Erythromycin ethylsuccinate (CHEM016687)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-22 03:40:31 UTC
Update Date2016-11-09 01:15:27 UTC
Accession NumberCHEM016687
Identification
Common NameErythromycin ethylsuccinate
ClassSmall Molecule
DescriptionErythromycin 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, as well as 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 of antibiotics 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, which lists 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. In 2016, it was the 281st most prescribed medication in the United States, with more than a million prescriptions.
Contaminant Sources
  • ToxCast & Tox21 Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
E.E.S.Kegg
ErypedKegg
Erythrocin WKegg
Erythromycin ethylsuccinic acidGenerator
PediamycinMeSH
Eyrthromycin ethyl succinateMeSH
EMycin eMeSH
Ethylsuccinate, erythromycinMeSH
Ethyl succinate, eyrthromycinMeSH
e-Mycin eMeSH
Succinate, eyrthromycin ethylMeSH
Wyamycin eMeSH
ErythropedMeSH
MonomycinMeSH
Chemical FormulaC43H75NO16
Average Molecular Mass862.064 g/mol
Monoisotopic Mass861.509 g/mol
CAS Registry Number1264-62-6
IUPAC Name(2S,3R,4S,6R)-4-(dimethylamino)-2-{[(3R,4S,5S,6R,7R,9R,11R,12R,13S,14R)-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-2,10-dioxo-1-oxacyclotetradecan-6-yl]oxy}-6-methyloxan-3-yl 1-ethyl butanedioate
Traditional Nameerythromycin ethylsuccinate
SMILES[H][C@@]1(C)C[C@]([H])(N(C)C)[C@@]([H])(OC(=O)CCC(=O)OCC)[C@]([H])(O[C@]2([H])[C@@]([H])(C)[C@]([H])(O[C@@]3([H])C[C@@](C)(OC)[C@@]([H])(O)[C@]([H])(C)O3)[C@@]([H])(C)C(=O)O[C@]([H])(CC)[C@@](C)(O)[C@]([H])(O)[C@@]([H])(C)C(=O)[C@]([H])(C)C[C@@]2(C)O)O1
InChI IdentifierInChI=1S/C43H75NO16/c1-15-29-43(11,52)36(48)24(5)33(47)22(3)20-41(9,51)38(25(6)34(26(7)39(50)57-29)59-32-21-42(10,53-14)37(49)27(8)56-32)60-40-35(28(44(12)13)19-23(4)55-40)58-31(46)18-17-30(45)54-16-2/h22-29,32,34-38,40,48-49,51-52H,15-21H2,1-14H3/t22-,23-,24+,25+,26-,27+,28+,29-,32+,34+,35-,36-,37+,38-,40+,41-,42-,43-/m1/s1
InChI KeyNSYZCCDSJNWWJL-YXOIYICCSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as aminoglycosides. These are molecules or a portion of a molecule composed of amino-modified sugars.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbohydrates and carbohydrate conjugates
Direct ParentAminoglycosides
Alternative Parents
Substituents
  • Aminoglycoside core
  • Macrolide
  • Glycosyl compound
  • O-glycosyl compound
  • Tricarboxylic acid or derivatives
  • Fatty acid ester
  • Fatty acyl
  • Monosaccharide
  • Oxane
  • Tertiary alcohol
  • Amino acid or derivatives
  • Carboxylic acid ester
  • Ketone
  • Lactone
  • Cyclic ketone
  • Secondary alcohol
  • Tertiary aliphatic amine
  • Tertiary amine
  • Organoheterocyclic compound
  • Ether
  • Dialkyl ether
  • Oxacycle
  • Acetal
  • Polyol
  • Carboxylic acid derivative
  • Organic oxide
  • Amine
  • Organopnictogen compound
  • Alcohol
  • Hydrocarbon derivative
  • Organonitrogen compound
  • Organic nitrogen compound
  • Carbonyl group
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.15 g/LALOGPS
logP2.94ALOGPS
logP3.37ChemAxon
logS-3.8ALOGPS
pKa (Strongest Acidic)12.66ChemAxon
pKa (Strongest Basic)7.87ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count14ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area226.28 ŲChemAxon
Rotatable Bond Count14ChemAxon
Refractivity215.6 m³·mol⁻¹ChemAxon
Polarizability92.62 ųChemAxon
Number of Rings3ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00or-0400292360-67f1f63e8243646b74ffSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0690-3300792200-f7ca6db6abf02e9ecc92Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9100320000-10e13d75a9b2afb6ca98Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03dj-1530042590-78e4af62ae182527e022Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004m-2301292520-4ddf5bf740f618ac7917Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0005-6910531400-dcba8d134d89b1118a3cSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDDBSALT001220
HMDB IDNot Available
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkErythromycin
Chemspider IDNot Available
ChEBI IDNot Available
PubChem Compound ID443953
Kegg Compound IDC12796
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General ReferencesNot Available