Erythromycin

Erythromycin

Clinical data
Trade names	Eryc, Erythrocin, others
AHFS/Drugs.com	Monograph
MedlinePlus	a682381
Pregnancy category	AU: A US: B (No risk in non-human studies)
Routes of administration	by mouth, IV, IM, topical, eye drops
ATC code	D10AF02 (WHO) J01FA01 (WHO) S01AA17 (WHO) QJ51FA01 (WHO)
Legal status
Legal status	AU: S4 (Prescription only) UK: POM (Prescription only) US: ℞-only
Pharmacokinetic data
Bioavailability	Depends on the ester type between 30% - 65%
Protein binding	90%
Metabolism	liver (under 5% excreted unchanged)
Biological half-life	1.5 hours
Excretion	bile
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	114-07-8 Y
PubChem CID	3255
IUPHAR/BPS	1456
DrugBank	DB00199 Y
ChemSpider	12041 Y
UNII	63937KV33D
KEGG	D00140 Y
ChEBI	CHEBI:42355 Y
ChEMBL	CHEMBL532 Y
ECHA InfoCard	100.003.673
Chemical and physical data
Formula	C37H67NO13
Molar mass	733.94 g·mol−1
3D model (Jmol)	Interactive image
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

Erythromycin is an antibiotic useful for the treatment of a number of bacterial infections. This includes respiratory tract infections, skin infections, chlamydia infections, and syphilis. It may also be used during pregnancy to prevent in the newborn. Erythromycin may be used to improve delayed stomach emptying. It can be given intravenously and by mouth. An eye ointment is routinely recommended after delivery to prevent eye infections in the newborn.

Common side effects include abdominal cramps, vomiting, and diarrhea. More serious side effects may include Clostridium difficile colitis, liver problems, prolonged QT, and allergic reactions. It is generally safe in those who are allergic to penicillin. Erythromycin also appears to be safe to use during pregnancy. 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. This risk also applies if taken directly by the baby during this age. It is in the macrolide family and works by decreasing bacterial protein production.

Erythromycin was first isolated in 1952 from the bacteria Saccharopolyspora erythraea. It is on the World Health Organization's List of Essential Medicines, the most effective and safe medicines needed in a health system. It is available as a generic medication and is not very expensive. The wholesale price in the developing world is between 0.03 and 0.06 USD per tablet.