Antibacterial sulfonamides

We have proposed rapid methods for determining 12 sulfonamide antibacterial in bovine and fish tissues (14,15), milk, and eggs (16). These methods are based on analyte extraction from the matrix dispersed on sand by hot water followed by injection, directly (14) or after little manipulation (15, 16), of a large aliquot of the extract on an LC column. 

We have proposed rapid methods for determining 12 sulfonamide antibacterials in bovine and fish tissues (Bogialli et al., 2003a, 2003b), milk, and eggs (Bogialli et al,... 

One of the side effects noted in the clinical use of the sulfonamide antibacterial agents was a diuretic effect caused by inhibition of the enzyme carbonic anhydrase. Attempts to capitalize on this side effect so as to obtain agents with greatly enhanced diuretic activity first met success when a heterocyclic ring was substituted for the benzene ring of the sulfonamide. Treatment of the hydrazine derivative, 151, with phosgene leads... 

Mechanism of Action. Pyrimethamine blocks the production of folic acid in susceptible protozoa by inhibiting the function of the dihydrofolate reductase enzyme. Folic acid helps catalyze the production of nucleic and amino acids in these parasites. Therefore, this drug ultimately impairs nucleic acid and protein synthesis by interfering with folic acid production. The action of sulfadoxine and other sulfonamide antibacterial agents was discussed in Chapter 33. These agents also inhibit folic acid synthesis in certain bacterial and protozoal cells. 

Bogialli S, Curini R, Di Corda A et al. (2003) Confirmatory analysis of sulfonamide antibacterials in bovine liver and kidney extraction with hot water and liquid chromatography coupled to a single- or triple-quadrupole mass spectrometer. Rapid Communications in Mass Spectrometry 17 1146-1156... 

Usually, phenazopyridine is given in combination with urinary antiseptics. For example, it is available as Azo-Gan-trisin. a fixed-dose combination with the sulfonamide antibacterial sulfisoxazole. and a.s Urobiotic, a combination with the antibiotic oxytctracycline and the sulfonamide sulfa-methizole (Chapter 10). The drug is rapidly excreted in the urine, to which it gives an orange-red color. Stains in fabrics may be removed by soaking in a 0.25% solution of. sodium dithionite. 

Sulfadoxine and Pyrimethamine. The combination of sulfadoxine and pyrimethamine (Fansidar) (Fig. 9-S) uses a drug from the sulfonamide antibacterial group and a pyri-... 

Sulfonyl chlorides (51) are used in the manufacture of many biologically active compounds like the sulfonamide antibacterial drugs (see Chapter 2, p. 25 and Chapter 11, pp. 222-6) and pesticides such as the acaricide tetradifon (60) (see Chapter 11, p. 235), which is synthesised from 1,2,4-trichlorobenzene (61) (Scheme 36). 

A wide variety of organosulfur compounds show useful biological activity examples include the sulfonamide antibacterials and diuretics, penicillin and cephalosporin antibiotics, the antiulcer drug ranitidine, and agrochemicals such as the thiophosphoryl (P=S) insecticides like malathion, herbicides like chlorsulfuron, many fungicides like the dithiocarbamates (see Chapter 9, p. 148) and captan (see Chapter 9, p. 151), and sulfone acaricides like tetradifon (see Chapter 7, p. 104). 

This discovery led to the synthesis of some 15 000 sulfonamides. Antibacterial activity was demonstrated to be confined to compounds of general structure (16) in which both R and R groups may be varied, although R is usually hydrogen as shown in compound... 

Sulfonamides Antibacterial agents Hypersensitivity, hemolytic anemia, fever, lupus-like syndromes... 

Nifedipine 218 and other related 1,4-dihydropyridines are important as antihypertensive agents (Ca antagonists). They are prepared by a classical Hantzsch synthesis from acetoacetic ester, arylaldehyde and NH3 [72]. Sulfapyridine 219 was one of the first sulfonamide antibacterial agents to be used. Cerivastatin (Lipobay) 220, a powerful HMG-CoA reductase inhibitor, is applied for treatment of primary hypercholesteremia types Ila and b. 

The client with a partial-thickness burn to the entire right leg who is being treated with silver sulfadiazine (Silvadene), a sulfonamide antibacterial agent, develops leukopenia. Which action would the nurse suspect that the HCP would prescribe ... 

Huang et al. described a simple, rapid method for the quantitative monitoring of five sulfonamide antibacterial residues in milk. The analytes were concentrated by SBSE based on poly(vinylimidazole-divinylbenzene) monolithic material as coating, and analyzed by HPLC with diode-array detection. The extraction procedure was very simple. Milk was first diluted with water and then directly subjected to sorptive extraction without a requirement for additional steps to eliminate fats and protein in the samples. Under the optimized experimental conditions, low detection limits (S/N = 3) (where S/N = signal-to-noise ratio) and quantification limits (S/N = 10) were achieved for the target compounds within the range of 1.30-7.90 and 4.29-26.3 p.g/1 from spiked milk, respectively. Good linearities were obtained for the sulfonamides with correlation coefficients (R ) above 0.996. Finally, the proposed method was successfully applied to the determination of sulfonamides in different milk samples. 

Sheridan R, Policastro B, Thomas S, Rice D, Analysis and occurrence of 14 sulfonamide antibacterials and... 

Sheridan R, Policasreo B, Thomas S, Rice D, Analysis and occurrence of 14 sulfonamide antibacterials and chloramphenicol in honey by solid phase extraction followed by LC-MS/MS analysis, J. Agric. Food Chem. 2008 56 3509-3516. 

At the present time, the largest use of sulfonamide antibacterials is as urinary antiseptics, e.g. those caused by E. coli and Proteus mirabilis. They are also used in treating nocardiosis (of lungs or foot), trachoma (eye), lymphogranuloma venereum, dermatitis herpatiformis, and valued for the prophylaxis of streptococcal infections in those prone to them, and in preventing recurrence of rheumatic fever. 

Many synthetic pyridine derivatives are important as therapeutic agents, for example Isoniazide is a major antituberculosis agent, Sulphapyridine is one of the sulfonamide antibacterials, Prialdoxime is an antidote for poisoning by organophosphates, and Lacidipine is one of several antihypertensive 1,4-dihy-dropyridines. Some herbicides (Paraquat) and fungicides (Davicil) are also pyridine derivatives. 

SuUa drugs (Section 20.10) Sulfonamide antibacterial agents, most of which have the general structure P-H2NCSH4SO2NHR. Sulfe drugs... 

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