ri- or plasmid mediated. fampin and ethambutol hydrochloride.'920 Azithromycin is Overall, the microbiologic spectrum of the activity of less active than clarithromycin against M avium-intracel- clarithromycin and azithromycin mirrors that of eryth- lulare, whereas other atypical pathogens such as M che- romycin, with increased
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