Erythromycin
Systematic (IUPAC) name
6-(4-dimethylamino-3-hydroxy-6-methyl-oxan-2-yl)oxy-14-ethyl-7,12,13-trihydroxy- 4-(5-hydroxy-4-methoxy-4,6-dimethyl-oxan-2-yl)oxy-3,5,7,9,11,13-hexamethyl- 1-oxacyclotetradecane-2,10-dione Image File history File links Download high-resolution version (1100x1081, 85 KB) File links The following pages on the English Wikipedia link to this file (pages on other projects are not listed): Erythromycin ... IUPAC nomenclature is a system of naming chemical compounds and of describing the science of chemistry in general. ...
Identifiers
CAS number	114-07-8
ATC code	J01FA01
PubChem	3255
DrugBank	APRD00953
Chemical data
Formula	C37H67NO13
Mol. mass	733.93 g/mol
Pharmacokinetic data
Bioavailability	100%
Protein binding	90%
Metabolism	liver (under 5% excreted unchanged)
Half life	1.5 hours
Excretion	bile
Therapeutic considerations
Pregnancy cat.	A(AU) B(US) CAS registry numbers are unique numerical identifiers for chemical compounds, polymers, biological sequences, mixtures and alloys. ... The Anatomical Therapeutic Chemical Classification System is used for the classification of drugs. ... A section of the Anatomical Therapeutic Chemical Classification System. ... PubChem is a database of chemical molecules. ... The DrugBank database available at the University of Alberta is a unique bioinformatics and cheminformatics resource that combines detailed drug (i. ... This article or section does not cite any references or sources. ... General Name, symbol, number carbon, C, 6 Chemical series nonmetals Group, period, block 14, 2, p Appearance black (graphite) colorless (diamond) Standard atomic weight 12. ... General Name, Symbol, Number hydrogen, H, 1 Chemical series nonmetals Group, Period, Block 1, 1, s Appearance colorless Atomic mass 1. ... General Name, Symbol, Number nitrogen, N, 7 Chemical series nonmetals Group, Period, Block 15, 2, p Appearance colorless gas Standard atomic weight 14. ... General Name, Symbol, Number oxygen, O, 8 Chemical series nonmetals, chalcogens Group, Period, Block 16, 2, p Appearance colorless (gas) very pale blue (liquid) Standard atomic weight 15. ... The molecular mass (abbreviated Mr) of a substance, formerly also called molecular weight and abbreviated as MW, is the mass of one molecule of that substance, relative to the unified atomic mass unit u (equal to 1/12 the mass of one atom of carbon-12). ... In pharmacology, bioavailability is used to describe the fraction of an administered dose of unchanged drug that reaches the systemic circulation, one of the principal pharmacokinetic properties of drugs. ... A drugs efficacy may be affected by the degree to which it binds to the proteins within blood plasma. ... Drug metabolism is the metabolism of drugs, their biochemical modification or degradation, usually through specialized enzymatic systems. ... It has been suggested that Effective half-life be merged into this article or section. ... Excretion is the process of eliminating waste products of metabolism and other materials that are of no use. ... The pregnancy category of a pharmaceutical agent is an assessment of the risk of fetal injury due to the pharmaceutical, if it is used as directed by the mother during pregnancy. ... For other uses, see Australia (disambiguation). ... Motto: (Out Of Many, One) (traditional) In God We Trust (1956 to date) Anthem: The Star-Spangled Banner Capital Washington D.C. Largest city New York City None at federal level (English de facto) Government Federal constitutional republic  - President George Walker Bush (R)  - Vice President Dick Cheney (R) Independence from...
Legal status	Prescription Only (S4)(AU) ℞-only(US) The regulation of therapeutic goods, that is drugs and therapeutic devices, varies by jurisdiction. ... The Standard for the Uniform Scheduling of Drugs and Poisons, abbreviated SUSDP, is a document used in the regulation of drugs and poisons in Australia. ... For other uses, see Australia (disambiguation). ... A prescription drug is a licensed medicine that is regulated by legislation to require a prescription before it can be obtained. ... Motto: (Out Of Many, One) (traditional) In God We Trust (1956 to date) Anthem: The Star-Spangled Banner Capital Washington D.C. Largest city New York City None at federal level (English de facto) Government Federal constitutional republic  - President George Walker Bush (R)  - Vice President Dick Cheney (R) Independence from...
Routes	oral, iv, im

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 and Legionellosis. It is also used to treat outbreaks of chlamydia, syphilis, acne 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. In pharmacology and toxicology, a route of administration is the path by which a drug, fluid, poison or other substance is brought into contact with the body 1. ... An intravenous drip in a hospital Intravenous therapy or IV therapy is the administration of liquid substances directly into a vein. ... Intramuscular injection is an injection of a substance directly into a muscle. ... The macrolides are a group of drugs (typically antibiotics) whose activity stems from the presence of a macrolide ring, a large lactone ring to which one or more deoxy sugars, usually cladinose and desosamine, are attached. ... Staphylococcus aureus - Antibiotics test plate. ... Penicillin nucleus Penicillin (sometimes abbreviated PCN) refers to a group of beta-lactam antibiotics used in the treatment of bacterial infections caused by susceptible, usually Gram-positive, organisms. ... An allergy is an abnormal, acquired sensitivity to a given substance, including pollen, drugs, or numerous environmental triggers. ... Species M. genitalium M. hominis M. pneumoniae etc. ... Legionellosis is an infection caused by the genus of Gram negative bacteria Legionella, notably Legionella pneumophila. ... Chlamydia is a common term for infection with any bacterium belonging to the phylum Chlamydiae. ... Syphilis is a sexually transmitted disease caused by Treponema pallidum. ... Gonorrhea (gonorrhoea in British English) is amongst the most common sexually transmitted diseases in the world and is caused by Gram-negative bacterium Neisseria gonorrheae. ... A lactone is a cyclic ester in organic chemistry. ...

Erythromycin is produced from a strain of the actinomycete Saccharopolyspora erythraea, formerly known as Streptomyces erythraeus. Orders Subclass Acidimicrobidae     Acidimicrobiales Subclass Actinobacteridae     Actinomycetales     Bifidobacteriales Subclass Coriobacteridae     Coriobacteriales Subclass Rubrobacteridae     Rubrobacterales Subclass Sphaerobacteridae     Sphaerobacterales The Actinobacteria or Actinomycetes are a group of Gram-positive bacteria. ...

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 (designation changed to "Saccharopolyspora erythraea") found in the samples. Eli Lilly and Company (NYSE: LLY) is a global pharmaceutical company and one of the worlds largest corporations. ... 1949 (MCMXLIX) was a common year starting on Saturday (the link is to a full 1949 calendar). ...

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 from). Erythromycin was formerly also called Ilotycin. Year 1952 (MCMLII) was a leap year starting on Tuesday (link will display full calendar) of the Gregorian calendar. ... Iloilo is a province of the Philippines located in the Western Visayas region. ...

In 1981, Nobel laureate (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. Harvard University (incorporated as The President and Fellows of Harvard College) is a private university in Cambridge, Massachusetts, USA and a member of the Ivy League. ... Harvard Square, May 2000 Cambridge is a city in the greater Boston area in Massachusetts, United States. ... Robert Burns Woodward (April 10, 1917–July 8, 1979) was an American organic chemist. ...

The antiobiotic 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. Clarithromycin is a macrolide antibiotic used to treat pharyngitis, tonsillitis, acute maxillary sinusitis, acute bacterial exacerbation of chronic bronchitis, pneumonia (especially atypical pneumonias associated with Chlamydia pneumoniae or TWAR), skin and skin structure infections, and, in HIV and AIDS patients to prevent, and to treat, disseminated Mycobacterium avium complex (MAC). ... Taisho Pharmaceutical is a Japanese drug company based in Tokyo. ...

Available forms

Erythromycin is available in enteric-coated tablets, slow release capsules, oral suspensions, ophthalmic solutions, ointments, gels and injections.

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, Erypar, EryPed, Eryped 200, Eryped 400, Erythrocin Stearate Filmtab, Erythrocot, E-Base, Erythroped, Ilosone, MY-E, Pediamycin, Zineryt, Abboticin, Abboticin-ES, Erycin and PCE Dispertab.

Mechanism of action

Erythromycin prevents bacteria from growing by interfering with their protein synthesis. Erythromycin binds to the 23S rRNA molecule in the 50S of the bacterial ribosome, blocking the exit of the growing peptide chain thus inhibiting the translocation of peptides. Phyla/Divisions Actinobacteria Aquificae Bacteroidetes/Chlorobi Chlamydiae/Verrucomicrobia Chloroflexi Chrysiogenetes Cyanobacteria Deferribacteres Deinococcus-Thermus Dictyoglomi Fibrobacteres/Acidobacteria Firmicutes Fusobacteria Gemmatimonadetes Nitrospirae Omnibacteria Planctomycetes Proteobacteria Spirochaetes Thermodesulfobacteria Thermomicrobia Thermotogae Bacteria (singular, bacterium) are a major group of living organisms. ... An overview of protein synthesis. ... Figure 1: Ribosome structure indicating small subunit (A) and large subunit (B). ... Peptides (from the Greek πεπτος, digestible), are the family of short molecules formed from the linking, in a defined order, of various α-amino acids. ...

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, such as erythromycin ethylsuccinate. 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. A carboxylic acid ester. ... Succinate is the anion of succinic acid. ... A phagocyte is a cell that ingests and destroys foreign matter such as microorganisms or debris via a process known as phagocytosis. ...

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 elimination half-life is 1.5 hours. Demethylation is the chemical process resulting in the removal a methyl group (CH3) from a molecule. ... The liver is an organ present in vertebrates and some other animals. ... Bile (or gall) is a bitter, yellow or green alkaline fluid secreted by hepatocytes from the liver of most vertebrates. ... This article or section is in need of attention from an expert on the subject. ... The elimination half-life of a drug (or any xenobiotic agent) refers to the timecourse necessary for the quantity of the xenobiotic agent in the body (or plasma concentration) to be reduced to half of its original level through various elimination processes. ...

Side-effects

Erythromycin inhibits the cytochrome P450 system, particularly CYP3A4, which can cause it to affect the metabolism of many different drugs. If CYP3A4 substrates such as simvastatin (Zocor), lovastatin (Mevacor) or atorvastatin (Lipitor) are taken concomitantly with erythromycin, levels of the substrates will increase, often causing adverse effects. A noted drug interaction involves erythromycin and simvastatin, resulting in increased simvastatin levels and the potential for rhabdomyolysis. Cytochrome P450 Oxidase (CYP2E1) Cytochrome P450 oxidase (commonly abbreviated CYP) is a generic term for a large number of related, but distinct, oxidative enzymes (EC 1. ... Simvastatin (INN) (IPA: ) is a hypolipidemic drug belonging to the class of pharmaceuticals called statins. It is used to control hypercholesterolemia (elevated cholesterol levels) and to prevent cardiovascular disease. ... Lovastatin is a member of the drug class of statins, used for lowering cholesterol (hypolipidemic agent) in those with hypercholesterolemia and so preventing cardiovascular disease. ... Atorvastatin (INN) (IPA: ) is a member of the drug class known as statins, used for lowering cholesterol and thereby reducing cardiovascular disease. ...

Gastrointestinal disturbances such as diarrhea, nausea, abdominal pain and vomiting are fairly common so it tends not to be prescribed as a first-line drug. However, erythromycin may be useful in treating gastroparesis due to this pro-motility effect. Intravenous erythromycin may also be used in endoscopy as an adjunct to clear gastric contents. Types 5-7 on the Bristol Stool Chart are often associated with diarrhea Diarrhea (in American English) or diarrhoea (in British English) is a condition in which the sufferer has frequent watery, loose bowel movements (from the Greek word διάρροια; literally meaning through-flowing). Acute infectious diarrhea is a common cause... For other uses, see Nausea (disambiguation). ... Abdominal pain can be one of the symptoms associated with transient disorders or serious disease. ... Vomiting (also throwing up or emesis) is the forceful expulsion of the contents of ones stomach through the mouth and sometimes the nose. ... Gastroparesis, also called delayed gastric emptying, is a disorder in which the stomach takes too long to empty its contents. ... Endoscopic still of esophageal ulcers seen after banding of esophageal varices, at time of esophagogastroduodenosocopy In medicine (gastroenterology), esophagogastroduodenoscopy is a diagnostic endoscopic procedure that visualises the upper part of the gastrointestinal tract up to the duodenum. ... In anatomy, the stomach is a bean-shaped hollow muscular organ of the gastrointestinal tract involved in the second phase of digestion, following mastication. ...

More serious side-effects, such as arrhythmia, reversible deafness are rare. Allergic reactions, while uncommon, may occur, ranging from urticaria to anaphylaxis. Cholestasis, Stevens-Johnson syndrome and toxic epidermal necrolysis are some other rare side effects that may occur. A cardiac arrhythmia, also called cardiac dysrhythmia, is a disturbance in the regular rhythm of the heartbeat. ... This article discusses the way the word deaf is used and how deafness is perceived by hearing and Deaf communities. ... Anaphylaxis is an acute systemic (multi-system) and severe Type I Hypersensitivity allergic reaction in humans and other mammals. ... In medicine, cholestasis is a condition where bile cannot flow from the liver to the duodenum. ... Stevens-Johnson syndrome (SJS) is a severe and life-threatening condition. ... Toxic epidermal necrolysis is a life-threatening and usually drug-induced dermatological condition that occurs more often in women than in men. ...

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. Infantile pyloric stenosis is a pediatric condition where there is a congenital narrowing of the pylorus (the opening at the lower end of the stomach). ...

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). Ventricular tachycardia (V-tach or VT) is a fast rhythm that originates in one of the ventricles of the heart. ... Verapamil (brand names: Isoptin®, Verelan®, Calan®) is a medical drug that acts as an L-type calcium channel blocker. ... Diltiazem is a member of the group of drugs known as Benzothiapines , which are a class of calcium channel blockers, used in the treatment of hypertension, angina pectoris, and some types of arrhythmia. ... Cytochrome P450 3A4 (abbreviated CYP3A4) (EC 1. ... Schematic representation of normal ECG trace (sinus rhythm), with waves, segments, and intervals labeled. ... Terfenadine is an antihistamine formerly used for the treatment of allergic conditions. ... Astemizole is a second generation antihistamine that has a long duration of action. ... Cisapride is a parasympathomimetic which acts as a serotonin 5-HT4 agonist. ... Pimozide (sold as Orap®) is an antipsychotic drug. ...

References

• Ray WA, Murray KT, Meredith S, Narasimhulu SS, Hall K, Stein CM. Oral Erythromycin and the Risk of Sudden Death from Cardiac Causes. N Engl J Med 2004;351:1089-96.
• British National Formulary "BNF 49" March 2005.

The New England Journal of Medicine (NEJM) is a peer-reviewed medical journal published by the Massachusetts Medical Society. ...

External links

• U.S. Patent 2,653,899