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Erythromycin is an antibiotic useful for the treatment of a number of bacterial infections.
Common side effects include abdominal cramps, vomiting, and diarrhea.
Erythromycin was first isolated in 1952 from the bacteria Saccharopolyspora erythraea.
Contents
1 Medical uses
1.1 Available forms
2 Adverse effects
3 Interactions
4 Pharmacology
4.1 Mechanism of action
4.2 Pharmacokinetics
4.3 Metabolism
5 Chemistry
5.1 Composition
5.2 Synthesis
5.3 Erythromycin related compounds
6 History
7 Society and culture
7.1 Cost
7.2 Brand names
8 See also
9 References
10 External links
Medical uses
Erythromycin can be used to treat bacteria responsible for causing infections of the skin and upper respiratory tract, including Streptococcus, Staphylococcus, Haemophilus and Corynebacterium genera. The following represents MIC susceptibility data for a few medically significant bacteria:
Haemophilus influenzae : 0.015 to 256 μg/ml
Staphylococcus aureus : 0.023 to 1024 μg/ml
Streptococcus pyogenes : 0.004 to 256 μg/ml
Corynebacterium minutissimum : 0.015 to 64 μg/ml
Available forms
Enteric-coated erythromycin capsule from Abbott Labs
Erythromycin is available in enteric-coated tablets, slow-release capsules, oral suspensions, ophthalmic solutions, ointments, gels, enteric-coated capsules, non enteric-coated tablets, non enteric-coated capsules, and injections.
The following erythromycin combinations are available for oral dosage:
erythromycin base (capsules, tablets)
erythromycin estolate (capsules, oral suspension, tablets), contraindicated during pregnancy
erythromycin ethylsuccinate (oral suspension, tablets)
erythromycin stearate (oral suspension, tablets)
For injection the available combinations are:
erythromycin gluceptate
erythromycin lactobionate
For ophthalmic use
erythromycin base (ointment)
Adverse effects
Gastrointestinal disturbances, such as diarrhea, nausea, abdominal pain, and vomiting, are very common because erythromycin is a motilin agonist. Because of this, erythromycin tends not to be prescribed as a first-line drug. It may be useful in treating gastroparesis due to this promotility effect. Intravenous erythromycin may also be used in endoscopy as an adjunct to clear gastric contents.
More serious side effects include arrhythmia with prolonged QT intervals including torsades de pointes, and reversible deafness. Allergic reactions range from urticaria to anaphylaxis. Cholestasis, Stevens–Johnson syndrome, and toxic epidermal necrolysis are some other rare side effects that may occur.
Studies have shown evidence both for and against the association of pyloric stenosis and exposure to erythromycin prenatally and postnatally.
Erythromycin estolate has been associated with reversible hepatotoxicity in pregnant women in the form of elevated serum glutamic-oxaloacetic transaminase and is not recommended during pregnancy. Some evidence suggests similar hepatotoxicity in other populations.
It can also affect the central nervous system, causing psychotic reactions, nightmares and night sweats.
It may also alter the effectiveness of combined oral contraceptive pills because of its effect on the gut flora. Erythromycin is an inhibitor of the cytochrome P450 system, which means it can have a rapid effect on levels of other drugs metabolised by this system, e.g., warfarin.
Interactions
Erythromycin is metabolized by enzymes of the cytochrome P450 system, in particular, by isozymes of the CYP3A superfamily, CYP3A.
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. Hence, erythromycin should not be administered to people using these drugs, or drugs that also prolong the QT interval. Other examples include terfenadine (Seldane, Seldane-D), astemizole (Hismanal), cisapride (Propulsid, withdrawn in many countries for prolonging the QT time) and pimozide (Orap). Theophylline, which is used mostly in asthma, is also contraindicated.
Erythromycin and doxycycline can have a synergistic effect when combined and kill bacteria ( E. coli) with a higher potency than the sum of the two drugs together. This synergistic relationship is only temporary. After approximately 72 hours, the relationship shifts to become antagonistic, whereby a 50/50 combination of the two drugs kills less bacteria than if the two drugs were administered separately.
Pharmacology
Mechanism of action
Erythromycin displays bacteriostatic activity or inhibits growth of bacteria, especially at higher concentrations, Erythromycin interferes with aminoacyl translocation, preventing the transfer of the tRNA bound at the A site of the rRNA complex to the P site of the rRNA complex. Without this translocation, the A site remains occupied, thus the addition of an incoming tRNA and its attached amino acid to the nascent polypeptide chain is inhibited. This interferes with the production of functionally useful proteins, which is the basis of this antimicrobial action.
Erythromycin increases gut motility by binding to Motillin, thus it is a Motillin receptor agonist in addition to its antimicrobial properties.
Pharmacokinetics
Erythromycin is easily inactivated by gastric acid; therefore, all orally administered formulations are given as either enteric-coated or more-stable salts or esters, such as erythromycin ethylsuccinate. Erythromycin is very rapidly absorbed, and diffuses 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 by the hepatic enzyme CYP3A4. Its main elimination route is in the bile with little renal excretion, 2%-15% unchanged drug. Erythromycin’s elimination half-life ranges between 1.5 and 2.0 hours and is between 5 and 6 hours in patients with end-stage renal disease. Erythromycin levels peak in the serum 4 hours after dosing; ethylsuccinate peaks 0.5-2.5 hours after dosing, but can be delayed if digested with food.
Erythromycin crosses the placenta and enters breast milk. The American Association of Pediatrics determined erythromycin is safe to take while breastfeeding.
Chemistry
Composition
Standard-grade erythromycin is primarily composed of four related compounds known as erythromycins A, B, C, and D. Each of these compounds can be present in varying amounts and can differ by lot. Erythromycin A has been found to have the most antibacterial activity, followed by erythromycin B. Erythromycins C and D are about half as active as erythromycin A. Some of these related compounds have been purified and can be studied and researched individually.
Synthesis
Over the three decades after the discovery of erythromycin A and its activity as an antimicrobial, many attempts were made to synthesize it in the laboratory. The presence of 10 stereospecific carbons and several points of distinct substitution has made the total synthesis of erythromycin A a formidable task.
Erythromycin related compounds
Azithromycin
Carbomycin
Cethromycin
Clarithromycin
Dirithromycin
Mitemcinal
Oleandomycin
Roxithromycin
Spiramycin
Telithromycin
Tylosin
History
Erythromycin was discovered by Abelardo Aguilar when working for the pharmaceutical company Eli Lilly and Company as a researcher.
In 1949 Abelardo B. Aguilar, a Filipino scientist, sent some soil samples to his employer Eli Lilly. Eli Lilly’s research team, led by J. M. McGuire, managed to isolate erythromycin from the metabolic products of a strain of Streptomyces erythreus (designation changed to ” Saccharopolyspora erythraea “) found in the samples.
Lilly filed for patent protection of the compound and U.S. patent 2,653,899 was granted in 1953. The product was launched commercially in 1952 under the brand name Ilosone (after the Philippine region of Iloilo where it was originally collected). Erythromycin was formerly also called Ilotycin.
In 1981, Nobel laureate (1965 in chemistry) and professor of chemistry at Harvard University Robert B. Woodward (posthumously), along with a large number of members from his research group, reported the first stereocontrolled asymmetric chemical synthesis of erythromycin A.
The antibiotic clarithromycin was invented by scientists at the Japanese drug company Taisho Pharmaceutical in the 1970s as a result of their efforts to overcome the acid instability of erythromycin.
Scientists at Chugai Pharmaceuticals discovered an erythromycin-derived motilin agonist called mitemcinal that is believed to have strong prokinetic properties (similar to erythromycin) but lacking antibiotic properties. Erythromycin is commonly used off-label for gastric motility indications such as gastroparesis. If mitemcinal can be shown to be an effective prokinetic agent, it would represent a significant advance in the gastrointestinal field, as treatment with this drug would not carry the risk of unintentional selection for antibiotic-resistant bacteria.
Society and culture
Cost
It is available as a generic medication and was inexpensive for many years.
In the United States in 2014 the price increased to seven dollars per tablet.
The price of Erythromycin rose three times between 2010 and 2015, from 24 cents per tablet in 2010 to $8.96 in 2015.
Brand names
Brand names include Robimycin, E-Mycin, E.E.S. Granules, E.E.S.-200, E.E.S.-400, E.E.S.-400 Filmtab, Erymax, Ery-Tab, Eryc, Ranbaxy, Erypar, EryPed, Eryped 200, Eryped 400, Erythrocin Stearate Filmtab, Erythrocot, E-Base, Erythroped, Ilosone, MY-E, Pediamycin, Zineryt, Abboticin, Abboticin-ES, Erycin, PCE Dispertab, Stiemycine, Acnasol, and Tiloryth.
See also
Erythromycin/tretinoin, a combination of tretinoin and the antibiotic erythromycin

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