Ayerlucil;Famet;Lucosil;Methazol;Microsul;Proklar;Renasul;Rufol;Salimol;Solfametizolo [Dcit];Sulamethizole;Sulfa Gram;Sulfamethazole;Sulfamethiazole;Sulfamethizol;Sulfamethizole [Usan:Inn:Jan];Sulfamethizolum [INN-Latin];Sulfamethylthiadiazole;Sulfametizol [INN-Spanish];Sulfapyelon;Sulfstat;Sulfurine;Sulphamethizole;Sulphamethyltiadiazole;Tetracid;Thidicur;Thiosulfil;Thiosulfil Forte;Ultrasul;Urocydal;Urodiaton;Urolucosil;Urosulfin;Uroz;

A sulfathiazole antibacterial agent. [PubChem]

• Forest pharmaceuticals inc
• Wyeth ayerst laboratories

• Prescript Pharmaceuticals
• Professional Co.
• Teva Pharmaceutical Industries Ltd.

Synthesis Reference

Not Available

General Reference

Ratanajamit C, Skriver MV, Norgaard M, Jepsen P, Schonheyder HC, Sorensen HT: Adverse pregnancy outcome in users of sulfamethizole during pregnancy: a population-based observational study. J Antimicrob Chemother. 2003 Nov;52(5):837-41. Epub 2003 Sep 30. Pubmed Kerrn MB, Frimodt-Moller N, Espersen F: Effects of sulfamethizole and amdinocillin against Escherichia coli strains (with various susceptibilities) in an ascending urinary tract infection mouse model. Antimicrob Agents Chemother. 2003 Mar;47(3):1002-9. Pubmed Watanabe H, Hastings JW: Inhibition of bioluminescence in Photobacterium phosphoreum by sulfamethizole and its stimulation by thymine. Biochim Biophys Acta. 1990 Jun 26;1017(3):229-34. Pubmed

Type	small molecule

Classes

Benzenesulfonamides Sulfanilamides

Substructures

Thiadiazoles Sulfonyls Aliphatic and Aryl Amines Benzene and Derivatives Benzenesulfonamides Heterocyclic compounds Aromatic compounds Sulfanilamides Sulfonamides Imines Anilines

antibacterials 抗细菌;

Indication	For the treatment of urinary tract infection
Pharmacodynamics	Sulfamethizole 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.
Mechanism of action	Sulfamethizole is a competitive inhibitor of bacterial enzyme dihydropteroate synthetase. The normal para-aminobenzoic acid (PABA) substrate is prevented from binding. The inhibited reaction is necessary in these organisms for the synthesis of folic acid.
Absorption	Rapidly absorbed.
Volume of distribution	Not Available
Protein binding	98-99%
Metabolism	Hepatic.
Route of elimination	Not Available
Half life	3-8 hours
Clearance	Not Available
Toxicity	Not Available
Affected organisms	Enteric bacteria and other eubacteria
Pathways	Not Available

Properties
State	solid
Experimental Properties	Property Value Source melting point 208 °C PhysProp water solubility 1050 mg/L (at 37 °C) YALKOWSKY,SH & DANNENFELSER,RM (1992) logP 0.54 HANSCH,C ET AL. (1995) logS -2.41 ADME Research, USCD
Predicted Properties	Property Value Source water solubility 6.11e-01 g/l ALOGPS logP 0.53 ALOGPS logP 0.21 ChemAxon logS -2.6 ALOGPS pKa (strongest acidic) 6.71 ChemAxon pKa (strongest basic) 1.95 ChemAxon physiological charge -1 ChemAxon hydrogen acceptor count 5 ChemAxon hydrogen donor count 2 ChemAxon polar surface area 97.97 ChemAxon rotatable bond count 2 ChemAxon refractivity 66.84 ChemAxon polarizability 26.26 ChemAxon

Drug	Interaction
Chlorpropamide	Sulfonamide/sulfonylurea: possible hypoglycemia
Fosphenytoin	The sulfonamide increases the effect of hydantoin
Methenamine mandelate	Possible crystallization of urates with this combination
Methotrexate	The sulfamide increases the toxicity of methotrexate
Phenytoin	The sulfonamide increases the effect of hydantoin

Not Available