erythromycin

Also known as Robimycin, C-Solve-2, Ilotycin, Erythra-Derm, Emgel, Pce, Staticin, Erygel

Erythromycin (sometimes abbreviated ETM in reports) is an antibiotic used for the treatment of a number of bacterial infections. This includes respiratory tract infections, skin infections, chlamydia infections, pelvic inflammatory disease, and syphilis. It may also be used during pregnancy to prevent Group B streptococcal infection in the newborn, and 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.

Key facts

Drug.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
Drug.C: 37
Drug.H: 67
Drug.N: 1
Drug.O: 13
Drug.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
Drug.Jmol: none
Drug.StdInChI: 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
Drug.StdInChIKey: ULGZDMOVFRHVEP-RWJQBGPGSA-N
Drug.KEGG: D00140
Drug.ChEBI: 42355
Drug.ChEMBL: 532
Drug.PDB_ligand: ERY
Drug.ATC_suffix: AF02
Drug.legal_AU: S4
Drug.legal_UK: POM
Drug.Watchedfields: changed
Drug.verifiedrevid: 464189839

via Wikipedia infobox

Chemical data

Formula: C37H67NO13
Molecular weight: 733.9 g/mol
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-oxacyclotetradecane-2,10-dione
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
InChIKey: ULGZDMOVFRHVEP-RWJQBGPGSA-N
XLogP: 2.7
Polar surface area: 194 Å²
H-bond donors: 5
H-bond acceptors: 14
Formal charge: 0

via PubChem

Research

44,469 papers

Erythromycin.The Medical clinics of North America · 1987
Erythromycin.The Medical clinics of North America · 1982
Erythromycin, lincomycin, and clindamycin.Pediatric clinics of North America · 1983
Erythromycin.Zentralblatt fur Bakteriologie, Parasitenkunde, Infektionskrankheiten und Hygiene. Zweite naturwissenschaftliche Abt.: Allgemeine, landwirtschaftliche und technische Mikrobiologie · 1972
Erythromycin.Indian pediatrics · 1988

via PubMed

Wikidata facts

Mass: 733.461

Show 5 more facts

chemical formula: C₃₇H₆₇NO₁₃
isomeric 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
canonical SMILES: CCC1C(C(C(C(=O)C(CC(C(C(C(C(C(=O)O1)C)OC2CC(C(C(O2)C)O)(C)OC)C)OC3C(C(CC(O3)C)N(C)C)O)(C)O)C)C)O)(C)O
World Health Organisation international non-proprietary name: erythromycin
Commons category: Erythromycin

Sources (5)

via Wikidata · CC0

~17 min read

Article

17 sections

Contents

Medical uses
Available forms
Adverse effects
Interactions
Pharmacology
Mechanism of action
Pharmacokinetics
Metabolism
Chemistry
Composition
Synthesis
History
Society and culture
Economics
Brand names
Veterinary uses
References

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