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Erythromycin Estolate

Basic information Safety Supplier Related

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
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Erythromycin Estolate Chemical Properties

Melting point:
135-140°C dec.
Boiling point:
743℃
Density 
1.0053 (rough estimate)
refractive index 
1.6550 (estimate)
Flash point:
>110°(230°F)
storage temp. 
-20°C Freezer
solubility 
chloroform: soluble4.0ML, clear, colorless (200 mg + 4.0 mL Chloroform)
pka
6.9(at 25℃)
form 
neat
color 
white
Water Solubility 
Freely soluble in organic solvents, practically insoluble in water /n
Sensitive 
Light Sensitive
CAS DataBase Reference
3521-62-8
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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
Toxicity
LD50 orally in rats: >5000 mg/kg (Goldenthal)

MSDS

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Erythromycin Estolate Usage And Synthesis

Chemical Properties

Long Needles

Originator

Ilosone,Dista,US,1958

Uses

Used as an antibacterial agent. LD50 >5000 mg/kg for oral administration to rats

Uses

Macrolides Antibiotics

Manufacturing Process

16.7 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 name

Antibio-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 Function

Antibacterial

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 Description

Erythromycin 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.

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