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HomeProduct name listErythromycin Estolate

Erythromycin Estolate

Synonym(s):Erythromycin 2′-propionate dodecyl sulfate

  • CAS NO.:3521-62-8
  • Empirical Formula: C52H97NO18S
  • Molecular Weight: 1056.39
  • MDL number: MFCD00084691
  • EINECS: 222-532-4
  • SAFETY DATA SHEET (SDS)
  • Update Date: 2024-11-19 23:02:33
Erythromycin Estolate Structural

What is Erythromycin Estolate?

Description

Erythromycin 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 properties

Long Needles

Originator

Ilosone,Dista,US,1958

The Uses of Erythromycin Estolate

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

The Uses of Erythromycin Estolate

Macrolides Antibiotics

The Uses of Erythromycin Estolate

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

What are the applications of Application

Erythromycin Estolate is an antibacterial agent

Definition

ChEBI: 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 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.

Properties of Erythromycin Estolate

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.  Keep in dark place,Sealed in dry,Room Temperature
solubility  chloroform: soluble4.0ML, clear, colorless (200 mg + 4.0 mL Chloroform)
form  neat
pka 6.9(at 25℃)
form  Solid
color  white
Water Solubility  Freely soluble in organic solvents, practically insoluble in water /n
Sensitive  Light Sensitive
CAS DataBase Reference 3521-62-8

Safety information for Erythromycin Estolate

Signal word Danger
Pictogram(s)
ghs
Exclamation Mark
Irritant
GHS07
ghs
Health Hazard
GHS08
GHS Hazard Statements H302:Acute toxicity,oral
H317:Sensitisation, Skin
H334:Sensitisation, respiratory
Precautionary Statement Codes P261:Avoid breathing dust/fume/gas/mist/vapours/spray.
P264:Wash hands thoroughly after handling.
P264:Wash skin thouroughly after handling.
P280:Wear protective gloves/protective clothing/eye protection/face protection.
P301+P312:IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.
P302+P352:IF ON SKIN: wash with plenty of soap and water.

Computed Descriptors for Erythromycin Estolate

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