Page last updated: 2024-12-07

trifluoromethylsulfonamide

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

Description

Trifluoromethylsulfonamide (TFMSA) is a versatile building block in organic synthesis, commonly employed as a reagent for the preparation of various compounds. It is a strong acid with a pKa of -1.5, making it a useful catalyst for various chemical transformations. TFMSA is also used in the preparation of pharmaceuticals, agrochemicals, and materials science.'

trifluoromethylsulfonamide: RN given refers to parent [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID79001
CHEMBL ID67511
SCHEMBL ID130
MeSH IDM0250694

Synonyms (38)

Synonym
trifluoro-methanesulfonamide
bdbm50044311
trifluoromethylsulfonamide
trifluoromethyl sulfonamide
methanesulfonamide, 1,1,1-trifluoro-
trifluoromethane sulfonamide
trifluoromethanesulfonamide, 95%
1BCD ,
CHEMBL67511 ,
1,1,1-trifluoromethanesulfonamide
T1290
421-85-2
trifluoromethanesulfonamide
AKOS003622043
trifluoromethanesulphonamide ,
triflamide
FT-0632111
BP-21470
trifluoromethylsulphonamide
trifiuoromethylsulphonamide
trifluorometanesulfonamide
trifiuoromethanesulfonamide
SCHEMBL130
CS-B0881
ch2f3no2s
mfcd00068714
J-525091
DTXSID10194944
AC2628
BBL101971
SY014031
STL555768
Q27460359
DS-11388
triflimidic acid
SB66436
EN300-96724
perfluoromethane sulfonamide
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Protein Targets (6)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Chain A, CARBONIC ANHYDRASE IIHomo sapiens (human)Ki0.00200.00200.00200.0020AID977610
Carbonic anhydrase 2Homo sapiens (human)IC50 (µMol)0.01300.00021.10608.3000AID47747
Carbonic anhydrase 2Homo sapiens (human)Ki0.00200.00000.72369.9200AID47925
Carbonic anhydrase 2Bos taurus (cattle)IC50 (µMol)0.00200.00200.72891.8600AID1573025
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Activation Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Carbonic anhydrase 1Homo sapiens (human)Kd0.05000.00071.368910.0000AID526859
Carbonic anhydrase 2Homo sapiens (human)Kd0.11050.00000.41575.5500AID526861; AID526862
Carbonic anhydrase 7Homo sapiens (human)Kd0.03250.00010.37616.6700AID526863; AID526864
Carbonic anhydrase 13Homo sapiens (human)Kd0.02350.00070.384910.0000AID526865; AID526866
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (12)

Processvia Protein(s)Taxonomy
one-carbon metabolic processCarbonic anhydrase 1Homo sapiens (human)
morphogenesis of an epitheliumCarbonic anhydrase 2Homo sapiens (human)
positive regulation of synaptic transmission, GABAergicCarbonic anhydrase 2Homo sapiens (human)
positive regulation of cellular pH reductionCarbonic anhydrase 2Homo sapiens (human)
angiotensin-activated signaling pathwayCarbonic anhydrase 2Homo sapiens (human)
regulation of monoatomic anion transportCarbonic anhydrase 2Homo sapiens (human)
secretionCarbonic anhydrase 2Homo sapiens (human)
regulation of intracellular pHCarbonic anhydrase 2Homo sapiens (human)
neuron cellular homeostasisCarbonic anhydrase 2Homo sapiens (human)
positive regulation of dipeptide transmembrane transportCarbonic anhydrase 2Homo sapiens (human)
regulation of chloride transportCarbonic anhydrase 2Homo sapiens (human)
carbon dioxide transportCarbonic anhydrase 2Homo sapiens (human)
one-carbon metabolic processCarbonic anhydrase 2Homo sapiens (human)
angiotensin-activated signaling pathwayCarbonic anhydrase 2Bos taurus (cattle)
regulation of monoatomic anion transportCarbonic anhydrase 2Bos taurus (cattle)
regulation of intracellular pHCarbonic anhydrase 2Bos taurus (cattle)
positive regulation of dipeptide transmembrane transportCarbonic anhydrase 2Bos taurus (cattle)
positive regulation of synaptic transmission, GABAergicCarbonic anhydrase 7Homo sapiens (human)
positive regulation of cellular pH reductionCarbonic anhydrase 7Homo sapiens (human)
neuron cellular homeostasisCarbonic anhydrase 7Homo sapiens (human)
regulation of chloride transportCarbonic anhydrase 7Homo sapiens (human)
regulation of intracellular pHCarbonic anhydrase 7Homo sapiens (human)
one-carbon metabolic processCarbonic anhydrase 7Homo sapiens (human)
one-carbon metabolic processCarbonic anhydrase 13Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (6)

Processvia Protein(s)Taxonomy
arylesterase activityCarbonic anhydrase 1Homo sapiens (human)
carbonate dehydratase activityCarbonic anhydrase 1Homo sapiens (human)
protein bindingCarbonic anhydrase 1Homo sapiens (human)
zinc ion bindingCarbonic anhydrase 1Homo sapiens (human)
hydro-lyase activityCarbonic anhydrase 1Homo sapiens (human)
cyanamide hydratase activityCarbonic anhydrase 1Homo sapiens (human)
arylesterase activityCarbonic anhydrase 2Homo sapiens (human)
carbonate dehydratase activityCarbonic anhydrase 2Homo sapiens (human)
protein bindingCarbonic anhydrase 2Homo sapiens (human)
zinc ion bindingCarbonic anhydrase 2Homo sapiens (human)
cyanamide hydratase activityCarbonic anhydrase 2Homo sapiens (human)
zinc ion bindingCarbonic anhydrase 2Bos taurus (cattle)
cyanamide hydratase activityCarbonic anhydrase 2Bos taurus (cattle)
zinc ion bindingCarbonic anhydrase 7Homo sapiens (human)
carbonate dehydratase activityCarbonic anhydrase 7Homo sapiens (human)
protein bindingCarbonic anhydrase 13Homo sapiens (human)
zinc ion bindingCarbonic anhydrase 13Homo sapiens (human)
carbonate dehydratase activityCarbonic anhydrase 13Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (7)

Processvia Protein(s)Taxonomy
cytosolCarbonic anhydrase 1Homo sapiens (human)
extracellular exosomeCarbonic anhydrase 1Homo sapiens (human)
cytoplasmCarbonic anhydrase 2Homo sapiens (human)
cytosolCarbonic anhydrase 2Homo sapiens (human)
plasma membraneCarbonic anhydrase 2Homo sapiens (human)
myelin sheathCarbonic anhydrase 2Homo sapiens (human)
apical part of cellCarbonic anhydrase 2Homo sapiens (human)
extracellular exosomeCarbonic anhydrase 2Homo sapiens (human)
cytoplasmCarbonic anhydrase 2Homo sapiens (human)
plasma membraneCarbonic anhydrase 2Homo sapiens (human)
apical part of cellCarbonic anhydrase 2Homo sapiens (human)
cytoplasmCarbonic anhydrase 2Bos taurus (cattle)
plasma membraneCarbonic anhydrase 2Bos taurus (cattle)
cytosolCarbonic anhydrase 7Homo sapiens (human)
cytoplasmCarbonic anhydrase 7Homo sapiens (human)
cytosolCarbonic anhydrase 13Homo sapiens (human)
myelin sheathCarbonic anhydrase 13Homo sapiens (human)
intracellular membrane-bounded organelleCarbonic anhydrase 13Homo sapiens (human)
cytoplasmCarbonic anhydrase 13Homo sapiens (human)
cytosolCarbonic anhydrase 13Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (26)

Assay IDTitleYearJournalArticle
AID47925Dissociation constant was reported against Carbonic anhydrase II2002Journal of medicinal chemistry, Aug-15, Volume: 45, Issue:17
Successful virtual screening for novel inhibitors of human carbonic anhydrase: strategy and experimental confirmation.
AID1573025Inhibition of bovine carbonic anhydrase 22018Journal of medicinal chemistry, 07-26, Volume: 61, Issue:14
Fluorine and Fluorinated Motifs in the Design and Application of Bioisosteres for Drug Design.
AID526859Binding affinity to human recombinant carbonic anhydrase 1 by thermal shift assay2010Bioorganic & medicinal chemistry, Nov-01, Volume: 18, Issue:21
4-[N-(substituted 4-pyrimidinyl)amino]benzenesulfonamides as inhibitors of carbonic anhydrase isozymes I, II, VII, and XIII.
AID730888Binding affinity to human recombinant carbonic anhydrase 12 expressed in Escherichia coli Rosetta (DE3) assessed as protein stability at pH 6 by fluorescent thermal shift assay2013Bioorganic & medicinal chemistry, Mar-15, Volume: 21, Issue:6
Characterization of human carbonic anhydrase XII stability and inhibitor binding.
AID526861Binding affinity to human recombinant carbonic anhydrase 2 by thermal shift assay2010Bioorganic & medicinal chemistry, Nov-01, Volume: 18, Issue:21
4-[N-(substituted 4-pyrimidinyl)amino]benzenesulfonamides as inhibitors of carbonic anhydrase isozymes I, II, VII, and XIII.
AID1572978Dissociation constant, pKa of the compound2018Journal of medicinal chemistry, 07-26, Volume: 61, Issue:14
Fluorine and Fluorinated Motifs in the Design and Application of Bioisosteres for Drug Design.
AID464215Inhibition of bovine carbonic anhydrase assessed as conversion of 4-nitrophenyl acetate to 4-nitrophnolate after 5 mins2010European journal of medicinal chemistry, Mar, Volume: 45, Issue:3
Synthesis and investigation of inhibition effect of fluorinated sulfonamide derivatives on carbonic anhydrase.
AID611568Inhibition of bovine carbonic anhydrase assessed as formation of p-nitrophenol from p-nitrophenyl acetate substrate after 30 mins by spectrophotometric method2011Bioorganic & medicinal chemistry, Jun-01, Volume: 19, Issue:11
Discovery of new chromone containing sulfonamides as potent inhibitors of bovine cytosolic carbonic anhydrase.
AID730889Intrinsic thermodynamic binding affinity to carbonic anhydrase 13 (unknown origin) by isothermal titration calorimetry assay2013Bioorganic & medicinal chemistry, Mar-15, Volume: 21, Issue:6
Characterization of human carbonic anhydrase XII stability and inhibitor binding.
AID526863Binding affinity to human recombinant carbonic anhydrase 7 by thermal shift assay2010Bioorganic & medicinal chemistry, Nov-01, Volume: 18, Issue:21
4-[N-(substituted 4-pyrimidinyl)amino]benzenesulfonamides as inhibitors of carbonic anhydrase isozymes I, II, VII, and XIII.
AID730886Binding affinity to human recombinant carbonic anhydrase 12 expressed in Escherichia coli Rosetta (DE3) assessed as protein stability at pH 10 by fluorescent thermal shift assay2013Bioorganic & medicinal chemistry, Mar-15, Volume: 21, Issue:6
Characterization of human carbonic anhydrase XII stability and inhibitor binding.
AID526866Binding affinity to human recombinant carbonic anhydrase 13 by isothermal titration calorimetry assay2010Bioorganic & medicinal chemistry, Nov-01, Volume: 18, Issue:21
4-[N-(substituted 4-pyrimidinyl)amino]benzenesulfonamides as inhibitors of carbonic anhydrase isozymes I, II, VII, and XIII.
AID27788Calculated partition coefficient (clogP) (MlogP)2002Journal of medicinal chemistry, Aug-15, Volume: 45, Issue:17
Successful virtual screening for novel inhibitors of human carbonic anhydrase: strategy and experimental confirmation.
AID526864Binding affinity to human recombinant carbonic anhydrase 7 by isothermal titration calorimetry assay2010Bioorganic & medicinal chemistry, Nov-01, Volume: 18, Issue:21
4-[N-(substituted 4-pyrimidinyl)amino]benzenesulfonamides as inhibitors of carbonic anhydrase isozymes I, II, VII, and XIII.
AID730887Binding affinity to human recombinant carbonic anhydrase 12 expressed in Escherichia coli Rosetta (DE3) assessed as protein stability at pH 5 by fluorescent thermal shift assay2013Bioorganic & medicinal chemistry, Mar-15, Volume: 21, Issue:6
Characterization of human carbonic anhydrase XII stability and inhibitor binding.
AID25313Acid dissociation constant was determined1993Journal of medicinal chemistry, Jul-23, Volume: 36, Issue:15
Sulfonylmethanesulfonamide inhibitors of carbonic anhydrase.
AID526862Binding affinity to human recombinant carbonic anhydrase 2 by isothermal titration calorimetry assay2010Bioorganic & medicinal chemistry, Nov-01, Volume: 18, Issue:21
4-[N-(substituted 4-pyrimidinyl)amino]benzenesulfonamides as inhibitors of carbonic anhydrase isozymes I, II, VII, and XIII.
AID526860Binding affinity to human recombinant carbonic anhydrase 1 by isothermal titration calorimetry assay2010Bioorganic & medicinal chemistry, Nov-01, Volume: 18, Issue:21
4-[N-(substituted 4-pyrimidinyl)amino]benzenesulfonamides as inhibitors of carbonic anhydrase isozymes I, II, VII, and XIII.
AID47747In vitro inhibition of purified human erythrocyte carbonic anhydrase II1993Journal of medicinal chemistry, Jul-23, Volume: 36, Issue:15
Sulfonylmethanesulfonamide inhibitors of carbonic anhydrase.
AID730890Intrinsic thermodynamic binding affinity to human recombinant carbonic anhydrase 12 expressed in Escherichia coli Rosetta (DE3) by isothermal titration calorimetry assay2013Bioorganic & medicinal chemistry, Mar-15, Volume: 21, Issue:6
Characterization of human carbonic anhydrase XII stability and inhibitor binding.
AID464216Inhibition of human carbonic anhydrase 2 assessed as conversion of 4-nitrophenyl acetate to 4-nitrophnolate after 5 mins2010European journal of medicinal chemistry, Mar, Volume: 45, Issue:3
Synthesis and investigation of inhibition effect of fluorinated sulfonamide derivatives on carbonic anhydrase.
AID526865Binding affinity to human recombinant carbonic anhydrase 13 by thermal shift assay2010Bioorganic & medicinal chemistry, Nov-01, Volume: 18, Issue:21
4-[N-(substituted 4-pyrimidinyl)amino]benzenesulfonamides as inhibitors of carbonic anhydrase isozymes I, II, VII, and XIII.
AID730898Binding affinity to human recombinant carbonic anhydrase 12 expressed in Escherichia coli Rosetta (DE3) in phosphate buffer at pH 7 by isothermal titration calorimetry assay2013Bioorganic & medicinal chemistry, Mar-15, Volume: 21, Issue:6
Characterization of human carbonic anhydrase XII stability and inhibitor binding.
AID597895Dissociation constant, pKa of the compound in DMSO2011Bioorganic & medicinal chemistry letters, Jun-01, Volume: 21, Issue:11
Synthesis and SAR study of tricyclic sulfones as γ-secretase inhibitors: C-6 and C-8 positions.
AID1811Experimentally measured binding affinity data derived from PDB1994FEBS letters, Aug-22, Volume: 350, Issue:2-3
The structure of a complex between carbonic anhydrase II and a new inhibitor, trifluoromethane sulphonamide.
AID977610Experimentally measured binding affinity data (Ki) for protein-ligand complexes derived from PDB1994FEBS letters, Aug-22, Volume: 350, Issue:2-3
The structure of a complex between carbonic anhydrase II and a new inhibitor, trifluoromethane sulphonamide.
[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-19900 (0.00)18.7374
1990's3 (25.00)18.2507
2000's1 (8.33)29.6817
2010's8 (66.67)24.3611
2020's0 (0.00)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 31.84

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 moderate demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index31.84 (24.57)
Research Supply Index2.56 (2.92)
Research Growth Index4.73 (4.65)
Search Engine Demand Index39.34 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (31.84)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews1 (8.33%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other11 (91.67%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]