Page last updated: 2024-11-06

4-nitro-4'-aminodiphenyl sulfone

Description Research Excerpts Clinical Trials Roles Classes Pathways Study Profile Bioassays Related Drugs Related Conditions Protein Interactions Research Growth Market Indicators

Description

4-nitro-4'-aminodiphenyl sulfone, also known as dapsone, is a synthetic sulfonamide drug that is primarily used to treat leprosy and dermatologic conditions such as dermatitis herpetiformis and acne. Dapsone's mechanism of action involves inhibiting the enzyme dihydrofolate reductase, which is essential for bacterial and parasitic growth. Its synthesis involves a multi-step process that typically begins with the reaction of chlorobenzene with sodium sulfite to form sodium benzenesulfonate. This is followed by nitration to produce 4-nitrobenzenesulfonate. The final step involves a nucleophilic aromatic substitution reaction between 4-nitrobenzenesulfonate and aniline to yield dapsone. Due to its effectiveness against leprosy, dapsone has been a vital tool in controlling the disease worldwide. Research on dapsone continues to explore its potential applications in the treatment of other inflammatory and autoimmune diseases, as well as its use as a prodrug for the delivery of other therapeutic agents. Dapsone's unique structural features and its diverse biological activities make it a subject of ongoing study in the fields of medicinal chemistry and pharmacology.'
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4-nitro-4'-aminodiphenyl sulfone: dapsone metabolite; structure given in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID74762
CHEMBL ID342457
SCHEMBL ID2762326
MeSH IDM0156733

Synonyms (36)

Synonym
nsc27185
nsc-27185
1948-92-1
4-nitro-4'-aminodiphenylsulfone
4-(4-nitrophenylsulfonyl)aniline
4-(4-nitrophenyl)sulfonylaniline
p-(p-nitrophenylsulfonyl)aniline
4-(4-nitrophenylsulfonyl)aniline, 96%
4-(4-nitrophenylsulfonyl)benzenamine
CHEMBL342457
AKOS000120860
benzenamine, 4-((4-nitrophenyl)sulfonyl)-
ge77ayq4nx ,
nsc 27185
unii-ge77ayq4nx
4-nitro-4'-aminodiphenyl sulfone
4-((4-nitrophenyl)sulfonyl)aniline
FT-0672745
benzenamine,4-[(4-nitrophenyl)sulfonyl]-
4-[(4-nitrophenyl)sulfonyl]aniline
4-(4-nitrobenzenesulfonyl)aniline
{4-[(4-nitrophenyl)sulfonyl]phenyl}amine
SCHEMBL2762326
4-(4'-nitro-benzenesulfonyl)-phenylamine
DTXSID4075162
sr-01000391085
SR-01000391085-1
mfcd00010648
4-amino-4'-nitrobiphenyl sulphone
E76624
CS-0188213
4-[(4-nitrophenyl)sulfonyl]benzenamine
4-nitro-4 inverted exclamation mark -aminodiphenyl sulfone
LS-08688
EN300-20870
Z104484152

Research Excerpts

Dosage Studied

ExcerptRelevanceReference
" Healthcare services must maintain strict adherence to the specific requirements of GPCANADs and drug instructions and strictly grasp the indications, contraindications, usage, and dosage of drugs, and strengthen the notification and management of off-label drug use."( Analysis of medical malpractice liability disputes related to novel antineoplastic drugs and research on risk prevention and control strategies.
Luo, J; Yu, R; Zheng, Z, 2023
)
0.91
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Bioassays (6)

Assay IDTitleYearJournalArticle
AID55880In vitro inhibition of Mycobacterium lufu dihydopterate synthase.1987Journal of medicinal chemistry, May, Volume: 30, Issue:5
A quantitative structure-activity relationship analysis of some 4-aminodiphenyl sulfone antibacterial agents using linear free energy and molecular modeling methods.
AID280386Inhibition of human CYP2C9 assessed as (S)-Flurbiprofen hydroxylation2007Journal of medicinal chemistry, Mar-22, Volume: 50, Issue:6
Use of simple docking methods to screen a virtual library for heteroactivators of cytochrome P450 2C9.
AID1653398Antimycobacterial activity against DDS sensitive Mycobacterium smegmatis ATCC 607 infected in mouse2019Bioorganic & medicinal chemistry, 07-01, Volume: 27, Issue:13
Insights of synthetic analogues of anti-leprosy agents.
AID55865Inhibition of dihydropteroate synthase of Escherichia coli1987Journal of medicinal chemistry, Mar, Volume: 30, Issue:3
Quantitative structure-activity analysis in dihydropteroate synthase inhibition by sulfones. Comparison with sulfanilamides.
AID1653399Antimycobacterial activity against DDS resistant Mycobacterium smegmatis ATCC 607 infected in mouse2019Bioorganic & medicinal chemistry, 07-01, Volume: 27, Issue:13
Insights of synthetic analogues of anti-leprosy agents.
AID55882Inhibition of Dihydropteroate synthase of Mycobacterium 607 and log (1/MIC) was reported1987Journal of medicinal chemistry, Mar, Volume: 30, Issue:3
Quantitative structure-activity analysis in dihydropteroate synthase inhibition by sulfones. Comparison with sulfanilamides.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (12)

TimeframeStudies, This Drug (%)All Drugs %
pre-19903 (25.00)18.7374
1990's0 (0.00)18.2507
2000's1 (8.33)29.6817
2010's2 (16.67)24.3611
2020's6 (50.00)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 12.69

According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be weak demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index12.69 (24.57)
Research Supply Index2.56 (2.92)
Research Growth Index5.25 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (12.69)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews3 (25.00%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other9 (75.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]