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Sulfapyridine

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Chemical compound

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Pharmaceutical compound
Sulfapyridine
Clinical data
AHFS/Drugs.comMicromedex Detailed Consumer Information
MedlinePlusa682204
ATC code
Identifiers
  • 4-Amino-N-pyridin-2-ylbenzenesulfonamide
CAS Number
PubChemCID
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard(EPA)
ECHA InfoCard100.005.130Edit this at Wikidata
Chemical and physical data
FormulaC11H11N3O2S
Molar mass249.29 g·mol−1
3D model (JSmol)
Melting point191 to 193 °C (376 to 379 °F)
  • O=S(=O)(Nc1ncccc1)c2ccc(N)cc2
  • InChI=1S/C11H11N3O2S/c12-9-4-6-10(7-5-9)17(15,16)14-11-3-1-2-8-13-11/h1-8H,12H2,(H,13,14) checkY
  • Key:GECHUMIMRBOMGK-UHFFFAOYSA-N checkY
 ☒NcheckY (what is this?)  (verify)

Sulfapyridine (INN; also known assulphapyridine) is asulfanilamideantibacterial medication. At one time, it was commonly referred to asM&B 693. Sulfapyridine is no longer prescribed for treatment of infections inhumans. However, it may be used to treatlinear IgA disease and has use inveterinary medicine.[1] It is a goodantibacterial drug, but its watersolubility is verypH dependent. Thus there is a risk ofcrystallization within thebladder orurethra, which could lead to pain or blockage. As with other sulfonamides, there is a significant risk ofagranulocytosis, and this, rather than the development of resistance by bacteria, is the main reason for its decline in use.

History

[edit]

Sulfapyridine was one of the first generation of sulfonamide antibiotics. It was first synthesised by chemistMontague Phillips, working under director of research Arthur Ewins at the British firmMay & Baker Ltd,Dagenham on 2 November 1937. This sample was recorded in their test log as T693.[2]

Animal testing was conducted by clinical pathologistLionel Whitby at the Bland-Sutton Institute of Pathology,Middlesex Hospital inLondon under the designation M&B 693. Whitby discovered the antibacterial properties of sulfapyridine againstpneumococci and a range of other bacteria in mice.[3]

Clinical trials were conducted between March and June 1938 atDudley Road Hospital,Birmingham by doctors G. Mary Evans and Wilfrid Gaisford. These trials demonstrated a 70% reduction in mortality in 100 patients withlobar pneumonia.[4]

May & Baker began marketing sulphapyridine in theUK under the trade name Dagenan in October 1938.[5]

During the aftermath to the disastrousconvoy SC7, in October 1940, Surgeon-Lieutenant John Robertson, RN, ofHMSLeith, saved the life of Commodore Lachlan MacKinnon, from the torpedoedAssyrian, who had developed pneumonia, by giving him M&B 693, despite Robertson never having used it before and not knowing the required dosage.[6]

M&B 693 was successfully used to treatWinston Churchill's bacterial pneumonia.[7][8]

The same source records that in 1944 M&B 693 also saved Nero, the Royal Circus lion, from pneumonia.[9]

It could either be taken in tablet form[10] or the powder could be placed in wounds. It was used so widely during the Second World War that May & Baker had difficulty keeping up with demand. It was later largely superseded bypenicillin and other sulfonamides.

Sulfapyridine may still be prescribed forDermatitis herpetiformis, also known as Duhring's disease.[11][12]

As of December 1990, the drug is no longer marketed.[13]

Related medications

[edit]

The drugsulfasalazine is structurally one molecule ofmesalamine linked to one molecule of sulfapyridine with anazo chemical linker.

References

[edit]
  1. ^"Sulfapyride".drugs.com.
  2. ^Lesch J (1997).The Inside Story of Medicines: A Symposium. American Institute of the History of Pharmacy. pp. 101–119.ISBN 9780931292316.
  3. ^Whitby L (28 May 1938). "Chemotherapy of pneumococcal and other infections with 2-(p-aminobenzenesulphonamide) pyridine".Lancet.231 (5987):1210–1212.doi:10.1016/S0140-6736(00)89787-1.
  4. ^Evans GM, Gaisford W (2 July 1938). "Treatment of pneumonia with 2-(p-aminobenzenesulphonamide) pyridine".Lancet.235 (5992):14–19.doi:10.1016/S0140-6736(00)87996-9.
  5. ^"The discovery of Dagenan".The Chemist and Druggist.129 (3051): 107. 30 July 1938.
  6. ^Lund P, Ludlam H (1974).Night of the U-boats. London: New English Library. p. 130.
  7. ^Vale JA, Scadding JW (December 2017)."Sir Winston Churchill: treatment for pneumonia in 1943 and 1944"(PDF).Journal of the Royal College of Physicians of Edinburgh.47 (4):390–93.doi:10.4997/JRCPE.2017.418.PMID 29537415.S2CID 261386634. Archived fromthe original(PDF) on April 8, 2024.
  8. ^Lesch JE (2007). "Chapter 7: M&B 693".The first miracle drugs: how the sulfa drugs transformed medicine(PDF). Oxford: Oxford University Press. pp. 158–159.ISBN 978-0-19-518775-5. Archived fromthe original(PDF) on 21 July 2019.This admirable M&B, from which I did not suffer any inconvenience, was used at the earliest moment; and after a week's fever the intruders were repulsed. I hope all our battles will be equally well conducted....
  9. ^Lesch JE (2007). "Chapter 7: M&B 693".The first miracle drugs: how the sulfa drugs transformed medicine(PDF). Oxford: Oxford University Press. p. 193.ISBN 978-0-19-518775-5. Archived fromthe original(PDF) on 21 July 2019.M&B seemed to be everywhere, even at the circus, where the medicine was reported to have pulled Nero, Royal circus lion, through pneumonia, and at the London Zoo, where Winnie the lioness was also treated with M&B 693 for pneumonia.
  10. ^"Sulfapyridine".go.drugbank.com. Retrieved11 January 2026.
  11. ^Daniel M P."Dermatitis Herpetiformis - Dermatologic Disorders".MSD Manual Professional Edition. www.msdmanuals.com. Retrieved11 January 2026.
  12. ^"Dermatitis Herpetiformis".clevelandclinic.org. Cleveland Clinic. Retrieved11 January 2026.
  13. ^"Sulfapyridine (oral route) - Side effects & dosage".Mayo Clinic. Retrieved11 January 2026.
Antifolates
(inhibit bacterial
purine metabolism,
thereby inhibiting
DNA and RNA
synthesis)
DHFR inhibitor
Sulfonamides
(DHPS inhibitor)
Short-acting
Intermediate-acting
Long-acting
Other/ungrouped
Combinations
Other DHPS inhibitors
Quinolones
(inhibit bacterial
topoisomerase
and/orDNA gyrase,
thereby inhibiting
DNA replication)
1st generation
Fluoroquinolones
2nd generation
3rd generation
4th generation
Veterinary
Newer non-fluorinated
Related (DG)
Anaerobic DNA
inhibitors
Nitroimidazole derivatives
RNA synthesis
Rifamycins/
RNA polymerase
Lipiarmycins
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