Dihydrostreptomycin streptomycins

Heitzman RJ, Dihydrostreptomycin and streptomycin, in Residues of Some Veterinary Drugs in Animals and Foods, FAO Food and Nutrition Paper 41/7, 1995, pp. 17—29 (available at ftp //ftp.fao.org/ag/agn/ jecfa/vetdrug/41-7-dihydrostreptomycin streptomycin.pdf accessed 11/20/10). 

Dihydrostreptomycin, in which the CHO group in the middle ring is replaced by CH2OH, is made by the catalytic reduction of streptomycin, and has similar antibacterial properties. 

Dihydrostreptomycin sulfate may be prepared from streptomycin sulfate by catalytic hydrogenation (Merck, Pfizer, Cyanamid), electrolytic reduction (Schenley, Olin Mathieson), or by sodium boro hydride reduction (Bristol), or by isolation from a fermentation process (Takeda). 

Li, Y. M., Debremaeker, D., Van Schepdael, A., Roets, E., and Hoogmartens, J. (2000). Simultaneous analysis of streptomycin, dihydrostreptomycin and their related substances by capillary zone electrophoresis. J. Liq. Chromatogr. Relat. Technol. 23, 2979—2990. 

Antidiarrhoeal formulations containing neomycin or streptomycin or dihydrostreptomycin including their respective salts or esters. 

Streptomycin and dihydrostreptomycin are aminoglycoside antibiotics closely related in structure, which are active against mainly gram-negative bacteria. Streptomycin is produced by certain strains of Streptomyces griseus dihydrostreptomycin can be prepared by reduction of streptomycin. 

They are active against many gram-negative bacteria but resistance develops rapidly and limits their use. Streptomycin and dihydrostreptomycin are less nephrotoxic than other aminoglycosides. They may cause neurological distur-... 

Administration of streptomycin intramuscularly is the method of choice for treating systemic infections. Oral forms of streptomycin or dihydrostreptomycin, frequently combined with sulfonamide drugs and other compounds, are also used in animals for treatment of enteric infections. In addition, streptomycin is used as a feed additive for growth promotion purposes. In some countries, the combination of streptomycin with procaine penicillin is used as an initial nonspecific therapy in farm animals, and in intramammary applications for treatment of mastitis. Intramuscular dosages are in the range 5-10 mg/kg bw, while oral dosages are 20 mg/kg bw. Dihydrostreptomycin is also used in veterinary medicine in intramammary and topical treatments. 

Results of pharmacokinetic studies of streptomycin are in most cases also applicable to dihydrostreptomycin and vice versa. In animals, the absorption of both streptomycin and dihydrostreptomycin is poor via the oral route but rapid after intramuscular administration. In cattle, peak serum levels were obtained 1 h after intramuscular injection of either streptomycin or dihydrostreptomycin (18), whereas serum concentrations produced in sheep and horses paralleled those obtained in cattle (19). As a result, most of an oral dose is recovered in the feces whereas most of a parenteral dose is recovered in the urine. However, if kidney function is severely impaired, little of an intramuscularly administered dose is excreted in the urine. 

In traditional electrophoresis, separation efficiency is limited by thermal diffusion and convection. Owing to long analysis times and low efficiencies, these procedures never enjoyed wide usage. Problems have arisen when trying to differentiate between structurally related drug residues such as streptomycin and dihydrostreptomycin, tetracyclines, lincomycin and clindamycin, and erythromycin and oleandomycin (83, 84). To overcome these problems, anticonvective media, such as polyacrylamide or agarose gels, have also been used. 

An indirect competitive ELISA has been also developed for the determination of streptomycin and dihydrosticptomyciri in milk (24). Prior to the analysis, the milk sample was skimmed and treated with oxalic acid. The antiserum was raised in rabbits using streptomycin linked to a bacterial protein as the antigen. To perform the test, microtiter plates were coated with streptomycin, and antiserum and milk samples were mixed to be added in the wells where they were incubated for 1 h. Depending on the amount of residues in the sample, more or less antibody remained available for binding to the streptomycin coat. A pig antirabbit antibody-enzyme conjugate was subsequently added and incubated for 90 min. Using a suitable substrate, streptomycin and dihydrostreptomycin could be detected down to 1.6 ppb, whereas quantification could be made possible up to 100 ppb when samples were used undiluted. 

Fig. 29.1 HPLC-PDA of (a) MSPD extract of control bovine kidney, (b) MSPD extract of bovine kidney fortified at the 20 ppm level, and (c) synthetic mixture of standards at levels of 15 ng per component injected. Peaks 1, spectinomycin 2, hygromycin B 3, streptomycin 4, dihydrostreptomycin. (Reprinted from Ref. 19 with permission from Elsevier Science.)...

GC Gerhardt, CDC Salisbury, JD MacNeil. Determination of streptomycin and dihydrostreptomycin in animal tissue by on-line sample enrichment liquid chromatography. J AOAC Int 77 334-337, 1994. 

Osterberg, A. C., J. J. Olsen, N. N. Yuda, C. E. Rauh, H. G Parr, and L. W. Will. 1957. Cochlear, vestibular, and acute toxicity studies of streptomycin and dihydrostreptomycin pantothenate salts, In Antibiotics Annual, 1956-1957, edited by H. VNfelch and F. Marti-lban ez, 564-573. New York Medical Encyclopedia. 

From these results, it may be concluded that the pseudo-disaccharide 44 is the first intermediate in the assembling of the three components of dihydrostreptomycin. The fact that no transfer-product was observed with streptidine is in agreement with the conclusions from a number of studies in which the importance of phosphorylated intermediates in the biosynthesis of streptomycin was established.36,64,65... 

Use of alkylamide phases, in which alkyl chains are attached to the silica surface via an alkylamide group, reduces interactions with free silanols, by an internal masking mechanism. Residual silanols interact by hydrogen bonding with the embedded amide groups and thus become less active toward analytes. The embedded polar amide groups lessen the hydrophobicity of these phases compared to that of C18 bonded phases prepared from the same silica. Improved peak shapes of ionizable compounds were reported and this stationary phase was successfully used under IPC conditions to analyze streptomycin and its dihydrostreptomycin derivative in food... 

Vinas, R, Balsalobre, N., and Hemdndez-Cdrdoba, M. Liquid chromatography on an amide stationary phase with post-column derivatization and flnorimetric detection for the determination of streptomycin and dihydrostreptomycin in foods. Talanta 2007, 72, 808-812. 

The lack of suitable chromophores for UV-Vis detection can be circumvented by derivatization, and the same strategy can be nsed to obtain the required fluorescence of an analyte if it does not naturally fluoresce. Many flnorophores were investigated and nsed. Determination of leukocyte DNA 6-thioguanine nucleotide levels relied on derivatization with chloroacetaldehyde [25]. A post-column derivatization with )8-naphthoqninone-4-sulfonate allowed the detection of streptomycin and dihydrostreptomycin in foods [26], A post-colnmn derivatization with 0-phthalaldehyde was used for the detection of biogenic amines and polyamines in vegetable products... 

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