Sulfanilamide

• Catalog No.: DB00259
• CAS Number: 63-74-1
• M. F.: C6H8N2O2S
• M. W.: 172.20492

SYNONYMS

• IUPAC name: 4-aminobenzene-1-sulfonamide
• IUPAC Traditional name: sulfanilamide
• Brand Name: Pysococcine; White Streptocide; Sulfanidyl; Streptocidum; Sulphanilamide Extra Pure; Sulfanilamide Vaginal Cream; Sulfonamide; Copticide; Deseptyl; Dipron; Prontalbin; Rubiazol A; Septamide Album; Septinal; Streptocide White; Sulfamine; Sulfanalone; Antistrept; Bacteramid; Erysipan; Exoseptoplix; Gerison; Orgaseptine; Prontosil I; Pronzin Album; Sanamid; Septanilam; Septoplix; Strepsan; Streptamid; Streptol; Streptosil; Streptrocide; Sulfamidyl; Sulfana; Sulfocidin; Sulfocidine; Sulfonamide P; Sulphanilamide Gr; Therapol; AVC; Albexan; Albosal; Ambeside; Astreptine; Astrocid; Bactesid; Colsulanyde; Desseptyl; Ergaseptine; Estreptocida; Fourneau 1162; Gombardol; Infepan; Lusil; Lysococcine; Neococcyl; Prontosil Album; Prontylin; Proseptal; Proseptine; Septolix; Septoplex; Stramid; Strepamide; Streptagol; Streptamin; Streptasol; Streptocid Album; Streptocide; Streptoclase; Streptocom; Strepton; Streptopan; Streptozol; Streptozone; Sulfanil; Tolder; Collomide; HSDB 223; Prontosil White; Proseptol; Stopton Album; Streptocid
• Synonyms: Sulfanilimidic Acid; P-Sulfamidoaniline; P-Aminobenzenesulfamide; P-Aminophenylsulfonamide; P-Aminobenzensulfonamide; P-Aminobenzenesulfonylamide; PABS; Sulphanilamide; P-Sulfamoylaniline; P-Anilinesulfonamide; P-Aminobenzenesulfonamide; Sulfonylamide; Sulphonamide

DATABASE IDS

• PubChem CID: 5333
• CAS Number: 63-74-1
• PubChem SID: 46508306

PROPERTIES

• Hydrophobicity(logP): -0.8
• Solubility: 7500 mg/L

DETAILS

Description (English)

• Drug Groups: approved
• Description: Sulfanilamide is a molecule containing the sulfonamide functional group attached to an aniline. [Wikipedia]
• Indication: For the treatment of vulvovaginitis caused by Candida albicans.
• Pharmacology: 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.
• 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
• 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.
• References: 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]
• External Links: Wikipedia; Drugs.com

REFERENCES

• 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