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Sulfanilamide information


Sulfanilamide
Clinical data
AHFS/Drugs.comsalonemide Consumer Drug Information
ATC code
  • J01EB06 (WHO) D06BA05 (WHO) QJ01EQ06 (WHO)
Identifiers
IUPAC name
  • 4-aminobenzenesulfonamide
CAS Number
  • 63-74-1 checkY
PubChem CID
  • 5333
DrugBank
  • DB00259 checkY
ChemSpider
  • 5142 checkY
UNII
  • 21240MF57M
KEGG
  • D08543 checkY
ChEBI
  • CHEBI:45373 checkY
ChEMBL
  • ChEMBL21 checkY
NIAID ChemDB
  • 019103
CompTox Dashboard (EPA)
  • DTXSID4023622 Edit this at Wikidata
ECHA InfoCard100.000.513 Edit this at Wikidata
Chemical and physical data
FormulaC6H8N2O2S
Molar mass172.20 g·mol−1
3D model (JSmol)
  • Interactive image
Density1.08 g/cm3
Melting point165 °C (329 °F)
SMILES
  • O=S(=O)(c1ccc(N)cc1)N
InChI
  • InChI=1S/C6H8N2O2S/c7-5-1-3-6(4-2-5)11(8,9)10/h1-4H,7H2,(H2,8,9,10) checkY
  • Key:FDDDEECHVMSUSB-UHFFFAOYSA-N checkY
  (verify)

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 previous wars.[2][3] Sulfanilamide is rarely if ever used systemically due to toxicity and because more effective sulfonamides are available for this purpose. Modern antibiotics have supplanted sulfanilamide on the battlefield; however, sulfanilamide remains in use today in the form of topical preparations, primarily for treatment of vaginal yeast infections such as vulvovaginitis caused by Candida albicans.[4][5][6][7]

The term "sulfanilamides" is also sometimes used to describe a family of molecules containing these functional groups. Examples include:

  • Furosemide, a loop diuretic
  • Sulfadiazine, an antibiotic
  • Sulfamethoxazole, an antibiotic
  1. ^ Actor P, Chow AW, Dutko FJ, McKinlay MA. "Chemotherapeutics". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a06_173. ISBN 978-3527306732.
  2. ^ Steinert D (2000). "The Use of Sulfanilamide in World War II". The History of WWII Medicine. Archived from the original on 2016-06-07.
  3. ^ "Class 9 Items: Drugs, Chemicals and Biological Stains Sulfa Drugs". Library of Congress Web Archives. Archived from the original on 2013-12-04. Retrieved 2014-06-13.
  4. ^ "Sulfanilamide". PubChem. National Center for Biotechnology Information (NCBI), U.S. National Library of Medicine.
  5. ^ Scholar E (2007-01-01). "Sulfanilamide". In Enna SJ, Bylund DB (eds.). xPharm: The Comprehensive Pharmacology Reference. New York: Elsevier. pp. 1–5. doi:10.1016/b978-008055232-3.62694-7. ISBN 978-0-08-055232-3. Retrieved 2021-10-02.
  6. ^ "US FDA Label: AVC (sulfanilamide) Vaginal Cream 15%" (PDF). United States Food & Drug Administration. Retrieved 3 October 2021.
  7. ^ "Drugs@FDA: FDA-Approved Drugs". www.accessdata.fda.gov. Retrieved 2021-10-02.

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Sulfanilamide

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Sulfanilamide (also spelled sulphanilamide) is a sulfonamide antibacterial drug. Chemically, it is an organic compound consisting of an aniline derivatized...

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Elixir sulfanilamide

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Elixir sulfanilamide was an improperly prepared sulfonamide antibiotic that caused mass poisoning in the United States in 1937. It is believed to have...

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Nazi human experimentation

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medical experiments revolving around food, seawater, epidemic jaundice, sulfanilamide, blood coagulation and phlegmon. According to the indictments at the...

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Prontosil

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became the first oral version of sulfanilamide by Bayer, which had actually obtained a German patent on sulfanilamide as early as 1909, without realizing...

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Timeline of antibiotics

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Neosalvarsan 1935 – Prontosil (an oral precursor to sulfanilamide), the first sulfonamide 1936 – Sulfanilamide 1938 – Sulfapyridine (M&B 693) 1939 – sulfacetamide...

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Antimetabolite

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cell DNA replication. Antimetabolites may also be antibiotics, such as sulfanilamide drugs, which inhibit dihydrofolate synthesis in bacteria by competing...

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Griess test

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aniline derivative and a coupling agent. The most common arrangements use sulfanilamide and N-(1-naphthyl)ethylenediamine: a typical commercial Griess reagent...

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Sulfonamide

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sometimes used as a synonym for sulfa drug, a derivative or variation of sulfanilamide. The first sulfonamide was discovered in Germany in 1932. Sulfonamides...

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Food and Drug Administration

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rapidly enacted into law following the public outcry over the 1937 Elixir Sulfanilamide tragedy, in which over 100 people died after using a drug formulated...

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Medication

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regulation of drug development and drug sales. In the U.S., the Elixir Sulfanilamide disaster led to the establishment of the Food and Drug Administration...

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Glycerol

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people died in the United States after ingesting DEG-contaminated elixir sulfanilamide, a drug used to treat infections. The origin of the gly- and glu- prefixes...

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Hypertension

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chlorothiazide, the first thiazide diuretic and developed from the antibiotic sulfanilamide, which became available in 1958. Subsequently, beta blockers, calcium...

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Sulfamethoxazole

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hypersensitivity to trimethoprim or sulfonamides. Sulfamethoxazole, a sulfanilamide, is a structural analog of para-aminobenzoic acid (PABA). They compete...

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Prodrug

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1932), must be cleaved in the body to release the active molecule, sulfanilamide. Since that time, many other examples have been identified. Terfenadine...

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Sulfapyridine

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Sulfapyridine (INN; also known as sulphapyridine) is a sulfanilamide antibacterial medication. At one time, it was commonly referred to as M&B 693. Sulfapyridine...

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Regulatory affairs

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Jungle by Upton Sinclair led to 1906 Pure Food and Drugs Act Elixir of Sulfanilamide led to the 1938 Food Drug and Cosmetic Act Thalidomide led to the 1962...

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Pharmaceutical industry

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drug's ingredients. In 1937 over 100 people died after ingesting "Elixir Sulfanilamide" manufactured by S.E. Massengill Company of Tennessee. The product was...

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Paul Gelmo

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was an Austrian chemist who worked on synthetic dyes and discovered sulfanilamide in 1908, although their antibiotic properties were discovered only in...

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List of medicine contamination incidents

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1937 Elixir sulfanilamide incident: S. E. Massengill Company used diethylene glycol as the solvent for the antibacterial sulfanilamide, leading to the...

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List of disasters in the United States by death toll

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explosion Sayreville, New Jersey Fatalities estimated 100+ 1937 Elixir sulfanilamide Mass poisoning United States 100 1978 Northeastern United States blizzard...

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Metronidazole

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vaginal tablets, oral metronidazole, and vaginal suppositories containing sulfanilamide, aminacrine hydrochloride, and allantoin in the treatment of symptomatic...

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1985 Austrian diethylene glycol wine scandal

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thousands of deaths worldwide since the first recorded case: the Elixir sulfanilamide incident in 1937. Most of the recalled wines contained up to a few grams...

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Assassination of Reinhard Heydrich

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amounts of morphine. Conflicting accounts exist concerning whether sulfanilamide, a new antibacterial drug, was given; Gebhardt testified at his 1947...

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Diethylene glycol

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sulfanilamide dissolved with diethylene glycol, to create a liquid alternative of this drug. The company tested the new product, Elixir sulfanilamide...

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Glossary of chemical formulae

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1824-81-3 C6H8N2O2S ethyl 2-aminothiazole-4-carboxylate 5398-36-7 sulfanilamide 63-74-1 C6H8O7 citric acid 77-92-9 C6H9N3O2 histidine His 71-00-1 ethyl...

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Sanami

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Sanami (born 1937), Japanese sport shooter Sanamid, alternative name of Sulfanilamide Sanamidol, alternative name of Omeprazole This disambiguation page lists...

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