Sulfanilamide (also spelled sulphanilamide) is a sulfonamide antibacterial. Chemically, it is a molecule containing the sulfonamide functional group attached to an aniline. As a sulfonamide antibiotic, it functions by competitively inhibiting (i.e., by acting as a substrate analogue) enzymatic reactions involving para-aminobenzoic acid (PABA).1 PABA is needed in enzymatic reactions that produce folic acid which acts as a coenzyme in the synthesis of purine, pyrimidine and other amino acids.
The term "sulfanilamides" is also used to describe a family of molecules containing these functional groups. Examples include:
- Furosemide, a loop diuretic
- Sulfadiazine, an antibiotic
- Sulfamethoxazole, an antibiotic
Gerhard Domagk, who directed the testing of the prodrug Prontosil in 1935,2 and Jacques and Thérèse Tréfouël, who along with Federico Nitti and Daniel Bovet in the laboratory of Ernest Fourneau at the Pasteur Institute, discovered the active component, 4-aminobenzenesulfonamide,3 are generally credited with the discovery of sulfanilamide as a chemotherapeutic agent. Domagk was awarded the Nobel Prize for his work.4
See also
- Sulfonamide (medicine)
- Nazi human experimentation -- Sulfonamide experiments
- Elixir sulfanilamide
External links
References
- ^ Michael Kent, Advanced Biology, Oxford University Press, 2000, p. 46 ISBN 9780199141951
- ^ G. Domagk, "Ein Beitrag zur Chemotherapie der bakteriellen Infektionen", Deutsche Medizinische Wochenschrift, 61, feb. 15, 1935, p. 250.
- ^ J. et T. Tréfouël, F. Nitti and D. Bovet, "Activité du p-aminophénylsulfamide sur l’infection streptococcique expérimentale de la souris et du lapin", C. R. Soc. Biol., 120, nov. 23, 1935, p. 756.
- ^ (French) Daniel Bovet, "Les étapes de la découverte de la sulfamidochrysoïdine dans les laboratoires de recherche de la firme Bayer à Wuppertal-Elberfeld (1927-1932)", in Une chimie qui guérit : Histoire de la découverte des sulfamides, Coll. "Médecine et Société", Payot, Paris, 1988, p. 307.
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Antibiotics and chemotherapeutics for dermatological use (D06)
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| Antibiotics |
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Tetracycline and derivatives
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Demeclocycline • Chlortetracycline • Oxytetracycline • Tetracycline
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Others
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Amphenicol: Chloramphenicol
Aminoglycosides: Neomycin • Gentamicin • Amikacin
Quinolone: Nadifloxacin
Streptogramin: Virginiamycin
Rifamycin: Rifaximin
other: Fusidic acid • Bacitracin • Tyrothricin • Mupirocin
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| Chemotherapeutics |
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Sulfonamides
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Silver sulfadiazine • Sulfathiazole • Mafenide • Sulfamethizole • Sulfanilamide • Sulfamerazine
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Antivirals
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Aciclovir • Penciclovir • Idoxuridine • Edoxudine
Imiquimod/Resiquimod • Podophyllotoxin
Docosanol • Tromantadine • Inosine • Lysozyme • Ibacitabine
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Other
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Metronidazole
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noco(i/b/d/q/u/r/p/m/k/v/f)/cong/tumr(n/e/d), sysi/epon
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proc, drug (D2/3/4/5/8/11)
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Antibacterials: nucleic acid inhibitors (J01E, J01M)
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Antifolates
(inhibits
purine metabolism,
thereby inhibiting
DNA and RNA synthesis) |
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DHFR inhibitor
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2,4-Diaminopyrimidine (Trimethoprim#, Brodimoprim, Tetroxoprim, Iclaprim†)
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Sulfonamides
(DHPS inhibitor)
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Short-
acting
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Sulfaisodimidine • Sulfamethizole • Sulfadimidine • Sulfapyridine • Sulfafurazole • Sulfanilamide (Prontosil) • Sulfathiazole • Sulfathiourea
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Intermediate-
acting
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Sulfamethoxazole • Sulfadiazine# • Sulfamoxole
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Long-
acting
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Sulfadimethoxine • Sulfalene • Sulfametomidine • Sulfametoxydiazine • Sulfamethoxypyridazine • Sulfaperin • Sulfamerazine • Sulfaphenazole • Sulfamazone
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Other/ungrouped
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sulfanilamide (Sulfacetamide, Sulfametrole)
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Combinations
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Trimethoprim/sulfamethoxazole#
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Topoisomerase
inhibitors/
quinolones/
(inhibits
DNA replication) |
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1st g.
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Cinoxacin‡ • Flumequine • Nalidixic acid • Oxolinic acid • Pipemidic acid • Piromidic acid • Rosoxacin
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Fluoro-
quinolones
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2nd g.
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Ciprofloxacin# • Enoxacin‡ • Fleroxacin‡ • Lomefloxacin • Nadifloxacin • Ofloxacin • Norfloxacin • Pefloxacin • Rufloxacin
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3rd g.
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Balofloxacin • Grepafloxacin‡ • Levofloxacin • Pazufloxacin • Sparfloxacin‡ • Temafloxacin‡ • Tosufloxacin
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4th g.
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Besifloxacin • Clinafloxacin† • Garenoxacin • Gemifloxacin • Moxifloxacin • Gatifloxacin‡ • Sitafloxacin • Trovafloxacin‡/Alatrofloxacin‡ • Prulifloxacin
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Vet.
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Danofloxacin • Difloxacin • Enrofloxacin • Ibafloxacin • Marbofloxacin • Orbifloxacin • Pradofloxacin • Sarafloxacin
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Related (DG)
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Aminocoumarins: Novobiocin
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Anaerobic DNA
inhibitors |
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Nitro- imidazole derivatives
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Metronidazole# • Tinidazole • Ornidazole
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Nitrofuran derivatives
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Nitrofurantoin# • Furazolidone‡ • Nifurtoinol
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| RNA synthesis |
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Rifamycins/
RNA polymerase
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Rifampicin • Rifabutin • Rifapentine • Rifaximin
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- #WHO-EM
- ‡Withdrawn from market
- Clinical trials:
- †Phase III
- §Never to phase III
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gr+f/gr+a(t)/gr-p(c)/gr-o
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