Page last updated: 2024-12-05

monoacetyldapsone

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

Description

Monoacetyldapsone (MAD) is a prodrug of dapsone, an anti-inflammatory and antimicrobial agent. It is synthesized by acetylation of dapsone, usually using acetic anhydride. MAD has improved oral bioavailability compared to dapsone, leading to higher plasma concentrations and prolonged therapeutic effects. This makes it particularly relevant for treating leprosy, where dapsone is a mainstay treatment, as it allows for less frequent dosing. MAD is also studied for its potential in treating inflammatory bowel diseases, as it exhibits anti-inflammatory properties and may modulate the gut microbiome. The exact mechanism of action of MAD is not fully understood, but it is thought to involve inhibition of dihydrofolate reductase, an enzyme involved in folate metabolism. '

monoacetyldapsone: used in leprosy chemotherapy [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

monoacetyldapsone : A secondary carboxamide resulting from acetylation of one of the amino groups of dapsone. [Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Cross-References

ID SourceID
PubMed CID11257
CHEMBL ID1246
CHEBI ID139473
SCHEMBL ID10920445
MeSH IDM0071025

Synonyms (59)

Synonym
a4yks8ulcn ,
3-13-00-01286 (beilstein handbook reference)
unii-a4yks8ulcn
565-20-8
n-acetyl-4,4'-diaminodiphenylsulfone
nsc-27184
acetamide, n-[4-[(4-aminophenyl)sulfonyl]phenyl]-
nsc27184
ccris 5693
nsc 27184
n-(4-((4-aminophenyl)sulfonyl)phenyl)acetamide
acetamide, n-(4-((4-aminophenyl)sulfonyl)phenyl)-
brn 2746651
acetanilide, 4'-sulfanilyl-
n-acetyl-4,4-diaminodiphenylsulfone
acetyldapsone
n-acetyldapsone
4'-sulfanilylacetanilide
n-[4-(4-aminophenyl)sulfonylphenyl]acetamide
n-[4-[(4-aminophenyl)sulfonyl]phenyl]-
monoacetyldapsone
p-sulfanilylacetanilide acetamide
n-{4-[(4-aminophenyl)sulfonyl]phenyl}acetamide
madds
smr000024670
MLS000090052 ,
NCGC00044286-02
n-[4-(4-aminobenzene-1-sulfonyl)phenyl]acetamide
n-acetyl-4,4'-diaminodiphenyl sulfone
CHEBI:139473
monoacetyl-dapsone
monoacetyl dapsone
n-[4-[(4-aminophenyl)sulfonyl]phenyl]acetamide
CHEMBL1246 ,
mono-n-acetyl dapsone
AKOS003272954
A831070
bdbm50391267
HMS2230L14
n-acetyl dapsone
AB06775
n-monoacetyl-4,4'-diaminodiphenyl sulfone
4-(acetamido)-4'-aminobiphenyl sulphone
HMS3371F07
SCHEMBL10920445
n-(4-[(4-aminophenyl)sulfonyl]phenyl)acetamide
WDOCBIHNYYQINH-UHFFFAOYSA-N
4-acetylamino-4'-aminodiphenyl sulfone
OPERA_ID_318
mfcd00672496
DTXSID70205040
n-acetyldapsone;madds
(s)-(+)-alpha-methyl-1h-imidazole-4-ethanaminedihydrobromide
n-(4-(4-aminophenylsulfonyl)phenyl)acetamide
Q27273637
n-acetyldapsone 100 microg/ml in acetonitrile
STARBLD0016694
n-[4-(4-aminobenzenesulfonyl)phenyl]acetamide
acetyl dapsone

Research Excerpts

Toxicity

ExcerptReferenceRelevance
" By early 2021, MADDS detected shifts in cocaine purity, alerted communities of a new toxic fentanyl analogue and a synthetic cannabinoid contaminant, and confirmed the increase of xylazine (a veterinary sedative) in Massachusetts."( Implementation and Uptake of the Massachusetts Drug Supply Data Stream: A Statewide Public Health-Public Safety Partnership Drug Checking Program.
Consigli, A; Del Pozo, B; Erowid, E; Erowid, F; Green, TC; Jarczyk, C; Michelson, L; Olson, R; Reilly, B; Ruiz, S; Thyssen, S; Wightman, R,
)
0.13

Pharmacokinetics

ExcerptReferenceRelevance
" After the last maintenance dose of Maloprim, the following kinetic parameters (mean values) were determined for DDS and PYR, respectively: maximum plasma concentration (Cmax) = 1,134 and 116 ng ml-1; elimination half-life (t1/2) = 23 and 105 h; plasma clearance (CL) = 37."( Multiple-dose pharmacokinetics and in vitro antimalarial activity of dapsone plus pyrimethamine (Maloprim) in man.
Edstein, MD; Rieckmann, KH; Veenendaal, JR, 1990
)
0.28
" This may relate to pharmacodynamic differences, but alternatively the concentration of oxidative metabolites rather than DDS or MADDS could be responsible for the therapeutic activity in dermatitis herpetiformis."( Pharmacokinetic observations on dapsone in dermatitis herpetiformis.
Ahmad, RA; Fry, L; Leonard, JN; Rogers, HJ; Swain, AF, 1983
)
0.27
" However, the suggested dosage regimen is based upon clinical experience with children with leprosy and dermatitis herpetiformis rather than pharmacokinetic and pharmacodynamic data obtained from the target patient population."( Pharmacokinetics of dapsone in human immunodeficiency virus-infected children.
Bassetti, D; Casazza, R; Cruciani, M; Gatti, G; Loy, A; Miletich, F, 1995
)
0.29
" Serial blood samples were obtained over 24 hours after dosing and analyzed for trimetrexate, dapsone, and monoacetyldapsone, and pharmacokinetic parameters were determined."( Pharmacokinetics of trimetrexate and dapsone in AIDS patients with Pneumocystis carinii pneumonia.
Chatterjee, DJ; Dubé, MP; Koda, RT; Li, WY; Sattler, FR; Stansell, JD, 1999
)
0.52

Bioavailability

ExcerptReferenceRelevance
"001) serum concentrations of PYR were found in Papua New Guineans than in Caucasians at both sampling times, an observation which may reflect differences in the bioavailability of PYR between the two racial groups."( Race-linked differences in serum concentrations of dapsone, monoacetyldapsone and pyrimethamine during malaria prophylaxis.
Cochrane, JP; Cook, IF; Edstein, MD, 1986
)
0.51

Dosage Studied

ExcerptRelevanceReference
"A high-performance liquid chromatographic method was developed to enable dapsone, monoacetyl dapsone and pyrimethamine to be measured simultaneously in plasma samples from volunteers in England and Malaysia who had been dosed with Maloprim."( Determination of plasma concentrations of dapsone, monoacetyl dapsone and pyrimethamine in human subjects dosed with maloprim.
Jones, CR; Ovenell, SM, 1979
)
0.26
" We conclude that cirrhosis is associated with minor changes in dapsone disposition and that dosage modification is not required."( The disposition of dapsone in cirrhosis.
Arns, PA; Branch, RA; Fleming, CM; May, DG; Porter, J; Richards, WO; Ryder, D; Wilkinson, GR, 1992
)
0.28
"20 patients with dermatitis herpetiformis maintained on once daily dosing of dapsone were studied to investigate the pharmacodynamics of dapsone in suppressing clinical disease."( The relationship between dapsone dose, serum concentration and disease severity in dermatitis herpetiformis.
Sanders, SW; Zone, JJ, 1986
)
0.27
" However, the suggested dosage regimen is based upon clinical experience with children with leprosy and dermatitis herpetiformis rather than pharmacokinetic and pharmacodynamic data obtained from the target patient population."( Pharmacokinetics of dapsone in human immunodeficiency virus-infected children.
Bassetti, D; Casazza, R; Cruciani, M; Gatti, G; Loy, A; Miletich, F, 1995
)
0.29
" Serial blood samples were obtained over 24 hours after dosing and analyzed for trimetrexate, dapsone, and monoacetyldapsone, and pharmacokinetic parameters were determined."( Pharmacokinetics of trimetrexate and dapsone in AIDS patients with Pneumocystis carinii pneumonia.
Chatterjee, DJ; Dubé, MP; Koda, RT; Li, WY; Sattler, FR; Stansell, JD, 1999
)
0.52
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (4)

ClassDescription
sulfoneAn organosulfur compound having the structure RS(=O)2R (R =/= H).
anilideAny aromatic amide obtained by acylation of aniline.
secondary carboxamideA carboxamide resulting from the formal condensation of a carboxylic acid with a primary amine; formula RC(=O)NHR(1).
acetamidesCompounds with the general formula RNHC(=O)CH3.
[compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Protein Targets (5)

Potency Measurements

ProteinTaxonomyMeasurementAverage (µ)Min (ref.)Avg (ref.)Max (ref.)Bioassay(s)
ATAD5 protein, partialHomo sapiens (human)Potency4.61090.004110.890331.5287AID504467
chromobox protein homolog 1Homo sapiens (human)Potency100.00000.006026.168889.1251AID540317
pyruvate kinase PKM isoform aHomo sapiens (human)Potency8.91250.04017.459031.6228AID1631; AID1634
gemininHomo sapiens (human)Potency3.88600.004611.374133.4983AID624296; AID624297
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Bioassays (38)

Assay IDTitleYearJournalArticle
AID504812Inverse Agonists of the Thyroid Stimulating Hormone Receptor: HTS campaign2010Endocrinology, Jul, Volume: 151, Issue:7
A small molecule inverse agonist for the human thyroid-stimulating hormone receptor.
AID651635Viability Counterscreen for Primary qHTS for Inhibitors of ATXN expression
AID588501High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Lethal Factor Protease, MLPCN compound set2010Current protocols in cytometry, Oct, Volume: Chapter 13Microsphere-based flow cytometry protease assays for use in protease activity detection and high-throughput screening.
AID588501High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Lethal Factor Protease, MLPCN compound set2006Cytometry. Part A : the journal of the International Society for Analytical Cytology, May, Volume: 69, Issue:5
Microsphere-based protease assays and screening application for lethal factor and factor Xa.
AID588501High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Lethal Factor Protease, MLPCN compound set2010Assay and drug development technologies, Feb, Volume: 8, Issue:1
High-throughput multiplex flow cytometry screening for botulinum neurotoxin type a light chain protease inhibitors.
AID504810Antagonists of the Thyroid Stimulating Hormone Receptor: HTS campaign2010Endocrinology, Jul, Volume: 151, Issue:7
A small molecule inverse agonist for the human thyroid-stimulating hormone receptor.
AID588499High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain A protease, MLPCN compound set2010Current protocols in cytometry, Oct, Volume: Chapter 13Microsphere-based flow cytometry protease assays for use in protease activity detection and high-throughput screening.
AID588499High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain A protease, MLPCN compound set2006Cytometry. Part A : the journal of the International Society for Analytical Cytology, May, Volume: 69, Issue:5
Microsphere-based protease assays and screening application for lethal factor and factor Xa.
AID588499High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain A protease, MLPCN compound set2010Assay and drug development technologies, Feb, Volume: 8, Issue:1
High-throughput multiplex flow cytometry screening for botulinum neurotoxin type a light chain protease inhibitors.
AID588459High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain F protease, Validation compound set2010Current protocols in cytometry, Oct, Volume: Chapter 13Microsphere-based flow cytometry protease assays for use in protease activity detection and high-throughput screening.
AID588459High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain F protease, Validation compound set2006Cytometry. Part A : the journal of the International Society for Analytical Cytology, May, Volume: 69, Issue:5
Microsphere-based protease assays and screening application for lethal factor and factor Xa.
AID588459High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain F protease, Validation compound set2010Assay and drug development technologies, Feb, Volume: 8, Issue:1
High-throughput multiplex flow cytometry screening for botulinum neurotoxin type a light chain protease inhibitors.
AID588461High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Lethal Factor Protease, Validation compound set2010Current protocols in cytometry, Oct, Volume: Chapter 13Microsphere-based flow cytometry protease assays for use in protease activity detection and high-throughput screening.
AID588461High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Lethal Factor Protease, Validation compound set2006Cytometry. Part A : the journal of the International Society for Analytical Cytology, May, Volume: 69, Issue:5
Microsphere-based protease assays and screening application for lethal factor and factor Xa.
AID588461High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Lethal Factor Protease, Validation compound set2010Assay and drug development technologies, Feb, Volume: 8, Issue:1
High-throughput multiplex flow cytometry screening for botulinum neurotoxin type a light chain protease inhibitors.
AID1745845Primary qHTS for Inhibitors of ATXN expression
AID588497High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain F protease, MLPCN compound set2010Current protocols in cytometry, Oct, Volume: Chapter 13Microsphere-based flow cytometry protease assays for use in protease activity detection and high-throughput screening.
AID588497High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain F protease, MLPCN compound set2006Cytometry. Part A : the journal of the International Society for Analytical Cytology, May, Volume: 69, Issue:5
Microsphere-based protease assays and screening application for lethal factor and factor Xa.
AID588497High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain F protease, MLPCN compound set2010Assay and drug development technologies, Feb, Volume: 8, Issue:1
High-throughput multiplex flow cytometry screening for botulinum neurotoxin type a light chain protease inhibitors.
AID588460High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain A protease, Validation Compound Set2010Current protocols in cytometry, Oct, Volume: Chapter 13Microsphere-based flow cytometry protease assays for use in protease activity detection and high-throughput screening.
AID588460High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain A protease, Validation Compound Set2006Cytometry. Part A : the journal of the International Society for Analytical Cytology, May, Volume: 69, Issue:5
Microsphere-based protease assays and screening application for lethal factor and factor Xa.
AID588460High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain A protease, Validation Compound Set2010Assay and drug development technologies, Feb, Volume: 8, Issue:1
High-throughput multiplex flow cytometry screening for botulinum neurotoxin type a light chain protease inhibitors.
AID1653404Effect of metallo-protein haemoglobin in rat assessed as peak methemoglobin level at 400 mg/kg, sc administered as single dose2019Bioorganic & medicinal chemistry, 07-01, Volume: 27, Issue:13
Insights of synthetic analogues of anti-leprosy agents.
AID1653409Anti-leprotic activity against Mycobacterium leprae infected in BALB/c mouse assessed as time delay in bacterial multiplication in footpad at 0.01 g/100g of diet administered via feed starting 60 or 75 day post infection up to 90 days by Shepard's kinetic2019Bioorganic & medicinal chemistry, 07-01, Volume: 27, Issue:13
Insights of synthetic analogues of anti-leprosy agents.
AID55887Inhibitory activity against dihydropteroic acid synthase (SYN) from Mycobacterium lufu (DDS resistant)2004Journal of medicinal chemistry, Jan-01, Volume: 47, Issue:1
Folate-synthesizing enzyme system as target for development of inhibitors and inhibitor combinations against Candida albicans-synthesis and biological activity of new 2,4-diaminopyrimidines and 4'-substituted 4-aminodiphenyl sulfones.
AID1653403Drug concentration in rat blood at 400 mg/kg, sc administered as single dose2019Bioorganic & medicinal chemistry, 07-01, Volume: 27, Issue:13
Insights of synthetic analogues of anti-leprosy agents.
AID55879In 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.
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.
AID55889Inhibitory activity against dihydropteroic acid synthase (SYN) from Plasmodium berghei2004Journal of medicinal chemistry, Jan-01, Volume: 47, Issue:1
Folate-synthesizing enzyme system as target for development of inhibitors and inhibitor combinations against Candida albicans-synthesis and biological activity of new 2,4-diaminopyrimidines and 4'-substituted 4-aminodiphenyl sulfones.
AID1653401Drug excretion in rat urine at 400 mg/kg, sc administered as single dose measured after 30 days2019Bioorganic & medicinal chemistry, 07-01, Volume: 27, Issue:13
Insights of synthetic analogues of anti-leprosy agents.
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.
AID55888Inhibitory activity against dihydropteroic acid synthase (SYN) from Mycobacterium lufu (DDS sensitive)2004Journal of medicinal chemistry, Jan-01, Volume: 47, Issue:1
Folate-synthesizing enzyme system as target for development of inhibitors and inhibitor combinations against Candida albicans-synthesis and biological activity of new 2,4-diaminopyrimidines and 4'-substituted 4-aminodiphenyl sulfones.
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.
AID1653388Antimalarial activity against Plasmodium berghei infected in albino mouse assessed survival against infection at 400 mg/kg, sc administered as single dose2019Bioorganic & medicinal chemistry, 07-01, Volume: 27, Issue:13
Insights of synthetic analogues of anti-leprosy agents.
AID55883Inhibitory activity against dihydropteroic acid synthase (SYN) from Candida albicans; No data2004Journal of medicinal chemistry, Jan-01, Volume: 47, Issue:1
Folate-synthesizing enzyme system as target for development of inhibitors and inhibitor combinations against Candida albicans-synthesis and biological activity of new 2,4-diaminopyrimidines and 4'-substituted 4-aminodiphenyl sulfones.
AID55885Inhibitory activity against dihydropteroic acid synthase (SYN) from Escherichia coli2004Journal of medicinal chemistry, Jan-01, Volume: 47, Issue:1
Folate-synthesizing enzyme system as target for development of inhibitors and inhibitor combinations against Candida albicans-synthesis and biological activity of new 2,4-diaminopyrimidines and 4'-substituted 4-aminodiphenyl sulfones.
AID1653402Half life in rat at 400 mg/kg, sc administered as single dose2019Bioorganic & medicinal chemistry, 07-01, Volume: 27, Issue:13
Insights of synthetic analogues of anti-leprosy agents.
AID1224864HCS microscopy assay (F508del-CFTR)2016PloS one, , Volume: 11, Issue:10
Increasing the Endoplasmic Reticulum Pool of the F508del Allele of the Cystic Fibrosis Transmembrane Conductance Regulator Leads to Greater Folding Correction by Small Molecule Therapeutics.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (81)

TimeframeStudies, This Drug (%)All Drugs %
pre-199041 (50.62)18.7374
1990's27 (33.33)18.2507
2000's6 (7.41)29.6817
2010's6 (7.41)24.3611
2020's1 (1.23)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 9.56

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 Index9.56 (24.57)
Research Supply Index4.53 (2.92)
Research Growth Index4.09 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (9.56)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials2 (2.22%)5.53%
Reviews2 (2.22%)6.00%
Case Studies4 (4.44%)4.05%
Observational0 (0.00%)0.25%
Other82 (91.11%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]