Erythromycin

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Erythromycin
Erythromycin A skeletal.svg
Erythromycin 3d structure.png
Clinical data
Trade names Eryc, Erythrocin, others [1]
AHFS/Drugs.com Monograph
MedlinePlus a682381
License data
Pregnancy
category
Routes of
administration 		By mouth, intravenous, intramuscular, topical, eye drops
Drug class Macrolide antibiotic
ATC code
Legal status
Legal status
  • AU: S4 (Prescription only)
  • UK: POM (Prescription only)
  • US: ℞-only
Pharmacokinetic data
Bioavailability Depends on the ester type; between 30% and 65%
Protein binding 90%
Metabolism Liver (under 5% excreted unchanged)
Elimination half-life 1.5 hours
Excretion Bile
Identifiers
  • (3R,4S,5S,6R,7R,9R,11R,12R,13S,14R)-6-{[(2S,3R,4S,6R)-4-(Dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy}-14-ethyl-7,12,13-trihydroxy-4-{[(2R,4R,5S,6S)-5-hydroxy-4-methoxy-4,6-dimethyloxan-2-yl]oxy}-3,5,7,9,11,13-hexamethyl-1-oxacyclotetradecane-2,10-dione
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
PDB ligand
CompTox Dashboard (EPA)
ECHA InfoCard 100.003.673 OOjs UI icon edit-ltr-progressive.svg
Chemical and physical data
Formula C37H67NO13
Molar mass 733.937 g·mol−1
  • CC[C@@H]1[C@@]([C@@H]([C@H](C(=O)[C@@H](C[C@@]([C@@H]([C@H]([C@@H]([C@H](C(=O)O1)C)O[C@H]2C[C@@]([C@H]([C@@H](O2)C)O)(C)OC)C)O[C@H]3[C@@H]([C@H](C[C@H](O3)C)N(C)C)O)(C)O)C)C)O)(C)O
  • InChI=1S/C37H67NO13/c1-14-25-37(10,45)30(41)20(4)27(39)18(2)16-35(8,44)32(51-34-28(40)24(38(11)12)15-19(3)47-34)21(5)29(22(6)33(43)49-25)50-26-17-36(9,46-13)31(42)23(7)48-26/h18-26,28-32,34,40-42,44-45H,14-17H2,1-13H3/t18-,19-,20+,21+,22-,23+,24+,25-,26+,28-,29+,30-,31+,32-,34+,35-,36-,37-/m1/s1 Yes check.svgY
  • Key:ULGZDMOVFRHVEP-RWJQBGPGSA-N Yes check.svgY
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Erythromycin is an antibiotic used for the treatment of a number of bacterial infections. [1] This includes respiratory tract infections, skin infections, chlamydia infections, pelvic inflammatory disease, and syphilis. [1] It may also be used during pregnancy to prevent Group B streptococcal infection in the newborn, [1] and to improve delayed stomach emptying. [3] It can be given intravenously and by mouth. [1] An eye ointment is routinely recommended after delivery to prevent eye infections in the newborn. [4]

Contents

Common side effects include abdominal cramps, vomiting, and diarrhea. [1] More serious side effects may include Clostridioides difficile colitis, liver problems, prolonged QT, and allergic reactions. [1] It is generally safe in those who are allergic to penicillin. [1] Erythromycin also appears to be safe to use during pregnancy. [2] While generally regarded as safe during breastfeeding, its use by the mother during the first two weeks of life may increase the risk of pyloric stenosis in the baby. [5] [6] This risk also applies if taken directly by the baby during this age. [7] It is in the macrolide family of antibiotics and works by decreasing bacterial protein production. [1]

Erythromycin was first isolated in 1952 from the bacteria Saccharopolyspora erythraea . [1] [8] It is on the World Health Organization's List of Essential Medicines. [9] In 2021, it was the 259th most commonly prescribed medication in the United States, with more than 1 million prescriptions. [10] [11]

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: [12]

It may be useful in treating gastroparesis due to this promotility effect. It has been shown to improve feeding intolerances in those who are critically ill. [13] Intravenous erythromycin may also be used in endoscopy to help clear stomach contents to enhance endoscopic visualization, potentially improving diagnostic accuracy and subsequent management. [14]

Available forms

Enteric-coated erythromycin capsule from Abbott Labs 000719lg Enteric coated erythomycin.jpg
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: [15]

For injection, the available combinations are: [15]

For ophthalmic use:

Adverse effects

Gastrointestinal disturbances, such as diarrhea, nausea, abdominal pain, and vomiting, are very common because erythromycin is a motilin agonist. [17]

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 and Stevens–Johnson syndrome are some other rare side effects that may occur. [18]

Studies have shown evidence both for and against the association of pyloric stenosis and exposure to erythromycin prenatally and postnatally. [19] Exposure to erythromycin (especially long courses at antimicrobial doses, and also through breastfeeding) has been linked to an increased probability of pyloric stenosis in young infants. [20] [21] Erythromycin used for feeding intolerance in young infants has not been associated with hypertrophic pyloric stenosis. [20]

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. [22]

It can also affect the central nervous system, causing psychotic reactions, nightmares, and night sweats. [23]

Interactions

Erythromycin is metabolized by enzymes of the cytochrome P450 system, in particular, by isozymes of the CYP3A superfamily. [24] The activity of the CYP3A enzymes can be induced or inhibited by certain drugs (e.g., dexamethasone), which can cause it to affect the metabolism of many different drugs, including erythromycin. If other CYP3A substrates — drugs that are broken down by CYP3A — such as simvastatin (Zocor), lovastatin (Mevacor), or atorvastatin (Lipitor) — are taken concomitantly with erythromycin, levels of the substrates increase, often causing adverse effects. A noted drug interaction involves erythromycin and simvastatin, resulting in increased simvastatin levels and the potential for rhabdomyolysis. Another group of CYP3A4 substrates are drugs used for migraine such as ergotamine and dihydroergotamine; their adverse effects may be more pronounced if erythromycin is associated. [23]

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. [25] 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), [26] astemizole (Hismanal), [27] cisapride [28] (Propulsid, withdrawn in many countries for prolonging the QT time) and pimozide (Orap). [29] Interactions with theophylline, which is used mostly in asthma, were also shown. [30]

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. [31]

It may alter the effectiveness of combined oral contraceptive pills because of its effect on the gut flora. A review found that when erythromycin was given with certain oral contraceptives, there was an increase in the maximum serum concentrations and AUC of estradiol and dienogest. [32] [33]

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. [34]

Pharmacology

Mechanism of action

Erythromycin displays bacteriostatic activity or inhibits growth of bacteria, especially at higher concentrations. [35] By binding to the 50s subunit of the bacterial rRNA complex, protein synthesis and subsequent structure and function processes critical for life or replication are inhibited. [35] 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. [36] 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.[ medical citation needed ] This interferes with the production of functionally useful proteins, which is the basis of this antimicrobial action.[ medical citation needed ]

Erythromycin increases gut motility by binding to motilin receptor, thus it is a motilin receptor agonist in addition to its antimicrobial properties. It can be therefore administered intravenously as a stomach emptying stimulant. [37]

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. [38]

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. [39]

Erythromycin crosses the placenta and enters breast milk. The American Association of Pediatrics determined erythromycin is safe to take while breastfeeding. [40] Absorption in pregnant patients has been shown to be variable, frequently resulting in levels lower than in nonpregnant patients. [41] [19]

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. [12] [42] 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 stereogenic carbons and several points of distinct substitution has made the total synthesis of erythromycin A a formidable task. [43] Complete syntheses of erythromycins’ related structures and precursors such as 6-deoxyerythronolide B have been accomplished, giving way to possible syntheses of different erythromycins and other macrolide antimicrobials. [44] Woodward successfully completed the synthesis of erythromycin A, which was published in 1981. [45] [46] [47]

History

In 1949 Abelardo B. Aguilar, a Filipino scientist, sent some soil samples to his employer at Eli Lilly. [48] Aguilar managed to isolate erythromycin from the metabolic products of a strain of Streptomyces erythreus (designation changed to Saccharopolyspora erythraea ) found in the samples. Aguilar received no further credit or compensation for his discovery. [49]

The scientist was allegedly promised a trip to the company's manufacturing plant in Indianapolis, but it was never fulfilled. In a letter to the company's president, Aguilar wrote: “A leave of absence is all I ask as I do not wish to sever my connection with a great company which has given me wonderful breaks in life.” The request was not granted. [50]

Aguilar reached out to Eli Lilly again in 1993, requesting royalties from sales of the drug over the years, intending to use them to put up a foundation for poor and sickly Filipinos. This request was also denied. He died in September of the same year. [50]

Lilly filed for patent protection on the compound which was granted in 1953. [51] 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.

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. [52]

Society and culture

Economics

It is available as a generic medication. [5]

In the United States, in 2014, the price increased to seven dollars per 500mg tablet. [53]

The US price of erythromycin rose three times between 2010 and 2015, from 24 cents per 500mg tablet in 2010 to $8.96 in 2015. [54] In 2017, a Kaiser Health News study found that the per-unit cost of dozens of generics doubled or even tripled from 2015 to 2016, increasing spending by the Medicaid program. Due to price increases by drug manufacturers, Medicaid paid on average $2,685,330 more for Erythromycin in 2016 compared to 2015 (not including rebates). [55] In the US by 2018, generic drug prices had climbed another 5% on average. [56]

The UK price listed in the BNF for erythromycin 500mg tablets was £36.40 for 100 tablets (36.4 pence each) as of August 2024. This price is not paid by NHS patients: there is no NHS prescription charge in Scotland, Wales, and Northern Ireland; while NHS patients in England without an exemption are liable for a flat rate prescription charge. As of May 2024, that charge was £9.90 for each prescribed medicine. [57]

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.

Veterinary uses

Erythromycin is also used in fishcare for the "broad spectrum treatment and control of bacterial disease". Body slime, mouth fungus, furunculosis, bacterial gill illness, and hemorrhagic septicaemia are all examples of bacterial diseases in fish that may be treated and controlled with this therapy. The usage of Erythromycin in fishcare is mainly limited to therapies targeting gram-positive bacteria. [58]

Related Research Articles

<span class="mw-page-title-main">Antibiotic</span> Antimicrobial substance active against bacteria

An antibiotic is a type of antimicrobial substance active against bacteria. It is the most important type of antibacterial agent for fighting bacterial infections, and antibiotic medications are widely used in the treatment and prevention of such infections. They may either kill or inhibit the growth of bacteria. A limited number of antibiotics also possess antiprotozoal activity. Antibiotics are not effective against viruses such as the ones which cause the common cold or influenza. Drugs which inhibit growth of viruses are termed antiviral drugs or antivirals. Antibiotics are also not effective against fungi. Drugs which inhibit growth of fungi are called antifungal drugs.

<span class="mw-page-title-main">Antimicrobial resistance</span> Resistance of microbes to drugs directed against them

Antimicrobial resistance occurs when microbes evolve mechanisms that protect them from the effects of antimicrobials. All classes of microbes can evolve resistance to the point that one or more drugs used to fight them are no longer effective. Fungi evolve antifungal resistance, viruses evolve antiviral resistance, protozoa evolve antiprotozoal resistance, and bacteria evolve antibiotic resistance. Together all of these come under the umbrella of antimicrobial resistance.

<span class="mw-page-title-main">Ciprofloxacin</span> Fluoroquinolone antibiotic

Ciprofloxacin is a fluoroquinolone antibiotic used to treat a number of bacterial infections. This includes bone and joint infections, intra-abdominal infections, certain types of infectious diarrhea, respiratory tract infections, skin infections, typhoid fever, and urinary tract infections, among others. For some infections it is used in addition to other antibiotics. It can be taken by mouth, as eye drops, as ear drops, or intravenously.

<span class="mw-page-title-main">Macrolide</span> Class of natural products

Macrolides are a class of mostly natural products with a large macrocyclic lactone ring to which one or more deoxy sugars, usually cladinose and desosamine, may be attached. The lactone rings are usually 14-, 15-, or 16-membered. Macrolides belong to the polyketide class of natural products. Some macrolides have antibiotic or antifungal activity and are used as pharmaceutical drugs. Rapamycin is also a macrolide and was originally developed as an antifungal, but has since been used as an immunosuppressant drug and is being investigated as a potential longevity therapeutic.

<span class="mw-page-title-main">Clarithromycin</span> Antibiotic medication

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<span class="mw-page-title-main">Clindamycin</span> Antibiotic

Clindamycin is a lincosamide antibiotic medication used for the treatment of a number of bacterial infections, including osteomyelitis (bone) or joint infections, pelvic inflammatory disease, strep throat, pneumonia, acute otitis media, and endocarditis. It can also be used to treat acne, and some cases of methicillin-resistant Staphylococcus aureus (MRSA). In combination with quinine, it can be used to treat malaria. It is available by mouth, by injection into a vein, and as a cream or a gel to be applied to the skin or in the vagina.

<span class="mw-page-title-main">Azithromycin</span> Antibiotic

Azithromycin, sold under the brand names Zithromax and Azasite, is an antibiotic medication used for the treatment of several bacterial infections. This includes middle ear infections, strep throat, pneumonia, traveler's diarrhea, and certain other intestinal infections. Along with other medications, it may also be used for malaria. It is administered by mouth, into a vein, or into the eye.

<span class="mw-page-title-main">Roxithromycin</span> Chemical compound

Roxithromycin is a semi-synthetic macrolide antibiotic. It is used to treat respiratory tract, urinary and soft tissue infections. Roxithromycin is derived from erythromycin, containing the same 14-membered lactone ring. but with an N-oxime side chain attached to the ring.

<span class="mw-page-title-main">Telithromycin</span> Chemical compound

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<span class="mw-page-title-main">Fusidic acid</span> Antibiotic

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Mycoplasma pneumonia is a form of bacterial pneumonia caused by the bacterium Mycoplasma pneumoniae.

<span class="mw-page-title-main">Ofloxacin</span> Antibiotic to treat bacterial infections

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<span class="mw-page-title-main">Tigecycline</span> Chemical compound

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<span class="mw-page-title-main">Norfloxacin</span> Chemical compound, antibiotic

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<span class="mw-page-title-main">Lincosamides</span> Group of antibiotics

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<span class="mw-page-title-main">Cefoxitin</span> Chemical compound

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<span class="mw-page-title-main">Mitemcinal</span> Chemical compound

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A prokinetic agent is a type of drug which enhances gastrointestinal motility by increasing the frequency or strength of contractions, but without disrupting their rhythm. They are used to treat certain gastrointestinal symptoms, including abdominal discomfort, bloating, constipation, heart burn, nausea, and vomiting; and certain gastrointestinal disorders, including irritable bowel syndrome, gastritis, gastroparesis, and functional dyspepsia.

<span class="mw-page-title-main">Solithromycin</span> Chemical compound

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<span class="mw-page-title-main">Omadacycline</span> Chemical compound

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