TOLBUTAMIDE

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Trade Names
Synonyms
Status
Molecule Category Free-form
ATC A10BB03 V04CA01
UNII 982XCM1FOI
EPA CompTox DTXSID8021359

Structure

InChI Key JLRGJRBPOGGCBT-UHFFFAOYSA-N
Smiles CCCCNC(=O)NS(=O)(=O)c1ccc(C)cc1
InChI
InChI=1S/C12H18N2O3S/c1-3-4-9-13-12(15)14-18(16,17)11-7-5-10(2)6-8-11/h5-8H,3-4,9H2,1-2H3,(H2,13,14,15)

Physicochemical Descriptors

Property Name Value
Molecular Formula C12H18N2O3S
Molecular Weight 270.35
AlogP 1.78
Hydrogen Bond Acceptor 3.0
Hydrogen Bond Donor 2.0
Number of Rotational Bond 5.0
Polar Surface Area 75.27
Molecular species ACID
Aromatic Rings 1.0
Heavy Atoms 18.0

Bioactivity

Mechanism of Action Action Reference
Sulfonylurea receptor 1, Kir6.2 blocker BLOCKER PubMed PubMed PubMed PubMed
Protein: Sulfonylurea receptor 1, Kir6.2
Description: ATP-binding cassette sub-family C member 8
Organism : Homo sapiens
Q09428 ENSG00000006071
Protein: Sulfonylurea receptor 1, Kir6.2
Description: ATP-sensitive inward rectifier potassium channel 11
Organism : Homo sapiens
Q14654 ENSG00000187486
Targets EC50(nM) IC50(nM) Kd(nM) Ki(nM) Inhibition(%)
Enzyme Cytochrome P450 Cytochrome P450 family 2 Cytochrome P450 family 2C Cytochrome P450 2C9
- - - 70000 88
Secreted protein
- - 6026 - -
Transporter Electrochemical transporter SLC superfamily of solute carriers SLC21/SLCO family of organic anion transporting polypeptides
- - - - 6-100
Transporter Electrochemical transporter SLC superfamily of solute carriers SLC22 family of organic cation and anion transporters
- - - 55500 -
Assay Description Organism Bioactivity Reference
Antitumor activity in vivo against the 6C3HED lymphosarcoma dosed for 10 days at 600 mg/kg Mus musculus 45.0 %
Inhibition of human liver OATP1B1 expressed in HEK293 Flp-In cells assessed as reduction in E17-betaG uptake at 20 uM by scintillation counting Homo sapiens 9.1 %
Inhibition of human liver OATP1B3 expressed in HEK293 Flp-In cells assessed as reduction in [3H]E17-betaG uptake at 20 uM incubated for 5 mins by scintillation counting Homo sapiens 5.8 %
Inhibition of human liver OATP2B1 expressed in HEK293 Flp-In cells assessed as reduction in [3H]E3S uptake at 20 uM incubated for 5 mins by scintillation counting Homo sapiens 15.5 %
Antiaggregatory activity in human platelet-rich plasma assessed as inhibition of collagen-induced aggregation at 300 uM pretreated 10 mins before addition of stimulus measured after 10 mins Homo sapiens 6.4 %
Inhibition of sodium fluorescein uptake in OATP1B1-transfected CHO cells at an equimolar substrate-inhibitor concentration of 10 uM Cricetulus griseus 125.25 %
Inhibition of sodium fluorescein uptake in OATP1B3-transfected CHO cells at an equimolar substrate-inhibitor concentration of 10 uM Cricetulus griseus 99.86 %
Hypoglycemic activity in 48-hrs fasted rat assessed as decrease in blood glucose level at 200 mg/kg, po after 1 hr Rattus norvegicus 28.0 %
Hypoglycemic activity in 48-hrs fasted rat assessed as decrease in blood glucose level at 200 mg/kg, po after 2 hrs Rattus norvegicus 47.0 %
Hypoglycemic activity in 48-hrs fasted rat assessed as decrease in blood glucose level at 200 mg/kg, po after 4 hrs Rattus norvegicus 48.0 %
Hypoglycemic activity in fasted glucose primed Sprague-Dawley rat assessed as plasma glucose level at 100 mg/kg administered via oral gavage measured after 2 hrs by glucose-oxidase method relative to control Rattus norvegicus 41.0 %
Hypoglycemic activity in fasted glucose primed Sprague-Dawley rat assessed as plasma glucose level at 50 mg/kg administered via oral gavage measured after 2 hrs by glucose-oxidase method relative to control Rattus norvegicus 43.0 %
Hypoglycemic activity in fasted glucose primed Sprague-Dawley rat assessed as plasma glucose level at 25 mg/kg administered via oral gavage measured after 2 hrs by glucose-oxidase method relative to control Rattus norvegicus 29.0 %
Hypoglycemic activity in fasted glucose primed Sprague-Dawley rat assessed as plasma glucose level at 12.5 mg/kg administered via oral gavage measured after 2 hrs by glucose-oxidase method relative to control Rattus norvegicus 16.0 %
Antibacterial activity against Staphylococcus aureus MRSA ATCC 43300 (CO-ADD:GP_020); MIC in CAMBH media, using NBS plates, by OD(600) Staphylococcus aureus subsp. aureus 4.92 %
Antibacterial activity against Escherichia coli ATCC 25922 (CO-ADD:GN_001); MIC in CAMBH media using NBS plates, by OD(600) Escherichia coli 0.97 %
Antibacterial activity against Klebsiella pneumoniae MDR ATCC 70063 (CO-ADD:GN_003); MIC in CAMBH media using NBS plates, by OD(600) Klebsiella pneumoniae 16.6 %
Antibacterial activity against Pseudomonas aeruginosa ATCC 27853 (CO-ADD:GN_042); MIC in CAMBH media using NBS plates, by OD(600) Pseudomonas aeruginosa 8.36 %
Antibacterial activity against Acinetobacter baumannii ATCC 19606 (CO-ADD:GN_034); MIC in CAMBH media using NBS plates, by OD600 Acinetobacter baumannii 35.1 %
Antifungal activity against Candida albicans ATCC 90028 (CO-ADD:FG_001); MIC in YNB media using NBS plates, by OD630 Candida albicans 1.06 %
Antifungal activity against Cryptococcus neoformans H99 ATCC 208821 (CO-ADD:FG_002); MIC in YNB media using NBS plates, by Resazurin OD(600-570) Cryptococcus neoformans 0.26 %
Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of Caco-2 cells at 10 uM after 48 hours by high content imaging Homo sapiens 3.6 %
Antihyperglycemic activity in alloxanized BALB/c mouse assessed as reduction in blood glucose level at 150 mg/kg, po measured after 8 hrs relative to control Mus musculus 47.23 %
SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate Severe acute respiratory syndrome coronavirus 2 21.67 %
Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of VERO-6 cells at 10 uM after 48 hours exposure to 0.01 MOI SARS CoV-2 virus by high content imaging Chlorocebus sabaeus 0.19 % Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of VERO-6 cells at 10 uM after 48 hours exposure to 0.01 MOI SARS CoV-2 virus by high content imaging Chlorocebus sabaeus 0.19 %
Inhibition of human CYP2C9 at 10 uM Homo sapiens 87.68 %

Related Entries

Cross References

Resources Reference
ChEBI 27999
ChEMBL CHEMBL782
DrugBank DB01124
DrugCentral 2696
FDA SRS 982XCM1FOI
Human Metabolome Database HMDB0015256
Guide to Pharmacology 6848
KEGG C07148
PharmGKB PA451718
PubChem 5505
SureChEMBL SCHEMBL15918
ZINC ZINC000001530703
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