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Substance Name: Erythromycin estolate [USAN:USP:BAN:JAN]
RN: 3521-62-8
UNII: XRJ2P631HP
InChIKey: AWMFUEJKWXESNL-JZBHMOKNSA-N

Note

  • A macrolide antibiotic, produced by Streptomyces erythreus. It is the lauryl sulfate salt of the propionic ester of erythromycin. This erythromycin salt 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

  • C40-H71-N-O14.C12-H26-O4-S

Molecular Weight

  • 1056.3933
 

Classification Codes

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

Name of Substance

  • Erythromycin estolate
  • Erythromycin estolate [USAN:USP:BAN:JAN]

MeSH Heading

  • Erythromycin estolate

Synonyms

  • Biomicron
  • EINECS 222-532-4
  • Eriscel
  • Eritroger
  • Eromycin
  • Ery-Toxinal dodecylsulfate
  • Erythromycin 2'-propionate dodecyl sulfate (salt)
  • Erythromycin 5-(3-propionate) dodecyl sulfate
  • Erythromycin estolate
  • Erythromycin propionate dodecylsulfate (salt)
  • Erythromycin propionate lauryl sulfate
  • Erythromycin propionate, compd. with dodecyl sulfate
  • Erythromycin propionate, compound with dodecyl sulfate
  • Erythromycin propionyl laurylsulfate
  • Erythromycin, propionate (ester), compd. with monododecyl sulfate
  • Erythromycine estolate
  • Erytrarco
  • Estomicina
  • Ilosone
  • Lauromicina
  • Lauryl sulfate propionyl erythromycin ester
  • Lubomycine B
  • Marcoeritrex
  • Neo-erycinum
  • NSC 263364
  • PELS
  • Propionic acid, 2'-ester with erythromycin, dodecyl sulfate salt
  • Propionylerythromycin lauryl sulfate
  • Prospiocine
  • Roxomicina
  • Stellamicina
  • Sulfuric acid, monododecyl ester, compd. with erythromycin 2'-propionate (1:1)
  • UNII-XRJ2P631HP

Systematic Names

  • Erythromycin, 2'-propanoate, dodecyl sulfate (salt)
  • Erythromycin, 2'-propionate, monododecyl sulfate (salt) (8CI)
  • Erythromycin, propionate (ester), compd. with monododecyl sulfate (1:1)
  • Sulfuric acid, monododecyl ester, compd. with erythromycin 2'-propanoate (1:1)

Registry Numbers

CAS Registry Number

  • 3521-62-8

FDA UNII

  • XRJ2P631HP

Other Registry Numbers

  • 12167-63-4
  • 28375-06-6
  • 31261-46-8

System Generated Number

  • 0003521628

Molecular Formulas

Molecular Formula

  • C40-H71-N-O14.C12-H26-O4-S

Molecular Formula Fragments

  • C12-H26-O4-S
  • C40-H71-N-O14
  • COMPONENT

Structure Descriptors

InChI

InChI=1S/C40H71NO14.C12H26O4S/c1-15-27-40(11,48)33(44)22(5)30(43)20(3)18-38(9,47)35(55-37-32(53-28(42)16-2)26(41(12)13)17-21(4)50-37)23(6)31(24(7)36(46)52-27)54-29-19-39(10,49-14)34(45)25(8)51-29;1-2-3-4-5-6-7-8-9-10-11-12-16-17(13,14)15/h20-27,29,31-35,37,44-45,47-48H,15-19H2,1-14H3;2-12H2,1H3,(H,13,14,15)/t20-,21-,22+,23+,24-,25+,26+,27-,29+,31+,32-,33-,34+,35-,37+,38-,39-,40-;/m1./s1

InChIKey

AWMFUEJKWXESNL-JZBHMOKNSA-N

Smiles

CCCCCCCCCCCCOS(=O)(=O)O.CC[C@H]1OC(=O)[C@H](C)[C@@H](O[C@H]2C[C@@](C)(OC)[C@@H](O)[C@H](C)O2)[C@H](C)[C@@H](O[C@@H]3O[C@H](C)C[C@@H]([C@H]3OC(=O)CC)N(C)C)[C@](C)(O)C[C@@H](C)C(=O)[C@H](C)[C@@H](O)[C@]1(C)O

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 oral > 6450mg/kg (6450mg/kg)   Drugs in Japan Vol. -, Pg. 211, 1990.
mouse LD50 subcutaneous > 6450mg/kg (6450mg/kg)   Drugs in Japan Vol. -, Pg. 211, 1990.
rat LD50 oral 1447mg/kg (1447mg/kg)   Toxicology and Applied Pharmacology. Vol. 18, Pg. 185, 1971.
rat LD50 subcutaneous > 6450mg/kg (6450mg/kg)   Drugs in Japan Vol. -, Pg. 211, 1990.
women TDLo unreported 100mg/kg/5D-I (100mg/kg) LIVER: CHANGE IN GALL BLADDER STRUCTURE OR FUNCTION Clinical Pharmacology and Therapeutics Vol. 6, Pg. 788, 1965.

Physical Properties

Physical Property Value Units Temp (deg C) Source
Melting Point 137 dec deg C   EXP
pKa Dissociation Constant 6.9 (none)   EXP
log P (octanol-water) 5.100 (none)   EST
Water Solubility 2.40E+04 mg/L   EXP
Atmospheric OH Rate Constant 3.29E-10 cm3/molecule-sec 25 EST

Physical property data is provided to ChemIDplus by SRC, Inc.