Sulfapyridine

Synonyms :
2-(P-Aminobenzenesulphonamido)pyridine, 2-Sulfanilamidopyridin, 2-Sulfanilamidopyridine, 2-Sulfanilylaminopyridine, 2-Sulfapyridine, 4-(2-Pyridinylsulfonyl)aniline, 4-[(2-Pyridylamino)sulfonyl]aniline, 4-Amino-N-pyridin-2-yl-benzenesulfonamide, 4-Amino-N,2-pyridinylbenzenesulfonamide, N-2-Pyridylsulfanilamide, N(1)-2-Pyridylsulfanilamide, N(1)-Pyridylsulfanilamide, Solfapiridina, Streptosilpyridine, Sulfapiridina, Sulfapyridin, Sulfapyridine, Sulfapyridinum, Sulphapyridine

Status : approved

Category

Dermatologic Agents

Therapeutic Classification

SULFONAMIDES AND TRIMETHOPRIM

ANTIINFECTIVES FOR SYSTEMIC USE
ANTIBACTERIALS FOR SYSTEMIC USE
SULFONAMIDES AND TRIMETHOPRIM
Anti-Infective Agents

Description

Antibacterial, potentially toxic, and previously used to treat certain skin diseases. No longer prescribed.

Used

For the treatment of dermatitis herpetiformis, benign mucous membrane pemphigoid and pyoderma gangrenosum

Mechanism Of Action

Sulfapyridine is a competitive inhibitor of the bacterial enzyme dihydropteroate synthetase. The inhibited reaction is necessary in these organisms for the synthesis of folic acid by means of processing the substrate para-aminobenzoic acid (PABA). Dihydropteroate synthetase activity is vital in the synthesis of folate, and folate is required for cells to make nucleic acids, such as DNA or RNA. So if DNA molecules cannot be built, the cell cannot divide.

Dosage

Form Route Strength
Tablet oral 500 mg

Pharmacodynamics

Sulfapyridine is a sulfonamide antibiotic. The sulfonamides are synthetic bacteriostatic antibiotics with a wide spectrum against most gram-positive and many gram-negative organisms. However, many strains of an individual species may be resistant. Sulfonamides inhibit multiplication of bacteria by acting as competitive inhibitors of p-aminobenzoic acid in the folic acid metabolism cycle. Bacterial sensitivity is the same for the various sulfonamides, and resistance to one sulfonamide indicates resistance to all. Most sulfonamides are readily absorbed orally. However, parenteral administration is difficult, since the soluble sulfonamide salts are highly alkaline and irritating to the tissues. The sulfonamides are widely distributed throughout all tissues. High levels are achieved in pleural, peritoneal, synovial, and ocular fluids. Although these drugs are no longer used to treat meningitis, CSF levels are high in meningeal infections. Their antibacterial action is inhibited by pus.

Toxic Effect

LD50 is 15800 mg/kg (orally in rats).

Metabolism

Hepatic.

Absorption

Approximately 60-80%

Half Life

6-14 hours.

Protein Binding

Approximately 50% bound to plasma proteins.

Chemical Classification

This compound belongs to the class of organic compounds known as aminobenzenesulfonamides. These are organic compounds containing a benzenesulfonamide moiety with an amine group attached to the benzene ring.

Aminobenzenesulfonamides

Organic compounds

Benzenoids

Benzene and substituted derivatives

Benzenesulfonamides

Chemical Name

2-(P-Aminobenzenesulphonamido)pyridine

Brands

name Dosage form Country
Dagenan Tab 500mg tablet Canada

Drug Drug Interactions

  •  Mecamylamine  : May enhance the adverse/toxic effect of Mecamylamine.

Calculated Property

kind Value Source
logP 0.84 ALOGPS
logS -3 ALOGPS
Water Solubility 2.35e-01 g/l ALOGPS
logP 1.01 ChemAxon
IUPAC Name 4-amino-N-(pyridin-2-yl)benzene-1-sulfonamide ChemAxon
Traditional IUPAC Name ronin ChemAxon
Molecular Weight 249.289 ChemAxon
Monoisotopic Weight 249.057197301 ChemAxon
SMILES NC1=CC=C(C=C1)S(=O)(=O)NC1=CC=CC=N1 ChemAxon
Molecular Formula C11H11N3O2S ChemAxon
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) ChemAxon
InChIKey InChIKey=GECHUMIMRBOMGK-UHFFFAOYSA-N ChemAxon
Polar Surface Area (PSA) 85.08 ChemAxon
Refractivity 65.75 ChemAxon
Polarizability 24.97 ChemAxon
Rotatable Bond Count 2 ChemAxon
H Bond Acceptor Count 4 ChemAxon
H Bond Donor Count 2 ChemAxon
pKa (strongest acidic) 6.24 ChemAxon
pKa (strongest basic) 2.63 ChemAxon
Physiological Charge -1 ChemAxon
Number of Rings 2 ChemAxon
Bioavailability 1 ChemAxon
Rule of Five 1 ChemAxon
Ghose Filter 1 ChemAxon
MDDR-Like Rule 0 ChemAxon

Affected organism

Humans and other mammals

Target within organism

  • Dihydropteroate synthase type-1 : in Mycobacterium fortuitum