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Compound Detail

CHEMBL1055

CHLORTHALIDONE
💊 Approved Drug
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💊 Approved Drug
NS(=O)(=O)c1cc(C2(O)NC(=O)c3ccccc32)ccc1Cl
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL1055
Name CHLORTHALIDONE
Phase Approved
Structure Type MOL
InChI Key JIVPVXMEBJLZRO-UHFFFAOYSA-N
Therapeutic ✓ Yes

Known Names

Chlortalidone Chlortalidonum Chlorthalidone Chlorthalidone component of clorpres Chlorthalidone component of combipres Chlorthalidone component of demi-regroton Chlorthalidone component of edarbyclor Chlorthalidone component of kerledex Chlorthalidone component of lopressidone Chlorthalidone component of regroton Chlorthalidone component of tenoretic Clortalidona +6 more
12
Targets
14
Activities
2
Assay Types
17
PK Parameters
20
Publications
18
Known Names
20
Indications
1
Mechanisms

Molecular Properties

338.8
MW (Da)
0.92
ALogP
4
HBA
3
HBD
109.5
PSA (Ų)
0.76
QED
0
Ro5 Violations
2
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 1960
Availability Prescription
Chirality Racemic

Routes of Administration

Oral

Flags

Natural Product
USAN Year 1961

Extended Properties

Molecular Formula C14H11ClN2O4S
MW 338.77
Aromatic Rings 2
Heavy Atoms 22
NP-Likeness -0.64

Mechanism of Action

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

Indications

Angina Pectoris Cardiovascular Diseases Glomerulonephritis Heart Failure Heart Failure Hypertension Kidney Failure, Chronic Nephrotic Syndrome Toxemia Atherosclerosis Cerebrovascular Disorders Coronary Disease Death, Sudden, Cardiac Diabetes Mellitus Diabetes Mellitus, Type 2 Essential Hypertension Heart Diseases Hypercholesterolemia Myocardial Infarction Myocardial Ischemia

ATC Classification

C03BA04
chlortalidone
Level 1: CARDIOVASCULAR SYSTEM
Level 2: DIURETICS

Activity Summary

Ki 12 meas. best 8.55
IC50 2 meas. best 6.58

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Carbonic anhydrase 7
CHEMBL2326
 Ki 8.55 8.55 2.8 1
Carbonic anhydrase 12
CHEMBL3242
 Ki 8.35 8.35 4.5 1
Carbonic anhydrase 5B, mitochondrial
CHEMBL3969
 Ki 8.05 8.05 9.0 1
Carbonic anhydrase 13
CHEMBL2186
 Ki 7.82 7.82 15.0 1
Carbonic anhydrase 9
CHEMBL3594
 Ki 7.64 7.64 23.0 1
Carbonic anhydrase 2
CHEMBL205
 Ki 6.86 6.86 138.0 1
Carbonic anhydrase 4
CHEMBL3729
 Ki 6.71 6.71 196.0 1
Carbonic anhydrase 1
CHEMBL261
 IC50 6.58 6.58 260.0 1
Carbonic anhydrase 1
CHEMBL261
 Ki 6.46 6.46 348.0 1
Carbonic anhydrase 2
CHEMBL205
 IC50 6.17 6.17 677.0 1
Carbonic anhydrase 5A, mitochondrial
CHEMBL4789
 Ki 6.04 6.04 917.0 1
Carbonic anhydrase 6
CHEMBL3025
 Ki 5.87 5.87 1347.0 1
Carbonic anhydrase 14
CHEMBL3510
 Ki 5.38 5.38 4130.0 1
Carbonic anhydrase 3
CHEMBL2885
 Ki 4.96 4.96 11000.0 1

Pharmacokinetic Data

Parameter Value Units Species
CL 1.5 mL.min-1.kg-1 Homo sapiens
CL 1.5 mL.min-1.kg-1 Homo sapiens
CL 0.5 mL.min-1.kg-1 Homo sapiens
CL 1.5 mL.min-1.kg-1 Homo sapiens
CL 0.04 mL.min-1.kg-1 Homo sapiens
Cmax 10921.86 nM Homo sapiens
Excretion 65.0 % Homo sapiens
Excretion 65.0 % Homo sapiens
F 79.0 % Homo sapiens
F 64.0 % Homo sapiens
Fu 0.24 - Homo sapiens
Fu 0.24 - Homo sapiens
MRT 43.0 hr Homo sapiens
T1/2 36.0 hr Homo sapiens
T1/2 47.0 hr Homo sapiens
Tmax 13.8 hr Homo sapiens
Vd 0.14 L.kg-1 Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Carbonic anhydrase 7 Ki = 2.8 nM 8.55 Inhibition of human recombinant full length CA7 by stopped-flow CO2 hydration me... 19119014
Carbonic anhydrase 12 Ki = 4.5 nM 8.35 Inhibition of human recombinant CA12 catalytic domain by stopped-flow CO2 hydrat... 19119014
Carbonic anhydrase 5B, mitochondrial Ki = 9.0 nM 8.05 Inhibition of human recombinant full length CA5B by stopped-flow CO2 hydration m... 19119014
Carbonic anhydrase 13 Ki = 15.0 nM 7.82 Inhibition of mouse recombinant full length CA13 by stopped-flow CO2 hydration m... 19119014
Carbonic anhydrase 9 Ki = 23.0 nM 7.64 Inhibition of human recombinant CA9 catalytic domain by stopped-flow CO2 hydrati... 19119014
Carbonic anhydrase 2 Ki = 138.0 nM 6.86 Inhibition of human recombinant full length CA2 by stopped-flow CO2 hydration me... 19119014
Carbonic anhydrase 4 Ki = 196.0 nM 6.71 Inhibition of human recombinant full length CA4 by stopped-flow CO2 hydration me... 19119014
Carbonic anhydrase 1 IC50 = 260.0 nM 6.58 Known Inhibitors of Carbonic Anhydrase: Compounds which are CAIs are well known ... -
Carbonic anhydrase 1 Ki = 348.0 nM 6.46 Inhibition of human recombinant full length CA1 by stopped-flow CO2 hydration me... 19119014
Carbonic anhydrase 2 IC50 = 677.0 nM 6.17 DRUGMATRIX: Carbonic Anhydrase II enzyme inhibition (substrate: 4-Nitrophenyl ac... -
Carbonic anhydrase 5A, mitochondrial Ki = 917.0 nM 6.04 Inhibition of human recombinant full length CA5A by stopped-flow CO2 hydration m... 19119014
Carbonic anhydrase 6 Ki = 1347.0 nM 5.87 Inhibition of human recombinant full length CA6 by stopped-flow CO2 hydration me... 19119014
Carbonic anhydrase 14 Ki = 4130.0 nM 5.38 Inhibition of human recombinant full length CA14 by stopped-flow CO2 hydration m... 19119014
Carbonic anhydrase 3 Ki = 11000.0 nM 4.96 Inhibition of human recombinant full length CA3 by stopped-flow CO2 hydration me... 19119014

Literature References

PubMed DOI Target Context # Activities
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
18426954 10.1124/dmd.108.020479 ADMET 4
- 10.6019/CHEMBL3301361 No relevant target 3
37468498 10.1038/s41467-023-40064-9 5-hydroxytryptamine receptor 1A 2
19445515 10.1021/jm900403j Homo sapiens 2
18666772 10.1021/jm8005228 No relevant target 2
- 10.6019/CHEMBL4651402 SARS-CoV-2 2
- 10.6019/CHEMBL4808148 Histone deacetylase 6 2
37468498 10.1038/s41467-023-40064-9 Muscarinic acetylcholine receptor M2 2
37468498 10.1038/s41467-023-40064-9 Progesterone receptor 2
37468498 10.1038/s41467-023-40064-9 Gamma-aminobutyric acid receptor subunit alpha-1 2
37468498 10.1038/s41467-023-40064-9 Mu-type opioid receptor 2
10891117 10.1021/jm0000564 ADMET 2
10891117 10.1021/jm0000564 No relevant target 2
37468498 10.1038/s41467-023-40064-9 Alpha-2A adrenergic receptor 2
26948801 10.1016/j.drudis.2016.02.015 Homo sapiens 2
37468498 10.1038/s41467-023-40064-9 5-hydroxytryptamine receptor 2A 2

Data from ChEMBL 36 via Core Engine