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)

pka

pKa 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 Reference

144-83-2(CAS DataBase Reference)

NIST Chemistry Reference

Sulfapyridine(144-83-2)

EPA Substance Registry System

Sulfapyridine (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

Toxicity

LD50 orally in mice: 7.5 mg/g (Wien)

MSDS

• Language:English Provider:4-((2-Pyridylamino)sulfonyl)aniline
• Language:English Provider:SigmaAldrich

Sulfapyridine Usage And Synthesis

Description

Sulfapyridine 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 Properties

White to Off-White Solid

Uses

Used in treatment of dermatitis herpetiformis; antibacterial.

Uses

antibacterial, dermatitis herpetiformis therapy

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.

General Description

Sulfapyridine’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 Description

Odorless or almost odorless white or yellowish-white crystalline powder. Very slightly bitter taste. Aqueous solution is neutral.

Air & Water Reactions

Insoluble in water.

Reactivity Profile

Sulfapyridine is an amino acid. Slowly darkens on exposure to light . Soluble in both acidic and basic aqueous solutions

Fire Hazard

Flash point data for Sulfapyridine are not available; however, Sulfapyridine is probably combustible.

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.

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.]

Sulfapyridine(144-83-2)Related Product Information

• 2-Aminophenol
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• ANILINE BLACK