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Sulfapyridine

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CAS:144-83-2
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  • Sulfapyridine
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  • 2025-11-10
  • CAS:144-83-2
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Sulfapyridine Basic information
Product Name:Sulfapyridine
Synonyms:2-(4-Aminobenzenesulfonamido)pyridine N'-2-Pyridylsulfanilide 2-Sulfanilamidopyridine;Sulfapyridine Solution, 100ppm;CTG-B43a;CTG-B45d;HRIHFB2206;Monoclonal Anti-THAP11 antibody produced in mouse;THAP11;Sulfapyridine (Dagenan)
CAS:144-83-2
MF:C11H11N3O2S
MW:249.29
EINECS:205-642-7
Product Categories:SULPHAPYRIDINE;Pharmaceuticals;Sulfapyridine;Aromatics Compounds;Aromatics;Sulfur & Selenium Compounds;Intermediates & Fine Chemicals
Mol File:144-83-2.mol
Sulfapyridine Structure
Sulfapyridine Chemical Properties
Melting point 191-193°C
Boiling point 473.5±51.0 °C(Predicted)
density 1.3220 (rough estimate)
refractive index 1.6740 (estimate)
storage temp. Keep in dark place,Sealed in dry,Room Temperature
solubility DMSO (Slightly), Methanol (Slightly)
form Solid
pkapKa 8.48(H2O t = 25 I = 0.05) (Uncertain)
color White to Off-White
Water Solubility <0.1 g/100 mL at 22 ºC
Merck 14,8938
BRN 222065
Stability:Stable. Combustible. Protect from light. Incompatible with strong oxidizing agents.
CAS DataBase Reference144-83-2(CAS DataBase Reference)
NIST Chemistry ReferenceSulfapyridine(144-83-2)
EPA Substance Registry SystemSulfapyridine (144-83-2)
Safety Information
Hazard Codes Xi
Risk Statements 36/37/38
Safety Statements 22-24/25-36-26
WGK Germany 2
RTECS DA9625000
HazardClass IRRITANT
HS Code 29350010
ToxicityLD50 orally in mice: 7.5 mg/g (Wien)
MSDS Information
ProviderLanguage
4-((2-Pyridylamino)sulfonyl)aniline English
SigmaAldrich English
Sulfapyridine Usage And Synthesis
DescriptionSulfapyridine is a sulfonamide antibiotic with antibacterial and anti-inflammatory activities. It is also a metabolite of sulfasalazine formed through bacterial conversion in the colon. It is active against strains of Y. enterocolitica and Salmonella (MICs = 3.1-25 and 25-100 μg/ml, respectively), as well as S. aureus (MBC = 0.8 μM). It is an inhibitor of recombinant P. carinii dihydropteroate synthetase (DHPS; IC50 = 0.18 μM). Sulfapyridine scavenges peroxyl radicals in an oxygen radical absorbance capacity (ORAC) assay. It inhibits histamine release induced by compound 48/80 from isolated rat peritoneal mast cells in a dose-dependent manner. Sulfapyridine (1 μg/kg) also inhibits compound 48/80-induced systemic allergic reaction in rats. Formulations containing sulfapyridine have previously been used in the treatment of dermatological conditions and ulcerative colitis.
Chemical PropertiesWhite to Off-White Solid
Usesantibacterial, dermatitis herpetiformis therapy
UsesUsed in treatment of dermatitis herpetiformis; antibacterial.
DefinitionChEBI: A sulfonamide consisting of pyridine with a 4-aminobenzenesulfonamido group at the 2-position.
Antimicrobial activityLike all sulfanilamides, this drug possesses antibacterial activity with respect to streptococci, pneumococci, staphylococci, meningococci, gonococci, colon bacillus, pathogenic dysentery, and so on. It is a long-lasting drug. Synonyms of this drug are bacillopirin, plurazol, sulfidin, and thiaseptol.
General DescriptionSulfapyridine’s plasma half-life is 9 hours.This compound is a white, crystalline, odorless, and tastelesssubstance. It is stable in air but slowly darkens on exposureto light. It is soluble in water (1:3,500), in alcohol(1:440), and in acetone (1:65) at 25°C. It is freely soluble indilute mineral acids and aqueous solutions of sodium andpotassium hydroxide. The pKa is 8.4. Its outstanding effectin curing pneumonia was first recognized by Whitby; however,because of its relatively high toxicity, it has been supplantedlargely by sulfadiazine and sulfamerazine. Severalcases of kidney damage have resulted from acetylsulfapyridinecrystals deposited in the kidneys. It also causes severenausea in most patients. Because of its toxicity, it is usedonly for dermatitis herpetiformis.
Sulfapyridine was the first drug to have an outstandingcurative action on pneumonia. It gave impetus to the studyof the whole class of N1 heterocyclically substituted derivativesof sulfanilamide.
General DescriptionOdorless or almost odorless white or yellowish-white crystalline powder. Very slightly bitter taste. Aqueous solution is neutral.
Air & Water ReactionsInsoluble in water.
Reactivity ProfileSulfapyridine is an amino acid. Slowly darkens on exposure to light . Soluble in both acidic and basic aqueous solutions
Fire HazardFlash point data for Sulfapyridine are not available; however, Sulfapyridine is probably combustible.
Safety ProfileModerately toxic by intraperitoneal and intravenous routes. Slightly toxic by ingestion. Experimental reproductive effects. Human mutation data reported. Questionable carcinogen with experimental tumorigenic data. When heated to decomposition it emits very toxic fumes of NO, and SOx.
SynthesisSulfapyridine, N1 -(2-pyridyl)-sulfanilamide (33.1.21), is also synthesized by an analogous scheme from 4-acetylaminobenzenesulfonyl chloride and 2-amino pyridine.
Purification MethodsCrystallise sulfapyridine from 90% acetone and dry it at 90o. Its solubility in Me2CO, EtOH and H2O is 1.5%, 0.22% and 0.02%, respectively. [Winterbottom J Am Chem Soc 62 160 1940, Beilstein 22 III/IV 3978.]
References[1] A L LORINCZ  R W P. Sulfapyridine and sulfone type drugs in dermatology.[J]. Archives of dermatology, 1962, 85: 2-16. DOI: 10.1001/archderm.1962.01590010008002
[2] DIANA COUTO. Scavenging of reactive oxygen and nitrogen species by the prodrug sulfasalazine and its metabolites 5-aminosalicylic acid and sulfapyridine.[J]. Redox Report, 2010, 15 6: 259-267. DOI: 10.1179/135100010x12826446921707
[3] JAN JESPER ANDREASEN  SUSANNE H H  LEIF PERCIVAL ANDERSEN. In vitro susceptibility of diarrhoea producing Gram negative enteric bacteria to sulfasalazine, 5-aminosalicylic acid, sulfapyridine and four quinolones[J]. Apmis, 1988, 96 1-6: 568-570. DOI: 10.1111/j.1699-0463.1988.tb05346.x
[4] W B WOOD  R A. STUDIES ON THE ANTIBACTERIAL ACTION OF THE SULFONAMIDE DRUGS?: II. THE POSSIBLE RELATION OF DRUG ACTIVITY TO SUBSTANCES OTHER THANp-AMINOBENZOIC ACID.[J]. Journal of Experimental Medicine, 1942, 75 4: 383-394. DOI: 10.1084/jem.75.4.383
[5] Y L HONG. Inhibition of recombinant Pneumocystis carinii dihydropteroate synthetase by sulfa drugs.[J]. Antimicrobial Agents and Chemotherapy, 1995, 39 8: 1756-1763. DOI: 10.1128/aac.39.8.1756
[6] H M KIM. Inhibitory effect of mast cell-mediated immediate-type allergic reactions by sulfapyridine.[J]. Immunopharmacology and Immunotoxicology, 2000, 22 2: 253-266. DOI: 10.3109/08923970009016419
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