Albexan;Albosal;Ambeside;Antistrept;Astreptine;Astrocid;AVC;Bacteramid;Bactesid;Collomide;Colsulanyde;Copticide;Deseptyl;Desseptyl;Dipron;Ergaseptine;Erysipan;Estreptocida;Exoseptoplix;Fourneau 1162;Gerison;Gombardol;HSDB 223;Infepan;Lusil;Lysococcine;Neococcyl;Orgaseptine;Prontalbin;Prontosil Album;Prontosil I;Prontosil White;Prontylin;Pronzin Album;Proseptal;Proseptine;Proseptol;Pysococcine;Rubiazol A;Sanamid;Septamide Album;Septanilam;Septinal;Septolix;Septoplex;Septoplix;Stopton Album;Stramid;Strepamide;Strepsan;Streptagol;Streptamid;Streptamin;Streptasol;Streptocid;Streptocid Album;Streptocide;Streptocide White;Streptocidum;Streptoclase;Streptocom;Streptol;Strepton;Streptopan;Streptosil;Streptozol;Streptozone;Streptrocide;Sulfamidyl;Sulfamine;Sulfana;Sulfanalone;Sulfanidyl;Sulfanil;Sulfanilamide Vaginal Cream;Sulfocidin;Sulfocidine;Sulfonamide;Sulfonamide P;Sulphanilamide Extra Pure;Sulphanilamide Gr;Therapol;Tolder;White Streptocide;

P-Aminobenzenesulfamide;P-Aminobenzenesulfonamide;P-Aminobenzenesulfonylamide;P-Aminobenzensulfonamide;P-Aminophenylsulfonamide;P-Anilinesulfonamide;P-Sulfamidoaniline;P-Sulfamoylaniline;PABS;Sulfanilimidic Acid;Sulfonylamide;Sulphanilamide;Sulphonamide;

Sulfanilamide is a molecule containing the sulfonamide functional group attached to an aniline. [Wikipedia]

• Azur pharma international ltd
• Teva pharmaceuticals usa inc

• Mallinckrodt Inc.
• Pharmedix
• Pharmelle LLC
• Physicians Total Care Inc.
• Sanofi-Aventis Inc.

Synthesis Reference	Not Available
General Reference	Nzila A: Inhibitors of de novo folate enzymes in Plasmodium falciparum. Drug Discov Today. 2006 Oct;11(19-20):939-44. Epub 2006 Sep 7. Pubmed

Type	small molecule

Classes

Benzenesulfonamides Sulfanilamides

Substructures

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

antibacterials 抗细菌;

Indication	For the treatment of vulvovaginitis caused by Candida albicans.
Pharmacodynamics	Sulfanilamide 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	Sulfanilamide is a competitive inhibitor of bacterial enzyme dihydropteroate synthetase. This enzyme normally uses para-aminobenzoic acid (PABA) for synthesizing the necessary folic acid. The inhibited reaction is normally necessary in these organisms for the synthesis of folic acid. Without it, bacteria cannot replicate.
Absorption	Sulfonamides are absorbed through the vaginal mucosa. There are no pharmacokinetic data available describing how much of an intravaginal dose reaches the systemic circulation.
Volume of distribution	Not Available
Protein binding	Not Available
Metabolism	Not Available
Route of elimination	Not Available
Half life	Not Available
Clearance	Not Available
Toxicity	Oral, mouse LD50 = 3700 mg/kg; Intravenous, mouse LD50 = 621 mg/kg; Oral, rabbit LD50 = 1300 mg/kg. Side effects include itching, burning, skin rash, redness, swelling, or other sign of irritation not present before use of this medicine and long-term use of sulfonamides may cause cancer of the thyroid gland.
Affected organisms	Candida albicans and other yeasts
Pathways	Not Available

Properties
State	solid
Experimental Properties	Property Value Source melting point 165.5 °C PhysProp water solubility 7500 mg/L (at 25 °C) MERCK INDEX (1976) logP -0.62 HANSCH,C ET AL. (1995) logS -1.36 ADME Research, USCD pKa 10.6 (at 20 °C) SERJEANT,EP & DEMPSEY,B (1979)
Predicted Properties	Property Value Source water solubility 1.04e+01 g/l ALOGPS logP -0.16 ALOGPS logP -0.25 ChemAxon logS -1.2 ALOGPS pKa (strongest acidic) 10.99 ChemAxon pKa (strongest basic) 2.27 ChemAxon physiological charge 0 ChemAxon hydrogen acceptor count 3 ChemAxon hydrogen donor count 2 ChemAxon polar surface area 86.18 ChemAxon rotatable bond count 1 ChemAxon refractivity 42.92 ChemAxon polarizability 16.25 ChemAxon

Not Available