Sulfonamide

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.

[1] 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)

[2] 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.

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