Studies of Erythromycin Maltobionate, a New Derivative of Erythromycin

Manna, P. K.; Basu, S.

doi:10.1081/ddc-100102188

Cited by 3 publications

(2 citation statements)

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“…It then shows an irregular oral absorption, a limited stability in the gastric environment, and a low solubility on water (2 mg/ml). To overcome such limits, different derivatives have been proposed, like salts, esters, and prodrugs, with the common aim at increasing the overall bioavailability and potency of the antibiotic, along with a better toxicological profile (10).…”

Section: Chemistrymentioning

confidence: 99%

“…Among the described salts of ERY are the nalidixate (8), taurate (9), maltobionate (10), melibionate (11), penicillanate (12), and fumarate (13), all obtained by reaction of ERY free base with the respective acids. Other derivatives, such as ethylsuccinate, estolate, gluceptate, stearate, and lactobionate are already on the market as medicinal products (14).…”

Section: Introductionmentioning

confidence: 99%

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Amphiphilic Erythromycin-Lipoamino Acid Ion Pairs: Characterization and In Vitro Microbiological Evaluation

et al. 2011

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A series of amphiphilic ion pairs of erythromycin (ERY) with lipoamino acids (LAAs) were produced. The ion pairs were prepared by evaporation of a water/ethanol co-solution of the drug and LAA bearing an alkyl side chain of 10-16 carbon atoms. For the sake of comparison, equimolar physical mixtures were prepared by triturating ERY and the LAA in the absence of any solvent. FTIR spectroscopy confirmed the structure of ion pairs, while differential scanning calorimetry and powder X-ray diffractometry were used to assess the formation of new saline species. The solubility pattern of the coevaporates in different aqueous and organic solvents confirmed their amphiphilic properties. ERY-LAA ion pairs were submitted to an in vitro microbiological assay against different bacterial strains, both susceptible and resistant to macrolides. The presence of the LAA moiety was shown not altering the antibacterial spectrum of activity of the drug. These results can be the basis for a further evaluation of ERY-LAA ion pairs as a mean to improve the penetration of the drug inside bacterial cells and to optimize the loading of ERY in lipid-based nanocarriers.

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Section: Chemistrymentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Amphiphilic Erythromycin-Lipoamino Acid Ion Pairs: Characterization and In Vitro Microbiological Evaluation

et al. 2011

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Antibiotics, Macrolides

Kirst

2001

Kirk-Othmer Encyclopedia of Chemical Technology

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Macrolide antibiotics are well‐established antimicrobial agents in clinical and veterinary medicine. These agents can be administered orally and are generally used to treat infections in the respiratory tract, skin and soft tissues, and genital tract caused by gram‐positive organisms, Mycoplasma species, and certain susceptible gram‐negative and anaerobic bacteria. The macrolide class is large and structurally diverse. Macrolides are produced by fermentation of soil microorganisms. Additionally, structural modifications using both chemical and microbiological means have yielded biologically active semisynthetic derivatives. The term macrolide was introduced to denote the class of substances produced by Streptomyces species containing a macrocyclic lactone. Traditional macrolide antibiotics are divided into three families according to the size of the aglycone, which can be a 12‐, 14‐, or 16‐membered ring. Naturally occurring 14‐membered macrolides include erythromycin A and erythromycin B, as well as others. Erythromycin has been the principal subject of modification of 14‐membered macrolides; its semisynthetic derivatives include erythromycin ethyl succinate, roxithromycin, clarithromycin, azithromycin, dirithromycin, and others. More recently, the ketolide family has been discovered that exhibits activity against certain macrolide‐resistant strains, from which telithromycin and ABT‐773 are in clinical trials. The 16‐membered macrolides are divided into leucomycin‐ and tylosin‐related groups, which differ in the substitution pattern of their aglycones. Natural products include josamycin (leucomycin A 3 ), spiramycin, and others. The most prominent member of the second group is tylosin, an important veterinary antibiotic. Semisynthetic 16‐membered macrolides include miokamycin, rokitamycin, AIV‐tylosin, and tilmicosin. The advent of molecular biology has opened new possibilities for producing novel macrolides by genetic manipulations of biosynthetic pathways from macrolide‐producing microorganisms (combinatorial biosynthesis) that complement traditional chemical and microbiological approaches. Macrolides inhibit growth of gram‐positive bacteria, Mycoplasma species, and certain gram‐negative and anaerobic bacteria. Susceptible gram‐positive bacteria include many species of Staphylococcus and Streptococcus ; susceptible gram‐negative bacteria include Bordetella pertussis, Legionella pneumophila, Moraxella catarrhalis , Campylobacter sp., Chlamydia sp., and Helicobacter pylori . Some derivatives have shown promising activity against non‐tuberculous mycobacteria. Macrolides inhibit growth of bacteria by inhibiting protein synthesis on ribosomes. Bacterial resistance to macrolides is often accompanied by cross‐resistance to lincosamide and streptogramin B antibiotics (MLS‐resistance). Bacterial resistance to antibiotics usually results from modification of a target site, enzymatic inactivation, or reduced uptake into or increased efflux from bacterial cells. The principal side effects of macrolides are gastrointestinal problems, such as pain, indigestion, diarrhea, nausea, and vomiting. Macrolide antibiotics are used clinically to treat infections resulting from susceptible organisms in the upper and lower respiratory tract, skin and soft tissues, and genital tract. They are generally used orally, although they can be given intravenously. Macrolides are regarded as among the safest of antibiotics. A few macrolides are used in veterinary medicine, such as tylosin and tilmicosin which are used to control respiratory diseases and other infections in poultry, pigs, and cattle.

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