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63-74-1 molecular structure
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4-aminobenzene-1-sulfonamide

ChemBase ID: 144
Molecular Formular: C6H8N2O2S
Molecular Mass: 172.20492
Monoisotopic Mass: 172.03064851
SMILES and InChIs

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

Cite this record

CBID:144 http://www.chembase.cn/molecule-144.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
4-aminobenzene-1-sulfonamide
IUPAC Traditional name
sulfanilamide
Brand Name
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
Sulfana
Sulfanalone
Sulfanidyl
Sulfanil
Sulfanilamide Vaginal Cream
Sulfocidin
Sulfocidine
Sulfonamide
Sulfonamide P
Sulphanilamide Extra Pure
Sulphanilamide Gr
Therapol
Tolder
White Streptocide
Synonyms
P-Aminobenzenesulfamide
P-Sulfamoylaniline
P-Sulfamidoaniline
P-Anilinesulfonamide
P-Aminophenylsulfonamide
P-Aminobenzensulfonamide
P-Aminobenzenesulfonylamide
P-Aminobenzenesulfonamide
PABS
Sulfanilimidic Acid
Sulfonylamide
Sulphanilamide
Sulphonamide
Sulfanilamide
4-Aminobenzenesulfonamide
4-aminobenzenesulfonamide
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
CAS Number
63-74-1
EC Number
200-563-4
MDL Number
MFCD00007939
Beilstein Number
511852
Merck Index
148925
PubChem SID
46508306
24860368
160963607
24870531
24899829
PubChem CID
5333

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem ALOGPS 2.1
Acid pKa 10.990055  H Acceptors
H Donor LogD (pH = 5.5) -0.2499021 
LogD (pH = 7.4) -0.2497514  Log P -0.24964938 
Molar Refractivity 42.9163 cm3 Polarizability 16.782362 Å3
Polar Surface Area 86.18 Å2 Rotatable Bonds
Lipinski's Rule of Five true 
Log P -0.16  LOG S -1.22 
Solubility (Water) 1.04e+01 g/l 

PROPERTIES

PROPERTIES

Physical Property Safety Information Pharmacology Properties Product Information Bioassay(PubChem)
Solubility
7500 mg/L expand Show data source
Acetone expand Show data source
Water expand Show data source
Apperance
White Solid expand Show data source
Melting Point
163-166 °C expand Show data source
163-168°C expand Show data source
164-166 °C expand Show data source
164-166 °C(lit.) expand Show data source
164-166°C expand Show data source
164-167°C expand Show data source
Density
1.08 expand Show data source
1.08 g/ml expand Show data source
Hydrophobicity(logP)
-0.8 expand Show data source
Storage Condition
-20°C expand Show data source
Refrigerator expand Show data source
Room Temperature (15-30°C) expand Show data source
RTECS
WO8400000 expand Show data source
European Hazard Symbols
Irritant Irritant (Xi) expand Show data source
MSDS Link
Download expand Show data source
Download expand Show data source
Download expand Show data source
Download expand Show data source
Download expand Show data source
Download expand Show data source
Download expand Show data source
Download expand Show data source
Download expand Show data source
German water hazard class
3 expand Show data source
Risk Statements
R:36/37/38 expand Show data source
Safety Statements
S:20-25-26-37/39 expand Show data source
TSCA Listed
expand Show data source
GHS Pictograms
GHS07 expand Show data source
GHS Hazard statements
H302 expand Show data source
GHS Precautionary statements
P264-P270-P301+P312-P330-P501A expand Show data source
Personal Protective Equipment
Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter expand Show data source
Gene Information
human ... CA1(759), CA2(760), CA5A(763), CA5B(11238), CA9(768)mouse ... Car13(71934), Car5a(12352) expand Show data source
Purity
≥98.0% (NT) expand Show data source
≥99% expand Show data source
≥99% (calc. to the dried substance) expand Show data source
≥99.7% expand Show data source
98% expand Show data source
99% expand Show data source
Grade
JIS special grade expand Show data source
puriss. p.a. expand Show data source
purum expand Show data source
VETRANAL™, analytical standard expand Show data source
Salt Data
Free Base expand Show data source
Certificate of Analysis
Download expand Show data source
Download expand Show data source
Suitability
suitable for 1694 per US EPA expand Show data source
Ignition Residue
≤0.1% (as SO4) expand Show data source
≤0.5% expand Show data source
Impurities
≤0.002% heavy metals (as Pb) expand Show data source
Antion Traces
chloride (Cl-): ≤100 mg/kg expand Show data source
sulfate (SO42-): ≤200 mg/kg expand Show data source
Loss on Drying
≤0.5% loss on drying, 105 °C expand Show data source
Pharmacopeia Traceability
traceable to USP 1633007 expand Show data source
Linear Formula
H2NC6H4SO2NH2 expand Show data source

DETAILS

DETAILS

DrugBank DrugBank MP Biomedicals MP Biomedicals Sigma Aldrich Sigma Aldrich Selleck Chemicals Selleck Chemicals TRC TRC
DrugBank - DB00259 external link
Item Information
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
Sigma Aldrich - 86060 external link
Application
Sulfanilamide is used as a competitive inhibitor of dihydropteroate synthetase to block the synthesis of folic acid.
Sigma Aldrich - 46874 external link
Legal Information
VETRANAL is a trademark of Sigma-Aldrich Co. LLC
Sigma Aldrich - S9251 external link
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
Selleck Chemicals - S1685 external link
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]
Clinical Trials
Features
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.
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
[1] McCullough JL, et al. Antimicrob Agents Chemother, 1973, 3(6), 665-669.
[2] Meneau I, et al. Antimicrob Agents Chemother, 2004, 48(7), 2610-2616.
[3] Kasekarn W, et al. Mol Biochem Parasitol, 2004, 137(1), 43-53.
[4] Hughes WT, et al. Antimicrob Agents Chemother, 1996, 40(4), 962-965.
Toronto Research Chemicals - S689100 external link
The active metabolite of the antibacterial dye, Sulfamidochrysoidine. Inhibits folic acid synthesis in prokaryotes. Antibacterial.

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