Streptomycin salts

Maltol is mainly isolated from naturally occurring sources such as beechwood and other wood tars pine needles chicory and the bark of young larch trees. It may also be synthesized by the alkaline hydrolysis of streptomycin salts or by a number of other synthetic methods. 

Maltol 3-Hydroxy-2 methyl-4H pyran-4-one 3-hydroxy-2-methyl-4-py rone 3-hydroxy-2-methyl- y-py-rone larixinic acid Palatone Veltol. C6H603 mol wt 126,11. C 57.14%, H 4.80%, O 38.06%. Found in the bark of young larch trees (Larix decidua Mill.) in pine needles (Abies alba Mill., Pinaoeae), in chicory, in wood tars and oils, in roasted malt. Isoln from these sources and structure Kiliani, Bazlen, Ber. 27, 3115 (1894) Feuerstein, Ber. 34r 1804 (1901) Erdmann, Schaefer, Ber. 43, 2398 (1910) Reichstein. Be it ter, Ber. 63, 824 (1930) cf. Pera toner, Tam-burelic, Chem. Zentr. 76, 11 680 (1905). Also obtained by alkaline hydrolysis of streptomycin salts Schenck, Spiel -... 

Two forms ("a and j8 ) of streptomycin salts are known. j9-Salts are crystalline, sparin y soluble in water, and different from ordinary amorphous salts (o-salts). In die j3-form, the aldehyde group was thought to be bound by cydizadon with the methylamino group." In... 

For each test compound concentration, vehicle, negative or positive controls, make 8.25 mL of serum culture medium containing 70% rat serum, 30% sterile Tyrode s salt buffer with less than 1 mg/500 mL phenol red (free acid indicator) and 35 p,g/mL streptomycin sulfates. 

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

Medium for resuspension of supernatants Ml99 (with Hanks salts and HEPES) 100 pg/ml penicillin 100 pg/ml streptomycin 10% FCS... 

TSM buffer TS buffer containing 5% (w/v) powdered milk, 100 U/mL penicillin, 100 pg/mL streptomycin, and 1 mM sodium azide This buffer can be stored for several days at 4°C Note that sodium azide is poisonous and can form explosive copper salts m drain pipes if not handled properly... 

Keller, H., W Kripe, H. Sous, and H. Mickter. 1956b. The pantothenates of streptomycin, viomycin, and neomycin New and less toxic salts. Antibiotics Annual, 1955-1956, edited by H. Welch and F. Marti-lban ez, 35-38. New York Medical Encyclopedia. 

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. 

Muranishi, S., N. Muranishi, and H. Sezaki. 1979. Improvement of absolute bioavailability of normally poorly absorbed drugs Inducement of the intestinal absorption of streptomycin and gentamicin by lipid-bile salt mixed micelles in rat and rabbit. Int J Pharm 2 101. 

Muranishi, N., et al. 1980. Mechanism for the inducement of the intestinal absorption of poorly absorbed drugs by mixed micelles. I. Effects of various lipid-bile salt mixed micelles on the intestinal absorption of streptomycin in rat. Int J Pharm 4 271. 

Heparin and its salts are incompatible with many drugs including alteplase, amikacin sulfate, amiodarone hydrochloride, ampicillin sodium, aprotinin, benzylpenicillin potassium or sodium, cephalothin sodium, ciprofloxacin lactate, cytarabine, dacarbazine, daunorubicin hydrochloride, diazepam, dobutamine hydrochloride, doxorubicin hydrochloride, droperidol, erythromycin lactobionate, gentamicin sulfate, haloperidol lactate, hyaluronidase, hydrocortisone sodium succinate, kanamycin sulfate, methicillin sodium, netilmicin sulfate, some opioid analgesics, oxytetracycline hydrochloride, some phenothiazines, polymyxin B sulfate, streptomycin sulfate, tetracycline hydrochloride, tobramycin sulfate, vancomycin hydrochloride, vinblastine sulfate, cisatracurium besylate, labetalol hydrochloride, nicardipine hydrochloride, cefmetazole, sodium ions, and fat emulsion.110 112... 

Fried and Wintersteiner first prepared a crystalline salt of streptomycin. Crude streptomycin phosphotungstate was converted to a crude picrate which was fractionated by flowing chromatography. One or more of the fractions, after removal of the picric acid, yielded a highly active amorphous product from which a crystalline streptomycin reineck-ate was obtained. 

Folkers and coworkers - found that when sufliciently pure concentrates of streptomycin were treated with methyl orange (the sodium salt of helianthine) a crystalline salt was formed with the sulfonic acid group of this dye. On recrystallization from aqueous methanol, pure streptomycin helianthate was obtained. The helianthate could be converted to streptomycin hydrochloride, sulfate or any other suitable salt for chemical or therapeutic purposes. All of these salts with the common inorganic acids are amorphous. They - also obtained a crystalline salt of streptomycin and p-(2-hydroxy-l-napthylazo)-benzenesulfonic acid from streptomycin hydrochloride and the azo dye Orange II. Streptomycin helianthate was converted directly into a crystalline streptomycin trihydrochloride-calcium chloride double salt. The chemistry of streptomycin was thus put on a crystalline basis. 

The molecular formula of streptomycin was established as C2iH37 39-N7O12 by elementary analyses of the crystalline streptomycin trihydrochloride-calcium chloride double salt, of crystalline streptomycin trihelianthate and of amorphous streptomycin trihydrochloride of high purity. The composition of crystalline streptomycin reineckate was in agreement with this formula as was also the analysis of the calcium chloride double salt performed in another laboratory. ... 

Acid hydrolysis of streptomycin trihydrochloride yielded an optically inactive, strongly basic degradation product which was readily isolated and purified as its picrate. This base, designated streptidine, was also obtained as the crystalline sulfate (anhydrous and monohydrate forms), dihydrochloride, dihydriodide, carbonate, and a variety of other crystalline salts. Analytical data on all of these salts indicated the molecular formula C8Hi8Ne04-2HX. Fried, Boyack and Wintersteiner have described the free base. 

Streptidine was best isolated by allowing a solution of streptomycin hydrochloride in N sulfuric acid to stand at 37° for forty-five hours. The sulfate monohydrate was precipitated in nicely crystalline form by adding three to five volumes of acetone to the reaction mixture. The substance is also isolable from the alkaline hydrolyzate of streptomycin. Streptidine and its salts have no true melting points and are optically inactive throughout the visible spectrum. The sulfate monohydrate has been definitely characterized by its x-ray diffraction pattern. 

Hydrogenation of the crystalline streptomycin trihydrochloride-calcium chloride double salt in aqueous solution with platinum oxide catalyst at atmospheric pressure or with Raney nickel catalyst at 100-140 atmospheres and 150° also yielded dihydrostreptomycin. Acid hydrolysis of dihydrostreptomycin gave streptidine and N-methyl-L-glucosamine. Hence, the reduction involved the nitrogen-free moiety, streptose. 

Wolfrom and coworkers had found that the mercaptolysis of the crystalline calcium chloride double salt of streptomycin trihydrochloride yielded, after chromatographic purification, two anomeric forms of ethyl tetraacetylthiostreptobiosaminide diethyl mercaptal. Mercaptolysis of dihydrostreptomycin yielded an amorphous ethyl dihydrothio-streptobiosaminide hydrochloride which formed crystalline N-acetyl and pentaacetyl derivatives. The ability of the ring in this latter compound to resist hydrolysis and to form a thioglycoside instead of a thio-... 

Besides the group of psychotropic compounds, we must quote here the antibiotics as drugs where a rapid recent development of techniques can be observed. D.c. polarographic techniques for the determination of chloramphenicol [242], tetracycline [243] and streptomycin [244] are available. The polarographic determination of penicillin G potassium salt is only indirect and is preceded by the introduction of a nitroso group [245]. The synthesis of chloramphenicol comprises the chemical reduc-... 

Mixed micelles consist of fatty acids solubilized by surfactants or bile salts. The effects of mixed micelles on drug absorption were reviewed by Muranishi Mixed micelles are effective absorption enhancers for compounds such as heparin, streptomycin, gentamycin, and insulin. The effect of mixed micelles on drug absorption tends to be greater at the distal region of the GI tract. The mechanism for increased absorption is not known. Some publications claim that they are safe to use. Others report a disordering effect on intestinal epithelial cells. 

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