{{drugbox |
| image=Erythromycin-2D-skeletal.png
| IUPAC_name = <small>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</small>
| CAS_number = 114-07-8
| ATC_prefix=J01
| ATC_suffix=FA01
| PubChem=3255
| DrugBank=APRD00953
| C=37 | H=67 | N=1 | O=13 
| molecular_weight = 733.93 g/mol
| bioavailability = 100%
| protein_bound = 90%
| metabolism = liver (under 5% excreted unchanged)
| elimination_half-life = 1.5 hours
| excretion = bile
| pregnancy_AU = A
| pregnancy_US = B
| pregnancy_category = 
| legal_AU = S4
| legal_US = Rx-only
| routes_of_administration = oral, iv, im
}}
'''Erythromycin''' is a chlamydia, syphilis, acne, and gonorrhea. In structure, this macrocyclic compound contains a 14-membered lactone ring with ten asymmetric centers and two sugars (<small>L</small>-cladinose and <small>D</small>-desoamine), making it a compound very difficult to produce via synthetic methods.

Erythromycin is produced from a strain of the actinomycete ''Saccharopolyspora 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'' (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 Philippine region of Iloilo where it was originally collected from). Erythromycin was formerly also called '''Ilotycin'''. 

In 1981, Nobel laureate (1965 in chemistry) and Professor of Chemistry at Robert B. Woodward, along with a large number of members from his research group, posthumously reported the first stereocontrolled asymmetric chemical synthesis of Erythromycin A.

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.

== 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, PCE Dispertab, Stiemycine and Acnasol.

== Mechanism of action ==
Erythromycin may possess bacteriocidal activity, particularly at higher concentrations<ref>Katzung PHARMACOLOGY, 9e Section VIII. Chemotherapeutic Drugs Chapter 44.
Chloramphenicol, Tetracyclines, Macrolides, Clindamycin, & Streptogramins</ref>. The mechanism is not fully elucidated however. By binding to the 50S subunit of the bacterial 70S rRNA complex, protein synthesis and subsequently structure/function processes critical for life or replication are inhibited<ref>Katzung PHARMACOLOGY, 9e Section VIII. Chemotherapeutic Drugs Chapter 44.
Chloramphenicol, Tetracyclines, Macrolides, Clindamycin, & Streptogramins</ref>. 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 and 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 and is therefore the basis of antimicrobial action.

== Pharmacokinetics ==
Erythromycin is easily inactivated by gastric acid; therefore, all orally-administered formulations are given as either enteric-coated or more-stable laxatives 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. Its main elimination route is in the bile, and a small portion in the urine. Erythromycin's elimination half-life is 1.5 hours.

== Adverse 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. 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.<ref name="BCFI">[http://www.bcfi.be/GGR/MPG/MPG_HABA.cfm Erythromycin]. Belgian Center for Pharmacotherapeutical Information. Retrieved July 20, 2008.</ref>

{{Geneesmiddel
| naam = 
| afbeelding = Erythromycin-2D-skeletal.png
| onderschrift = 
| width = 300
| IUPAC_naam = 6-(4-dimethylamino-3-hydroxy- 6-methyl-oxan-2-yl)oxy-14-ethyl-7,12,13-trihydroxy-  -(5-hydroxy-4-methoxy-4,6-dimethyl-oxan-2-yl)oxy- 3,5,7,9,11,13-hexamethyl- 1-oxacyclotetradecaan-2,10-dion
| beschikbaarheid = 
| metabolisatie = Hepatisch
| halfwaardetijd = 
| excretie = Biliair
| groep = Antibacteriële middelen
| subklasse = Macroliden
| merknamen = Erythrocine, Erythroforte, Benzamycin, Acneryne, Aknemycin, Inderm, Stimycine, Zineryt
| indicaties = Bacteriële infectie, acne
| voorschrift = Vereist
| toediening = iv, im
| dosering = 
| zwangerschap = B (VS), A (AUS)
| lactatie = 
| rijvaardigheid = 
| alcohol = 
| voeding = 
| overdosis = 
| CAS_number = 114-07-8
| ATC_prefix = J01
| ATC_suffix = FA01
| PubChem = 3255
| DrugBank = APRD00953
| repertorium = 
| chemische_formule = C<sub>37</sub>H<sub>67</sub>N<sub>1</sub>O<sub>13</sub>
| moleculair_gewicht = 733,93
| smeltpunt = 
| kleur = 
| oplosbaarheid = 
| dichtheid = 
| aggregatietoestand = 
}}
'''Erytromycine''' is een antibioticum behorend tot de groep der macroliden. Het heeft een breed werkingsspectrum tegen vele Gram-positieve microorganismen en wordt gebruikt bij de behandeling van luchtweginfecties,met name bij mensen die overgevoelig zijn voor penicillines. Daarnaast kunnen atypische pneumonieën, huidinfecties en ''Campylobacter'' gastro-enteritis met erytromycine behandeld worden. Een bijwerking van erytromycine is versterking van de maagdarmmotiliteit, welke gebruikt kan worden om de maaglediging te bevorderen. 

Een nadeel is dat deze maaglediging vrij vaak de verkeerde kant op gaat (overgeven), een ander dat het middel drie maal daags moet worden gegeven. Andere macroliden azithromycine, clarithromycine hebben deze nadelen minder maar zijn duurder. 