File:Erythromycin_A_skeletal.svg · Wikimedia Commons · See Wikimedia Commons
erythromycin
Sign in to saveAlso 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.
OverviewAI-generated
Erythromycin is a chemical compound with the formula C₃₇H₆₇NO₁₃. Its molecular mass is listed as 733.461, while its weight is recorded as 733.9. The substance has a charge of 0.
Chemical properties include an xlogp value of 2.7 and a topological polar surface area of 194. The molecule contains 5 hydrogen bond donors and 14 hydrogen bond acceptors. Its canonical SMILES representation is 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.
The compound is associated with a PubMed query count of 44469. It is referenced by 946 other encyclopedia articles.
Synthesized by Vinony from 15 facts across 4 sources: Wikidata, PubMed, PubChem, Vinony graph. Generated from structured data (not the Wikipedia text) and checked against those facts — may still contain errors.
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 Ų
- 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
- Has use
- antibiotic
Show 11 more facts
- route of administration
- intravenous infusion and defusion
- chemical formula
- C₃₇H₆₇NO₁₃
- significant drug interaction
- tacrolimus
- found in taxon
- Pseudoalteromonas
- medical condition treated
- anthrax
- 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
- has characteristic
- bitterness
- subject has role
- essential medicine
via Wikidata · CC0
~17 min read
Encyclopedic overview
17 sectionsContents
- 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
{{Infobox drug | Watchedfields = changed | verifiedrevid = 464189839 | image = Erythromycin A skeletal.svg | image_class = skin-invert-image | width = 200 | alt = | image2 = Erythromycin A 3D.png | image_class2 = bg-transparent | width2 = | alt2 = | caption = Above: Erythromycin A molecular structure Below: 3D representation of an erythromycin A molecule | pronounce = | tradename = Eryc, Erythrocin, others | Drugs.com = | MedlinePlus = a682381 | DailyMedID = Erythromycin | pregnancy_AU = A | pregnancy_AU_comment = | pregnancy_category = | routes_of_administration = By mouth, intravenous, intramuscular, topical, eye drops | class = Macrolide antibiotic | ATC_prefix = D10 | ATC_suffix = AF02 | ATC_supplemental =
| legal_AU = S4 | legal_AU_comment = | legal_BR = | legal_BR_comment = | legal_CA = | legal_CA_comment = | legal_DE = | legal_DE_comment = | legal_NZ = | legal_NZ_comment = | legal_UK = POM | legal_UK_comment = | legal_US = Rx-only | legal_US_comment = | legal_EU = | legal_EU_comment = | legal_UN = | legal_UN_comment = | legal_status =
Excerpted from Wikipedia’s “erythromycin” article, available under the CC BY-SA 4.0 licence.