Page last updated: 2024-11-06

n(4)-acetylsulfamethoxazole

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

Description

N-acetylsulfamethoxazole : A sulfonamide compound having a 4-acetamidophenyl group attached to the sulfur atom and a 1,2-oxazol-3-yl group attached to the nitrogen atom. [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 CID65280
CHEMBL ID3560298
CHEBI ID31169
SCHEMBL ID1502536
MeSH IDM0075954

Synonyms (93)

Synonym
NCGC00183871-02
NCGC00183871-03
UPCMLD0ENAT5582698:001
SDCCGMLS-0065402.P001
sulfisomezole-n(sup 4)-acetate
acetamide, n-(4-(((5-methyl-3-isoxazolyl)amino)sulfonyl)phenyl)-
4'-((5-methyl-3-isoxazolyl)sulfamoyl)acetanilide
n(sup 4)-acetylsulfulfamethoxazole
brn 0285801
n(sup 4)-acetylsulfisomezole
n-(4-(((5-methylisoxazol-3-yl)amino)sulphonyl)phenyl)acetamide
einecs 244-330-5
n-(4-(((5-methyl-3-isoxazolyl)amino)sulfonyl)phenyl)acetamide
acetanilide, 4'-((5-methyl-3-isoxazolyl)sulfamoyl)-
OPREA1_529808
OPREA1_653133
acetylsulfamethoxazole
21312-10-7
acetylsulfamethoxazole (jan)
D01601
n4-acetylsulfamethoxazole
MAYBRIDGE1_006926
SR-01000419910-2
STK039900
n-{4-[(5-methyl-1,2-oxazol-3-yl)sulfamoyl]phenyl}acetamide
sulfisomezole-n(4)-acetate
n(4)-acetylsulfisomezole
n-acetylsulfamethoxazole
n-{4-[(5-methylisoxazol-3-yl)sulfamoyl]phenyl}acetamide
n(4)-acetylsulfulfamethoxazole
sulfamethoxazole acetate
CHEBI:31169 ,
smx-acetate
AKOS000495698
HMS561C18
n-[4-[(5-methyl-1,2-oxazol-3-yl)sulfamoyl]phenyl]acetamide
n(4)-acetylsulfamethoxazole
AB00684062-01
NCGC00183871-01
4-acetylamino-n-(5-methyl-3-isoxazolyl)benzenesulfonamide
dtxcid3028970
cas-21312-10-7
tox21_113591
n-acetyl sulfamethoxazole
dtxsid8049044 ,
n-(4-(n-(5-methylisoxazol-3-yl)sulfamoyl)phenyl)acetamide
A815261
CCG-42821
3i1988834q ,
n(4)-acetylsulphamethoxazole
unii-3i1988834q
acetylsulfamethoxazole [jan]
n-[4-[[(5-methyl-3-isoxazolyl)amino]sulfonyl]phenyl]acetamide
n4-acetylsulfisomezole
stx 606
sulfisomezole-n4-acetate
FT-0617403
EPITOPE ID:116043
NCGC00183871-04
tox21_113591_1
n-(4-((5-methylisoxazol-3-yl)sulfamoyl)phenyl)acetamide
sulfamethoxazole impurity a [ep impurity]
sulfamethoxazole n4-acetylsulfamethoxazole [mi]
n-4-acetylsulphamethoxazole
sulfamethoxazole n4-acetylsulfamethoxazole
n-(4-(((5-methylisoxazol-3-yl)amino)sulfonyl)phenyl)acetamide
SCHEMBL1502536
GXPIUNZCALHVBA-UHFFFAOYSA-N
acetamide, n-[4-[[(5-methyl-3-isoxazolyl)amino]sulfonyl]phenyl]-
n-(4-([(5-methyl-3-isoxazolyl)amino]sulfonyl)phenyl)acetamide #
CHEMBL3560298
mfcd00205417
n4-acetylsulphamethoxazole
n4-acetylsulfamethoxazole, analytical standard
SR-01000419910-1
sr-01000419910
Y10986
sulfamethoxazole impurity a, european pharmacopoeia (ep) reference standard
n-[4-[(5-methylisoxazol-3-yl)sulphamoyl]phenyl]acetamide
sulfamethoxazole imp. a (ep); sulfamethoxazole usp related compound a; sulfamethoxazole usp rc a; n-[4-[(5-methylisoxazol-3-yl)sulphamoyl]phenyl]acetamide; sulfamethoxazole related compound a; sulfamethoxazole impurity a
acetyl-sulfamethoxazole
Z32429922
n4-acetylsulfulfamethoxazole
n-(4-{[(5-methyl-3-isoxazolyl)amino]sulfonyl}phenyl)acetamide
n4-acetyl-n1-(5-methyl-3-isoxazolyl)sulfanilamide
n4-acetyl-smx
n-acetyl-sulfamethoxazole
DS-5239
Q27114190
BCP10149
CS-W013982
HY-W013266
EN300-7357311

Research Excerpts

Pharmacokinetics

ExcerptReferenceRelevance
" Following oral administration of a single dose, the pharmacokinetic parameters of SMZ and its N4-acetylated metabolite (N4SMZ) were similar in both groups."( Pharmacokinetics of the trimethoprim-sulphamethoxazole combination in the elderly.
Advenier, C; Cordonnier, P; Ducreuzet, C; Gobert, C; Lajoie, D; Pays, M; Varoquaux, O, 1985
)
0.27
" Comparison of the pharmacokinetic parameters in this study with those of our previous findings indicates that the elimination of trimethoprim-sulfamethoxazole follows a first-order process within the dose ranges assessed."( Multiple-dose pharmacokinetics of 12 milligrams of trimethoprim and 60 milligrams of sulfamethoxazole per kilogram of body weight per day in healthy volunteers.
Laizure, SC; Sanders, PL; Stein, DS; Stevens, RC, 1993
)
0.29
" Despite being used as prophylactic treatment for respiratory infections associated with high altitude, little information is available on the pharmacokinetic properties of sulfamethoxazole in subjects living at high altitude, especially in a Chinese population."( Comparison of the pharmacokinetics of sulfamethoxazole in male chinese volunteers at low altitude and acute exposure to high altitude versus subjects living chronically at high altitude: an open-label, controlled, prospective study.
Feng, WL; Gao, F; Ge, RL; Guan, W; Li, XY; Li, ZQ, 2009
)
0.35
"0 software to get the related pharmacokinetic parameters."( [Pharmacokinetics of sulfamethoxazole in healthy Han volunteers living at plain and in native Han and Tibetan healthy volunteers living at high altitude].
Li, XY; Li, YP; Liu, YN; Yuan, M; Zhu, JB, 2011
)
0.37

Bioavailability

ExcerptReferenceRelevance
"The ATP-binding cassette transporter P-glycoprotein (P-gp) is known to limit both brain penetration and oral bioavailability of many chemotherapy drugs."( A High-Throughput Screen of a Library of Therapeutics Identifies Cytotoxic Substrates of P-glycoprotein.
Ambudkar, SV; Brimacombe, KR; Chen, L; Gottesman, MM; Guha, R; Hall, MD; Klumpp-Thomas, C; Lee, OW; Lee, TD; Lusvarghi, S; Robey, RW; Shen, M; Tebase, BG, 2019
)
0.51

Dosage Studied

ExcerptRelevanceReference
" Further studies are indicated in patients to optimize the dosing regimen of trimethoprim-sulfamethoxazole in the treatment of PCP."( Pharmacokinetics and adverse effects of 20-mg/kg/day trimethoprim and 100-mg/kg/day sulfamethoxazole in healthy adult subjects.
Laizure, SC; Stein, DS; Stevens, RC; Williams, CL, 1991
)
0.28
" A study of plasma concentrations of TMP, SMZ and N4SMZ during continuous dosing in seven elderly patients treated for urinary or respiratory infections showed that steady state was reached after 3 days of treatment and that plasma drug concentrations were about two to three times higher than those observed after a single dose."( Pharmacokinetics of the trimethoprim-sulphamethoxazole combination in the elderly.
Advenier, C; Cordonnier, P; Ducreuzet, C; Gobert, C; Lajoie, D; Pays, M; Varoquaux, O, 1985
)
0.27
" Clinical trials are indicated to evaluate this dosing scheme, which may decrease exposure to potentially excessive concentrations of trimethoprim and sulfamethoxazole."( Multiple-dose pharmacokinetics of 12 milligrams of trimethoprim and 60 milligrams of sulfamethoxazole per kilogram of body weight per day in healthy volunteers.
Laizure, SC; Sanders, PL; Stein, DS; Stevens, RC, 1993
)
0.29
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Roles (2)

RoleDescription
marine xenobiotic metaboliteAny metabolite produced by metabolism of a xenobiotic compound in marine macro- and microorganisms.
drug metabolitenull
[role 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]

Drug Classes (2)

ClassDescription
isoxazolesOxazoles in which the N and O atoms are adjacent.
sulfonamideAn amide of a sulfonic acid RS(=O)2NR'2.
[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 (3)

Potency Measurements

ProteinTaxonomyMeasurementAverage (µ)Min (ref.)Avg (ref.)Max (ref.)Bioassay(s)
RAR-related orphan receptor gammaMus musculus (house mouse)Potency13.33320.006038.004119,952.5996AID1159521
nuclear receptor subfamily 1, group I, member 3Homo sapiens (human)Potency2.66030.001022.650876.6163AID1224838
Spike glycoproteinSevere acute respiratory syndrome-related coronavirusPotency1.00000.009610.525035.4813AID1479145
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Ceullar Components (1)

Processvia Protein(s)Taxonomy
virion membraneSpike glycoproteinSevere acute respiratory syndrome-related coronavirus
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (34)

Assay IDTitleYearJournalArticle
AID1296008Cytotoxic Profiling of Annotated Libraries Using Quantitative High-Throughput Screening2020SLAS discovery : advancing life sciences R & D, 01, Volume: 25, Issue:1
Cytotoxic Profiling of Annotated and Diverse Chemical Libraries Using Quantitative High-Throughput Screening.
AID1347092qHTS of pediatric cancer cell lines to identify multiple opportunities for drug repurposing: Primary screen for A673 cells2018Oncotarget, Jan-12, Volume: 9, Issue:4
Quantitative high-throughput phenotypic screening of pediatric cancer cell lines identifies multiple opportunities for drug repurposing.
AID1347107qHTS of pediatric cancer cell lines to identify multiple opportunities for drug repurposing: Primary screen for Rh30 cells2018Oncotarget, Jan-12, Volume: 9, Issue:4
Quantitative high-throughput phenotypic screening of pediatric cancer cell lines identifies multiple opportunities for drug repurposing.
AID1347105qHTS of pediatric cancer cell lines to identify multiple opportunities for drug repurposing: Primary screen for MG 63 (6-TG R) cells2018Oncotarget, Jan-12, Volume: 9, Issue:4
Quantitative high-throughput phenotypic screening of pediatric cancer cell lines identifies multiple opportunities for drug repurposing.
AID1347094qHTS of pediatric cancer cell lines to identify multiple opportunities for drug repurposing: Primary screen for BT-37 cells2018Oncotarget, Jan-12, Volume: 9, Issue:4
Quantitative high-throughput phenotypic screening of pediatric cancer cell lines identifies multiple opportunities for drug repurposing.
AID1347096qHTS of pediatric cancer cell lines to identify multiple opportunities for drug repurposing: Primary screen for U-2 OS cells2018Oncotarget, Jan-12, Volume: 9, Issue:4
Quantitative high-throughput phenotypic screening of pediatric cancer cell lines identifies multiple opportunities for drug repurposing.
AID1347106qHTS of pediatric cancer cell lines to identify multiple opportunities for drug repurposing: Primary screen for control Hh wild type fibroblast cells2018Oncotarget, Jan-12, Volume: 9, Issue:4
Quantitative high-throughput phenotypic screening of pediatric cancer cell lines identifies multiple opportunities for drug repurposing.
AID1347103qHTS of pediatric cancer cell lines to identify multiple opportunities for drug repurposing: Primary screen for OHS-50 cells2018Oncotarget, Jan-12, Volume: 9, Issue:4
Quantitative high-throughput phenotypic screening of pediatric cancer cell lines identifies multiple opportunities for drug repurposing.
AID1347098qHTS of pediatric cancer cell lines to identify multiple opportunities for drug repurposing: Primary screen for SK-N-SH cells2018Oncotarget, Jan-12, Volume: 9, Issue:4
Quantitative high-throughput phenotypic screening of pediatric cancer cell lines identifies multiple opportunities for drug repurposing.
AID1347407qHTS to identify inhibitors of the type 1 interferon - major histocompatibility complex class I in skeletal muscle: primary screen against the NCATS Pharmaceutical Collection2020ACS chemical biology, 07-17, Volume: 15, Issue:7
High-Throughput Screening to Identify Inhibitors of the Type I Interferon-Major Histocompatibility Complex Class I Pathway in Skeletal Muscle.
AID1347086qHTS for Inhibitors of the Functional Ribonucleoprotein Complex (vRNP) of Lymphocytic Choriomeningitis Arenaviruses (LCMV): LCMV Primary Screen - GLuc reporter signal2020Antiviral research, 01, Volume: 173A cell-based, infectious-free, platform to identify inhibitors of lassa virus ribonucleoprotein (vRNP) activity.
AID1347108qHTS of pediatric cancer cell lines to identify multiple opportunities for drug repurposing: Primary screen for Rh41 cells2018Oncotarget, Jan-12, Volume: 9, Issue:4
Quantitative high-throughput phenotypic screening of pediatric cancer cell lines identifies multiple opportunities for drug repurposing.
AID1347102qHTS of pediatric cancer cell lines to identify multiple opportunities for drug repurposing: Primary screen for Rh18 cells2018Oncotarget, Jan-12, Volume: 9, Issue:4
Quantitative high-throughput phenotypic screening of pediatric cancer cell lines identifies multiple opportunities for drug repurposing.
AID1347095qHTS of pediatric cancer cell lines to identify multiple opportunities for drug repurposing: Primary screen for NB-EBc1 cells2018Oncotarget, Jan-12, Volume: 9, Issue:4
Quantitative high-throughput phenotypic screening of pediatric cancer cell lines identifies multiple opportunities for drug repurposing.
AID1347425Rhodamine-PBP qHTS Assay for Modulators of WT P53-Induced Phosphatase 1 (WIP1)2019The Journal of biological chemistry, 11-15, Volume: 294, Issue:46
Physiologically relevant orthogonal assays for the discovery of small-molecule modulators of WIP1 phosphatase in high-throughput screens.
AID1347089qHTS of pediatric cancer cell lines to identify multiple opportunities for drug repurposing: Primary screen for TC32 cells2018Oncotarget, Jan-12, Volume: 9, Issue:4
Quantitative high-throughput phenotypic screening of pediatric cancer cell lines identifies multiple opportunities for drug repurposing.
AID1347090qHTS of pediatric cancer cell lines to identify multiple opportunities for drug repurposing: Primary screen for DAOY cells2018Oncotarget, Jan-12, Volume: 9, Issue:4
Quantitative high-throughput phenotypic screening of pediatric cancer cell lines identifies multiple opportunities for drug repurposing.
AID651635Viability Counterscreen for Primary qHTS for Inhibitors of ATXN expression
AID1347154Primary screen GU AMC qHTS for Zika virus inhibitors2020Proceedings of the National Academy of Sciences of the United States of America, 12-08, Volume: 117, Issue:49
Therapeutic candidates for the Zika virus identified by a high-throughput screen for Zika protease inhibitors.
AID1347082qHTS for Inhibitors of the Functional Ribonucleoprotein Complex (vRNP) of Lassa (LASV) Arenavirus: LASV Primary Screen - GLuc reporter signal2020Antiviral research, 01, Volume: 173A cell-based, infectious-free, platform to identify inhibitors of lassa virus ribonucleoprotein (vRNP) activity.
AID1347097qHTS of pediatric cancer cell lines to identify multiple opportunities for drug repurposing: Primary screen for Saos-2 cells2018Oncotarget, Jan-12, Volume: 9, Issue:4
Quantitative high-throughput phenotypic screening of pediatric cancer cell lines identifies multiple opportunities for drug repurposing.
AID1347099qHTS of pediatric cancer cell lines to identify multiple opportunities for drug repurposing: Primary screen for NB1643 cells2018Oncotarget, Jan-12, Volume: 9, Issue:4
Quantitative high-throughput phenotypic screening of pediatric cancer cell lines identifies multiple opportunities for drug repurposing.
AID1347424RapidFire Mass Spectrometry qHTS Assay for Modulators of WT P53-Induced Phosphatase 1 (WIP1)2019The Journal of biological chemistry, 11-15, Volume: 294, Issue:46
Physiologically relevant orthogonal assays for the discovery of small-molecule modulators of WIP1 phosphatase in high-throughput screens.
AID1745845Primary qHTS for Inhibitors of ATXN expression
AID1347091qHTS of pediatric cancer cell lines to identify multiple opportunities for drug repurposing: Primary screen for SJ-GBM2 cells2018Oncotarget, Jan-12, Volume: 9, Issue:4
Quantitative high-throughput phenotypic screening of pediatric cancer cell lines identifies multiple opportunities for drug repurposing.
AID1347093qHTS of pediatric cancer cell lines to identify multiple opportunities for drug repurposing: Primary screen for SK-N-MC cells2018Oncotarget, Jan-12, Volume: 9, Issue:4
Quantitative high-throughput phenotypic screening of pediatric cancer cell lines identifies multiple opportunities for drug repurposing.
AID1508630Primary qHTS for small molecule stabilizers of the endoplasmic reticulum resident proteome: Secreted ER Calcium Modulated Protein (SERCaMP) assay2021Cell reports, 04-27, Volume: 35, Issue:4
A target-agnostic screen identifies approved drugs to stabilize the endoplasmic reticulum-resident proteome.
AID1347104qHTS of pediatric cancer cell lines to identify multiple opportunities for drug repurposing: Primary screen for RD cells2018Oncotarget, Jan-12, Volume: 9, Issue:4
Quantitative high-throughput phenotypic screening of pediatric cancer cell lines identifies multiple opportunities for drug repurposing.
AID1347100qHTS of pediatric cancer cell lines to identify multiple opportunities for drug repurposing: Primary screen for LAN-5 cells2018Oncotarget, Jan-12, Volume: 9, Issue:4
Quantitative high-throughput phenotypic screening of pediatric cancer cell lines identifies multiple opportunities for drug repurposing.
AID1347083qHTS for Inhibitors of the Functional Ribonucleoprotein Complex (vRNP) of Lassa (LASV) Arenavirus: Viability assay - alamar blue signal for LASV Primary Screen2020Antiviral research, 01, Volume: 173A cell-based, infectious-free, platform to identify inhibitors of lassa virus ribonucleoprotein (vRNP) activity.
AID1347101qHTS of pediatric cancer cell lines to identify multiple opportunities for drug repurposing: Primary screen for BT-12 cells2018Oncotarget, Jan-12, Volume: 9, Issue:4
Quantitative high-throughput phenotypic screening of pediatric cancer cell lines identifies multiple opportunities for drug repurposing.
AID1346987P-glycoprotein substrates identified in KB-8-5-11 adenocarcinoma cell line, qHTS therapeutic library screen2019Molecular pharmacology, 11, Volume: 96, Issue:5
A High-Throughput Screen of a Library of Therapeutics Identifies Cytotoxic Substrates of P-glycoprotein.
AID1346986P-glycoprotein substrates identified in KB-3-1 adenocarcinoma cell line, qHTS therapeutic library screen2019Molecular pharmacology, 11, Volume: 96, Issue:5
A High-Throughput Screen of a Library of Therapeutics Identifies Cytotoxic Substrates of P-glycoprotein.
AID1159607Screen for inhibitors of RMI FANCM (MM2) intereaction2016Journal of biomolecular screening, Jul, Volume: 21, Issue:6
A High-Throughput Screening Strategy to Identify Protein-Protein Interaction Inhibitors That Block the Fanconi Anemia DNA Repair Pathway.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (35)

TimeframeStudies, This Drug (%)All Drugs %
pre-199012 (34.29)18.7374
1990's9 (25.71)18.2507
2000's1 (2.86)29.6817
2010's6 (17.14)24.3611
2020's7 (20.00)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 12.06

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 Index12.06 (24.57)
Research Supply Index3.66 (2.92)
Research Growth Index5.73 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (12.06)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials2 (5.56%)5.53%
Reviews0 (0.00%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other34 (94.44%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]