Page last updated: 2024-12-09

1-(4-chlorophenyl)-3-(4-sulfamoylphenyl)urea

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

1-(4-chlorophenyl)-3-(4-sulfamoylphenyl)urea is a compound that is commonly known as **glibenclamide** or **glyburide**.

**Why it's important for research:**

* **Diabetes treatment:** Glibenclamide is a **sulfonylurea drug** widely used in the treatment of **type 2 diabetes**. It works by stimulating the release of insulin from the pancreas, helping regulate blood sugar levels.
* **Research tool:** It is used as a research tool to study the **mechanisms of insulin secretion** and the **role of the sulfonylurea receptor (SUR)** in various cellular processes.
* **Potential for other applications:** Research is ongoing to explore its potential in other areas, such as **cancer therapy** and **neuroprotection**.

**Here's a breakdown of its key features and importance:**

* **Structure:** Glibenclamide is a complex molecule with a urea linker connecting two aromatic rings. One ring carries a chlorine atom, and the other a sulfamoyl group.
* **Mechanism of action:** It binds to the SUR1 subunit of the ATP-sensitive potassium channel (KATP) in pancreatic beta cells. This binding leads to the closure of the channel, which triggers the release of insulin.
* **Therapeutic benefits:** Glibenclamide helps improve glycemic control in patients with type 2 diabetes by increasing insulin secretion. It is an effective medication for managing the disease, although its use may be limited in some cases.
* **Research applications:** As a potent inhibitor of KATP channels, glibenclamide is used extensively in research to:
* **Investigate the role of KATP channels in various cellular processes.**
* **Study the mechanism of insulin secretion.**
* **Develop new drugs that target KATP channels for various medical conditions.**

**In conclusion,** glibenclamide is a significant compound for both clinical and research purposes. Its use in the treatment of type 2 diabetes and its role as a research tool for understanding cellular mechanisms make it a valuable asset in the pharmaceutical and scientific communities.

Cross-References

ID SourceID
PubMed CID730672
CHEMBL ID1446150
CHEBI ID112239
SCHEMBL ID671549

Synonyms (20)

Synonym
smr000230984
MLS000704335 ,
OPREA1_331972
OPREA1_659254
4-{[(4-chloroanilino)carbonyl]amino}benzenesulfonamide
AI-204/31750036 ,
STK019184
4-{[(4-chlorophenyl)carbamoyl]amino}benzenesulfonamide
CHEBI:112239
AKOS000489358
1-(4-chlorophenyl)-3-(4-sulfamoylphenyl)urea
CHEMBL1446150
4-{([(4'-chlorophenyl)amino]carbonylamino)}benzenesulfonamide
173550-69-1
SCHEMBL671549
HACQCGHVZICZSC-UHFFFAOYSA-N
bdbm56662
cid_730672
Q27192341
DTXSID10352643
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (1)

ClassDescription
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 (16)

Potency Measurements

ProteinTaxonomyMeasurementAverage (µ)Min (ref.)Avg (ref.)Max (ref.)Bioassay(s)
glp-1 receptor, partialHomo sapiens (human)Potency7.07950.01846.806014.1254AID624417
ATAD5 protein, partialHomo sapiens (human)Potency10.31830.004110.890331.5287AID504467
TDP1 proteinHomo sapiens (human)Potency16.36010.000811.382244.6684AID686978
nuclear factor erythroid 2-related factor 2 isoform 2Homo sapiens (human)Potency10.32250.00419.984825.9290AID504444
nuclear receptor ROR-gamma isoform 1Mus musculus (house mouse)Potency18.85410.00798.23321,122.0200AID2546; AID2551
gemininHomo sapiens (human)Potency6.51310.004611.374133.4983AID624296
Glycoprotein hormones alpha chainHomo sapiens (human)Potency10.00004.46688.344810.0000AID624291
ATP-dependent phosphofructokinaseTrypanosoma brucei brucei TREU927Potency9.56620.060110.745337.9330AID485367; AID504636; AID504637
[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)
kallikrein-5 preproproteinHomo sapiens (human)IC50 (µMol)50.00001.359211.306050.0000AID1431
Carbonic anhydrase 12Homo sapiens (human)Ki0.00530.00021.10439.9000AID587002
Carbonic anhydrase 1Homo sapiens (human)Ki2.15000.00001.372610.0000AID586999
Carbonic anhydrase 2Homo sapiens (human)Ki0.78100.00000.72369.9200AID551577; AID587000
Carbonic anhydrase Mycobacterium tuberculosis H37RvKi0.06310.01202.72389.1200AID551580
Beta-carbonic anhydrase 1Mycobacterium tuberculosis H37RvKi0.00480.00483.38419.8400AID551579
Carbonic anhydrase 9Homo sapiens (human)Ki0.05800.00010.78749.9000AID587001
Carbonic anhydrase Nakaseomyces glabratus CBS 138Ki0.00700.00701.21749.1700AID744415
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (31)

Processvia Protein(s)Taxonomy
estrous cycleCarbonic anhydrase 12Homo sapiens (human)
chloride ion homeostasisCarbonic anhydrase 12Homo sapiens (human)
one-carbon metabolic processCarbonic anhydrase 12Homo sapiens (human)
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)
G protein-coupled receptor signaling pathwayGlycoprotein hormones alpha chainHomo sapiens (human)
positive regulation of cell population proliferationGlycoprotein hormones alpha chainHomo sapiens (human)
hormone-mediated signaling pathwayGlycoprotein hormones alpha chainHomo sapiens (human)
regulation of signaling receptor activityGlycoprotein hormones alpha chainHomo sapiens (human)
positive regulation of steroid biosynthetic processGlycoprotein hormones alpha chainHomo sapiens (human)
positive regulation of cell migrationGlycoprotein hormones alpha chainHomo sapiens (human)
thyroid gland developmentGlycoprotein hormones alpha chainHomo sapiens (human)
luteinizing hormone secretionGlycoprotein hormones alpha chainHomo sapiens (human)
organ growthGlycoprotein hormones alpha chainHomo sapiens (human)
follicle-stimulating hormone signaling pathwayGlycoprotein hormones alpha chainHomo sapiens (human)
positive regulation of transcription by RNA polymerase IIGlycoprotein hormones alpha chainHomo sapiens (human)
negative regulation of organ growthGlycoprotein hormones alpha chainHomo sapiens (human)
follicle-stimulating hormone secretionGlycoprotein hormones alpha chainHomo sapiens (human)
thyroid hormone generationGlycoprotein hormones alpha chainHomo sapiens (human)
response to hypoxiaCarbonic anhydrase 9Homo sapiens (human)
morphogenesis of an epitheliumCarbonic anhydrase 9Homo sapiens (human)
response to xenobiotic stimulusCarbonic anhydrase 9Homo sapiens (human)
response to testosteroneCarbonic anhydrase 9Homo sapiens (human)
secretionCarbonic anhydrase 9Homo sapiens (human)
one-carbon metabolic processCarbonic anhydrase 9Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (9)

Processvia Protein(s)Taxonomy
zinc ion bindingCarbonic anhydrase 12Homo sapiens (human)
carbonate dehydratase activityCarbonic anhydrase 12Homo sapiens (human)
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)
hormone activityGlycoprotein hormones alpha chainHomo sapiens (human)
protein bindingGlycoprotein hormones alpha chainHomo sapiens (human)
follicle-stimulating hormone activityGlycoprotein hormones alpha chainHomo sapiens (human)
carbonate dehydratase activityCarbonic anhydrase 9Homo sapiens (human)
protein bindingCarbonic anhydrase 9Homo sapiens (human)
zinc ion bindingCarbonic anhydrase 9Homo sapiens (human)
molecular function activator activityCarbonic anhydrase 9Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (16)

Processvia Protein(s)Taxonomy
plasma membraneCarbonic anhydrase 12Homo sapiens (human)
membraneCarbonic anhydrase 12Homo sapiens (human)
basolateral plasma membraneCarbonic anhydrase 12Homo sapiens (human)
apical plasma membraneCarbonic anhydrase 12Homo sapiens (human)
plasma membraneCarbonic anhydrase 12Homo sapiens (human)
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)
extracellular regionGlycoprotein hormones alpha chainHomo sapiens (human)
extracellular spaceGlycoprotein hormones alpha chainHomo sapiens (human)
Golgi lumenGlycoprotein hormones alpha chainHomo sapiens (human)
follicle-stimulating hormone complexGlycoprotein hormones alpha chainHomo sapiens (human)
pituitary gonadotropin complexGlycoprotein hormones alpha chainHomo sapiens (human)
extracellular spaceGlycoprotein hormones alpha chainHomo sapiens (human)
nucleolusCarbonic anhydrase 9Homo sapiens (human)
plasma membraneCarbonic anhydrase 9Homo sapiens (human)
membraneCarbonic anhydrase 9Homo sapiens (human)
basolateral plasma membraneCarbonic anhydrase 9Homo sapiens (human)
microvillus membraneCarbonic anhydrase 9Homo sapiens (human)
plasma membraneCarbonic anhydrase 9Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (27)

Assay IDTitleYearJournalArticle
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.
AID1745845Primary qHTS for Inhibitors of ATXN expression
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.
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.
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.
AID587000Inhibition of human cytosolic carbonic anhydrase 2 preincubated for 15 min by CO2 hydration assay2011Journal of medicinal chemistry, Mar-24, Volume: 54, Issue:6
Ureido-substituted benzenesulfonamides potently inhibit carbonic anhydrase IX and show antimetastatic activity in a model of breast cancer metastasis.
AID587002Inhibition of tumor-associated human carbonic anhydrase 12 preincubated for 15 min by CO2 hydration assay2011Journal of medicinal chemistry, Mar-24, Volume: 54, Issue:6
Ureido-substituted benzenesulfonamides potently inhibit carbonic anhydrase IX and show antimetastatic activity in a model of breast cancer metastasis.
AID551579Inhibition of Mycobacterium tuberculosis recombinant beta-carbonic anhydrase Rv1284 preincubated for 15 mins by stopped-flow CO2 hydrase assay2011Bioorganic & medicinal chemistry letters, Jan-01, Volume: 21, Issue:1
Inhibition of β-carbonic anhydrases with ureido-substituted benzenesulfonamides.
AID586999Inhibition of human cytosolic carbonic anhydrase 1 preincubated for 15 min by CO2 hydration assay2011Journal of medicinal chemistry, Mar-24, Volume: 54, Issue:6
Ureido-substituted benzenesulfonamides potently inhibit carbonic anhydrase IX and show antimetastatic activity in a model of breast cancer metastasis.
AID551577Inhibition of human recombinant carbonic anhydrase 2 preincubated for 15 mins by stopped-flow CO2 hydrase assay2011Bioorganic & medicinal chemistry letters, Jan-01, Volume: 21, Issue:1
Inhibition of β-carbonic anhydrases with ureido-substituted benzenesulfonamides.
AID744415Inhibition of recombinant full length Candida glabrata NCE103 expressed in Escherichia coli BL21 preincubated for 15 mins by stopped-flow CO2 hydrase assay2013Bioorganic & medicinal chemistry letters, May-01, Volume: 23, Issue:9
Carbonic anhydrase inhibitors: inhibition of the β-class enzyme from the pathogenic yeast Candida glabrata with sulfonamides, sulfamates and sulfamides.
AID744416Inhibition of Cryptococcus neoformans Can2 expressed in Candida albicans RH1 preincubated for 15 mins by stopped-flow CO2 hydrase assay2013Bioorganic & medicinal chemistry letters, May-01, Volume: 23, Issue:9
Carbonic anhydrase inhibitors: inhibition of the β-class enzyme from the pathogenic yeast Candida glabrata with sulfonamides, sulfamates and sulfamides.
AID551583Selectivity ratio, ratio of Ki for Mycobacterium tuberculosis recombinant beta-carbonic anhydrase Rv3273 to Ki for Candida albicans recombinant beta-carbonic anhydrase2011Bioorganic & medicinal chemistry letters, Jan-01, Volume: 21, Issue:1
Inhibition of β-carbonic anhydrases with ureido-substituted benzenesulfonamides.
AID551578Inhibition of Candida albicans recombinant beta-carbonic anhydrase preincubated for 15 mins by stopped-flow CO2 hydrase assay2011Bioorganic & medicinal chemistry letters, Jan-01, Volume: 21, Issue:1
Inhibition of β-carbonic anhydrases with ureido-substituted benzenesulfonamides.
AID551582Selectivity ratio, ratio of Ki for Mycobacterium tuberculosis recombinant beta-carbonic anhydrase Rv1284 to Ki for Candida albicans recombinant beta-carbonic anhydrase2011Bioorganic & medicinal chemistry letters, Jan-01, Volume: 21, Issue:1
Inhibition of β-carbonic anhydrases with ureido-substituted benzenesulfonamides.
AID587001Inhibition of tumor-associated human carbonic anhydrase 9 preincubated for 15 min by CO2 hydration assay2011Journal of medicinal chemistry, Mar-24, Volume: 54, Issue:6
Ureido-substituted benzenesulfonamides potently inhibit carbonic anhydrase IX and show antimetastatic activity in a model of breast cancer metastasis.
AID551584Selectivity ratio, ratio of Ki for Mycobacterium tuberculosis recombinant beta-carbonic anhydrase Rv3273 to Ki for human recombinant carbonic anhydrase 22011Bioorganic & medicinal chemistry letters, Jan-01, Volume: 21, Issue:1
Inhibition of β-carbonic anhydrases with ureido-substituted benzenesulfonamides.
AID551580Inhibition of Mycobacterium tuberculosis recombinant beta-carbonic anhydrase Rv3273 preincubated for 15 mins by stopped-flow CO2 hydrase assay2011Bioorganic & medicinal chemistry letters, Jan-01, Volume: 21, Issue:1
Inhibition of β-carbonic anhydrases with ureido-substituted benzenesulfonamides.
AID744414Selectivity ratio of Ki for human carbonic anhydrase-2 to Ki for recombinant full length Candida glabrata NCE1032013Bioorganic & medicinal chemistry letters, May-01, Volume: 23, Issue:9
Carbonic anhydrase inhibitors: inhibition of the β-class enzyme from the pathogenic yeast Candida glabrata with sulfonamides, sulfamates and sulfamides.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (8)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's0 (0.00)18.2507
2000's1 (12.50)29.6817
2010's6 (75.00)24.3611
2020's1 (12.50)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 12.25

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 Index12.25 (24.57)
Research Supply Index2.20 (2.92)
Research Growth Index4.44 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (12.25)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews0 (0.00%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other8 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]