Erythromycin oleandomycin with

O Hara, K. Kanda,T. Kono, M. Structure of a phosphorylated derivative of oleandomycin, obtained by reaction of oleandomycin with an extract of an erythromycin-resistant strain of Escherichia coli. J. Antibiot., 41,823-827 (1988)... 

The most impressive application of 2-thiopyridyl and 2-thiopyrimidinyl donors is in the area of antibiotics. Thus, Woodward et al. [481] successfully completed the total synthesis of erythromycin by using S Pyrm glycoside of D-desosamine and S Pyr-glycoside of L-cladinose as glycosyl donors to the subsequent glycosylation with erythronalide A. This methodology was also successfully used in the synthesis of oleandomycin [482,483], erythromycin A [484] and erythromycin B [485]. 

Erythromycin and oleandomycin are examples with a 14-membered ring. The former is a mixture of three closely related compounds erythromycin A, B, and C erythromycin A is the major and most important component. The latter consists of a single component. 

Health hazards from drug residues in food depend on the frequency and degree of human exposure. Increase in the degree of human exposure occurs when injection sites are accidentally consumed. Continuous exposure is more probable when a side or quarter of a contaminated food animal is purchased by a consumer for deep-freeze use. Basic antibiotics such as chloramphenicol, erythromycin, tylosin, and oleandomycin, are more likely to accumulate in tissue at a higher concentration than in plasma due both to ion trapping, which results from a pH difference between blood and tissue, and to the innate lipid solubility of the compounds (1). A factor with the potential to reduce the drug residues intake is that most animal tissues are cooked before eating, which may decrease 269... 

In liquid chromatographic analysis of macrolides and lincosamides, most popular is the ultraviolet detector (Table 29.4). Tylosin, tilmicosin, spiramycin, sedecamycin, and josamycin exhibit relatively strong ultraviolet absorption, but erythromycin, lincomycin, pirlimycin, and oleandomycin show extremely weak absorption in the ultraviolet region. Hence, detection at 200-210 nm has been reported for the determination of lincomycin (146). However, a combination of poor sensitivity and interference from coextractives necessitated extensive cleanup and concentration of the extract. Precolumn derivatization of pirlimycin with 9-fluorenylmethyl chloroformate has also been described to impart a chromophore for ultraviolet detection at 264 nm (140). 

Recommendations have been presented for correction of theophylline doses dnring concomitant medication with some of the above dmgs (SEDA-8, 130) (45). Concomitant therapy with aUopnrinol, cimetidine, erythromycin, furosemide, isoprenahne, or propranolol requires a reduction in dose of abont 20-30% for oleandomycin the reduction shonld be abont 50%. 

The 12-membered ring macrolides are not represented by clinical agents in the United States. The most prominent members of the 14-unit rings are the erythromycins (EM) and oleandomycins. Oleandomycin (which forms a spiro-oxirane with the C8 of EM-A) and its triacetate, has been discontinued in the United States. 

Duthu, G.S. Assay of erythromycin from human serum by high performance liquid chromatography with electrochemical detection. J.Liq.Chromatogr, 1984, 7, 1023-1032 [serum electrochemical detection also josamycin, oleandomycin, tylosin]... 

The most well-established system for heterologous expression involves the hosts S. coelicolor or its close relative S. lividans, and a bifimctional actino-myces- . coli vector with control elements for PKS gene expression that have been derived from the actinorhodin gene cluster [59]. This host-vector system has successfuUy been used to reconstitute functionally the polyketide pathways associated with biosynthesis of frenolicin [60], tetracenomycin [59], oxytetra-cycline [61], erythromycin [62], picromycin/methymycin [63], oleandomycin... 

The interactions of ergot derivatives with erythromycin and troleandomycin are well documented, well establish, and clinically important, whereas information about clarithromycin appears to be eonfined to three possible cases and that relating to oleandomycin to one case. There are no adverse reports about midecamycin, but it is expected to interact similarly. The concurrent use of all of these macrolides and ergot derivatives should be avoided. Some of the cases cited were effectively treated with sodium nitroprusside or naftidrofuryl oxalate, with or without heparin. "" " Spiramycin, and josamycin would not be expected to interact because they do not inhibit CYP3A4. However, there is one unexplained and unconfirmed report of an interaction with josamycin. "... 

Total syntheses of the following antibiotics and/or their aglycones are dealt with methymycin, erythromycin, pikromycin, oleandomycin, ingramycin (albo-cycline), carbomycin B, leucomycin A3 (josamycin), tylosin, mycinamicins, rosaramicin, A26771B and elaiophylin (azalomycin B). Since the total synthesis of the macrolide-like immunosuppressant FK-506 has been recently reported, it is also reviewed here. Today, erythromycin A, oleandomycin, leucomycin A3 (josamycin), tylosin and mycinamicin II are clinically important antibiotics. 

Oleandomycin, a 14-membered ring macrolide antibiotic, was isolated in 1956 from fermentation broths of Streptomyces antibioticus [360]. Some years later, oleandomycin was assigned the structure 340 on the basis of its chemical degradation [361]. Oleandomycin is effective, but less potently, against the same spectrum of bacteria as erythromycin, namely Gram-positive bacteria such as staphylococci, streptococci, and pneumococci. The antimicrobial activity of oleandomycin, when combined with tetracycline, is potentiated. In fact, in such a combination it is sold as an antibacterial agent for upper and lower respiratory tract infection. 

MaerolldM, macrolide antibiotics a group of antibiotics from various strains of Streptomyces, all with the same complex macrocyclic structure. M. inhibit protein synthesis by blocking transpeptidation, and translocation on the 50S ribosomal subunit (similar to Chloramphenicol, see). Examples of M. are erythromycin (Fig.), spiramycin, oleandomycin, carbo-mycin, angolamycin, leucomycin, picromycin. Almost all M. are used therapeutically as broad spectrum antibiotics. 

J. Zhou, Y. Chen and R. Cassidy, Separation and determination of the macrolide antibiotics (erythromycin, spiramycin and oleandomycin) by capillary electrophoresis coupled with fast reductive voltammetric detection. Electrophoresis, 2000, 21, 1349-1353. 

Spraying was with anisaldehyde/sulfuric acid/ethanol (1 1 9) and heating at 1 lO C for 2 min. The identification was aided by the difference in color observed after spraying with anisaldehyde red for oleandomycin and troleandomycin, gray-green to brown for erythromycin and its esters (41). 

For the quantitative determination of erythromycin and oleandomycin in animal tissues, milk, and eggs, a TLC method has been described (44) in which 25 g of sample are homogenized with 90 ml of acetonitrile and 2 ml of saturated sodium carbonate solution and centrifuged. Then 3 g of sodium chloride are added to the supemate and the extraction is done with 50 ml of dichloromethane. The organic layer is dried with 5 g of anhydrous sodium sulfate, filtered through cotton wool, evaporated to dryness, and dissolved in ethyl acetate, followed by different washing steps. 

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