Molecular structure of amoxicillin
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Amoxicillin (INN) or amoxycillin (former BAN) is a moderate-spectrum β-lactam antibiotic used to treat bacterial infections caused by susceptible microorganisms. It is usually the drug of choice within the class because it is better absorbed, following oral administration, than other beta-lactam antibiotics. Amoxicillin is susceptible to degradation by β-lactamase-producing bacteria, and so may be given with Clavulanic acid to increase its susceptability (see below). It is currently marketed by GlaxoSmithKline under the trade name Amoxil®. more...

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Mode of action

Amoxicillin acts by inhibiting the synthesis of bacterial cell walls. It inhibits cross-linkage between the linear peptidoglycan polymer chains that make up a major component of the cell wall of Gram-positive bacteria.

Microbiology

Amoxicillin is a moderate-spectrum antibiotic active against a wide range of Gram-positive, and a limited range of Gram-negative organisms. Some examples of susceptible and resistant organisms, from the Amoxil® Approved Product Information (GSK, 2003), are listed below.

Susceptible Gram-positive organisms

Streptococcus spp., Diplococcus pneumoniae, non β-lactamase-producing Staphylococcus spp., and Streptococcus faecalis.

Susceptible Gram-negative organisms

Haemophilus influenzae, Neisseria gonorrhoeae, Neisseria meningitidis, Escherichia coli, Proteus mirabilis and Salmonella spp.

Resistant organisms

Penicillinase producing organisms, particularly penicillinase producing Staphylococcus spp. Penicillinase-producing N. gonorrhoeae and H. influenzae are also resistant

All strains of Pseudomonas spp., Klebsiella spp., Enterobacter spp., indole-positive Proteus spp., Serratia marcescens, and Citrobacter spp. are resistant.

The incidence of β-lactamase-producing resistant organisms, including E. coli, appears to be increasing.

Doubling the routinely given concentration (in pediatrics) of amoxicillin has been shown to eradicate intermediately resistant organisms (Red Book, 2003 Report of the Committee on Infectious Diseases, American Academy of Pediatrics).

Formulations

Amoxicillin in trihydrate form is avaialable as capsules or syrup for oral use, and as the sodium salt for intravenous administration.

Amoxicillin and Clavulanic acid

Amoxicillin (in either trihydrate or sodium salt forms) may be combined with Clavulanic acid (as potassium clavulanate), a β-lactamase inhibitor, to increase the spectrum of action against Gram-negative organisms, and to overcome bacterial antibiotic resistance mediated through β-lactamase production. This formulation is referred to as Co-amoxiclav (British Approved Name), but more commonly by proprietary names such as Augmentin® and Clamoxyl®.

Proprietary Preparations

The patent for amoxicillin has expired. Thus amoxicillin is marketed under many trade names including: Actimoxi®, Amoxibiotic®, Amoxicilina®, Pamoxicillin®, Lamoxy®, Ospamox®, Polymox®, Trimox®, Tolodina®, Wymox® and Zimox®.

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Medication errors
From American Family Physician, 6/1/92 by Peter H. Rheinstein

Mistakes are, unfortunately, a part of every human activity, including health care. Throughout the course of any drug therapy, medication mishaps can occur at different stages of the process, such as prescribing, dispensing, administering or monitoring. The causes of errors include deficient knowledge of the product, poor communication with the patient, similarities in product names, ambiguous directions for drug use, unclear medical abbreviations, poor handwriting and similarities in product appearance. The wrong bottle may be pulled from the pharmacy shelf, a drug order may be transcribed incorrectly or a drug label may give insufficient prominence to product potency or may inadequately describe potency. Medical personnel may be prone to error because of fatigue and job stress, faulty institutional procedures and techniques, and inadequate training. Any health care professional may cause or contribute to a medication error.

On March 31, 1992, Dateline NBC, a national television news show, reported on patient injuries and deaths from medication errors caused by health care personnel. The U.S. Food and Drug Administration receives reports of medication errors through its drug experience and drug quality reporting systems, as well as the agency's Medical Advertising Information Line. However, many medication errors probably go undetected. The clinical significance of most such errors is minimal, with little or no adverse consequence to the patient. Some medication errors, however, result in great patient morbidity or even mortality. Medication errors also may compromise patient confidence in the health care system and increase health care costs.

Lidocaine (Xylocaine) has been involved in several serious medication errors. Administered for cardiac arrhythmias, lidocaine is packaged in 1- and 2-g prefilled syringes (20 percent lidocaine intended for dilution in an intravenous bottle or bag). Health care professionals have accidentally used these high-potency syringes instead of the 2 percent lidocaine prefilled syringe (100 mg) as bolus injections to stop ventricular arrhythmias.

In response to reports of patient deaths due to improper lidocaine administration, the FDA in 1987 asked its Anesthesia and Life Support Drugs Advisory Committee whether the high-potency syringes (20 percent) were too dangerous to keep on the market because of the confusion with the low-potency syringes (2 percent). The advisory committee concluded that high-potency syringes were necessary to provide physicians with dosage flexibility. The committee advised that the possibility of errors should be addressed through education and, perhaps, changes in packaging, but not only by eliminating an important therapeutic option.

Lidocaine is only one of a number of substances available in high-potency prefilled syringes. These syringes carry warnings that the contents must be diluted before use. In recent years, manufacturers of these products have added a "hood" to the syringe. This hood is a plastic shield or adapter that surrounds the needle, permitting injection into the port of an intravenous bag but preventing direct venous injection or injection into intravenous tubing. Unfortunately, hoods do not prevent injection into the injection ports on some intravenous tubing sets. In some instances, health professionals have removed the hoods and have then made the mistake of administering a direct infusion of concentrated lidocaine. Special adapters should never be removed from prefilled syringes, and the presence of such an adapter should serve as notice that the contents of the syringe are for a special purpose.

Prescriptions and hospital orders are early points at which medication errors can arise. One common problem for physicians is unfamiliarity with the medication ordering systems in different organized health care settings. Physicians must become thoroughly familiar with the drug formulary system, the extent to which delegation of authority is allowed, standard medication times and approved abbreviations.

Recently, the Washington state legislature considered a bill that would have required standardized labeling, including color coding, for certain injectable drug products. However, the bill was not passed. If labeling is to be standardized, the process should probably be handled at the national level after research to discover whether such a system would have a beneficial, detrimental or null effect on the rate of medication error. In response to the proposed Washington state bill, the pharmaceutical industry established the Committee to Reduce Medication Errors-Injectables to examine ways of improving pharmaceutical packaging in an effort to reduce the error rate. Earlier this year, that committee produced a report discussing ways to make labels on injectable drugs easier to read.

The FDA and the United States Pharmacopeia (USP) are both involved in establishing requirements for the labeling of injectable drugs. A new USP requirement for potassium chloride (injection concentrate) took effect on May 15, 1992. As of this date, the words "must be diluted" must appear on the container cap and the overseal, in a color that stands out from the background. In addition, the statement "must be diluted" must be imprinted printed on the label. As of January 15, 1993, the container cap and overseal of the container must be black. These steps are being instituted as the result of many cases of medication error involving this product.

Earlier this year, the USP began the Medication Error Reporting (MER) program in conjunction with the Institute for Safe Medication Practices. This program focuses on product design and characteristics. The MER program offers a 24-hour toll-free telephone line (800-23-ERROR) with an answering device that provides a series of instructions to the caller filing a report. Reports may also be submitted in writing to the USP, Drug Problem Reporting Director, 12601 Twinbrook Pkwy., Rockville, MD 20852. Errors or near-errors that have been reported through the program include the administration of the wrong drug or strength or dose, confusion over look-alike or sound-alike drugs, incorrect routes of administration, miscalculations and prescribing and transcribing errors.

In addition to the USP program, the FDA accepts reports of medication errors or potential errors on its toll-free medical advertising information line, 800-AD-USFDA. The FDA is most interested in reports of errors that might be prevented through changes in labeling, packaging, product name or other factors that lie within the agency's regulatory purview. Recent examples are the elimination of numbers from the trade names for transdermal patches such as Transderm V and NitroDur II, because when prescriptions were telephoned to pharmacies or written on inpatient charts, the name of the drug might be misinterpreted as a quantity to be applied.

The FDA receives all medication error reports, whether made initially to the USP or directly to the FDA. One purpose of the toll-free reporting numbers is to identify and reduce risks before errors occur and to publicize the potential for error in an effort to educate health care workers about risks associated with specific products. The agency also works with the pharmaceutical industry to make changes in labeling and packaging of drug products, when design may contribute to medication error. Each report is evaluated for possible agency action or for discussion with a pharmaceutical manufacturer. The FDA's Center for Drug Evaluation and Research has a Labeling and Nomenclature Committee to assist in this process. The FDA's goal is to be a catalyst to reduce and prevent medication errors by seeing that manufacturers name and package their products in ways that minimize confusion and mistakes.

Because of the vast number of drug products on the market, the various routes of administration, the variety of directions for use and the variety and complexity of medication delivery systems, the likelihood of medication error is increasing. Physicians can influence drug product standards and help educate their colleagues by sharing their experiences and observations about risky drug names or procedures.

Health care professionals should exercise continuous care to prevent drug mishaps and to make sure that drugs are used properly. In addition, the FDA welcomes reports from health care professionals about look-alike drug packages, sound-alike drug names and easily confused prescriptions. Table 1 shows examples of products whose names were changed because of look-alike or sound-alike confusion.

COPYRIGHT 1992 American Academy of Family Physicians
COPYRIGHT 2004 Gale Group

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