4-aminobenzene-1-sulfonamide

• ChemBase ID: 144
• Molecular Formular: C6H8N2O2S
• Molecular Mass: 172.20492
• Monoisotopic Mass: 172.03064851
• SMILES: S(=O)(=O)(N)c1ccc(N)cc1
• Canonical SMILES: Nc1ccc(cc1)S(=O)(=O)N
• InChI: InChI=1S/C6H8N2O2S/c7-5-1-3-6(4-2-5)11(8,9)10/h1-4H,7H2,(H2,8,9,10)
• InChIKey: FDDDEECHVMSUSB-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-aminobenzene-1-sulfonamide
• IUPAC Traditional name: sulfanilamide
• Brand Name: Sulfana; Sulfanalone; Sulfanidyl; Sulfanil; Sulfanilamide Vaginal Cream; Sulfocidin; Sulfocidine; Sulfonamide; Sulfonamide P; Sulphanilamide Extra Pure; Sulphanilamide Gr; Therapol; Tolder; White Streptocide; AVC; Albexan; Albosal; Ambeside; Antistrept; Astreptine; Astrocid; 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
• Synonyms: 4-Aminobenzenesulfonamide; 4-aminobenzenesulfonamide; Sulfanilamide; P-Aminobenzenesulfamide; P-Sulfamoylaniline; P-Sulfamidoaniline; P-Anilinesulfonamide; P-Aminophenylsulfonamide; P-Aminobenzensulfonamide; P-Aminobenzenesulfonylamide; P-Aminobenzenesulfonamide; PABS; Sulfanilimidic Acid; Sulfonylamide; Sulphanilamide; Sulphonamide; Sulfanilamide; 4-(Aminosulfonyl)aniline; Sulfanilamide; 4-Aminophenylsulfonamide; 4-Sulfamoylaniline; A-349; Albexan; Albosal; Ambeside; Antistrept; Astreptine; Astrocid; Bacteramid; Bactesid; Collomide; Deseptyl; Dipron; Ergaseptine; Erysipan; Sulphanilamide; 对氨基苯磺酰胺; 磺胺

Database IDs

• CAS Number: 63-74-1
• EC Number: 200-563-4
• MDL Number: MFCD00007939
• Beilstein Number: 511852
• Merck Index: 148925
• PubChem SID: 46508306; 160963607; 24899829; 24870531; 24860368
• PubChem CID: 5333

CALCULATED PROPERTIES

JChem

• Acid pKa: 10.990055
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): -0.2499021
• LogD (pH = 7.4): -0.2497514
• Log P: -0.24964938
• Molar Refractivity: 42.9163 cm^3
• Polarizability: 16.782362 Å^3
• Polar Surface Area: 86.18 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: -0.16
• LOG S: -1.22
• Solubility (Water): 1.04e+01 g/l

PROPERTIES

Physical Property

• Solubility: 7500 mg/L; Acetone; Water
• Apperance: White Solid
• Melting Point: 163-166 °C; 163-168°C; 164-166 °C; 164-166 °C(lit.); 164-166°C; 164-167°C
• Density: 1.08; 1.08 g/ml
• Hydrophobicity(logP): -0.8

Safety Information

• Storage Condition: -20°C; Refrigerator; Room Temperature (15-30°C)
• RTECS: WO8400000
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: R:36/37/38
• Safety Statements: S:20-25-26-37/39
• TSCA Listed: 是
• GHS Pictograms: GHS07
• GHS Hazard statements: H302
• GHS Precautionary statements: P264-P270-P301+P312-P330-P501A
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Pharmacology Properties

• Gene Information: human ... CA1(759), CA2(760), CA5A(763), CA5B(11238), CA9(768)mouse ... Car13(71934), Car5a(12352)

Product Information

• Purity: ≥98.0% (NT); ≥99%; ≥99% (calc. to the dried substance); ≥99.7%; 98%; 99%
• Grade: JIS special grade; puriss. p.a.; purum; VETRANAL™, analytical standard
• Salt Data: Free Base
• Suitability: suitable for 1694 per US EPA
• Ignition Residue: ≤0.1% (as SO4); ≤0.5%
• Impurities: ≤0.002% heavy metals (as Pb)
• Antion Traces: chloride (Cl-): ≤100 mg/kg; sulfate (SO42-): ≤200 mg/kg
• Loss on Drying: ≤0.5% loss on drying, 105 °C
• Pharmacopeia Traceability: traceable to USP 1633007
• Linear Formula: H2NC6H4SO2NH2

DETAILS

MP Biomedicals - 02102988

Crystalline

DrugBank - DB00259

• 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

Selleck Chemicals - S1685

Research Area

• Description: Infection

Biological Activity

• Description: Sulfanilamide (Sulphanilamide) is a competitive inhibitor for bacterial enzyme dihydropteroate synthetase with IC50 of 320 μM.
• Targets: Dihydropteroate synthetase (DHPS)
• IC50: 320 μM ^[1]
• In Vitro: Sulfanilamide containing the sulfonamide functional group displays inhibitory activity for dihydropteroate synthetase partially purified from Escherichia coli which normally uses para-aminobenzoic acid (PABA) for synthesizing the necessary folic acid acting as a coenzyme in the synthesis of purine, pyrimidine and other amino acids, exhibiting an IC 50 of 320 μM for dihydropteroate synthetasea and Km of 2.5 uM for PABA. ^[1] Sulfanilamide shows IC50 of 286.8 μg/mL for recombinant S. cerevisiae strains with wild-type FOL1 genes, but the single mutation ^55Trp to ^55Ala or ^57Pro to ^57Ser within the putative active site of the fungal DHPS confers resistance to Sulfanilamide with IC50 of >800 μg/mL. ^[2] Sulfanilamide moderately inhibits the growth of bacterial cells harboring plasmodium falciparum pKOS-pfPPPK-DHPS (His) with IC50 of 380 uM. ^[3]
• In Vivo: Administration of Sulfanilamide with the dosage of 100 mg/kg/day is effective in the prevention of P. carinii infection in the immunosuppressed rat model. When the dosage of sulfaguanidine and Sulfanilamide reduced to 10 mg/kg/day, breakthrough P. carinii infection occurs in the rats. ^[4]

Protocol

• Protocol: Kinase Assay ^[1]
• Assay of dihydropteroate synthetase activity: The dihydropteroate synthetase activity is measured by a modification of the radioactive assay based on the incorporation of ^14C-PABA into dihydropteroate. The reaction mixture in test tubes (1 by 7 cm) is prepared in 0.4 mL of 100 mM Tris-HCl buffer (pH 8.5) (containing 10 mM of MgCl₂, 50 mM of 2-ME, 0.12 mM of hydroxymethyldihydropteridine pyrophosphate, 0.01 mM of 14C-PABA, a set of concentrations of Sulfanilamide and 0.2 mg partially purified dihydropteroate synthetase extract), and incubated for 1 hour at 37 °C. The reactions are stopped immediately by the addition of 25 μM of EDTA (pH 8.3) to each reaction mixture, then evaporated to dryness under reduced pressure and redissolved in 0.075 mL of 0.05 M Tris (pH 8.0). 0.05 mL of the above mixture is applied (each in an area of 1.0 by 4.0 cm) to Whatman 3MM chromatography paper. The chromatograms are developed by descending chromatography with 0.1 M potassium phosphate buffer (pH 7.0), for 4 hours at 25 °C. Under these conditions, pteroate (dihydropteroate is oxidized to pteroate during the evaporation step) remains at the origin, whereas unreacted ^14C-PABA migrates with an Rf value of 0.78. Areas corresponding to the origin of the developed chromatograms are cut out and counted in a liquid scintillation counter. The concentration of Sulfanilamide required for 50% inhibition of dihydropteroate synthetase activity represents IC50.
• Protocol: Animal Study ^[4]
• Animal Models: Male Sprague-Dawley rats
• Formulation: Thoroughly mixed into the daily ration of pulverized food and compounded into pellets.
• Doses: 100 mg/kg
• Administration: Orally taken every day

References

• References: [1] McCullough JL, et al. Antimicrob Agents Chemother, 1973, 3(6), 665-669.
• References: [2] Meneau I, et al. Antimicrob Agents Chemother, 2004, 48(7), 2610-2616.
• References: [3] Kasekarn W, et al. Mol Biochem Parasitol, 2004, 137(1), 43-53.
• References: [4] Hughes WT, et al. Antimicrob Agents Chemother, 1996, 40(4), 962-965.

Sigma Aldrich - 46874

Legal Information
VETRANAL is a trademark of Sigma-Aldrich Co. LLC

Sigma Aldrich - 86060

Application
Sulfanilamide is used as a competitive inhibitor of dihydropteroate synthetase to block the synthesis of folic acid.

Sigma Aldrich - S9251

Biochem/physiol Actions
Sulfonamide antibiotic that blocks the synthesis of dihydrofolic acid by inhibiting the enzyme dihydropteroate synthase.Mode of Action: A competitive inhibitor of dihydropteroate synthestase to block the synthesis of folic acid.Anti-microbial Spectrum: Gram positive, Gram negative, Chlamydia Mode of Resistance: Alteration of dihydropteroate synthase or alternative pathway for folic acid synthesis.
Packaging
100, 500 g in poly bottle

Toronto Research Chemicals - S689100

The active metabolite of the antibacterial dye, Sulfamidochrysoidine. Inhibits folic acid synthesis in prokaryotes. Antibacterial.

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
• Meneau I, et al. Antimicrob Agents Chemother, 2004, 48(7), 2610-2616.
• Kasekarn W, et al. Mol Biochem Parasitol, 2004, 137(1), 43-53.
• Hughes WT, et al. Antimicrob Agents Chemother, 1996, 40(4), 962-965.
• McCullough JL, et al. Antimicrob Agents Chemother, 1973, 3(6), 665-669.
• Colebrook, L., et al.: Lancet, 233, 1291 (1937)
• Dye, C., et al.: Nat. Rev. Microbiol., 7, 81 (1937)
• Isik, S., et al.: Bioorg. Med. Chem., 17, 1158 (1937)
• Intermediate for preparation of 2,6-disubstituted anilines, by electrophilic substitution followed by removal of the sulfonamide blocking group by desulfonation with sulfuric acid. See, e.g.: Org. Synth. Coll., 3, 262 (1955).