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| AHFS/Drugs.com | salonemideConsumer Drug Information |
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| ECHA InfoCard | 100.000.513 |
| Chemical and physical data | |
| Formula | C6H8N2O2S |
| Molar mass | 172.20 g·mol−1 |
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| Density | 1.08 g/cm3 |
| Melting point | 165 °C (329 °F) |
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Sulfanilamide (also spelledsulphanilamide) is asulfonamideantibacterial drug. Chemically, it is anorganic compound consisting of ananilinederivatized with asulfonamide group.[1] Powdered sulfanilamide was used by theAllies inWorld War II to reduce infection rates and contributed to a dramatic reduction in mortality rates compared to previous wars.[2][3] Sulfanilamide is rarely if ever usedsystemically due totoxicity and because more effective sulfonamides are available for this purpose. Modernantibiotics have supplanted sulfanilamide on the battlefield; however, sulfanilamide remains in use today in the form oftopical preparations, primarily for treatment ofvaginal yeast infections such asvulvovaginitis caused byCandida albicans.[4][5][6][7]
The term "sulfanilamides" is also sometimes used to describe a family of molecules containing thesefunctional groups. Examples include:
As a sulfonamide antibiotic, sulfanilamide functions bycompetitively inhibiting (that is, by acting as a substrate analogue of) enzymatic reactions involvingpara-aminobenzoic acid (PABA).[8][9] Specifically, itcompetitively inhibits the enzymedihydropteroate synthase.[5][10] PABA is needed in enzymatic reactions that producefolic acid, which acts as acoenzyme in the synthesis ofpurines andpyrimidines.Mammals do not synthesize their own folic acid so are unaffected by PABA inhibitors, which selectively kill bacteria.[11]
However, this effect can be reversed by adding the end products of one-carbon transfer reactions, such asthymidine,purines,methionine, andserine. PABA can also reverse the effects of sulfonamides.[5][12][11]
Sulfanilamide was first prepared in 1908 by the Austrian chemist Paul Josef Jakob Gelmo (1879–1961)[13][14] as part of his dissertation for a doctoral degree from theTechnische Hochschule ofVienna.[15] It was patented in 1909.[16]
Gerhard Domagk, who directed the testing of theprodrugProntosil in 1935,[17] andJacques Tréfouël andThérèse Tréfouël, who along with Federico Nitti andDaniel Bovet in the laboratory ofErnest Fourneau at thePasteur Institute, determined sulfanilamide as the active form,[18] are generally credited with the discovery of sulfanilamide as a chemotherapeutic agent. Domagk was awarded the Nobel Prize for his work.[19]
In 1937,Elixir sulfanilamide, a medicine consisting of sulfanilamide dissolved indiethylene glycol, poisoned and killed more than one hundred people as a result of acutekidney failure, prompting new US regulations for drug testing. In 1938, theFood, Drug and Cosmetic Act was passed. It was only the solvent and not the sulfanilamide that was the problem, as sulfanilamide was widely and safely used at the time in both tablet and powder form.[20]
Sulfanilamide is a yellowish-white or white crystal or fine powder. It has adensity of 1.08 g/cm3 and amelting point of 164.5-166.5 °C. ThepH of a 0.5%aqueous solution of Sulfanilamide is 5.8 to 6.1. It has a λmax of 255 and 312 nm.[5]
Solubility: One gram of sulphanilamide dissolves in approximately 37 mlalcohol or in 5 mlacetone. It is practically insoluble inchloroform,ether, orbenzene.[5]
Sulfanilamide iscontraindicated in those known to behypersensitive to sulfonamides, innursing mothers, duringpregnancy near term, and in infants less than two months of age.[5]
Since sulfanilamide is used almost exclusively in topical vaginal preparations these days, adverse effects are typically limited tohypersensitivity or local skin reactions. Ifabsorbed, systemic side effects commonly seen with sulfanilamides may occur.[5]
A small amount of sulfanilamide is absorbed following topical application or when administered as avaginal cream orsuppository (through the vaginal mucosa). It ismetabolized byacetylation like othersulfonamides and excreted through the urine.[5]
