Sulfapyridine

In a few cases, A/ -heterocycHc sulfanilamides have been prepared by the condensation of an active heterocycHc haHde with the sulfonamide nitrogen of sulfanilamide or its A/-acetyl derivative in the presence of an acid-binding agent. Sulfapyridine, sulfadiazine, and sulfapyrazine have been made by this method (1), but the most important appHcation is probably for the synthesis of sulfachlorapyridazine (9) and sulfamethoxypyridazine (10) (45). 

Reaction of 2-aininopyridine (35) with A/-acetylsulfanilyl chloride, followed by hydrolysis, gives sulfapyridine [144-83-2] (36), an antibacterial (36). 

Mesomerism involving sulfonyl groups is relatively weak, and in the case of the sulfonyliminopyridones (279) destabilization caused by the factors previously mentioned for the acyliminopyridones should be less important. Early ultraviolet spectral comparisons showed that acetylsulfapyridine and sulfapyridine (cf. reference 354) exist in aqueous solution as mixtures of comparable amounts of 279 and 280. A recent investigation of 2-, 3-, and 4-methanesulfonamido-... 

Aromatic amines and phenols [1-4] e.g. resorcinol, catechol, aminonaphthols Indol m-dinitrobenzene Ruene [2] Sulfapyridine [2, 3] ... 

Note The dipping solution can also be used as a spray solution. Aromatic amines react J more sensitively than do phenols [1]. The presence of acetone in the reagent increases the sensitivity for some substances, e.g. for sulfapyridine [2]. ... 

The prototypical aminosalicylate is sulfasalazine, which is comprised of mesalamine linked by a diazo bond to the carrier molecule sulfapyridine. This linkage prevents premature absorption of mesalamine in the small intestine. Once sulfasalazine is delivered to the colon, bacterial degradation of... 

Newer mesalamine products utilize non-sulfapyridine methods for drug delivery. Olsalazine uses two mesalamine molecules linked together, while balsalazide uses the inert carrier molecule 4-aminobenzoyl-P-alanine. Both drugs use a diazo bond similar to sulfasalazine. Other mesalamine formulations are pH-dependent formulations that release mesalamine at various points throughout the GI tract. 

Sulfasalazine is associated with various adverse effects, most of which are thought to be due to the sulfapyridine component. Common adverse effects that may be dose related include headache, dyspepsia, nausea, vomiting, and fatigue.19 Idiosyncratic effects include bone marrow suppression, reduction in sperm counts in males, hepatitis, and pulmonitis. Hypersensitivity reactions may occur in patients allergic to sulfonamide-containing medications. 

The use of non-sulfapyridine-based aminosalicylates has led to greater tolerability. Although the adverse effects are similar to those of sulfasalazine, they occur at a much lower rate. Olsalazine, in particular, is associated with a higher incidence of secretory diarrhea. These agents can also be used safely in patients with a reported sulfonamide allergy. 

The bioslurry treatment successfully removed several of the PhC to non-detectable levels after 26 days three histamine H2-receptor antagonists (ranitidine, famotidine, cimetidine), two (1-blockers (atenolol, sotalol), one barbiturate (butalbital) and one antidiabetic compound (glibenclamide). The elimination of the sulfonamide antibiotics sulfapyridine (100%), sulfamethazine (91.0%) and... 

Fig. 5 TPs of sulfapyridine after degradation by T. versicolor (adapted from Rodriguez-Rodriguez et al. [24])...

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