Erythromycin propionyl ester

Stubbs, C. Kanfer, I. High-performance liquid chromatography of erythromycin propionyl ester and erythromycin base in biological fluids. J.Chromatogr., 1988, 427, 93-101 [extracted erythromycin, erythromycin propionate oleandomycin (IS) electrochemical detection column temp 35 serum urine SPE pharmacokinetics LOQ 250 ng/mL]... 

Erythromycin Ethyl Succinate Erythromycin Propionyl Ester... 

Cholestatic jaundice This side effect occurs, especially with the estolate form of erythromycin, presumably as the result of a hypersensitivity reaction to the estolate form (the lauryl salt of the propionyl ester of erythromycin). It has also been reported for other forms of the drug. 

Most of the data on rokitamycin have been published in Japanese and Italian journals. As a propionyl ester of leucomycin, rokitamycin has an antimicrobial spectrum similar to that of erythromycin, it is especially potent against L. pneumophila, M. pneumoniae, and Chlamydia. Like other 16-membered macrolides, it is active against bacteria that are inducibly resistant to erythromycin but inactive against strains that are constitutively resistant to macrolide-lincosamide-streptogramin B antibiotics. 

Synonyms for this compound include erythromycin propionate lauryl sulfate erythromycin propionate dodecyl sulfate lauryl sulfate salt of the propionic ester of erythromycin monopropionylerythromycin lauryl sulfate and propionyl erythromycin lauryl sulfate. 

The maximum ultraviolet absorption of aqueous solutions of monopropiony1 erythromycin is at 285 nm. Monopropionyl erythromycin was used because propionyl erythromycin lauryl sulfate is practically insoluble. Murphy4 has reported that the ultraviolet spectrum of the esters of erythromycin are not significantly... 

Erythromycin estolate differs from other forms of erythromycin in that it is extremely stable to acid hydrolysis.5 Erythromycin liberated from the ester by mild alkaline hydrolysis is subject to rapid decomposition in strongly acid solutions. Kavanagh has stated that deterioration of erythromycin increases with an increase in temperature and decreases with an increase in pH up to 8.0. Buffered aqueous solutions of erythromycin base are quite stable at this pH. Acetone solutions of the ester form are stable, while acetone solutions of the propionyl erythromycin lauryl sulfate preparation are not. Powders and dry formulations are stable for at least five years. Liquid preparations become unacceptable after 2 years due to undesirable taste. 

Ester derivatives of erythromycin, shown in Table 4, were synthesized soon after its discovery (124—126). They are readily prepared by acylation of the 2-hydroxyl group the neighboring 3r-dimethylamino group directs acylation to this site. Commonly used esters of erythromycin are propionate, acetate, ethyl succinate, and ethyl carbonate (30). 2r-Esters do not bind bacterial ribosomes, however, and consequently must be hydrolyzed back to the parent to exert antibacterial activity (127). Ester derivatives are still being prepared (128,129). 2,-0-Acetylerythromycin stearate, also known as erythromycin acistrate, is an example undergoing clinical trial (11,130,131). Two salts of 2,-0-propionyl-erythromycin, N-acetylcysteinate (erythromycin stinoprate) and mercaptosuccinate, were prepared to combine antibiotic and mucolytic properties in a single agent (132—134). 

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