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Erythromycin Estolate

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Erythromycin Estolate Basic information
Product Name:Erythromycin Estolate
Synonyms:eritroger;eromycin;erythromycin,propionate(ester),compd.withmonododecylsulfate(1:1);erythromycin5-(3-propionate)dodecylsulfate;erythromycinpropionate,compd.withdodecylsulfate;erythromycinpropionatelaurylsulfate;ERYTHROMYCIN ESTOLATE;ERYTHROMYCIN 2'-PROPANOATE DODECYL SULFATE SALT
CAS:3521-62-8
MF:C52H97NO18S
MW:1056.39
EINECS:222-532-4
Product Categories:Intermediates & Fine Chemicals;Pharmaceuticals
Mol File:3521-62-8.mol
Erythromycin Estolate Structure
Erythromycin Estolate Chemical Properties
Melting point 135-140°C dec.
Boiling point 743℃
density 1.0053 (rough estimate)
refractive index 1.6550 (estimate)
Fp >110°(230°F)
storage temp. Keep in dark place,Sealed in dry,Room Temperature
solubility chloroform: soluble4.0ML, clear, colorless (200 mg + 4.0 mL Chloroform)
pka6.9(at 25℃)
form Solid
color white
Water Solubility Freely soluble in organic solvents, practically insoluble in water /n
Sensitive Light Sensitive
Major Applicationpharmaceutical
pharmaceutical small molecule
InChIKeyAWMFUEJKWXESNL-QTEUPTDTNA-N
CAS DataBase Reference3521-62-8
Safety Information
Hazard Codes Xn,Xi
Risk Statements 22-42/43-36/37/38
Safety Statements 22-36-26
WGK Germany 3
RTECS KF5775000
HS Code 29419000
Storage Class11 - Combustible Solids
Hazard ClassificationsAcute Tox. 4 Oral
Resp. Sens. 1
Skin Sens. 1
ToxicityLD50 orally in rats: >5000 mg/kg (Goldenthal)
MSDS Information
ProviderLanguage
Erythromycin 2'-propionate dodecyl sulfate English
SigmaAldrich English
Erythromycin Estolate Usage And Synthesis
DescriptionErythromycin estolate was synthesized by the Lilly Research Laboratories in 1959. It shows a higher and longer lasting serum level than erythromycin and the other esters, ethylsuccinate and stearate, when administered orally. This antibiotic is stable against gastric acids, and after oral absorption it is hydrolyzed gradually into erythromycin. Long-term usage of erythromycin estolate is toxic to the liver. Erythromycin ethylsuccinate [41342-53-4], (C43H75NO16, Mr 862.07) and erythromycin stearate [643-22-1] (C37H67NO13 · C18H36O2, Mr 1018.43) also have been used orally, and erythromycin lactobionate [3847-29-8] (C37H67NO13 · C12H22NO12, Mr 1092.25) has been used by intravenous administration and opthalmic topical application
Chemical PropertiesLong Needles
OriginatorIlosone,Dista,US,1958
UsesUsed as an antibacterial agent. LD50 >5000 mg/kg for oral administration to rats.
UsesMacrolides Antibiotics
DefinitionChEBI: Erythromycin estolate is an aminoglycoside sulfate salt and an erythromycin derivative. It has a role as an enzyme inhibitor. It contains an erythromycin A 2'-propanoate.
Manufacturing Process16.7 grams of monopropionylerythromycin are dissolved in 50 ml of warm acetone. To the solution are added 6.4 grams of sodium lauryl sulfate dissolved in 50 ml of distilled water containing 2 ml of glacial acetic acid. The white crystalline precipitate of rnonopropionylerythromycin lauryl sulfate which separates is filtered off and dried. It melts at about 135° to 137°C.
Brand nameAntibio-aberel;Apo-erythro-s;Bio-exazol;Biometran;Biomicron;Chemthromycin;Cimetrin;Cusimicina balsamica;Doboiosol;Dowmicyn;Dreimicina;Duozplin vitaminado;Dynabiotal;Ees-200;Ees-400;E-mycine;Endoeritrina;Erimec;Erirobios;Eritrazol;Eritrobios;Eritrobiotic;Eritrocin;Eritrodes;Eritronicol;Eritropan;Eritroveinte;Eritrovienite;Eritrowolf;Eritro-wolf;Erymycin;Eryped;Ery-tar;Erythromictine;Erythro-prat;Ery-toxinal;Erytrodol;Erytro-prot;Eryt-toxinal;Espimina;Estimina;Estomiicina;Estomycin;Fesmicina;Ilosone pulvules;Ilosone ready-mix;Ilothycin;Kesso-mycin;Laucetin;Laurilin;Lauritran;Liferitrin;Loderm;Lubomycina;Lubomycine;Makrocyklina;Manilina;Marocid;Neo-ilolycina;Neo-iloticina;Niux;Novorythro;Propriocin enfante;Prospiocine;Proterytrin;Pulmomas;Purmycin;Ritromin;Roxo chemil;Roxochemil;Rp-mycin;Rubibacter;Selvicin;Spetrasone;Stella micina;Taimoxin;Togerin;Togrien;Tosinova;Tropoxin;Wyamycin s.
Therapeutic FunctionAntibacterial
World Health Organization (WHO)Erythromycin estolate, a macrolide antibiotic, was introduced in 1958 for the treatment of gram-positive infections. By the early 1970s its use had been associated with a higher incidence of hepatic toxicity than that seen with other salts and esters of erythromycin. This led to its withdrawal by some regulatory authorities whereas others required the addition of a warning in the product information. Evidence that the estolate ester is more hepatotoxic than other salts or esters has subsequently been disputed. It has been claimed to be the most effective ester for treatment of Legionnaire's disease and preparations remain widely available. (Reference: (BMJOAE) British Medical Journal, 286, 1954, 1983)
General DescriptionErythromycin estolate, erythromycin propionate lauryl sulfate(Ilosone), is the lauryl sulfate salt of the 2'-propionateester of erythromycin. Erythromycin estolate is acid stableand absorbed as the propionate ester. The ester undergoesslow hydrolysis in vivo. Only the free base binds to bacterialribosomes. Some evidence, however, suggests that theester is taken up by bacterial cells more rapidly than thefree base and undergoes hydrolysis by bacterial esteraseswithin the cells. The incidence of cholestatic hepatitis is reportedlyhigher with the estolate than with other erythromycinpreparations.
Erythromycin estolate occurs as long needles that aresparingly soluble in water but soluble in organic solvents. administration for the treatment of serious infections,such as Legionnaires disease, or when oral administrationis not possible. Solutions are stable for 1 week whenrefrigerated.
Tag:Erythromycin Estolate(3521-62-8) Related Product Information
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