Chemical structure of erythromycin.
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Eryc

Erythromycin is a macrolide antibiotic which has an antimicrobial spectrum similar to or slightly wider than that of penicillin, and is often used for people who have an allergy to penicillins. For respiratory tract infections, it has better coverage of atypical organisms, including mycoplasma. It is also used to treat outbreaks of chlamydia, syphilis, and gonorrhea. Structurally, this macrocyclic compound contains a 14-membered lactone ring with ten asymmetric centers and two sugars (L-cladinose and D-desoamine), making it a compound very difficult to produce via synthetic methods. more...

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Erythromycin is produced from a strain of the actinomyces Saccaropolyspora erythraea, formerly known as Streptomyces erythraeus.

History

Abelardo Aguilar, a Filipino scientist, sent some soil samples to his employer Eli Lilly in 1949. Eli Lilly’s research team, led by J. M. McGuire, managed to isolate Erythromycin from the metabolic products of a strain of Streptomyces erythreus found in the samples. The product was subsequently launched in 1952 under the brand name Ilosone® (after the Philippine region of Iloilo where it was originally collected from). Erythromycin was formerly also called Ilotycin®. In 1981, Nobel laurate (1965 in chemistry) and Professor of Chemistry at Harvard University (Cambridge, MA) Robert B. Woodward and a large team of researchers reported the first stereocontrolled asymmetric chemical synthesis of Erythromycin A.

Available forms

Erythromycin is available in enteric-coated tablets, oral suspensions, opthalmic solutions, ointments, gels and injections.

Mechanism of action

Erythromycin prevents bacteria from growing, by interfering with their protein synthesis. Erythromycin binds to the subunit 50S of the bacterial ribosome, and thus inhibits the translation of peptides.

Pharmacokinetics

Erythromycin is easily inactivated by gastric acids, therefore all orally administered formulations are given as either enteric coated or as more stable salts or esters. Erythromycin is very rapidly absorbed, and diffused into most tissues and phagocytes. Due to the high concentration in phagocytes, erythromycin is actively transported to the site of infection, where during active phagocytosis, large concentrations of erythromycin are released.

Metabolism

Most of erythromycin is metabolised by demethylation in the liver. Its main elimination route is in the bile, and a small portion in the urine. Erythromycin's half-life is 1.5 hours.

Side-effects

Gastrointestinal intestinal disturbances such as diarrhea, nausea, abdominal pain and vomiting are fairly common so it tends not to be prescribed as a first-line drug. More serious side-effects, such as reversible deafness are rare. Allergic reactions, while uncommon, may occur, ranging from urticaria to anaphylaxis. Cholestatic jaundice, Stevens-Johnson syndrome and toxic epidermal necrolysis are some other rare side effects that may occur.

Erythromycin has been shown to increase the probability of pyloric stenosis in children whose mothers took the drug during the late stages of pregnancy or while nursing.

Contraindications

Earlier case reports on sudden death prompted a study on a large cohort that confirmed a link between erythromycin, ventricular tachycardia and sudden cardiac death in patients also taking drugs that prolong the metabolism of erythromycin (like verapamil or diltiazem) by interfering with CYP3A4 (Ray et al 2004). Hence, erythromycin should not be administered in patients using these drugs, or drugs that also prolong the QT time. Other examples include terfenadine (Seldane, Seldane-D), astemizole (Hismanal), cisapride (Propulsid, withdrawn in many countries for prolonging the QT time) and pimozide (Orap).

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Antigastroesophageal reflux drugs
From Gale Encyclopedia of Medicine, 4/6/01 by Nancy Ross-Flanigan

Definition

These drugs are used to treat gastroesophageal reflux, the backward flow of stomach contents into the esophagus.

Purpose

The drug discussed here, cisapride (Propulsid), is used to treat nighttime heartburn resulting from gastroesophageal reflux disease (GERD). In this condition, food and stomach juices flow backward from the stomach into the esophagus, the part of the digestive tract through which food passes on its way from the mouth to the stomach. Normally, a muscular ring called the lower esophageal sphincter (LES) opens to allow food into the stomach and then closes to prevent the stomach's contents from flowing back into the esophagus. In people with GERD, this muscular ring is either weak or it relaxes at the wrong times. The main symptom is heartburn -- a burning sensation centered behind the breastbone and spreading upward toward the neck and throat.

Cisapride works by strengthening the lower esophageal sphincter and making the stomach empty more quickly. This shortens the amount of time that the esophagus comes in contact with the stomach contents. Other drugs, such as H2-blockers are sometimes prescribed to reduce the amount of acid in the stomach.

Description

Cisapride is available only with a physician's prescription. Cisapride is sold in tablet and liquid forms.

Recommended dosage

The dose depends on the patient. The average dose for adults and children age 12 and over is 5-20 mg taken two to four times a day. The medicine should be taken 15 minutes before meals and at bedtime. For children under 12, the dose is based on body weight and should be determined by the child's physician.

Precautions

This medicine is effective in treating only nighttime heartburn, not daytime heartburn.

Cisapride may increase the effects of alcohol and tranquilizers.

Cisapride has caused dangerous irregular heartbeats in a few people who took it with other medicines. Anyone who takes this drug should let the physician know all other medicines he or she is taking. Patients with heart problems should check with their physicians before taking cisapride.

Anyone who has bleeding, blockage, or leakage in the stomach or intestines should not take cisapride. Cisapride should not be used by anyone who has had an unusual reaction to the drug in the past. In addition, people with any of the following medical problems should make sure their physicians are aware of their conditions:

  • Epilepsy or history of seizures
  • Kidney disease
  • Liver disease.

The effects of taking cisapride during pregnancy have not been fully studied. Women who are pregnant or plan to become pregnant should check with their physicians before taking Cisapride. The drug passes into breast milk and may affect nursing babies. Women who are breastfeeding and need to take this medicine should check with their physicians. Avoiding breastfeeding while taking the drug may be necessary.

Side effects

The most common side effects are abdominal pain, bloating, gas, diarrhea, constipation, nausea, upper respiratory infections, inflammation of the nasal passages and sinuses, headache, and viral infections. Other side effects may occur. Anyone who has unusual or troublesome symptoms after taking this drug should get in touch with his or her physician.

Interactions

Cisapride may interact with a variety of 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 Cisapride should let the physician know all other medicines he or she is taking. Among the drugs that may interact with cisapride are:

  • Antifungal drugs such as ketoconazole (Nizoral), miconazole (Monistat), and fluconazole (Diflucan)
  • Antibiotics such as clarithromycin (Biaxin) and erythromycin (E-Mycin, ERYC)
  • Blood-thinners such as warfarin (Coumadin)
  • H2-blockers such as cimetidine (Tagamet) and ranitidine (Zantac)
  • Tranquilizers such as chlordiazepoxide (Librium), diazepam (Valium), and alprazolam (Xanax).

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

Key Terms

Esophagus
The part of the digestive tract between the pharynx and the stomach. (The pharynx is the space just behind the mouth.)
Inflammation
Pain, redness, swelling, and heat that usually develop in response to injury or illness.

Further Reading

For Your Information

    Organizations

  • National Digestive Diseases Information Clearinghouse. Address: 2 Information Way, Bethesda, MD 20892-3570. nddic@aerie.com. http://www.niddk.nih.gov/Brochures/NDDIC.htm.
  • Pediatric/Adolescent Gastroesophageal Reflux Association Inc. Address: P.O. Box 1153, Germantown, MD 20875-1153. (301) 601-9541. GERGROUP@aol.com. http://www.reflux.org.

    Other

  • Astra Merck Inc. GERD Information Resource Center. http://www.gerd.com.
  • Pharmaceutical Information Network GERD Information Center. http://pharminfo.com/disease/gerd/gerd_info.html

Gale Encyclopedia of Medicine. Gale Research, 1999.

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