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Compound Detail

CHEMBL406

INDAPAMIDE
💊 Approved Drug
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💊 Approved Drug
CC1Cc2ccccc2N1NC(=O)c1ccc(Cl)c(S(N)(=O)=O)c1

Basic Information

ChEMBL ID CHEMBL406
Name INDAPAMIDE
Phase Approved
Structure Type MOL
InChI Key NDDAHWYSQHTHNT-UHFFFAOYSA-N
Therapeutic ✓ Yes

Known Names

Arifon Bajaten Cardide sr Damide Ethibide xl Flubest Fludex Fludin Flupamid Indaflex Indamide Indamol +18 more
14
Targets
55
Activities
3
Assay Types
2
PK Parameters
20
Publications
30
Known Names
7
Indications
1
Mechanisms

Molecular Properties

365.8
MW (Da)
2.08
ALogP
4
HBA
2
HBD
92.5
PSA (Ų)
0.87
QED
0
Ro5 Violations
3
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 1983
Availability Prescription
Chirality Racemic

Routes of Administration

Oral

Flags

Natural Product
USAN Stem -pamide
USAN Year 1979

Extended Properties

Molecular Formula C16H16ClN3O3S
MW 365.84
Aromatic Rings 2
Heavy Atoms 24
NP-Likeness -1.65

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 Hypertension Toxemia Diabetes Mellitus, Type 2 Essential Hypertension Multiple Sclerosis, Chronic Progressive

ATC Classification

C03BA11
indapamide
Level 1: CARDIOVASCULAR SYSTEM
Level 2: DIURETICS

Activity Summary

Kd 40 meas. best 9.48
Ki 13 meas. best 9.64
IC50 2 meas. best 5.54

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Carbonic anhydrase 7
CHEMBL2326
Ki 9.64 9.64 0.2 2
Carbonic anhydrase 4
CHEMBL3729
Kd 9.48 8.295 0.3 2
Carbonic anhydrase 14
CHEMBL3510
Kd 9.42 8.31 0.4 2
Carbonic anhydrase 5B, mitochondrial
CHEMBL3969
Kd 9.34 8.285 0.5 2
Carbonic anhydrase 6
CHEMBL3025
Kd 9.0 7.25 1.0 3
Carbonic anhydrase 7
CHEMBL2326
Kd 8.84 6.846 1.5 5
Carbonic anhydrase 9
CHEMBL3594
Kd 8.69 7.53 2.0 2
Carbonic anhydrase 2
CHEMBL205
Kd 8.42 6.74 3.8 7
Carbonic anhydrase 13
CHEMBL3912
Kd 8.39 7.126 4.1 5
Carbonic anhydrase 5A, mitochondrial
CHEMBL4789
Kd 8.16 7.165 7.0 2
Carbonic anhydrase 12
CHEMBL3242
Ki 8.0 8.0 10.0 1
Carbonic anhydrase 12
CHEMBL3242
Kd 7.91 6.4867 12.2 3
Carbonic anhydrase 13
CHEMBL2186
Ki 7.89 7.89 13.0 1
Carbonic anhydrase 9
CHEMBL3594
Ki 7.44 7.44 36.0 1
Carbonic anhydrase 3
CHEMBL2885
Kd 6.98 5.4967 105.0 3
Carbonic anhydrase 4
CHEMBL3729
Ki 6.67 6.67 213.0 1
Carbonic anhydrase 1
CHEMBL261
Kd 6.58 5.3325 261.0 4
Carbonic anhydrase 5B, mitochondrial
CHEMBL3969
Ki 6.56 6.56 274.0 1
Carbonic anhydrase 5A, mitochondrial
CHEMBL4789
Ki 6.05 6.05 890.0 1
Carbonic anhydrase 6
CHEMBL3025
Ki 5.79 5.79 1606.0 1
Carbonic anhydrase 2
CHEMBL205
Ki 5.6 5.6 2520.0 1
Polyunsaturated fatty acid lipoxygenase ALOX15
CHEMBL4358
IC50 5.54 5.54 2918.0 1
Carbonic anhydrase 14
CHEMBL3510
Ki 5.3 5.3 4950.0 1
Carbonic anhydrase 1
CHEMBL261
Ki 4.29 4.29 51900.0 1

Pharmacokinetic Data

Parameter Value Units Species
CL 4.9 uL.min-1.(10^6cells)-1 Homo sapiens
CL 13.18 uL.min-1.(10^6cells)-1 Rattus norvegicus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Carbonic anhydrase 7 Ki = 0.23 nM 9.64 Inhibition of human recombinant full length CA7 by stopped-flow CO2 hydration me... 19119014
Carbonic anhydrase 7 Ki = 0.23 nM 9.64 Inhibition of human recombinant carbonic anhydrase 7 preincubated for 15 mins by... 24287559
Carbonic anhydrase 4 Kd = 0.33 nM 9.48 Binding affinity to recombinant human N-terminal His6-tagged carbonic anhydrase ... 29305297
Carbonic anhydrase 14 Kd = 0.38 nM 9.42 Binding affinity to recombinant human N-terminal His6-tagged carbonic anhydrase ... 29305297
Carbonic anhydrase 5B, mitochondrial Kd = 0.46 nM 9.34 Binding affinity to recombinant human full length N-terminal His6-tagged mitocho... 29305297
Carbonic anhydrase 6 Kd = 1.01 nM 9.0 Binding affinity to recombinant human N-terminal His6-tagged carbonic anhydrase ... 29305297
Carbonic anhydrase 7 Kd = 1.46 nM 8.84 Binding affinity to recombinant human N-terminal His-tagged carbonic anhydrase 7... 29305297
Carbonic anhydrase 9 Kd = 2.03 nM 8.69 Binding affinity to recombinant human carbonic anhydrase 9 (1 to 260 residues) e... 29305297
Carbonic anhydrase 2 Kd = 3.77 nM 8.42 Binding affinity to recombinant human full length N-terminal His-tagged carbonic... 29305297
Carbonic anhydrase 13 Kd = 4.11 nM 8.39 Binding affinity to recombinant human full length N-terminal His-tagged carbonic... 29305297
Carbonic anhydrase 5A, mitochondrial Kd = 6.96 nM 8.16 Binding affinity to recombinant human full length N-terminal His6-tagged mitocho... 29305297
Carbonic anhydrase 12 Ki = 10.0 nM 8.0 Inhibition of human recombinant CA12 catalytic domain by stopped-flow CO2 hydrat... 19119014
Carbonic anhydrase 12 Kd = 12.2 nM 7.91 Binding affinity to recombinant human carbonic anhydrase 12 (1 to 260 residues) ... 29305297
Carbonic anhydrase 13 Ki = 13.0 nM 7.89 Inhibition of mouse recombinant full length CA13 by stopped-flow CO2 hydration m... 19119014
Carbonic anhydrase 9 Ki = 36.0 nM 7.44 Inhibition of human recombinant CA9 catalytic domain by stopped-flow CO2 hydrati... 19119014
Carbonic anhydrase 5B, mitochondrial Kd = 59.0 nM 7.23 Binding affinity to recombinant human full length N-terminal His6-tagged mitocho... 29305297
Carbonic anhydrase 14 Kd = 63.0 nM 7.2 Binding affinity to recombinant human N-terminal His6-tagged carbonic anhydrase ... 29305297
Carbonic anhydrase 4 Kd = 77.0 nM 7.11 Binding affinity to recombinant human N-terminal His6-tagged carbonic anhydrase ... 29305297
Carbonic anhydrase 13 Kd = 100.0 nM 7.0 Binding affinity to human recombinant carbonic anhydrase 13 by thermal shift ass... 20926301
Carbonic anhydrase 13 Kd = 100.0 nM 7.0 Binding affinity to human recombinant carbonic anhydrase 13 by thermal shift ass... 24103428

Literature References

PubMed DOI Target Context # Activities
- 10.5281/zenodo.13943903 ADMET 89
31158845 10.1038/s41586-019-1291-3 ADMET 60
16472241 10.2174/1570163043334794 Hepatotoxicity 18
22194678 10.1371/journal.pcbi.1002310 Hepatotoxicity 14
15646539 10.1016/s0399-8320(04)95062-2 Unchecked 11
7328592 10.1021/jm00140a018 Rattus norvegicus 9
15646539 10.1016/s0399-8320(04)95062-2 NON-PROTEIN TARGET 8
39161321 10.1021/acs.jmedchem.4c01512 Carbonic anhydrase 2 4
7328592 10.1021/jm00140a018 NON-PROTEIN TARGET 3
37468498 10.1038/s41467-023-40064-9 Cannabinoid receptor 1 3
37468498 10.1038/s41467-023-40064-9 5-hydroxytryptamine receptor 2A 3
- 10.6019/CHEMBL3301361 ADMET 3
37468498 10.1038/s41467-023-40064-9 Alpha-1A adrenergic receptor 3
20014752 10.1021/tx900326k Hepatotoxicity 3
37468498 10.1038/s41467-023-40064-9 Alpha-2A adrenergic receptor 3
29305297 10.1016/j.bmc.2017.12.035 Carbonic anhydrase 6 2
29305297 10.1016/j.bmc.2017.12.035 Carbonic anhydrase 12 2
29305297 10.1016/j.bmc.2017.12.035 Carbonic anhydrase 9 2
29305297 10.1016/j.bmc.2017.12.035 Carbonic anhydrase 13 2
29305297 10.1016/j.bmc.2017.12.035 Carbonic anhydrase 7 2

Data from ChEMBL 36 via Core Engine