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Compound Detail

CHEMBL878

METOLAZONE
💊 Approved Drug
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💊 Approved Drug
Cc1ccccc1N1C(=O)c2cc(S(N)(=O)=O)c(Cl)cc2NC1C

Basic Information

ChEMBL ID CHEMBL878
Name METOLAZONE
Phase Approved
Structure Type MOL
InChI Key AQCHWTWZEMGIFD-UHFFFAOYSA-N
Therapeutic ✓ Yes

Known Names

Diulo Metazoline Metenix Metolazona Metolazone Metozalone Mykrox Normelan NSC-759581 Oldren SR 720-22 SR-720-22 +2 more
3
Targets
5
Activities
3
Assay Types
9
PK Parameters
20
Publications
14
Known Names
6
Indications
1
Mechanisms

Molecular Properties

365.8
MW (Da)
2.71
ALogP
4
HBA
2
HBD
92.5
PSA (Ų)
0.86
QED
0
Ro5 Violations
2
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 1973
Availability Prescription
Chirality Racemic

Routes of Administration

Oral

Flags

Black Box Warning Natural Product
USAN Year 1968

Extended Properties

Molecular Formula C16H16ClN3O3S
MW 365.84
Aromatic Rings 2
Heavy Atoms 24
NP-Likeness -1.18

Mechanism of Action

Mechanism Action Type Target Direct Efficacy
Thiazide-sensitive sodium-chloride cotransporter inhibitor INHIBITOR Solute carrier family 12 member 3

Indications

Cardiovascular Diseases Heart Failure Heart Failure Hypertension Toxemia Renal Insufficiency, Chronic

ATC Classification

C03BA08
metolazone
Level 1: CARDIOVASCULAR SYSTEM
Level 2: DIURETICS

Drug Warnings

Black Box Warning
General Warning
Country: United States

Activity Summary

Ki 3 meas. best 8.68
IC50 1 meas. best 4.9
Kd 1 meas. best 5.55

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Carbonic anhydrase 7
CHEMBL2326
Ki 8.68 8.68 2.1 1
Carbonic anhydrase 2
CHEMBL205
Ki 5.7 5.7 2000.0 1
Carbonic anhydrase 2
CHEMBL205
Kd 5.55 5.55 2800.0 1
Plasmodium falciparum
CHEMBL364
IC50 4.9 4.9 12589.2 1

Pharmacokinetic Data

Parameter Value Units Species
CL 1.4 mL.min-1.kg-1 Homo sapiens
CL 1.4 mL.min-1.kg-1 Homo sapiens
CL 0.3 mL.min-1.kg-1 Homo sapiens
CL 1.4 mL.min-1.kg-1 Homo sapiens
F 64.0 % Homo sapiens
Fu 0.05 - Homo sapiens
Fu 0.05 - Homo sapiens
MRT 19.0 hr Homo sapiens
T1/2 20.0 hr Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Literature References

PubMed DOI Target Context # Activities
- 10.5281/zenodo.13943903 ADMET 89
31158845 10.1038/s41586-019-1291-3 ADMET 51
21051535 10.1124/dmd.110.034629 ADMET 21
22194678 10.1371/journal.pcbi.1002310 Hepatotoxicity 14
15646539 10.1016/s0399-8320(04)95062-2 Unchecked 11
15646539 10.1016/s0399-8320(04)95062-2 NON-PROTEIN TARGET 8
20070106 10.1021/jm901371v Homo sapiens 8
15658873 10.1021/jm049711o ADMET 5
18426954 10.1124/dmd.108.020479 ADMET 4
39161321 10.1021/acs.jmedchem.4c01512 Carbonic anhydrase 3 3
39161321 10.1021/acs.jmedchem.4c01512 Carbonic anhydrase 2 3
11384238 10.1021/jm001101a Homo sapiens 3
37468498 10.1038/s41467-023-40064-9 Mu-type opioid receptor 2
26948801 10.1016/j.drudis.2016.02.015 Homo sapiens 2
37468498 10.1038/s41467-023-40064-9 Gamma-aminobutyric acid receptor subunit alpha-1 2
37468498 10.1038/s41467-023-40064-9 Alpha-2A adrenergic receptor 2
- 10.6019/CHEMBL4808148 Histone deacetylase 6 2
37468498 10.1038/s41467-023-40064-9 5-hydroxytryptamine receptor 1A 2
11300874 10.1021/jm001020e ADMET 2
37468498 10.1038/s41467-023-40064-9 Progesterone receptor 2

Data from ChEMBL 36 via Core Engine