Sulfapyridine
Sulfapyridine
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Sulfapyridine

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Catalog Number PR144832
CAS 144-83-2
Structure
Synonyms 2-(4-Aminobenzenesulfonamido)pyridine
IUPAC Name 4-amino-N-pyridin-2-ylbenzenesulfonamide
Molecular Weight 249.29
Molecular Formula C11H11N3O2S
Canonical SMILES C1=CC=NC(=C1)NS(=O)(=O)C2=CC=C(C=C2)N
InChI 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)
InChI Key GECHUMIMRBOMGK-UHFFFAOYSA-N
Purity 98%
Drug Categories Amides; Amines; Aniline Compounds; Anti-Infective Agents; Antibacterials for Systemic Use; Antiinfectives for Systemic Use; Benzene Derivatives; Benzenesulfonamides; Cytochrome P-450 CYP2C9 Inhibitors; Cytochrome P-450 CYP2C9 Inhibitors (strength unknown); Cytochrome P-450 Enzyme Inhibitors; Dermatologicals; Genito Urinary System and Sex Hormones; Gynecological Antiinfectives and Antiseptics; Methemoglobinemia Associated Agents; Short-Acting Antibacterial Sulfonamides; Sulfanilamides; Sulfonamides; Sulfonamides and trimethoprim; Sulfones; Sulfur Compounds
Drug Interactions Abrocitinib-The metabolism of Abrocitinib can be decreased when combined with Sulfapyridine.
Acarbose-The therapeutic efficacy of Acarbose can be increased when used in combination with Sulfapyridine.
Acenocoumarol-The metabolism of Acenocoumarol can be decreased when combined with Sulfapyridine.
Acetaminophen-The risk or severity of methemoglobinemia can be increased when Acetaminophen is combined with Sulfapyridine.
Acetohexamide-The metabolism of Acetohexamide can be decreased when combined with Sulfapyridine.
Half-Life 6-14 hours.
Type Small Molecule
Pharmacology

Indications

Sulfapyridine is an effective therapeutic agent primarily prescribed for the treatment of several dermatological conditions, including dermatitis herpetiformis, benign mucous membrane pemphigoid, and pyoderma gangrenosum. These conditions are characterized by immune-mediated skin lesions, and sulfapyridine's ability to mitigate symptoms makes it valuable in clinical settings.

Pharmacodynamics

As a sulfonamide antibiotic, sulfapyridine exhibits bacteriostatic properties by targeting and inhibiting the growth of bacteria. Its mechanism of action involves acting as a competitive inhibitor of p-aminobenzoic acid, a critical component in the folic acid metabolism cycle of bacterial cells. Despite its broad-spectrum efficacy against numerous gram-positive and gram-negative organisms, it should be noted that resistance is common among various bacterial strains. Therefore, cross-resistance may occur between different sulfonamide antibiotics. The extensive tissue distribution of sulfapyridine allows it to reach high concentrations in fluids such as pleural, peritoneal, synovial, and ocular fluids, although its effectiveness can be reduced in the presence of pus.

Absorption

Sulfapyridine demonstrates moderate oral bioavailability, with approximately 60-80% of the drug being absorbed from the gastrointestinal tract. The drug's absorption profile supports its practical use in clinical management of its indicated conditions, ensuring sufficient systemic availability following oral administration.

Metabolism

Sulfapyridine undergoes metabolic processing primarily in the liver. Hepatic metabolism is crucial for its biotransformation and subsequent excretion. Understanding the metabolic pathway of sulfapyridine is essential for optimizing dosage regimens and mitigating potential adverse effects associated with its therapeutic use.

Mechanism of Action

Sulfapyridine functions as a competitive inhibitor of the bacterial enzyme dihydropteroate synthetase. This inhibition disrupts the synthesis of folic acid, as it interferes with the processing of para-aminobenzoic acid (PABA), a critical substrate in this pathway. The role of dihydropteroate synthetase is crucial for the production of folate, which is essential for the synthesis of nucleic acids, including DNA and RNA. Consequently, the inability to synthesize DNA impairs cellular division, effectively limiting bacterial growth and proliferation.

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