Sulfapyridine

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Sulfapyridine
Sulfapyridine.png
Clinical data
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MedlinePlus a682204
ATC code
Identifiers
  • 4-Amino-N-pyridin-2-ylbenzenesulfonamide
CAS Number
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Chemical and physical data
Formula C11H11N3O2S
Molar mass 249.29 g·mol−1
3D model (JSmol)
Melting point 191 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) Yes check.svgY
  • Key:GECHUMIMRBOMGK-UHFFFAOYSA-N Yes check.svgY
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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 is no longer prescribed for treatment of infections in humans. However, it may be used to treat linear IgA disease and has use in veterinary medicine. [1] It is a good antibacterial drug, but its water solubility is very pH dependent. Thus there is a risk of crystallization within the bladder or urethra, which could lead to pain or blockage. As with other sulfonamides, there is a significant risk of agranulocytosis, and this, rather than the development of resistance by bacteria, is the main reason for its decline in use.

Contents

History

M&B 693 was one of the first generation of sulfonamide antibiotics. It was discovered by Lionel Whitby at the British firm May & Baker Ltd and logged in their Test Book on 2 November, 1937 under Code No M&B 693.

During the aftermath to the disastrous convoy SC7, in October 1940, Surgeon-Lieutenant John Robertson, RN, of HMS Leith, saved the life of Commodore Lachlan MacKinnon, from the torpedoed Assyrian , who had developed pneumonia, by giving him M&B 693, despite Robertson never having used it before and not knowing the required dosage. [2]

M&B 693 was successfully used to treat Winston Churchill's bacterial pneumonia. [3] [4] The same source records that in 1944 M&B 693 also saved Nero, the Royal Circus lion, from pneumonia. [5]

It could either be taken in tablet form 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 It was later largely superseded by penicillin and other sulfonamides.

The drug sulfasalazine is structurally one molecule of mesalamine linked to one molecule of sulfapyridine with an azo chemical linker.

Related Research Articles

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An antibiotic is a type of antimicrobial substance active against bacteria. It is the most important type of antibacterial agent for fighting bacterial infections, and antibiotic medications are widely used in the treatment and prevention of such infections. They may either kill or inhibit the growth of bacteria. A limited number of antibiotics also possess antiprotozoal activity. Antibiotics are not effective against viruses such as the common cold or influenza; drugs which inhibit growth of viruses are termed antiviral drugs or antivirals rather than antibiotics. They are also not effective against fungi; drugs which inhibit growth of fungi are called antifungal drugs.

<span class="mw-page-title-main">Alexander Fleming</span> Scottish biologist, pharmacologist, botanist, and Nobel laureate (1881–1955)

Sir Alexander Fleming,, was a Scottish physician and microbiologist, best known for discovering the world's first broadly effective antibiotic substance, which he named penicillin. His discovery in 1928 of what was later named benzylpenicillin from the mould Penicillium rubens is described as the "single greatest victory ever achieved over disease". For this discovery, he shared the Nobel Prize in Physiology or Medicine in 1945 with Howard Florey and Ernst Boris Chain.

<span class="mw-page-title-main">Sulfonamide (medicine)</span> Molecular moiety or the drug class that uses it

Sulfonamide is a functional group that is the basis of several groups of drugs, which are called sulphonamides, sulfa drugs or sulpha drugs. The original antibacterial sulfonamides are synthetic (nonantibiotic) antimicrobial agents that contain the sulfonamide group. Some sulfonamides are also devoid of antibacterial activity, e.g., the anticonvulsant sultiame. The sulfonylureas and thiazide diuretics are newer drug groups based upon the antibacterial sulfonamides.

<span class="mw-page-title-main">Loop diuretic</span> Diuretics that act at the ascending limb of the loop of Henle in the kidney

Loop diuretics are diuretics that act on the Na-K-Cl cotransporter along the thick ascending limb of the loop of Henle in nephrons of the kidneys. They are primarily used in medicine to treat hypertension and edema often due to congestive heart failure or chronic kidney disease. While thiazide diuretics are more effective in patients with normal kidney function, loop diuretics are more effective in patients with impaired kidney function.

<span class="mw-page-title-main">Trimethoprim/sulfamethoxazole</span> Combination of 2 antibiotic drugs

Trimethoprim/sulfamethoxazole, sold under the brand name Bactrim among others, is a fixed-dose combination antibiotic medication used to treat a variety of bacterial infections. It consists of one part trimethoprim to five parts sulfamethoxazole. It is used to treat urinary tract infections, methicillin-resistant Staphylococcus aureus (MRSA) skin infections, travelers' diarrhea, respiratory tract infections, and cholera, among others. It is used both to treat and prevent pneumocystis pneumonia and toxoplasmosis in people with HIV/AIDS and other causes of immunosuppression. It can be given by mouth or intravenously.

<span class="mw-page-title-main">Mesalazine</span> Anti-inflammatory drug

Mesalazine, also known as mesalamine or 5-aminosalicylic acid (5-ASA), is a medication used to treat inflammatory bowel disease, including ulcerative colitis and Crohn's disease. It is generally used for mildly to moderately severe disease. It is taken by mouth or rectally. The formulations which are taken by mouth appear to be similarly effective.

<span class="mw-page-title-main">Sulfasalazine</span> Chemical compound

Sulfasalazine, sold under the brand name Azulfidine among others, is a medication used to treat rheumatoid arthritis, ulcerative colitis, and Crohn's disease. It is considered by some to be a first-line treatment in rheumatoid arthritis. It is taken by mouth.

<span class="mw-page-title-main">Prontosil</span> An early antimicrobial drug of nonantibiotic type

Prontosil is an antibacterial drug of the sulfonamide group. It has a relatively broad effect against gram-positive cocci but not against enterobacteria. One of the earliest antimicrobial drugs, it was widely used in the mid-20th century but is little used today because better options now exist. The discovery and development of this first sulfonamide drug opened a new era in medicine, because it greatly widened the success of antimicrobial chemotherapy in an era when many physicians doubted its still largely untapped potential. At the time, disinfectant cleaners and topical antiseptic wound care were widely used but there were very few antimicrobial drugs to use safely inside living bodies. Antibiotic drugs derived from microbes, which we rely on heavily today, did not yet exist. Prontosil was discovered in 1932 by a research team at the Bayer Laboratories of the IG Farben conglomerate in Germany.

<span class="mw-page-title-main">Sulfadiazine</span> Chemical compound

Sulfadiazine is an antibiotic. Used together with pyrimethamine, a dihydrofolate reductase inhibitor, it is the treatment of choice for toxoplasmosis, which is caused by a protozoan parasite. It is a second-line treatment for otitis media, prophylaxis of rheumatic fever, chancroid, chlamydia, and infections by Haemophilus influenzae. It is also used as adjunct therapy for chloroquine-resistant malaria and several forms of bacterial meningitis. It is taken by mouth. Sulfadiazine is available in multiple generic tablets of 500 mg. For urinary tract infections, the usual dose is 4 to 6 grams daily in 3 to 6 divided doses.

<span class="mw-page-title-main">Sulfanilamide</span> Chemical compound

Sulfanilamide is a sulfonamide antibacterial drug. Chemically, it is an organic compound consisting of an aniline derivatized with a sulfonamide group. 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. 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 mainly vulvovaginitis which is caused by Candida albicans.

<span class="mw-page-title-main">Sulfacetamide</span> Chemical compound

Sulfacetamide is a sulfonamide antibiotic.

<span class="mw-page-title-main">Sulfadimethoxine</span> Chemical compound

Sulfadimethoxine is a long-lasting sulfonamide antimicrobial medication used in veterinary medicine. It is used to treat many infections, including respiratory, urinary tract, enteric, and soft tissue infections and can be given as a standalone or combined with ormetoprim to broaden the target range. Like all sulfamides, sulfadimethoxine inhibits bacterial synthesis of folic acid by acting as a competitive inhibitor against PABA. It is the most common drug prescribed to dogs who have coccidiosis.

May & Baker was a British chemical company founded by John May and William Gerrard Baker in Wandsworth, London in 1839. They initially specialized in the manufacture of chemicals derived from mercury and bismuth. Over the years they diversified into other chemical fields including photographic chemicals, pharmaceuticals, agrochemicals, and chemicals for research and development.

<span class="mw-page-title-main">Ernest Fourneau</span> French scientist (1872–1949)

Ernest Fourneau was a French pharmacist who graduated in 1898 for the Paris university specialist in medicinal chemistry and pharmacology. He played a major role in the discovery of synthetic local anesthetics such as amylocaine, as well as in the synthesis of suramin. He authored more than two hundred scholarly works, and has been described as having "helped to establish the fundamental laws of chemotherapy that have saved so many human lives".

<span class="mw-page-title-main">Sulfonamide</span> Organosulfur compounds containing –S(=O)2–N< functional group

In organic chemistry, the sulfonamide functional group is an organosulfur group with the structure R−S(=O)2−NR2. It consists of a sulfonyl group connected to an amine group. 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.

Eleanor Albert Bliss was an immunologist who made significant advancements to the field of immunological research. She was also a dean and professor of biology at Bryn Mawr College.

<span class="mw-page-title-main">Cefiderocol</span> Antibiotic

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<span class="mw-page-title-main">Azabon</span> Chemical compound

Azabon is a central nervous system stimulant of the sulfonamide class that is also used as a nootropic. As it is a sulpha drug, care must be taken during administration, and certain individuals must avoid azabon altogether to prevent an allergic reaction. Despite being a sulfonamide, azabon has poor antibacterial potency, although this decreased activity is common among other benzenesulfonamides with two substituents on N1. Azabon is synthesized from 3-azabicyclo-[2.2.2]nonane, which is itself prepared by pyrolysis of aliphatic diamine.

References

  1. "Sulfapyride". drugs.com.
  2. Lund P, Ludlam H (1974). Night of the U-boats. London: New English Library. p. 130.
  3. 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 . Retrieved 7 August 2023.
  4. Lesch, John E. (2007). "7". The first miracle drugs: how the sulfa drugs transformed medicine (PDF). Oxford: Oxford university press. pp. 158–59. ISBN   978-0-19-518775-5 . Retrieved 7 August 2023. 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....
  5. Lesch, John E. (2007). "7". The first miracle drugs: how the sulfa drugs transformed medicine (PDF). Oxford: Oxford university press. p. 193. ISBN   978-0-19-518775-5 . Retrieved 7 August 2023. 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.