Structure via PubChem · Public domain (PubChem)
sulfapyridine
Sign in to saveAlso known as Coccoclase, Piridazol, Sulfanilamidopyridine, Eubasin, N(1)-Pyridylsulfanilamide, 4-(2-Pyridinylsulfonyl)aniline, 2-Sulfapyridine, 4-Amino-N,2-pyridinylbenzenesulfonamide
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. 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
In the Vinony graph
Vinony's link graph records 147 inbound references to sulfapyridine, and connects out to sulfamethazine, antibiotic and fidaxomicin.
It sits within the topics 2-Pyridyl compounds, 4-Aminophenyl compounds and Abandoned drugs.
Vinony links it to 14 Wikipedia language editions.
Chemical data
- Formula
- C11H11N3O2S
- Molecular weight
- 249.29 g/mol
- IUPAC name
- 4-amino-N-pyridin-2-ylbenzenesulfonamide
- SMILES
- C1=CC=NC(=C1)NS(=O)(=O)C2=CC=C(C=C2)N
- InChIKey
- GECHUMIMRBOMGK-UHFFFAOYSA-N
- XLogP
- 0
- Polar surface area
- 93.5 Ų
- H-bond donors
- 2
- H-bond acceptors
- 5
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Max clinical phase
- Approved
- Molecule type
- Small molecule
- First approval
- 1939
- Admin. routes
- oral
- Indications
- bacterial disease
via ChEMBL · EBI
Research
1,167 papers- Dapsone and sulfapyridine.Dermatologic clinics · 2001
- Dapsone and sulfapyridine.Clinics in dermatology · 1989
- Development of Novel Magneto-Biosensor for Sulfapyridine Detection.Biosensors · 2020
- Drug therapy: Sulfasalazine.The New England journal of medicine · 1975
- Mea culpa.Nature clinical practice. Gastroenterology & hepatology · 2008
via PubMed
Wikidata facts
- Subclass of
- chemical compound
- Mass
- 249.057
- Has use
- medication
Show 5 more facts
- chemical formula
- C₁₁H₁₁N₃O₂S
- canonical SMILES
- C1=CC=NC(=C1)NS(=O)(=O)C2=CC=C(C=C2)N
- World Health Organisation international non-proprietary name
- sulfapyridine
- defined daily dose
- 1
- Commons category
- Sulfapyridine
via Wikidata · CC0
~3 min read
Encyclopedic overview
3 sectionsContents
- History
- Related medications
- References
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. 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.
==History==
Excerpted from Wikipedia’s “sulfapyridine” article, available under the CC BY-SA 4.0 licence.