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Compound Detail

CHEMBL782

TOLBUTAMIDE
💊 Approved Drug
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💊 Approved Drug
CCCCNC(=O)NS(=O)(=O)c1ccc(C)cc1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL782
Name TOLBUTAMIDE
Phase Approved
Structure Type MOL
InChI Key JLRGJRBPOGGCBT-UHFFFAOYSA-N
Therapeutic ✓ Yes

Known Names

1-butyl-3-(p-tolylsulfonyl)urea Arkozal Butamide Diabetamid Glyconon Ipoglicone NSC-23813 NSC-87833 Orinase Pramidex Rastinon Tolbutamida +3 more
5
Targets
13
Activities
4
Assay Types
26
PK Parameters
20
Publications
15
Known Names
8
Indications
1
Mechanisms

Molecular Properties

270.4
MW (Da)
1.78
ALogP
3
HBA
2
HBD
75.3
PSA (Ų)
0.80
QED
0
Ro5 Violations
5
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 1961
Availability Discontinued
Chirality Achiral

Routes of Administration

Oral Parenteral

Flags

Natural Product

Extended Properties

Molecular Formula C12H18N2O3S
MW 270.35
Aromatic Rings 1
Heavy Atoms 18
NP-Likeness -1.38

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 Chronic Pain Endotoxemia Hepatitis C, Chronic Lymphoma Neoplasms Neoplasms

ATC Classification

A10BB03
tolbutamide
Level 1: ALIMENTARY TRACT AND METABOLISM
Level 2: DRUGS USED IN DIABETES
V04CA01
tolbutamide
Level 1: VARIOUS
Level 2: DIAGNOSTIC AGENTS

Activity Summary

IC50 5 meas. best 6.42
Ki 4 meas. best 4.26
Kd 3 meas. best 5.22
EC50 1 meas. best 5.8

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Cytochrome P450 2C9
CHEMBL3397
 IC50 6.42 6.144 380.0 5
Aorta
CHEMBL613606
 EC50 5.8 5.8 1600.0 1
Albumin
CHEMBL3253
 Kd 5.22 5.22 6025.6 1
Albumin
CHEMBL4817
 Kd 5.1 5.1 7970.0 1
Solute carrier family 22 member 6
CHEMBL1777665
 Ki 4.26 4.26 55500.0 2
Cytochrome P450 2C9
CHEMBL3397
 Ki 4.16 4.16 70000.0 1

Pharmacokinetic Data

Parameter Value Units Species
AUC 285.2 mg/dl Mus musculus
AUC 289.1 mg/dl Mus musculus
AUC 229.3 mg/dl Mus musculus
AUC 170.7 mg/dl Mus musculus
AUC 150.5 mg/dl Mus musculus
CL 0.3 mL.min-1.kg-1 Homo sapiens
CL 0.21 mL.min-1.kg-1 Homo sapiens
CL 0.2 mL.min-1.kg-1 Homo sapiens
CL 0.21 mL.min-1.kg-1 Homo sapiens
CL 0.21 mL.min-1.kg-1 Homo sapiens
CL 6.31 uL.min-1.(10^6cells)-1 Homo sapiens
CL 6.31 mL.min-1.g-1 Homo sapiens
CL 6.61 uL.min-1.(10^6cells)-1 Rattus norvegicus
CL 0.38 mL.min-1.kg-1 Homo sapiens
CL 4.68 uL.min-1.(10^6cells)-1 Homo sapiens
CL 0.207 uL.min-1.(10^6cells)-1 Homo sapiens
CL 0.06 mL.min-1.kg-1 Homo sapiens
F 80.0 % Homo sapiens
F 85.0 % Homo sapiens
Fu 0.05 - Homo sapiens
Fu 0.05 - Homo sapiens
Fu 0.8434 - Rattus norvegicus
Fu 0.16 - Not specified
Fu 0.985 - Homo sapiens
MRT 9.5 hr Homo sapiens
T1/2 7.0 hr Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Cytochrome P450 2C9 IC50 = 380.0 nM 6.42 Inhibition of CYP2C9 in human liver microsomes incubated for 15 to 40 mins in pr... 35679690
Cytochrome P450 2C9 IC50 = 380.0 nM 6.42 Inhibition of CYP2C9 in human liver microsomes using tolbutamide as substrate me... 36577220
Cytochrome P450 2C9 IC50 = 404.0 nM 6.39 Inhibition of CYP2C9 (unknown origin) 35797898
Cytochrome P450 2C9 IC50 = 421.0 nM 6.38 Inhibition of CYP2C9 (unknown origin) 36442370
Aorta EC50 = 1600.0 nM 5.8 Vasodilatory activity in Wistar rat thoracic aorta assessed as relaxation of L-p... 22565215
Albumin Kd = 6025.6 nM 5.22 Binding affinity to human serum albumin by PAMPA method 18348514
Cytochrome P450 2C9 IC50 = 7690.0 nM 5.11 Inhibition of CYP2C9 (unknown origin) 38996652
Albumin Kd = 7970.0 nM 5.1 Binding affinity to Wistar rat serum albumin 21071520
Solute carrier family 22 member 6 Ki = 55500.0 nM 4.26 Inhibition of rat Oat1 expressed in Xenopus oocytes 21571536
Solute carrier family 22 member 6 Ki = 55500.0 nM 4.26 TP_TRANSPORTER: inhibition of PAH uptake in Xenopus laevis oocytes 10854830
Cytochrome P450 2C9 Ki = 70000.0 nM 4.16 Binding affinity measured on human cytochrome P450 2C9 (CYP2C9) enzyme 10956186

Literature References

PubMed DOI Target Context # Activities
- 10.6019/CHEMBL3885861 Rattus norvegicus 1380
22194678 10.1371/journal.pcbi.1002310 Hepatotoxicity 14
15646539 10.1016/s0399-8320(04)95062-2 Unchecked 11
20070106 10.1021/jm901371v Homo sapiens 8
15646539 10.1016/s0399-8320(04)95062-2 NON-PROTEIN TARGET 8
6512531 10.1021/np50035a003 Oryctolagus cuniculus 7
22565215 10.1016/j.bmcl.2012.03.103 Unchecked 7
30818176 10.1016/j.ejmech.2019.02.036 Mus musculus 6
30818176 10.1016/j.ejmech.2019.02.036 MIN6 6
17249729 10.1021/np0680580 Rattus norvegicus 6
17723306 10.1016/j.bmc.2007.08.005 Unchecked 6
- 10.6019/CHEMBL3301361 ADMET 5
6345781 10.1021/jm00361a007 Rattus norvegicus 5
20869876 10.1016/j.bmc.2010.08.052 Albumin 4
1255659 10.1021/jm00225a004 Rattus norvegicus 4
17583514 10.1016/j.bmc.2007.05.075 Unchecked 4
15165145 10.1021/np030513u Rattus norvegicus 4
18426954 10.1124/dmd.108.020479 ADMET 4
9214731 10.1021/np9605403 Mus musculus 4
6345781 10.1021/jm00361a007 Oryctolagus cuniculus 4

Data from ChEMBL 36 via Core Engine