ChemFOnt: Showing chemical card for Dapsone (CFc000008788)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:55:43 UTC

Chemfont ID

CFc000008788

Molecule Identification

Common Name

Dapsone

Definition

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)

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
1,1'-Sulfonylbis(4-aminobenzene)	ChEBI
4,4'-Dapsone	ChEBI
4,4'-Diaminodiphenyl sulfone	ChEBI
4,4'-Sulfonylbisaniline	ChEBI
4,4'-Sulfonylbisbenzenamine	ChEBI
4-(4-Amino-benzenesulfonyl)-phenylamine	ChEBI
4-(4-Aminophenylsulfonyl)aniline	ChEBI
4-(4-Aminophenylsulfonyl)benzenamine	ChEBI
4-Aminophenyl sulfone	ChEBI
Bis(4-aminophenyl)sulfone	ChEBI
Bis(p-aminophenyl) sulfone	ChEBI
DADPS	ChEBI
Dapsona	ChEBI
Dapsonum	ChEBI
DDS	ChEBI
DIAPHENYLsulfone	ChEBI
p,P'-diaminodiphenyl sulfone	ChEBI
p,p-Sulphonylbisbenzamine	ChEBI
p,p-Sulphonylbisbenzenamine	ChEBI
p-Aminophenyl sulfone	ChEBI
Aczone	Kegg
1,1'-Sulphonylbis(4-aminobenzene)	Generator
4,4'-Diaminodiphenyl sulphone	Generator
4,4'-Sulphonylbisaniline	Generator
4,4'-Sulphonylbisbenzenamine	Generator
4-(4-Amino-benzenesulphonyl)-phenylamine	Generator
4-(4-Aminophenylsulphonyl)aniline	Generator
4-(4-Aminophenylsulphonyl)benzenamine	Generator
4-Aminophenyl sulphone	Generator
Bis(4-aminophenyl)sulphone	Generator
Bis(p-aminophenyl) sulphone	Generator
DIAPHENYLsulphone	Generator
p,P'-diaminodiphenyl sulphone	Generator
p,p-Sulfonylbisbenzamine	Generator
p,p-Sulfonylbisbenzenamine	Generator
p-Aminophenyl sulphone	Generator
1,1'-Sulfonylbis[4-aminobenzene]	HMDB
4,4'-Diaminodiphenylsulfone	HMDB
4,4'-Sulfonylbisbenzeneamine	HMDB
4,4'-Sulfonyldianilin	HMDB
4,4'-Sulfonyldianiline	HMDB
DDS, Pharmaceutical	HMDB
Mex-america brand OF dapsone	HMDB
Sulfona	HMDB
4,4' Diaminophenyl sulfone	HMDB
4,4'-Diaminophenyl sulfone	HMDB
Dapson-fatol	HMDB
Disulone	HMDB
Fatol brand OF dapsone	HMDB
Orsade brand OF dapsone	HMDB
Sulfone, 4,4'-diaminophenyl	HMDB
Sulfonyldianiline	HMDB
Avlosulfone	HMDB
Dapsoderm-X	HMDB
Diaminodiphenylsulfone	HMDB

Chemical Formula

C₁₂H₁₂N₂O₂S

Average Molecular Weight

248.301

Monoisotopic Molecular Weight

248.061948328

IUPAC Name

4-(4-aminobenzenesulfonyl)aniline

Traditional Name

dapsone

CAS Registry Number

80-08-0

SMILES

NC1=CC=C(C=C1)S(=O)(=O)C1=CC=C(N)C=C1

InChI Identifier

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

InChI Key

MQJKPEGWNLWLTK-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as benzenesulfonyl compounds. These are aromatic compounds containing a benzenesulfonyl group, which consists of a monocyclic benzene moiety that carries a sulfonyl group.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Benzenesulfonyl compounds

Direct Parent

Benzenesulfonyl compounds

Alternative Parents

Substituents

Benzenesulfonyl group
Aniline or substituted anilines
Sulfonyl
Sulfone
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Primary amine
Organosulfur compound
Organonitrogen compound
Amine
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

sulfone (CHEBI:4325 )
substituted aniline (CHEBI:4325 )

Functional Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 21059682)

Excreta

Biofluid or Excreta

Urine (PMID: 21059682)

Cellular substructure

Source

Exogenous

Exogenous (HMDB: HMDB0014395)

Process

Not Available

Role

Industrial application

Antiinfective agent (HMDB: HMDB0014395)

Pharmaceutical industry

Antimicrobial agent

Antimalarial (HMDB: HMDB0014395)

Leprostatic drug (HMDB: HMDB0014395)
Anti-inflammatory drug (HMDB: HMDB0014395)

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.28 g/L	ALOGPS
logP	1.19	ALOGPS
logP	1.27	ChemAxon
logS	-2.9	ALOGPS
pKa (Strongest Basic)	2.39	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	86.18 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	68.99 m³·mol⁻¹	ChemAxon
Polarizability	25.05 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon