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Cefuroxime Axetil (Ceftin(R)) a Brief Review

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Cefuroxime Axetil (Ceftin(R)) a Brief Review Infectious Diseases in Obstetrics and Gynecology 5:211-214 (1997) (C) 1997 Wiley-Liss, Inc. Cefuroxime Axetil (Ceftin(R)) A Brief Review Rachel Deanne Leder I and Deborah Stier Carson2. 1Pharmacy Practice, St., Louis College of Pharmacy, St. Louis, MO eDepartment of Family Medicine, Medical University of South Carolina, Charleston, SC KEY WORDS cefuroxime axetil; antimicrobial; uncomplicated gonorrhea efuroxime axetil (Ceftin (R), Glaxo Wellcome, tablet. Cefuroxime axetil is converted to the active Research Triangle Park, NC) is the oral pro- moiety, cefuroxime, in less than 3 min once ab- drug formulation of the injectable antibiotic cefu- sorbed. Due to the rapid conversion it is not pos- roxime sodium. It has essentially the same antibac- sible to detect cefuroxime axetil in the systemic terial activity as its parent moiety, making cefurox- circulation. Peak serum concentration achieved af- ime the only second-generation cephalosporin with ter a single 250 mg dose in the fed state is 4.7 both an intravenous and oral formulation. mcg/ml and is reached after 2.1 h post-ingestion. 3 The administration of food with cefuroxime axetil STRUCTURE AND DERIVATION substantially increases its absorption. ,4,s The bio- Cefuroxime axetil is the 1-acetoxyethyl ester of ce- availability was shown to increase from 36% to 52% furoxime. The axetil salt renders the molecule when a 5;00 mg dose was taken in a fasting state more lipophilic, thus allowing enhanced oral ab- compared to being administered after food. s The sorption. Once cefuroxime axetil reaches the in- mechanism for this increased bioavailability is not testinal mucosa and portal blood flow it rapidly un- completely understood. It has been proposed that dergoes de-esterification to yield the active parent food-induced cholecystokinin release which causes compound cefuroxime. the gall bladder to contract and release bile may be responsible for improving absorption. 6 MECHANISM OF ACTION Cefuroxime axetil, as cefuroxime, is approxi- Cefuroxime axetil is a second-generation cephalo- mately 30% protein bound and has a volume of sporin that contains the classic [3-1actam ring struc- distribution of about 17 1. 7 Distribution of this an- ture. Bactericidal activity in vivo is resultant of its tibiotic into body fluids and tissues is variable, binding to essential target proteins, termed the however, it does penetrate well (35-90%) into the penicillin-binding proteins, which are located in tonsil tissue, sinus tissue, and bronchial mucosa. 8 the bacterial cell wall. Inhibition of these proteins Once de-esterified and released into systemic leads to bacterial cell wall elongation and leakage, circulation, cefuroxime is not metabolized further, thus the bacteria are unable to divide and mature, z but is eliminated unchanged in the urine. In pa- tients with normal renal function, the plasma elimi- PHARMACO KI N ETI CS nation half-life after a dose of 500 mg of cefuroxime Cefuroxime axetil is available as a tablet and a fla- is 1.4. h. The elimination half-life increases as the vored suspension. Although the tablets have un- renal function declines. In patients with creatinine dergone three product reformulations in an attempt clearances <10 ml/min the elimination half-life ex- to standardize absorption, the bioavailability issues tends to approximately 16.8 h. 9 Based on these re- have been resolved with the currently marketed suits, it is recommended that the dosing interval be *Correspondence to: Dr. Deborah Stier Carson, Department of Family Medicine, 171 Ashley Avenue, Medical University of South Carolina, Charleston, SC 29425. Received April 1997 Antimicrobial Symposium Accepted 23 June 1997 CEFUROXIME AXETIL (CEFTIN(R)) LEDER AND CARSON TABLE I. Dosage guidelines for renal dysfunction one of the few oral cephalosporins with some ac- tivity against isolates of S. pneumoniae that are in- Estimated creatinine 13 clearance Recommended dosage termediately resistant to penicillin. It also has the that lead to 30-49 ml/min/I.73 m Standard individual dose good activity against pathogens given every 12 h skin and soft tissue infections, including methicil- 10-29 ml/min/I.73 m Standard individual dose lin-sensitive staphylococci and S. pyogenes. The 24 h given every most frequently encountered urinary tract infection < 10 ml/min/I.73 m Standard individual dose given every 48 h pathogens, Escherichia coli, Proteus mirabilis, and Klebsidla pneumoniae, are also susceptible to cefu- aAdapted from Konishi et al. roxime axetil. Cefuroxime axetil has coverage for both the penicillinase-positive and -negative extended in patients with renal dysfunction (see strains of Neisseria gonorrhea, and thus is an alterna- Table 1). tive choice for uncomplicated gonorrhea. It has ac- SIDE EFFECTS AND INTERACTIONS tivity against Borrelia burgdorferi, the bacteria re- sponsible for Lyme disease, and some anaerobic Cefuroxime axetil is associated with a low inci- bacteria such as Peptococcus species. Most strains of dence of adverse effects and is generally well tol- Clostridium difficile and Bacteroides fragilis are resis- erated. The most frequently reported adyerse ef- tant, and therefore render this antibiotic a poor fects are primarily gastrointestinal in nature, in- choice for most obstetric and gynecological surger- cluding diarrhea/loose stools (3.7%), nausea (2.6%), ies.lO, 14 and vomiting (2.6%). 1<11 In clinical trials com- Pseudomonas species, Campylobacter species, Ad- prised of large cohorts of patients (n 912) using netobacter calcoaceticus, most strains of Serratia multiple doses of cefuroximc axetil, only 2.2% of species, Proteus vulgaris, and certain strains of patients discontinued treatment due to adverse re- terococci are resistant to therapy with cefuroxime actions. Of those who discontinued treatment, 85% axetil. 1 Resistance is being reported for some nos- did so because of gastrointestinal complaints. 1 ocomial isolates of Enterobacteriaceae, primarily K. Other occasionally reported adverse events as- pneumoniae and E. coli. This is due to bacterial pro- sociated with cefuroxime axetil include antibiotic- duction of novel plasmid-mediated 13-1actamases. is associated colitis and liver function abnormalities. Hypersensitivity reactions including Stevens- CLINICAL APPLICATIONS Johnson syndrome, erythema multiforme, and toxic Multiple clinical trials have investigated the thera- epidermal necrolysis have been reported rarely peutic efficacy of cefuroxime axetil in upper and during post-marketing surveillance. 1,11 lower respiratory tract infections, uncomplicated Concurrent use of cefuroxime with probenecid urinary tract infections, skin and soft tissue infec- may increase the serum concentration of cefurox- tions, uncomplicated gonorrhea, and early stage ime. Use with warfarin may increase the hypopro- Lyme disease. Although cefuroxime axetil has la- thrombotic effect of the anticoagulant; therefore, beled indications for all of the previously men- closer monitoring of the patient's international nor- tioned infections, 1 it is generally not the preferred malized ratio during cefuroxime therapy is recom- antibiotic for initial treatment since equally effica- mended. 1 cious and less expensive options are available. For general use in obstetrics and gynecological infec- SPECTRUM OF ANTIMICROBIAL ACTIVITY tions, cefuroxime axetil may be considered a useful Cefuroxime axetil has a wide spectrum of bacteri- alternative for treating uncomplicated gonorrhea cidal activity both in vivo and in vitro against many and urinary tract infections (UTIs). It is considered gram-positive bacteria, some gram-negative bacte- safe to use in pregnancy (pregnancy category B). 16 ria, and few anaerobic bacteria. It even covers those strains that produce 13-1actamases. lz It is highly ef- Uncomplicated Gonorrhea fective against many of the common respiratory For treatment of uncomplicated gonorrhea, the pathogens including Streptococcus pneumoniae, Hae- Centers for Disease Control and Prevention (CDC) mophilus influenzae, and Moraxdla catarrhalis. It is recommends ceftriaxone 125 mg IM once plus a 7 212 INFECTIOUS DISEASES IN OBSTETRICS AND GYNECOLOGY CEFUROXIME AXE TIL (CEFTIN(R) LEDER AND CARSON day course of doxycycline for the presumptive con- TABLE 2. Comparison of cost of commonly current infection with Chlamydia. This regimen has prescribed antibiotics used to treat obstetric and a greater than 95% cure rate for anal and genital gynecological infections infections while also achieving cure rates of->90% AWP cost for pharyngeal infections. Another advantage for Daily for 7 day ceftriaxone is it may also abort incubating syphilis, Drug dosage supplyb a concern when treatment is not accompanied by a Amoxicillin 7 day course of doxycycline. Cefuroxime axetil g Generic 250 mg q 8 h $4.41 Amoxil (R) $4.54 as a dose is considered an alternative orally single Clavulanate potassium regimen. However, a single dose of this shorter- -Augmentin (R) 500 mg q 12 h $40.32 acting cephalosporin will not cover incubating Cefaclor syphilis nor C. trachomatis. 17 Clinical trials con- Generic 250 mg q 8 h $40.90 Ceclor(R) $46.49 ducted using 1-1.5 g single doses of cefuroxime Cefuroxime axetiI-Ceftin (R) 250 mg q 12 h $44.94 axetil either alone or in combination with proben- g x dose $12.84 (R) x ecid have produced cure rates of 96-100% in Ceftriaxone-Rocephin 125 mg IM $12.04 Doxycycline-generic 100 mg q 12 h $2.24 gonococcal genitorectal infections in both men and Trimethoprim-sulfamethoxazole women. 18-z4 However, these
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