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Compound Detail

CHEMBL1481

GLIMEPIRIDE
💊 Approved Drug
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💊 Approved Drug
CCC1=C(C)CN(C(=O)NCCc2ccc(S(=O)(=O)NC(=O)N[C@H]3CC[C@H](C)CC3)cc2)C1=O

Basic Information

ChEMBL ID CHEMBL1481
Name GLIMEPIRIDE
Phase Approved
Structure Type MOL
InChI Key WIGIZIANZCJQQY-RUCARUNLSA-N
Therapeutic ✓ Yes

Known Names

Amaryl Glimepirida Glimepiride Glimepiride component of avandaryl Glimepiride component of duetact HOE 490 HOE-490 Niddaryl NSC-759809
6
Targets
11
Activities
3
Assay Types
30
PK Parameters
20
Publications
9
Known Names
7
Indications
1
Mechanisms

Molecular Properties

490.6
MW (Da)
3.07
ALogP
5
HBA
3
HBD
124.7
PSA (Ų)
0.54
QED
0
Ro5 Violations
7
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 1995
Availability Prescription
Chirality Single Enantiomer

Routes of Administration

Oral

Flags

Natural Product
USAN Stem gli-
USAN Year 1992

Extended Properties

Molecular Formula C24H34N4O5S
MW 490.63
Aromatic Rings 1
Heavy Atoms 34
NP-Likeness -0.88

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 Mellitus, Type 2 Atherosclerosis Coronary Disease Hypercholesterolemia Hypertension

ATC Classification

A10BB12
glimepiride
Level 1: ALIMENTARY TRACT AND METABOLISM
Level 2: DRUGS USED IN DIABETES

Activity Summary

IC50 9 meas. best 8.39
EC50 1 meas. best 6.1
Ki 1 meas. best 7.96

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Unchecked
CHEMBL612545
IC50 8.39 7.695 4.1 2
Unchecked
CHEMBL612545
Ki 7.96 7.96 11.0 1
Unchecked
CHEMBL612545
EC50 6.1 6.1 790.0 1
Aldo-keto reductase family 1 member C3
CHEMBL4681
IC50 6.07 6.07 850.0 1
ATP-binding cassette sub-family C member 3
CHEMBL5918
IC50 5.19 5.19 6390.0 1
Aldo-keto reductase family 1 member C1
CHEMBL5905
IC50 5.16 5.16 6860.0 1
Bile salt export pump
CHEMBL6020
IC50 4.8 4.69 15700.0 3
ATP-binding cassette sub-family C member 4
CHEMBL1743128
IC50 4.19 4.19 64000.0 1

Pharmacokinetic Data

Parameter Value Units Species
AUC 338.8 ng.hr.mL-1 Homo sapiens
AUC 315.2 ng.hr.mL-1 Homo sapiens
AUC 1665.69 ng.hr.mL-1 Homo sapiens
CL 0.5 mL.min-1.kg-1 Homo sapiens
CL 0.5 mL.min-1.kg-1 Homo sapiens
CL 0.5 mL.min-1.kg-1 Homo sapiens
CL 0.5 mL.min-1.kg-1 Homo sapiens
CL 23.2 uL.min-1.(10^6cells)-1 Homo sapiens
CL 5.1 mL.min-1.kg-1 Homo sapiens
CL 5.62 uL.min-1.(10^6cells)-1 Homo sapiens
CL 6.17 uL.min-1.(10^6cells)-1 Homo sapiens
CL 0.69 mL.min-1.kg-1 Homo sapiens
CL 47.8 mL/min Homo sapiens
CL/F 52.1 mL/min Homo sapiens
CL/F 48.5 mL/min Homo sapiens
CL/F 52.7 mL/min Homo sapiens
Cmax 209.93 nM Homo sapiens
Cmax 208.71 nM Homo sapiens
Cmax 210.34 nM Homo sapiens
Cmax 717.44 nM Homo sapiens
Cmax 627.76 nM Homo sapiens
Cmax 360.76 nM Homo sapiens
Cmax 1123.05 nM Homo sapiens
Cmax 1204.57 nM Homo sapiens
Cmax 1178.08 nM Homo sapiens
Cmax 629.8 nM Homo sapiens
Cmax 1123.0 nM Homo sapiens
F 100.0 % Homo sapiens
Fu 0.005 - Homo sapiens
Fu 0.005 - Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Unchecked IC50 = 4.06 nM 8.39 PubChem BioAssay. insulin secretion from INS-1E cells in the presence of 5 mM gl... -
Unchecked Ki = 11.0 nM 7.96 DRUGMATRIX: Potassium Channel [KATP] radioligand binding (ligand: [3H] Glyburide... -
Unchecked IC50 = 100.0 nM 7.0 DRUGMATRIX: Potassium Channel [KATP] radioligand binding (ligand: [3H] Glyburide... -
Unchecked EC50 = 790.0 nM 6.1 Agonist activity at SUR in Wistar rat pancreatic islets assessed as increase in ... 28720328
Aldo-keto reductase family 1 member C3 IC50 = 850.0 nM 6.07 Inhibition of N-terminal His-tagged human AKR1C3 expressed in Escherichia coli B... 32463235
ATP-binding cassette sub-family C member 3 IC50 = 6390.0 nM 5.19 Inhibition of human MRP3 overexpressed in Sf9 insect cell membrane vesicles asse... 23956101
Aldo-keto reductase family 1 member C1 IC50 = 6860.0 nM 5.16 Inhibition of N-terminal His-tagged human AKR1C1 expressed in Escherichia coli B... 32463235
Bile salt export pump IC50 = 15700.0 nM 4.8 Inhibition of human BSEP expressed in fall armyworm sf9 cell plasma membrane ves... 20829430
Bile salt export pump IC50 = 15700.0 nM 4.8 Inhibition of human BSEP overexpressed in Sf9 cell membrane vesicles assessed as... 23956101
Bile salt export pump IC50 = 34000.0 nM 4.47 Inhibition of recombinant human BSEP expressed in baculovirus infected sf9 cell ... 24799086
ATP-binding cassette sub-family C member 4 IC50 = 64000.0 nM 4.19 Inhibition of human MRP4 overexpressed in Sf9 cell membrane vesicles assessed as... 23956101

Literature References

Data from ChEMBL 36 via Core Engine