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The overall incidence of adverse drug reactions to sulfa antibiotics is approximately 3%, close to penicillin; [3] hence medications containing sulfonamides are prescribed carefully. Sulfonamide drugs were the first broadly effective antibacterials to be used systemically, and paved the way for the antibiotic revolution in medicine.
Sulfonamides are usually metabolized by several oxidative pathways, acetylation, and conjugation with sulfate or glucuronic acid. [20] However, there are some differences in biotransformation between certain species. Acetylation, which reduces the solubility of sulfonamides, is for example poor developed in dogs.
Sulfanilamide (also spelled sulphanilamide) is a sulfonamide antibacterial drug. Chemically, it is an organic compound consisting of an aniline derivatized with a sulfonamide group. [ 1 ] Powdered sulfanilamide was used by the Allies in World War II to reduce infection rates and contributed to a dramatic reduction in mortality rates compared to ...
For this reason, pharmaceutical companies produce sulfate and hydrochloride salts of the drug, both of which are over 300 times more water-soluble than their parent molecule. [clarification needed] [citation needed] Whereas the pH of a saturated morphine hydrate solution is 8.5, the salts are acidic.
Nature is abound with organosulfur compounds—sulfur is vital for life. Of the 20 common amino acids, two (cysteine and methionine) are organosulfur compounds, and the antibiotics penicillin and sulfa drugs both contain sulfur. While sulfur-containing antibiotics save many lives, sulfur mustard is a deadly chemical warfare agent.
Author of The Demon Under the Microscope, a history of the discovery of the sulfa drugs; A History of the Fight Against Tuberculosis in Canada (Chemotherapy) Presentation speech, Nobel Prize in Physiology and Medicine, 1939; The History of WW II Medicine "Five Medical Miracles of the Sulfa Drugs". Popular Science, June 1942, pp. 73–78.
Sulfation is widely used in the production of consumer products such as detergents, shampoos, and cosmetics. Since the sulfate group is highly polar, its conjugation to a lipophilic "tail" gives surfacant-like properties. Well known sulfates are sodium lauryl sulfate and sodium laureth sulfate. [2]
Some sultones are short-lived intermediates, used as strong alkylating agents to introduce a negatively charged sulfonate group. In the presence of water, they slowly hydrolyze to the hydroxy sulfonic acids. Sultone oximes are key intermediates in the synthesis of the anti-convulsant drug zonisamide. [4] Tisocromide is an example of a sultone.