Chemical structure of erythromycin.
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Erythromycin

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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Warning against using erythromycin while using protease inhibitors or certain other drugs
From AIDS Treatment News, 9/24/04

An article in the September 9, 2004 New England Journal of Medicine reported that patients using the antibiotic erythromycin at the same time as drugs that strongly inhibited cytochrome P-450 3A (CYP3A, an enzyme in the liver that helps remove many drugs from the body) had an increased risk of sudden death from cardiac (heart) causes. But those who used amoxicillin, a different antibiotic, instead of erythromycin, did not have the problem. The authors concluded "concurrent use of erythromycin and strong inhibitors of CYP3A should be avoided."

The patients in this study were using oral erythromycin (not the injected form, which is probably more dangerous because of the higher blood levels reached).

This study of Tennessee Medicaid recipients excluded those with HIV or other life-threatening conditions, so patients taking antiretrovirals were not included. But the mechanism of the drug interaction is well known (inhibition of the enzyme dangerously increases the erythromycin level, which can affect the heart rhythm) and it is clear that HIV protease inhibitors would also be a risk if used at the same time as the erythromycin.

In this study of medical records there were 194 person-years on erythromycin plus strong P-450 3A inhibitors at the same time, and three sudden deaths from cardiac causes. This is statistically significant, despite the small number of deaths, because none or one would have been expected.

Previous use of erythromycin in patients taking the enzyme inhibitors was also checked, and was not a problem. The dangerous blood levels occur when the drugs are used concurrently.

References

(1.) Ray WA, Murray KT, Meredith S, and others. Oral erythromycin and the risk of sudden death from cardiac causes. Nero, England Journal of Medicine. 2004; volume 351, pages 1089-1096.

COPYRIGHT 2004 John S. James
COPYRIGHT 2004 Gale Group

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