4-(4-aminobenzenesulfonyl)aniline

• ChemBase ID: 135
• Molecular Formular: C12H12N2O2S
• Molecular Mass: 248.30088
• Monoisotopic Mass: 248.06194863
• SMILES: S(=O)(=O)(c1ccc(N)cc1)c1ccc(N)cc1
• Canonical SMILES: Nc1ccc(cc1)S(=O)(=O)c1ccc(cc1)N
• InChI: InChI=1S/C12H12N2O2S/c13-9-1-5-11(6-2-9)17(15,16)12-7-3-10(14)4-8-12/h1-8H,13-14H2
• InChIKey: MQJKPEGWNLWLTK-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-(4-aminobenzenesulfonyl)aniline
• IUPAC Traditional name: dapsone; 4-(4-aminobenzenesulfonyl)aniline
• Brand Name: Araldite Ht; Avlosulfon; Avlosulfone; Avlosulphone; Croysulfone; Croysulphone; Dimitone; Diphone; Dubronax; Dumitone; Eporal; ICI; Normet; Novophone; Recolip; Sulfadione; Sulfanona-Mae; Sulfon-Mere; Sulfona; Sulfona-Mae; Sulfone Ucb; Sulphon-Mere; Sumicure S; Tarimyl; Udolac; Aczone
• Synonyms: bis(4-AMINOPHENYL)SULFONE; 4,4′-Diaminodiphenyl sulfone; 4,4′-Sulfonyldianiline; Bis(4-aminophenyl) sulfone; 4-Aminophenyl sulfone; 4-[(4-Aminophenyl)sulfonyl]aniline; 4,4'-Diaminodiphenyl sulfone; DADPS, DDS, Avlosulfon, Croysulfone, Diphenasone, Disulone, Dumitone, Eporal, Novophone, Sulfona-Mae, Sulphadione, 4,4’-Sulfonylbisbenzeneamine; 1,1'-Sulfonylbis[4-aminobenzene]; 4,4'-Diaminodiphenyl Sulfone; NSC 6091; 4-Aminophenyl sulfone; Dapson; P, P'-Sulfonyldianiline; P-Aminophenyl Sulfone; P,P-Sulphonyldianiline; P,P-Sulphonylbisbenzenamine; P,P-Sulphonylbisbenzamine; P,P-Sulfonylbisbenzenamine; P,P-Sulfonylbisbenzamine; P,P-Diaminodiphenyl Sulphone; P,P'-Diaminodiphenyl Sulfone; N, N'-Diphenyl Sulfondiamide; Metabolite C; Sulfonyldianiline; Sulphadione; Sulphonyldianiline; Diphenasone; Diaphenylsulphone; Diaphenylsulphon; Diaphenylsulfone; Diaphenylsulfon; Diaminodiphenyl Sulfone; Diaminodifenilsulfona; Dds, Pharmaceutical; Dds, Diaphenylsulfone; DDS; Dapsonum; Dapson; DADPS; Acedapsone; Diamino-diphenyl sulphone; DSS; dapsone; Dapsone; 4,4'-二氨基二苯砜; 4,4′-磺酰基二苯胺; 双(4-氨基苯基)砜; 氨苯砜; 4-氨基苯砜; 4,4'-二氨基二苯砜; 4-氨基苯砜; 氨苯砜

Database IDs

• CAS Number: 80-08-0
• EC Number: 201-248-4
• MDL Number: MFCD00007887
• Beilstein Number: 788055
• Merck Index: 142822
• PubChem SID: 24869870; 24859802; 46505300; 160963598; 24891242
• PubChem CID: 2955
• CHEBI ID: 4325
• ATC CODE: D10AX05; J04BA02
• CHEMBL: 1043
• Chemspider ID: 2849
• DrugBank ID: DB00250
• KEGG ID: D00592
• Unique Ingredient Identifier: 8W5C518302
• Wikipedia Title: Dapsone
• Medline Plus: a682128

CALCULATED PROPERTIES

JChem

• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): 1.2698921
• LogD (pH = 7.4): 1.2702243
• Log P: 1.2702285
• Molar Refractivity: 68.991 cm^3
• Polarizability: 26.662663 Å^3
• Polar Surface Area: 86.18 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 1.19
• LOG S: -2.94
• Solubility (Water): 2.84e-01 g/l

PROPERTIES

Physical Property

• Solubility: 380 mg/L; Acetone; DMSO; Ethanol; Methanol
• Apperance: Off -White Solid
• Melting Point: 172-174°C; 175°C; 175-177 °C(lit.); 175-178°C; 175-179 °C
• Hydrophobicity(logP): 0.4

Safety Information

• Storage Condition: -20°C Freezer
• Storage Warning: IRRITANT
• RTECS: BY8925000
• European Hazard Symbols: X; Harmful (Xn)
• German water hazard class: 1
• Risk Statements: 22; R:22
• Safety Statements: 22; S:22
• TSCA Listed: false; 是
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H302
• GHS Precautionary statements: P261
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves

Pharmacology Properties

• Admin Routes: Oral
• Bioavailability: 70 to 80%
• Excretion: Renal
• Half Life: 20 to 30 hours
• Metabolism: Hepatic (mostly CYP2E1-mediated)
• Protein Bound: 70 to 90%
• Legal Status: ?-only (U.S.), POM (UK)
• Pregnancy Category: B2 (Australia); C (US)

Product Information

• Purity: ≥97.0% (NT); 97%; 98%
• Grade: purum; VETRANAL™, analytical standard
• Linear Formula: (H2NC6H4)2SO2

DETAILS

MP Biomedicals - 05212644

MP Biomedicals Rare Chemical collection

DrugBank - DB00250

• Drug Groups: approved; investigational
• Description: A sulfone active against a wide range of bacteria but mainly employed for its actions against mycobacterium leprae. Its mechanism of action is probably similar to that of the sulfonamides which involves inhibition of folic acid synthesis in susceptible organisms. It is also used with pyrimethamine in the treatment of malaria. (From Martindale, The Extra Pharmacopoeia, 30th ed, p157-8)
• Indication: For the treatment and management of leprosy and dermatitis herpetiformis.
• Pharmacology: Dapsone is a sulfone with anti-inflammatory immunosuppressive properties as well as antibacterial and antibiotic properties. Dapsone is the principal drug in a multidrug regimen recommended by the World Health Organization for the treatment of leprosy. As an anti-infective agent, it is also used for treating malaria and, recently, for Pneumocystic carinii pneumonia in AIDS patients. Dapsone is absorbed rapidly and nearly completely from the gastrointestinal tract. Dapsone is distributed throughout total body water and is present in all tissues. However, it tends to be retained in skin and muscle and especially in the liver and kidney: traces of the drug are present in these organs up to 3 weeks after therapy cessation.
• Toxicity: Overdosage might be expected to produce nasal congestion, syncope, or hallucinations. Measures to support blood pressure should be taken if necessary.
• Affected Organisms: Mycobacteria
• Biotransformation: Hepatic, mostly CYP2E1-mediated.
• Absorption: Bioavailability is 70 to 80% following oral administration.
• Half Life: 28 hours (range 10-50 hours)
• Protein Binding: 70 to 90%
• Elimination: Renal
• External Links: Wikipedia; RxList; Drugs.com

Sigma Aldrich - A74807

Packaging
100, 500 g in poly bottle

Sigma Aldrich - 46158

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

Toronto Research Chemicals - D193250

An antibacterial used in the treatment of dermatitis herpetiformis.

REFERENCES

• Francis, J., et al.: Br. J. Pharmacol., 5, 565 (1950)
• Uetrecht, J., et al.: Clin. Dermatol., 7, 111 (1950)
• Reszka, K., et al.: Chem. Res. Toxicol., 22, 1137 (1950)
• Santos, J., et al.: Bioorg. Med. Chem., 17, 3795 (1950)
• Varma, M., et al.: J. Med. Chem