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Substance Name: Erythromycin ethylsuccinate [USP:JAN]
RN: 1264-62-6
UNII: 1014KSJ86F
InChIKey: NSYZCCDSJNWWJL-YXOIYICCSA-N

Note

  • A macrolide antibiotic, produced by Streptomyces erythreus. This compound is an ester of erythromycin base and succinic acid. It acts primarily as a bacteriostatic agent. In sensitive organisms, it inhibits protein synthesis by binding to 50S ribosomal subunits. This binding process inhibits peptidyl transferase activity and interferes with translocation of amino acids during translation and assembly of proteins.

Molecular Formula

  • C43-H75-N-O16

Molecular Weight

  • 862.0565
 

Classification Codes

  • Anti-Bacterial Agents
  • Anti-Infective Agents
  • Antibacterial
  • Drug / Therapeutic Agent
  • Enzyme Inhibitors
  • Gastrointestinal Agents
  • Human Data
  • Protein Synthesis Inhibitors
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Names and Synonyms

Name of Substance

  • Erythromycin ethyl succinate
  • Erythromycin ethylsuccinate
  • Erythromycin ethylsuccinate [USP:JAN]

MeSH Heading

  • Erythromycin ethylsuccinate

Synonyms

  • 4-18-00-07416 (Beilstein Handbook Reference)
  • BRN 0077638
  • E-Mycin
  • E-Mycin E
  • E.E.S
  • E.E.S 200
  • E.E.S 400
  • E.E.S.
  • EES
  • EES (Antiobiotic)
  • EES Granules
  • EINECS 215-033-8
  • ERY-PED
  • EryPed
  • Erythrocin ethyl succinate
  • Erythromycin 2'-(ethyl succinate)
  • Erythromycin ethylsuccinate
  • Erythromycin, 2'-(ethyl butanedioate)
  • Erythromycin, ethyl succinate
  • Erythromycin, mono(ethyl succinate)
  • Erythromycin, mono(ethyl succinate) (ester)
  • Erythroped
  • HSDB 3075
  • Pediamycin
  • Pediamycin 400
  • Succinic acid, monoethyl ester, monoester with erythromycin
  • UNII-1014KSJ86F
  • Wyamycin
  • Wyamycin E

Systematic Names

  • Erythromycin 2'-(ethyl butanedioate)
  • Erythromycin ethyl succinate
  • Succinic acid, monoethyl ester, monoester with erythromycin

Mixture Name

  • Pediazole

Registry Numbers

CAS Registry Number

  • 1264-62-6

FDA UNII

  • 1014KSJ86F

Other Registry Numbers

  • 12125-46-1
  • 1334-36-7
  • 1386-36-3
  • 22372-15-2
  • 41342-53-4
  • 68206-56-4
  • 7121-45-1

System Generated Number

  • 0001264626

Structure Descriptors

InChI

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

InChIKey

NSYZCCDSJNWWJL-YXOIYICCSA-N

Smiles

CCOC(=O)CCC(=O)O[C@H]1[C@H](O[C@@H]2[C@@H](C)[C@H](O[C@H]3C[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)O[C@H](C)C[C@@H]1N(C)C

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
child TDLo oral 420mg/kg/7D-I (420mg/kg) GASTROINTESTINAL: NAUSEA OR VOMITING

LIVER: OTHER CHANGES
Canadian Medical Association Journal. Vol. 129, Pg. 411, 1983.
man TDLo oral 5714ug/kg (5.714mg/kg) BEHAVIORAL: ATAXIA American Journal of Emergency Medicine. Vol. 10, Pg. 616, 1992.
mouse LD50 oral > 10gm/kg (10000mg/kg)   Drugs in Japan Vol. 6, Pg. 126, 1982.
rat LD50 subcutaneous 4167mg/kg (4167mg/kg) GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA" Toxicology and Applied Pharmacology. Vol. 9, Pg. 445, 1966.