| Identification | More | [Name]
Sulfapyridine | [CAS]
144-83-2 | [Synonyms]
2-(4-AMINOBENZENESULFONAMIDO)PYRIDINE
2-SULFANILAMIDOPYRIDINE
2-sulfapyridine
4-((2-pyridylamino)sulfonyl)aniline
4-AMINO-N-2-PYRIDINYL-BENZENESULFONAMIDE
4-AMINO-N-[2-PYRIDYL]BENZENE SULFONAMIDE
4-AMINO-N-PYRIDIN-2-YL-BENZENESULFONAMIDE
AKOS 91331
LABOTEST-BB LT00772295
N1-(PYRIDIN-2-YL)SULFANILAMIDE
N'-2-PYRIDYLSULFANILIDE
SULFAPYRIDINE
TIMTEC-BB SBB003154
2-(p-Aminobenzenesulfonamido)pyridine
2-(p-Aminobenzenesulphonamido)pyridine
2-Sulfanilamidopyridin
2-Sulfanilylaminopyridine
4-(2-Pyridinylsulfonyl)aniline
4-amino-n-(2-pyridinyl)-benzenesulfonamid
4-amino-n-2-pyridinyl-benzenesulfonamid | [EINECS(EC#)]
205-642-7 | [Molecular Formula]
C5H5NO3S | [MDL Number]
MFCD00038036 | [Molecular Weight]
159.16 | [MOL File]
144-83-2.mol |
| Chemical Properties | Back Directory | [Appearance]
White to Off-White Solid | [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. ]
2-8°C
| [solubility ]
DMSO (Slightly), Methanol (Slightly) | [form ]
neat | [pka]
pKa 8.48(H2O
t = 25
I = 0.05) (Uncertain) | [color ]
White to Off-White | [Stability:]
Stable. Combustible. Protect from light. Incompatible with strong oxidizing agents. | [Water Solubility ]
<0.1 g/100 mL at 22 ºC | [Merck ]
8938 | [BRN ]
222065 | [Major Application]
forensics and toxicology
pharmaceutical (small molecule) | [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) | [InChIKey]
GECHUMIMRBOMGK-UHFFFAOYSA-N | [SMILES]
Nc1ccc(cc1)S(=O)(=O)Nc2ccccn2 | [CAS DataBase Reference]
144-83-2(CAS DataBase Reference) | [NIST Chemistry Reference]
Sulfapyridine(144-83-2) | [EPA Substance Registry System]
144-83-2(EPA Substance) |
| Safety Data | Back Directory | [Symbol(GHS) ]
GHS08 | [Signal word ]
Warning | [Hazard statements ]
H361fd | [Precautionary statements ]
P201-P202-P280-P308+P313-P405-P501 | [Hazard Codes ]
Xi | [Risk Statements ]
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
S22:Do not breathe dust .
S24/25:Avoid contact with skin and eyes .
S36:Wear suitable protective clothing .
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice . | [WGK Germany ]
2
| [RTECS ]
DA9625000
| [TSCA ]
TSCA listed | [REACH Registrations]
Active | [HazardClass ]
IRRITANT | [HS Code ]
29350010 | [Storage Class]
11 - Combustible Solids | [Hazard Classifications]
Repr. 2 | [Safety Profile]
Moderately 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. | [Toxicity]
LD50 orally in mice: 7.5 mg/g (Wien) |
| Hazard Information | Back Directory | [General Description]
Odorless or almost odorless white or yellowish-white crystalline powder. Very slightly bitter taste. Aqueous solution is neutral. | [Reactivity Profile]
SULFAPYRIDINE(144-83-2) is an amino acid. Slowly darkens on exposure to light . Soluble in both acidic and basic aqueous solutions | [Air & Water Reactions]
Insoluble in water. | [Fire Hazard]
Flash point data for this chemical are not available; however, SULFAPYRIDINE is probably combustible. | [Description]
Sulfapyridine is a sulfonamide antibiotic with antibacterial and anti-inflammatory activities.1 It is also a metabolite of sulfasalazine (Item No. 15025) formed through bacterial conversion in the colon.2 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).3,4 It is an inhibitor of recombinant P. carinii dihydropteroate synthetase (DHPS; IC50 = 0.18 μM).5 Sulfapyridine scavenges peroxyl radicals in an oxygen radical absorbance capacity (ORAC) assay.2 It inhibits histamine release induced by compound 48/80 (Item No. 22173) from isolated rat peritoneal mast cells in a dose-dependent manner.6 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 Properties]
White to Off-White Solid | [Uses]
antibacterial, dermatitis herpetiformis therapy | [Uses]
Used in treatment of dermatitis herpetiformis; antibacterial. | [Definition]
ChEBI: A sulfonamide consisting of pyridine with a 4-aminobenzenesulfonamido group at the 2-position. | [Antimicrobial activity]
Like 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. | [Synthesis]
Sulfapyridine, N1
-(2-pyridyl)-sulfanilamide (33.1.21), is also synthesized
by an analogous scheme from 4-acetylaminobenzenesulfonyl chloride and 2-amino pyridine. | [Purification Methods]
Crystallise 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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