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).

Amoxicillin and Clavulanic acid

Amoxicillin is sometimes combined with clavulanic acid, 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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Penicillins
From Gale Encyclopedia of Medicine, 4/6/01 by Nancy Ross-Flanigan

Definition

Penicillins are medicines that kill bacteria or prevent their growth.

Purpose

Penicillins are antibiotics (medicines used to treat infections caused by microorganisms). There are several types of penicillins, each used to treat different kinds of infections, such as skin infections, dental infections, ear infections, respiratory tract infections, urinary tract infections, gonorrhea, and other infections caused by bacteria. These drugs will not work for colds, flu, and other infections caused by viruses.

Description

Examples of penicillins are penicillin V (Beepen-VK, Pen-Vee K, V-cillin K, Veetids) and amoxicillin (Amoxil, Polymox, Trimox, Wymox). Penicillins are sometimes combined with other ingredients called beta-lactamase inhibitors, which protect the penicillin from bacterial enzymes that may destroy it before it can do its work. The drug Augmentin, for example, contains a combination of amoxicillin and a beta-lactamase inhibitor, clavulanic acid.

Penicillins are available only with a physician's prescription. They are sold in capsule, tablet (regular and chewable), liquid, and injectable forms.

Recommended dosage

The recommended dosage depends on the type of penicillin, the strength of the medicine, and the medical problem for which it is being taken. Check with the physician who prescribed the drug or the pharmacist who filled the prescription for the correct dosage.

Always take penicillins exactly as directed. Never take larger, smaller, more frequent, or less frequent doses. To make sure the infection clears up completely, take the medicine for as long as it has been prescribed. Do not stop taking the drug just because symptoms begin to improve. This is important with all types of infections, but it is especially important with "strep" infections, which can lead to serious heart problems if they are not cleared up completely.

Take this medicine only for the infection for which it was prescribed. Different kinds of penicillins cannot be substituted for one another. Do not save some of the medicine to use on future infections. It may not be the right treatment for other kinds of infections, even if the symptoms are the same.

Penicillins work best when they are at constant levels in the blood. To help keep levels constant, take the medicine in doses spaced evenly through the day and night. Do not miss any doses.

Some penicillins, notably penicillin V, should be taken on an empty stomach, but others may be taken with food. Check package directions or ask the physician or pharmacist for instructions on how to take the medicine.

Precautions

Symptoms should begin to improve within a few days of beginning to take this medicine. If they do not, or if they get worse, check with the physician who prescribed the medicine.

Penicillins may cause diarrhea. Certain diarrhea medicines may make the problem worse. Check with a physician before using any diarrhea medicine to treat diarrhea caused by taking penicillin. If diarrhea is severe, check with a physician as soon as possible. This could be a sign of a serious side effect.

Penicillins may change the results of some medical tests. Before having medical tests, patients who are taking penicillin should be sure to let the physician in charge know that they are taking this medicine.

Special conditions

People with certain medical conditions or who are taking certain other medicines can have problems if they take penicillins. Before taking these drugs, be sure to let the physician know about any of these conditions:

Allergies

People who have hay fever, asthma, eczema, or other general allergies (or who have had such allergies in the past) may be more likely to have severe reactions to penicillins. They should be sure their health care provider knows about their allergies.

Anyone who has had unusual reactions to penicillins or cephalosporins in the past should let his or her physician know before taking the drugs again. The physician should also be told about any allergies to foods, dyes, preservatives, or other substances.

Low-sodium diet

Some penicillin medicines contain large enough amounts of sodium to cause problems for people on low-sodium diets. Anyone on such a diet should make sure that the physician treating the infection knows about the special diet.

Diabetes

Penicillins may cause false positive results on urine sugar tests for diabetes. People with diabetes should check with their physicians to see if they need to change their diet or the doses of their diabetes medicine.

Phenylketonuria

Some formulations of Augmentin contain phenylalanine. People with phenylketonuria (PKU) should consult a physician before taking this medicine.

Other medical conditions

Before using penicillins, people with any of these medical problems should make sure their physicians are aware of their conditions:

  • Bleeding problems
  • Congestive heart failure
  • Cystic fibrosis
  • Kidney disease
  • Mononucleosis ("mono")
  • Stomach or intestinal problems, especially ulcerative colitis.
Use of certain medicines

Taking penicillins with certain other drugs may affect the way the drugs work or may increase the chance of side effects.

Side effects

The most common side effects are mild diarrhea, headache, vaginal itching and discharge, sore mouth or tongue, or white patches in the mouth or on the tongue. These problems usually go away as the body adjusts to the drug and do not require medical treatment unless they continue or they are bothersome.

More serious side effects are not common, but may occur. If any of the following side effects occur, get emergency medical help immediately:

  • Breathing problems, such as shortness of breath or fast or irregular breathing
  • Fever
  • Sudden lightheadedness or faintness
  • Joint pain
  • Skin rash, hives, itching, or red, scaly skin
  • Swelling or puffiness in the face.

Other rare side effects may occur. Anyone who has unusual symptoms after taking penicillin should get in touch with his or her physician.

Interactions

Birth control pills may not work properly when taken at the same time as penicillin. To prevent pregnancy, use additional methods of birth control while taking penicillin, such as latex condoms or spermicide.

Penicillins may interact with many other medicines. When this happens, the effects of one or both of the drugs may change or the risk of side effects may be greater. Anyone who takes penicillin should let the physician know all other medicines he or she is taking. Among the drugs that may interact with penicillins are:

  • Acetaminophen (Tylenol) and other medicines that relieve pain and inflammation
  • Medicine for overactive thyroid
  • Male hormones (androgens)
  • Female hormones (estrogens)
  • Other antibiotics
  • Blood thinners
  • Disulfiram (Antabuse), used to treat alcohol abuse
  • Antiseizure medicines such as Depakote and Depakene
  • Blood pressure drugs such as Capoten, Monopril, and Lotensin.

The list above does not include every drug that may interact with penicillins. Be sure to check with a physician or pharmacist before combining penicillins with any other prescription or nonprescription (over-the-counter) medicine.

Key Terms

Enzyme
A type of protein that brings about or speeds up chemical reactions.
Microorganism
An organism that is too small to be seen with the naked eye.
Mononucleosis
An infectious disease with symptoms that include severe fatigue, fever, sore throat, and swollen lymph nodes in the neck and armpits. Also called "mono."

Further Reading

Gale Encyclopedia of Medicine. Gale Research, 1999.

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