Diuretics sulfonamides

Dithiole-3-thione, methylation of, 391 Di-(trimethyisilyl) amine, reaction with A-4-thiazoline-2-thione, 396 Diuretic sulfonamide, 414 Diuretic properties, 150, 152 Dithiobiuret, 85... 

High-ceiling diuretics, sulfonamide (furosemide, bumetanide, torasemide, piretanide)... 

Some drugs, like the acne medications Accutane and Retin-A, as well as antibiotics, diuretics, sulfonamides, and estrogen, make the skin extremely sensitive to light. 

Cyclothia2ide [2259-96-3] is another example of a duorine-free pharmaceutical (diuretic, antihypertensive) based on y -chloroduoroben2ene [625-98-9] where duorine activation is subsequentiy provided by two sulfonamide groups (156). 

Muzolimine (710), a 1-substituted 2-pyrazolin-5-one derivative, is a highly active diuretic, differing from the structures of other diuretics since it contains neither a sulfonamide nor a carboxyl group. It has a saluretic effect similar to furosemide and acts in the proximal tubule and in the medullary portion of the ascending limb of the loop of Henle. Pharmacokinetic studies in dogs, healthy volunteers and in patients with renal insufficiency show that the compound is readily absorbed after oral administration (B-80MI40406). 

Diuretic activity can be retained in the face of replacement of one of the sulfonamide groups by a carboxylic acid or amide. Reaction of the dichlorobenzoic acid, 174, with chlorsulfonic acid gives the sulfonyl chloride, 175 this is then converted to the amide (176). Reaction of that compound with furfuryl ine leads to nucleophilic aromatic displacement of the highly activated chlorine at the 2 position. There is thus obtained the very potent diuretic furosemide (177). ... 

Chlorthalidone (49) is another thiazide-like diuretic agent that formally contains an isoindole ring. Transformation of the amine in benzophenone, 47, to a sulfonamide group by essentially the same process as was outlined for chlorexolone (46) affords Intermediate 43. This product cyclizes to the desired pseudoacid 1-ketoisoindole (49) on successive treatments with thionyl... 

The sulfonamide group has been used successfully to confer diuretic activity to both aromatic and simple heterocyclic compounds. 

Replacement of the sulfonamide group at the 7 position by chlorine markedly diminishes the diuretic effect in this series. One such compound, diazoxide (169), exhibits instead potent anti-... 

Each era of medicinal chemistry has been marked by intensive concentration on some structural type in a large number of laboratories. One need only look back in this book to the tables of sulfonamides, barbiturates, and thiazide diuretics, noting the small time span covered by the references to each list. The benzodiazepines have provided such a focus for the past decade. 

It has been documented in an earlier volume that appropriately substituted molecules with two strongly electron withdrawing substituents meta to one another in a benzene ring often possess diuretic properties and, even though the prototypes usually have two substituted sulfonamide moieties so disposed, other groups can replace at least one of them. An example of this is piretanide (24), where one such group is a carboxyl... 

Thiazide diuretics have a venerable history as antihypertensive agents until the advent of the angiotensin-converting enzyme (ACE) inhibitors this class of drugs completely dominated first line therapy for hypertension. The size of thi.s market led until surprisingly recently to the syntheses of new sulfonamides related to the thiazides. Preparation of one of the last of these compounds starts by exhaustive reduction of the Diels-Alder adduct from cyclopentadiene and malei-mide (207). Nitrosation of the product (208), followed by reduction of the nitroso group of 209,... 

Loop diuretics are contraindicated in patients with known hypersensitivity to the loop diuretics or to the sulfonamides, severe electrolyte imbalances, hepatic coma, or anuria, and in infants (ethacrynic acid). 

P-lactam antimicrobials, erythromycin, nitrofurantoin, rifampin, sulfonamide antimicrobials, and vancomycin 0 Diuretics (all classes), NSAIDs... 

Sulfonamides are compounds that contain a sulfonamide moiety (i.e., S02NH2). This group includes sulfonamide antibiotics, furosemide, thiazide diuretics, sulfonylureas, and celecoxib. The sulfonamide antibiotics contain an aromatic amine at the... 

Many benzenesulfonamides have diuretic properties, particularly those having two such functions situated meta to one another. To some extent a carboxyl group can serve in place of one of the sulfonamido groups. Bumetanide (8) is such a substance. Chlorosulfonation of p-chlorobenzoic acid leads to 5, which is nitrated, and then converted to sulfonamide 6 with ammonia. 

Changing the substitution pattern on the carbo-cyclic ring of the benzothiadiazine diuretics is well known to have a marked effect on the qualitative biological activity. Thus, the direct analogue of the diuretic chlorothiazide (199) in which chlorine replaces one sulfonamide group, diazoxide (200), shows negligible diuretic activity instead the compound is a potent antihypertensive vasodilator. 

For therapeutic drugs, the highest concentrations in the raw sludge corresponded to the analgesics diclofenac (209 ng g ) and ibuprofen (135 ng g-1), and the sulfonamide antibiotic sulfathiazole (143.0 ng g-1). Next in abundance were the diuretic compounds furosemide (79.9 ng g-1) and hydrochlorothiazide (41.3 ng g-1), and the analgesic ketoprofen (42.4 ng g-1). The remaining PhC were found at concentrations below 40 ng g The list of the 24 detected... 

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