GLIPIZIDE

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Trade Names
Synonyms
Status
Molecule Category Free-form
ATC A10BB07
UNII X7WDT95N5C
EPA CompTox DTXSID0040676

Structure

InChI Key ZJJXGWJIGJFDTL-UHFFFAOYSA-N
Smiles Cc1cnc(C(=O)NCCc2ccc(S(=O)(=O)NC(=O)NC3CCCCC3)cc2)cn1
InChI
InChI=1S/C21H27N5O4S/c1-15-13-24-19(14-23-15)20(27)22-12-11-16-7-9-18(10-8-16)31(29,30)26-21(28)25-17-5-3-2-4-6-17/h7-10,13-14,17H,2-6,11-12H2,1H3,(H,22,27)(H2,25,26,28)

Physicochemical Descriptors

Property Name Value
Molecular Formula C21H27N5O4S
Molecular Weight 445.55
AlogP 2.08
Hydrogen Bond Acceptor 6.0
Hydrogen Bond Donor 3.0
Number of Rotational Bond 7.0
Polar Surface Area 130.15
Molecular species ACID
Aromatic Rings 2.0
Heavy Atoms 31.0

Bioactivity

Mechanism of Action Action Reference
Sulfonylurea receptor 1, Kir6.2 blocker BLOCKER PubMed DailyMed
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 3 Cytochrome P450 family 3A Cytochrome P450 3A4
- 7447 - - -
Enzyme Hydrolase
- - - - 13
Transporter Electrochemical transporter SLC superfamily of solute carriers SLC21/SLCO family of organic anion transporting polypeptides
- - - - 1
Transporter Electrochemical transporter SLC superfamily of solute carriers SLC22 family of organic cation and anion transporters
- - - -
Assay Description Organism Bioactivity Reference
Inhibition of [125I]-I binding to ATP-inhibited Potassium channel receptor of Rat brain homogenate Rattus norvegicus 8.2 nM
Inhibition of 4-(4-(dimethylamino)styryl)-N-methylpyridinium uptake at human OCT1 expressed in HEK293 cells at 100 uM by confocal microscopy Homo sapiens -12.7 %
Inhibition of human FAAH at 1 uM Homo sapiens 12.54 %
DRUGMATRIX: Potassium Channel [KATP] radioligand binding (ligand: [3H] Glyburide) None 398.0 nM DRUGMATRIX: Potassium Channel [KATP] radioligand binding (ligand: [3H] Glyburide) None 45.0 nM
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 1.1 %
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 25.2 %
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 22.0 %
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 13.08 %
Antibacterial activity against Escherichia coli ATCC 25922 (CO-ADD:GN_001); MIC in CAMBH media using NBS plates, by OD(600) Escherichia coli 0.63 %
Antibacterial activity against Klebsiella pneumoniae MDR ATCC 70063 (CO-ADD:GN_003); MIC in CAMBH media using NBS plates, by OD(600) Klebsiella pneumoniae 8.44 %
Antibacterial activity against Pseudomonas aeruginosa ATCC 27853 (CO-ADD:GN_042); MIC in CAMBH media using NBS plates, by OD(600) Pseudomonas aeruginosa 16.96 %
Antibacterial activity against Acinetobacter baumannii ATCC 19606 (CO-ADD:GN_034); MIC in CAMBH media using NBS plates, by OD600 Acinetobacter baumannii 16.47 %
Antifungal activity against Candida albicans ATCC 90028 (CO-ADD:FG_001); MIC in YNB media using NBS plates, by OD630 Candida albicans 3.06 %
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 -1.88 %
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 -4.06 %
SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate Severe acute respiratory syndrome coronavirus 2 5.804 %
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 -0.04 % 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 -0.04 %

Cross References

Resources Reference
ChEBI 5384
ChEMBL CHEMBL1073
DrugBank DB01067
DrugCentral 1301
FDA SRS X7WDT95N5C
Human Metabolome Database HMDB0015200
Guide to Pharmacology 6821
PharmGKB PA449762
PubChem 3478
SureChEMBL SCHEMBL17094
ZINC ZINC000000537795
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