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Compound Detail

CHEMBL1072

BUMETANIDE
💊 Approved Drug
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💊 Approved Drug
CCCCNc1cc(C(=O)O)cc(S(N)(=O)=O)c1Oc1ccccc1

Basic Information

ChEMBL ID CHEMBL1072
Name BUMETANIDE
Phase Approved
Structure Type MOL
InChI Key MAEIEVLCKWDQJH-UHFFFAOYSA-N
Therapeutic ✓ Yes

Known Names

Betinex Bumetanida Bumetanide Bumex Burinex Lixil PF-1593 PF1593 RO 10-6338 RO-10-6338 RO-106338 RO10-6338 +2 more
4
Targets
6
Activities
2
Assay Types
13
PK Parameters
20
Publications
14
Known Names
14
Indications
1
Mechanisms

Molecular Properties

364.4
MW (Da)
3.04
ALogP
5
HBA
3
HBD
118.7
PSA (Ų)
0.62
QED
0
Ro5 Violations
8
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 1983
Availability Prescription
Chirality Achiral

Routes of Administration

Oral Parenteral

Flags

Black Box Warning Natural Product
USAN Stem -etanide
USAN Year 1976

Extended Properties

Molecular Formula C17H20N2O5S
MW 364.42
Aromatic Rings 2
Heavy Atoms 25
NP-Likeness -0.97

Mechanism of Action

Mechanism Action Type Target Direct Efficacy
Sodium-(potassium)-chloride cotransporter 2 inhibitor INHIBITOR Solute carrier family 12 member 1

Indications

Cardiovascular Diseases Heart Failure Heart Failure Kidney Diseases Nephrotic Syndrome Autistic Disorder Child Development Disorders, Pervasive Alzheimer Disease Down Syndrome Hypokalemic Periodic Paralysis Renal Insufficiency, Chronic Carcinoma, Hepatocellular Diabetes Mellitus, Type 2 Seizures

ATC Classification

C03CA02
bumetanide
Level 1: CARDIOVASCULAR SYSTEM
Level 2: DIURETICS

Drug Warnings

Black Box Warning
nephrotoxicity
Country: United States
Black Box Warning
General Warning
Country: United States

Activity Summary

IC50 3 meas. best 5.81
Ki 3 meas. best 5.26

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Solute carrier family 12 member 2
CHEMBL1615383
IC50 5.81 5.81 1540.0 1
Solute carrier family 22 member 6
CHEMBL1777665
Ki 5.26 5.26 5500.0 1
Carbonic anhydrase 2
CHEMBL205
Ki 5.16 5.16 6980.0 1
Aquaporin-4
CHEMBL5291512
IC50 4.0 4.0 100000.0 1

Pharmacokinetic Data

Parameter Value Units Species
CL 2.5 mL.min-1.kg-1 Homo sapiens
CL 2.5 mL.min-1.kg-1 Homo sapiens
CL 1.0 mL.min-1.kg-1 Homo sapiens
CL 2.5 mL.min-1.kg-1 Homo sapiens
CL 4.0 mL.min-1.g-1 Homo sapiens
CL 144.54 uL.min-1.(10^6cells)-1 Rattus norvegicus
F 80.0 % Homo sapiens
F 81.0 % Homo sapiens
Fu 0.031 - Homo sapiens
Fu 0.031 - Homo sapiens
MRT 1.1 hr Homo sapiens
T1/2 1.2 hr Homo sapiens
T1/2 1.0 hr Mus musculus

Activity Data Samples

Top measurements by pChEMBL value

Literature References

PubMed DOI Target Context # Activities
16472241 10.2174/1570163043334794 Hepatotoxicity 18
1255664 10.1021/jm00225a013 Canis familiaris 16
22194678 10.1371/journal.pcbi.1002310 Hepatotoxicity 14
592337 10.1021/jm00222a033 Canis familiaris 12
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
- 10.6019/CHEMBL3301361 No relevant target 5
- 10.6019/CHEMBL3301361 ADMET 4
37468498 10.1038/s41467-023-40064-9 Cannabinoid receptor 1 4
18426954 10.1124/dmd.108.020479 ADMET 4
37468498 10.1038/s41467-023-40064-9 Alpha-1A adrenergic receptor 4
691010 10.1021/jm00206a027 Rattus norvegicus 3
37468498 10.1038/s41467-023-40064-9 Alpha-2A adrenergic receptor 3
37468498 10.1038/s41467-023-40064-9 Histamine H1 receptor 3
37468498 10.1038/s41467-023-40064-9 Muscarinic acetylcholine receptor M2 3
37468498 10.1038/s41467-023-40064-9 5-hydroxytryptamine receptor 1A 3
37468498 10.1038/s41467-023-40064-9 5-hydroxytryptamine receptor 2A 3
20014752 10.1021/tx900326k Hepatotoxicity 3
37468498 10.1038/s41467-023-40064-9 5-hydroxytryptamine receptor 2B 3

Data from ChEMBL 36 via Core Engine