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Compound Detail

CHEMBL472

GLYBURIDE
💊 Approved Drug
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💊 Approved Drug
COc1ccc(Cl)cc1C(=O)NCCc1ccc(S(=O)(=O)NC(=O)NC2CCCCC2)cc1

Basic Information

ChEMBL ID CHEMBL472
Name GLYBURIDE
Phase Approved
Structure Type MOL
InChI Key ZNNLBTZKUZBEKO-UHFFFAOYSA-N
Therapeutic ✓ Yes

Known Names

Amglidia Calabren Cirara Daonil Diabeta Diabetamide 2.5 Diabetamide 5 Euglucon Glibenclamida Glibenclamide Glibenclamidum Gliken +16 more
29
Targets
70
Activities
4
Assay Types
30
PK Parameters
20
Publications
28
Known Names
9
Indications
1
Mechanisms

Molecular Properties

494.0
MW (Da)
3.64
ALogP
5
HBA
3
HBD
113.6
PSA (Ų)
0.52
QED
0
Ro5 Violations
8
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 1984
Availability Prescription
Chirality Achiral

Routes of Administration

Oral

Flags

Natural Product Chemical Probe
USAN Year 1969

Extended Properties

Molecular Formula C23H28ClN3O5S
MW 494.01
Aromatic Rings 2
Heavy Atoms 33
NP-Likeness -1.21

Mechanism of Action

Mechanism Action Type Target Direct Efficacy
Sulfonylurea receptor 1, Kir6.2 blocker BLOCKER Sulfonylurea receptor 1, Kir6.2

Indications

Diabetes Mellitus Diabetes Mellitus, Type 2 Diabetes, Gestational Brain Injuries Diabetes Mellitus, Type 1 Stroke Angina, Stable Ischemic Stroke Spinal Cord Injuries

ATC Classification

A10BB01
glibenclamide
Level 1: ALIMENTARY TRACT AND METABOLISM
Level 2: DRUGS USED IN DIABETES

Activity Summary

IC50 51 meas. best 8.96
Ki 13 meas. best 9.37
EC50 5 meas. best 8.52
Kd 1 meas. best 4.39

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Unchecked
CHEMBL612545
Ki 9.37 9.26 0.4 3
Unchecked
CHEMBL612545
IC50 8.96 6.8029 1.1 7
Rattus norvegicus
CHEMBL376
IC50 8.8 8.8 1.6 1
Unchecked
CHEMBL612545
EC50 8.52 7.4 3.0 3
Sulfonylurea receptor 1, Kir6.2
CHEMBL2096972
IC50 8.37 8.37 4.3 1
Cavia porcellus
CHEMBL369
IC50 8.1 8.1 8.0 1
Liver
CHEMBL613642
IC50 7.85 7.85 14.2 1
Sulfonylurea receptor 2, Kir6.2
CHEMBL2095198
Ki 6.89 6.89 130.0 1
Sulfonylurea receptor 2, Kir6.2
CHEMBL2095198
IC50 6.66 6.66 220.0 1
Peroxisome proliferator-activated receptor gamma
CHEMBL235
Ki 6.18 6.18 660.0 1
T-cell line
CHEMBL614685
IC50 6.0 6.0 1000.0 1
Solute carrier organic anion transporter family member 1B1
CHEMBL1697668
IC50 5.85 5.3967 1400.0 3
Bile salt export pump
CHEMBL6020
IC50 5.82 5.378 1500.0 5
Solute carrier family 22 member 6
CHEMBL1777665
Ki 5.8 5.8 1600.0 1
Cytochrome P450 2C9
CHEMBL3397
IC50 5.79 5.79 1602.0 1
CDGSH iron-sulfur domain-containing protein 1
CHEMBL1795168
Ki 5.78 5.78 1671.0 1
Peroxisome proliferator-activated receptor gamma
CHEMBL235
EC50 5.64 5.64 2300.0 1
Bile salt export pump
CHEMBL2073674
IC50 5.55 5.14 2800.0 3
Mesenchymal stem cells
CHEMBL5058627
EC50 5.55 5.55 2800.0 1
Bile salt export pump
CHEMBL2073674
Ki 5.21 5.21 6100.0 1
Solute carrier family 15 member 2
CHEMBL3325
Ki 5.11 5.11 7800.0 1
Leishmania donovani
CHEMBL367
IC50 5.01 5.01 9800.0 1
NACHT, LRR and PYD domains-containing protein 3
CHEMBL1741208
IC50 5.0 4.96 10000.0 2
NACHT, LRR and PYD domains-containing protein 3
CHEMBL3779755
IC50 5.0 5.0 10000.0 2
ATP-binding cassette sub-family C member 4
CHEMBL1743128
IC50 4.98 4.98 10500.0 1
Solute carrier family 22 member 7
CHEMBL2073671
Ki 4.91 4.91 12300.0 1
Plasmodium falciparum
CHEMBL364
IC50 4.9 4.66 12589.2 2
Cystic fibrosis transmembrane conductance regulator
CHEMBL4051
IC50 4.82 4.82 15000.0 1
Solute carrier family 15 member 1
CHEMBL2073691
Ki 4.6 4.6 25000.0 1
Bile salt export pump
CHEMBL6020
Ki 4.56 4.56 27500.0 1
ATP-binding cassette sub-family C member 3
CHEMBL5918
IC50 4.48 4.48 33000.0 1
CDGSH iron-sulfur domain-containing protein 1
CHEMBL1795168
IC50 4.41 4.41 39100.0 1
Urokinase plasminogen activator surface receptor
CHEMBL4883
Kd 4.39 4.39 40400.0 1
Voltage-gated inwardly rectifying potassium channel KCNH2
CHEMBL240
IC50 4.13 4.13 74000.0 4
Trypanosoma brucei rhodesiense
CHEMBL612348
IC50 4.06 4.06 87650.0 1
Trypanosoma cruzi
CHEMBL368
IC50 4.03 4.03 93930.0 1

Pharmacokinetic Data

Parameter Value Units Species
AUC 33113.0 mg/dl Rattus norvegicus
AUC 2610.0 ng.hr.mL-1 Rattus norvegicus
AUC 15230.0 ng.hr.mL-1 Rattus norvegicus
AUC 3000.0 ng.hr.mL-1 Rattus norvegicus
AUC 2350.0 ng.hr.mL-1 Rattus norvegicus
AUC 13270.0 ng.hr.mL-1 Rattus norvegicus
AUC 2380.0 ng.hr.mL-1 Rattus norvegicus
AUC 306.67 ng.hr.mL-1 Rattus norvegicus
AUC 916.0 ng.hr.mL-1 Rattus norvegicus
AUC 356.67 ng.hr.mL-1 Rattus norvegicus
AUC 1327.4 ng.hr.mL-1 Homo sapiens
CL 0.82 mL.min-1.kg-1 Homo sapiens
CL 0.8 mL.min-1.kg-1 Homo sapiens
CL 0.82 mL.min-1.kg-1 Homo sapiens
CL 0.82 mL.min-1.kg-1 Homo sapiens
CL 14.45 uL.min-1.(10^6cells)-1 Homo sapiens
CL 22.0 mL.min-1.g-1 Homo sapiens
CL 347.0 mL.min-1.kg-1 Homo sapiens
CL 6.54 uL.min-1.(10^6cells)-1 Homo sapiens
CL 10.1 uL.min-1.(10^6cells)-1 Homo sapiens
CL 0.205 mL.min-1.g-1 Rattus norvegicus
CL 0.052 mL.min-1.g-1 Rattus norvegicus
CL 0.176 mL.min-1.g-1 Rattus norvegicus
CL 1.3 mL.min-1.kg-1 Homo sapiens
CL 69.0 mL.min-1.kg-1 Homo sapiens
CL 1.2 mL.min-1.kg-1 Rattus norvegicus
CL 5.8 mL.min-1.kg-1 Macaca fascicularis
CL 1.2 mL.min-1.kg-1 Homo sapiens
Cmax 215.0 nM -
Cmax 708.49 nM Rattus norvegicus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Unchecked Ki = 0.432 nM 9.37 DRUGMATRIX: Potassium Channel [KATP] radioligand binding (ligand: [3H] Glyburide... -
Unchecked Ki = 0.608 nM 9.22 Inhibition of [125I]-I binding to ATP-inhibited Potassium channel receptor of Ra... 2124268
Unchecked Ki = 0.65 nM 9.19 Displacement of [3H]Glyburide from ATP-sensitive potassium channel in hamster pa... 23403082
Unchecked IC50 = 1.1 nM 8.96 Inhibition of rat K+ATP channel 20875743
Rattus norvegicus IC50 = 1.6 nM 8.8 The inhibitory concentration was measured on the rat insulinoma cell line RIN-m5... 11356099
Unchecked EC50 = 3.0 nM 8.52 Stimulation of insulin secretion in rat INS-1E cells after 1 hr by alphaLISA ass... 24484900
Unchecked IC50 = 3.804 nM 8.42 DRUGMATRIX: Potassium Channel [KATP] radioligand binding (ligand: [3H] Glyburide... -
Sulfonylurea receptor 1, Kir6.2 IC50 = 4.3 nM 8.37 Inhibition of human SUR1/Kir6.2 expressed in CHO cells 11356099
Unchecked IC50 = 5.7 nM 8.24 Displacement of [3H]Glyburide from ATP-sensitive potassium channel in hamster pa... 23403082
Unchecked EC50 = 7.0 nM 8.15 Stimulation of insulin secretion in rat INS-1E cells after 1 hr by alphaLISA ass... 24484900
Cavia porcellus IC50 = 8.0 nM 8.1 The inhibitory concentration was measured on guinea pig cardiomyocytes 11356099
Unchecked IC50 = 8.08 nM 8.09 PubChem BioAssay. insulin secretion from INS-1E cells in the presence of 5 mM gl... -
Liver IC50 = 14.24 nM 7.85 Induction of mitochondrial dysfunction in Sprague-Dawley rat liver mitochondria ... 24799086
Sulfonylurea receptor 2, Kir6.2 Ki = 130.0 nM 6.89 Binding affinity was determined by displacement of [3H]P1075 from its binding si... 9464357
Sulfonylurea receptor 2, Kir6.2 IC50 = 220.0 nM 6.66 Inhibition of human SUR2A/Kir6.2 expressed in Xenopus oocytes 11356099
Peroxisome proliferator-activated receptor gamma Ki = 660.0 nM 6.18 Binding affinity to PPARgamma (unknown origin) by TR-FRET assay 30672698
T-cell line IC50 = 1000.0 nM 6.0 In vitro inhibition of Rb efflux in human T-cells; 1-10 -
Solute carrier organic anion transporter family member 1B1 IC50 = 1400.0 nM 5.85 Inhibition of OATP1B1 (unknown origin) expressed in HEK293 cells using estradiol... 22587986
Bile salt export pump IC50 = 1500.0 nM 5.82 Inhibition of recombinant human BSEP expressed in baculovirus infected sf9 cell ... 24799086
Solute carrier family 22 member 6 Ki = 1600.0 nM 5.8 TP_TRANSPORTER: inhibition of PAH uptake in Xenopus laevis oocytes 10854830

Literature References

PubMed DOI Target Context # Activities
- 10.6019/CHEMBL3885861 Rattus norvegicus 1440
- 10.6019/CHEMBL3885881 Rattus norvegicus 199
22393122 10.1124/dmd.111.043513 Rattus norvegicus 24
22393122 10.1124/dmd.111.043513 Liver microsome 23
- 10.1039/C3MD00377A Rattus norvegicus 20
23827180 10.1016/j.ejmech.2013.05.014 Rattus norvegicus 18
27397496 10.1016/j.bmcl.2016.06.071 Rattus norvegicus 18
16472241 10.2174/1570163043334794 Hepatotoxicity 18
- 10.1007/s00044-011-9690-5 Rattus norvegicus 15
22194678 10.1371/journal.pcbi.1002310 Hepatotoxicity 14
20346546 10.1016/j.ejmech.2010.02.049 Rattus norvegicus 13
25203779 10.1016/j.ejmech.2014.09.007 Rattus norvegicus 11
37393789 10.1016/j.ejmech.2023.115591 Rattus norvegicus 11
32985885 10.1021/acs.jmedchem.0c01033 ADMET 11
15646539 10.1016/s0399-8320(04)95062-2 Unchecked 11
19140696 10.1021/np800642d Rattus norvegicus 10
22393122 10.1124/dmd.111.043513 ADMET 9
36854648 10.1021/acs.jmedchem.2c01663 CT26 9
20879744 10.1021/np100447a Mus musculus 8
- 10.1007/s00044-012-0237-1 Rattus norvegicus 8

Data from ChEMBL 36 via Core Engine