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80-08-0 molecular structure
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4-(4-aminobenzenesulfonyl)aniline

ChemBase ID: 135
Molecular Formular: C12H12N2O2S
Molecular Mass: 248.30088
Monoisotopic Mass: 248.06194863
SMILES and InChIs

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

Cite this record

CBID:135 http://www.chembase.cn/molecule-135.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
4-(4-aminobenzenesulfonyl)aniline
IUPAC Traditional name
4-(4-aminobenzenesulfonyl)aniline
dapsone
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
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-Aminophenyl)sulfonyl]aniline
4,4′-Diaminodiphenyl sulfone
4,4′-Sulfonyldianiline
Bis(4-aminophenyl) sulfone
4-Aminophenyl sulfone
bis(4-AMINOPHENYL)SULFONE
4-Aminophenyl 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
4,4'-Diaminodiphenyl sulfone
Dapson
NSC 6091
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
CAS Number
80-08-0
EC Number
201-248-4
MDL Number
MFCD00007887
Beilstein Number
788055
Merck Index
142822
PubChem SID
24869870
24891242
24859802
46505300
160963598
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

CALCULATED PROPERTIES

JChem ALOGPS 2.1
H Acceptors H Donor
LogD (pH = 5.5) 1.2698921  LogD (pH = 7.4) 1.2702243 
Log P 1.2702285  Molar Refractivity 68.991 cm3
Polarizability 26.662663 Å3 Polar Surface Area 86.18 Å2
Rotatable Bonds Lipinski's Rule of Five true 
Log P 1.19  LOG S -2.94 
Solubility (Water) 2.84e-01 g/l 

PROPERTIES

PROPERTIES

Physical Property Safety Information Pharmacology Properties Product Information Bioassay(PubChem)
Solubility
380 mg/L expand Show data source
Acetone expand Show data source
DMSO expand Show data source
Ethanol expand Show data source
Methanol expand Show data source
Apperance
Off -White Solid expand Show data source
Melting Point
172-174°C expand Show data source
175°C expand Show data source
175-177 °C(lit.) expand Show data source
175-178°C expand Show data source
175-179 °C expand Show data source
Hydrophobicity(logP)
0.4 expand Show data source
Storage Condition
-20°C Freezer expand Show data source
Storage Warning
IRRITANT expand Show data source
RTECS
BY8925000 expand Show data source
European Hazard Symbols
X expand Show data source
Harmful Harmful (Xn) 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
German water hazard class
1 expand Show data source
Risk Statements
22 expand Show data source
R:22 expand Show data source
Safety Statements
22 expand Show data source
S:22 expand Show data source
TSCA Listed
false expand Show data source
expand Show data source
GHS Pictograms
GHS07 expand Show data source
GHS Signal Word
Warning expand Show data source
GHS Hazard statements
H302 expand Show data source
GHS Precautionary statements
P261 expand Show data source
Personal Protective Equipment
dust mask type N95 (US), Eyeshields, Gloves expand Show data source
Admin Routes
Oral expand Show data source
Bioavailability
70 to 80% expand Show data source
Excretion
Renal expand Show data source
Half Life
20 to 30 hours expand Show data source
Metabolism
Hepatic (mostly CYP2E1-mediated) expand Show data source
Protein Bound
70 to 90% expand Show data source
Legal Status
?-only (U.S.), POM (UK) expand Show data source
Pregnancy Category
B2 (Australia) expand Show data source
C (US) expand Show data source
Purity
≥97.0% (NT) expand Show data source
97% expand Show data source
98% expand Show data source
Grade
purum expand Show data source
VETRANAL™, analytical standard expand Show data source
Certificate of Analysis
Download expand Show data source
Download expand Show data source
Linear Formula
(H2NC6H4)2SO2 expand Show data source

DETAILS

DETAILS

DrugBank DrugBank TRC TRC MP Biomedicals MP Biomedicals Wikipedia Wikipedia Sigma Aldrich Sigma Aldrich
DrugBank - DB00250 external link
Item Information
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
Toronto Research Chemicals - D193250 external link
An antibacterial used in the treatment of dermatitis herpetiformis.
MP Biomedicals - 05212644 external link
MP Biomedicals Rare Chemical collection
Sigma Aldrich - 46158 external link
Legal Information
VETRANAL is a trademark of Sigma-Aldrich Co. LLC
Sigma Aldrich - A74807 external link
Packaging
100, 500 g in poly bottle

REFERENCES

REFERENCES

From Suppliers Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • • 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
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PATENTS

PATENTS

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INTERNET

INTERNET

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