Organosulfur compounds containing –S(=O)2–N< functional group
For the medical use of chemicals within this group, see Sulfonamide (medicine).
Not to be confused with Sulfamide.
The structure of the sulfonamide group
In organic chemistry, the sulfonamide functional group (also spelled sulphonamide) is an organosulfur group with the structure R−S(=O)2−NR2. It consists of a sulfonyl group (O=S=O) connected to an amine group (−NH2). Relatively speaking this group is unreactive. Because of the rigidity of the functional group, sulfonamides are typically crystalline; for this reason, the formation of a sulfonamide is a classic method to convert an amine into a crystalline derivative which can be identified by its melting point. Many important drugs contain the sulfonamide group.[1]
A sulfonamide (compound) is a chemical compound that contains this group. The general formula is R−SO2NR'R" or R−S(=O)2−NR'R", where each R is some organic group; for example, "methanesulfonamide" (where R = methane, R' = R" = hydrogen) is CH3SO2NH2. Any sulfonamide can be considered as derived from a sulfonic acid by replacing a hydroxyl group (−OH) with an amine group.
In medicine, the term "sulfonamide" is sometimes used as a synonym for sulfa drug, a derivative or variation of sulfanilamide. The first sulfonamide was discovered in Germany in 1932.[2]
^Actor, P.; Chow, A. W.; Dutko, F. J.; McKinlay, M. A. "Chemotherapeutics". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a06_173. ISBN 978-3527306732.{{cite encyclopedia}}: CS1 maint: multiple names: authors list (link)
^Levy, Stuart B. (2002). The antibiotic paradox : how the misuse of antibiotics destroys their curative powers (2 ed.). Cambridge, Massachusetts: Perseus Publ. p. 51. ISBN 9780738204406.
In organic chemistry, the sulfonamide functional group (also spelled sulphonamide) is an organosulfur group with the structure R−S(=O)2−NR2. It consists...
This is a list of sulfonamides used in medicine. Short-acting Sulfacetamide Sulfadiazine Sulfadimidine Sulfafurazole (sulfisoxazole) Sulfisomidine (sulfaisodimidine)...
sulphanilamide) is a sulfonamide antibacterial drug. Chemically, it is an organic compound consisting of an aniline derivatized with a sulfonamide group. Powdered...
cross-reactivity between sulfonamide-containing drugs. In smaller studies, the lack of cross-reactivity between sulfonamide antibiotics and sulfonamide non-antibiotics...
general rather than cross reactivity from structural components of the sulfonamide-based drug. Prescribers should examine the evidence carefully and assess...
include nausea, vomiting, loss of appetite, and skin rashes. It is a sulfonamide and bacteriostatic. It resembles a component of folic acid. It prevents...
about September 1943, experiments to investigate the effectiveness of sulfonamide, a synthetic antimicrobial agent, were conducted at Ravensbrück. Wounds...
A primary amine will form a soluble sulfonamide salt. Acidification of this salt then precipitates the sulfonamide of the primary amine. A secondary amine...
failure to prescribe sulfonamide for Heydrich, Himmler suggested to Gebhardt that he should conduct experiments proving that sulfonamide was useless in the...
to consume for individuals with diabetes or prediabetes. People with sulfonamide allergies can experience allergic reactions to saccharin, although it...
Sulfacetamide is a sulfonamide antibiotic. Sulfacetamide 10% topical lotion, sold under the brand name Klaron or Ovace, is approved for the treatment...
Sulfonamide hypersensitivity syndrome is similar to anticonvulsant hypersensitivity syndrome, but the onset is often sooner in the treatment course, generally...
perfluorinated compound, having an eight-carbon chain and a terminal sulfonamide functional group. PFOSA, a persistent organic pollutant, was an ingredient...
Anticonvulsants (also known as antiepileptic drugs, antiseizure drugs, or anti-seizure medications (ASM)) are a diverse group of pharmacological agents...
Perfluorobutane sulfonamide, also known as FBSA or H-FBSA, is a perfluorinated surfactant. FBSA and its N-alkylated derivatives have been patented by...
microorganism fighting another), whereas non-antibiotic antibacterials (such as sulfonamides and antiseptics) are fully synthetic. However, both classes have the...
extractum and Strychnos nux vomica in high doses, for meteorism. Enbasin: Sulfonamide, intragluteal 5 cc, for diverse infections. Euflat: Bile extract, Radix...
is believed to be safe if the baby is otherwise healthy. It is in the sulfonamide class of medications. Sulfadiazine was approved for medical use in the...
Penoxsulam is sulfonamide and triazolopyrimidine herbicide that acts as an acetolactate synthase inhibitor. It is primarily used for rice production....
only 10% of patients with allergy to antibiotic sulfonamides were also allergic to diuretic sulfonamides, but it is unclear if this represents true cross...
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