Erythromycin

Not to be confused with Azithromycin.

Erythromycin
Above: Erythromycin A molecular structure Below: 3D representation of an erythromycin A molecule
Clinical data
Trade namesEryc, Erythrocin, others[1]
AHFS/Drugs.comMonograph
MedlinePlusa682381
License data
Pregnancy
category
Routes of
administration		By mouth, intravenous, intramuscular, topical, eye drops
Drug classMacrolide antibiotic
ATC code
Legal status
Legal status
  • AU: S4 (Prescription only)
  • UK: POM (Prescription only)
  • US: ℞-only
Pharmacokinetic data
BioavailabilityDepends on the ester type; between 30% and 65%
Protein binding90%
MetabolismLiver (under 5% excreted unchanged)
Elimination half-life1.5 hours
ExcretionBile
Identifiers
IUPAC name
  • (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 InfoCard100.003.673
Chemical and physical data
FormulaC37H67NO13
Molar mass733.937 g·mol−1
SMILES
  • 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
  • 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 Y
  • Key:ULGZDMOVFRHVEP-RWJQBGPGSA-N Y
  (verify)

Erythromycin (sometimes abbreviated ETM in reports)[3] 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.[4] It can be given intravenously and by mouth.[1] An eye ointment is routinely recommended after delivery to prevent eye infections in the newborn.[5]

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.[6][7] This risk also applies if taken directly by the baby during this age.[8] 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][9] It is on the World Health Organization's List of Essential Medicines.[10] In 2022, it was the 271st most commonly prescribed medication in the United States, with more than 800,000 prescriptions.[11][12]

  1. ^ a b c d e f g h i j "Erythromycin". The American Society of Health-System Pharmacists. Archived from the original on 6 September 2015. Retrieved 1 August 2015.
  2. ^ a b "Prescribing medicines in pregnancy database". Australian Government. 23 August 2015. Archived from the original on 8 April 2014.
  3. ^ Logan CM, Rice MK (1987). Logan's Medical and Scientific Abbreviations (Hardbound book). J. B. Lippincott. p. 182. ISBN 0-397-54589-4.
  4. ^ Camilleri M, Parkman HP, Shafi MA, Abell TL, Gerson L (January 2013). "Clinical guideline: management of gastroparesis". The American Journal of Gastroenterology. 108 (1): 18–37, quiz 38. doi:10.1038/ajg.2012.373. PMC 3722580. PMID 23147521.
  5. ^ Matejcek A, Goldman RD (November 2013). "Treatment and prevention of ophthalmia neonatorum". Canadian Family Physician. 59 (11): 1187–90. PMC 3828094. PMID 24235191.
  6. ^ Hamilton RJ (2013). Tarascon pocket pharmacopoeia (2013 delux lab-coat ed., 14th ed.). [Sudbury, Mass.]: Jones & Bartlett Learning. p. 72. ISBN 9781449673611. Archived from the original on 1 August 2020. Retrieved 9 September 2017.
  7. ^ Kong YL, Tey HL (June 2013). "Treatment of acne vulgaris during pregnancy and lactation". Drugs. 73 (8): 779–87. doi:10.1007/s40265-013-0060-0. PMID 23657872. S2CID 45531743.
  8. ^ Maheshwai N (March 2007). "Are young infants treated with erythromycin at risk for developing hypertrophic pyloric stenosis?". Archives of Disease in Childhood. 92 (3): 271–3. doi:10.1136/adc.2006.110007. PMC 2083424. PMID 17337692. Archived from the original on 7 November 2012.
  9. ^ Vedas JC (2000). Biosynthesis : polyketides and vitamins. Berlin [u.a.]: Springer. p. 52. ISBN 9783540669692. Archived from the original on 1 August 2020. Retrieved 9 September 2017.
  10. ^ World Health Organization (2021). World Health Organization model list of essential medicines: 22nd list (2021). Geneva: World Health Organization. hdl:10665/345533. WHO/MHP/HPS/EML/2021.02.
  11. ^ "The Top 300 of 2022". ClinCalc. Archived from the original on 30 August 2024. Retrieved 30 August 2024.
  12. ^ "Erythromycin Drug Usage Statistics, United States, 2013 - 2022". ClinCalc. Retrieved 30 August 2024.
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