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Compound Detail

CHEMBL435

HYDROCHLOROTHIAZIDE
💊 Approved Drug
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💊 Approved Drug
NS(=O)(=O)c1cc2c(cc1Cl)NCNS2(=O)=O
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL435
Name HYDROCHLOROTHIAZIDE
Phase Approved
Structure Type MOL
InChI Key JZUFKLXOESDKRF-UHFFFAOYSA-N
Therapeutic ✓ Yes

Known Names

Apo-hydro Apresazide Carozide Chlorosulthiadil Copalia-hct Dafiro-hct Dihydrochlorurite Esidrex Esidrix Exforge-hct Hidroclorotiazida Hidrotiazida +18 more
8
Targets
88
Activities
3
Assay Types
7
PK Parameters
20
Publications
30
Known Names
20
Indications
1
Mechanisms

Molecular Properties

297.8
MW (Da)
-0.35
ALogP
5
HBA
3
HBD
118.4
PSA (Ų)
0.65
QED
0
Ro5 Violations
1
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 1959
Availability Prescription
Chirality Achiral

Routes of Administration

Oral

Flags

Natural Product
USAN Stem -thiazide

Extended Properties

Molecular Formula C7H8ClN3O4S2
MW 297.75
Aromatic Rings 1
Heavy Atoms 17
NP-Likeness -1.23

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 Edema Glomerulonephritis Heart Failure Heart Failure Hypertension Kidney Failure, Chronic Liver Cirrhosis Myocardial Infarction Nephrotic Syndrome Toxemia Atherosclerosis Coronary Disease Death, Sudden, Cardiac Diabetes Mellitus, Type 2 Essential Hypertension Hypercholesterolemia Kidney Calculi Polycystic Kidney, Autosomal Dominant

ATC Classification

C03AA03
hydrochlorothiazide
Level 1: CARDIOVASCULAR SYSTEM
Level 2: DIURETICS
C03AX01
hydrochlorothiazide, combinations
Level 1: CARDIOVASCULAR SYSTEM
Level 2: DIURETICS

Activity Summary

Ki 84 meas. best 8.14
Kd 3 meas. best 5.58
IC50 1 meas.

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Carbonate dehydratase
CHEMBL3745586
 Ki 8.14 8.14 7.2 1
Unchecked
CHEMBL612545
 Ki 8.14 6.3933 7.2 36
AGAP002992-PA
CHEMBL3399914
 Ki 7.5 7.5 31.5 1
Carbonic anhydrase 2
CHEMBL205
 Ki 6.54 6.54 290.0 22
Carbonic anhydrase, alpha family
CHEMBL3621035
 Ki 6.53 6.53 296.0 1
Carbonic anhydrase 1
CHEMBL261
 Ki 6.48 6.48 328.0 18
Astrosclerin-3
CHEMBL1944499
 Ki 6.41 6.41 394.0 1
Carbonic anhydrase 2
CHEMBL205
 Kd 5.58 5.36 2600.0 2
Delta carbonic anhydrase
CHEMBL3097982
 Ki 5.37 5.37 4270.0 1

Pharmacokinetic Data

Parameter Value Units Species
F 79.0 % Homo sapiens
F 71.0 % Homo sapiens
F 55.0 % Homo sapiens
T1/2 5.6 hr Homo sapiens
T1/2 48.0 hr -
T1/2 48.0 hr Homo sapiens
Tmax 2.0 hr Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Unchecked Ki = 7.2 nM 8.14 Inhibition of Sulfurihydrogenibium yellowstonense YO3AOP1 recombinant carbonic a... 22883029
Carbonate dehydratase Ki = 7.2 nM 8.14 Inhibition of recombinant Sulfurihydrogenibium yellowstonense YO3AOP1 carbonic a... 26691758
AGAP002992-PA Ki = 31.5 nM 7.5 Inhibition of Anopheles gambiae carbonic anhydrase pre-incubated for 15 mins by ... 25882523
Unchecked Ki = 50.2 nM 7.3 Inhibition of Leishmania donovani chagasi recombinant beta-carbonic anhydrase pr... 24314394
Unchecked Ki = 50.2 nM 7.3 Inhibition of recombinant Leishmania donovani chagasi beta-carbonic anhydrase ex... 23977960
Unchecked Ki = 58.7 nM 7.23 Inhibition of recombinant Nostoc commune gamma-carbonic anhydrase preincubated f... 25773015
Unchecked Ki = 58.7 nM 7.23 Inhibition of Nostoc commune gamma carbonic anhydrase preincubated for 15 mins b... 26832216
Unchecked Ki = 58.7 nM 7.23 Inhibition of Nostoc commune gamma carbonic anhydrase by CO2 hydration assay 26174556
Unchecked Ki = 68.0 nM 7.17 Inhibition of Vibrio cholerae beta carbonic anhydrase pre-incubated for 15 mins ... 33214843
Unchecked Ki = 79.5 nM 7.1 Inhibition of recombinant Vibrio cholerae carbonic anhydrase expressed in Escher... 23181552
Unchecked Ki = 79.5 nM 7.1 Inhibition of Vibrio cholerae alpha-carbonic anhydrase using CO2 as substrate pr... 26850377
Unchecked Ki = 87.0 nM 7.06 Inhibition of Vibrio cholerae beta-carbonic anhydrase using CO2 as substrate pre... 26850377
Unchecked Ki = 87.0 nM 7.06 Inhibition of Vibrio cholerae beta carbonic anhydrase incubated for 15 mins by s... 26920803
Unchecked Ki = 133.0 nM 6.88 Inhibition of recombinant Enterobacter sp. B13 beta carbonic anhydrase incubated... 26920803
Unchecked Ki = 134.0 nM 6.87 Inhibition of Trypanosoma cruzi CL Brener recombinant alpha-carbonic anhydrase e... 23391336
Unchecked Ki = 153.0 nM 6.82 Inhibition of Plasmodium falciparum Eta-carbonic anhydrase pre-incubated for 15 ... 25533402
Carbonic anhydrase 2 Ki = 290.0 nM 6.54 Inhibition of human recombinant carbonic anhydrase 2 at pH 7.5 by stopped flow C... 21757360
Carbonic anhydrase 2 Ki = 290.0 nM 6.54 Inhibition of human recombinant carbonic anhydrase 2 preincubated for 15 mins by... 23181552
Carbonic anhydrase 2 Ki = 290.0 nM 6.54 Inhibition of human carbonic anhydrase 2 after 15 mins by CO2 hydrase assay at p... 21377369
Carbonic anhydrase 2 Ki = 290.0 nM 6.54 Inhibition of human recombinant carbonic anhydrase 2 after 15 mins by stopped fl... 22285172

Literature References

PubMed DOI Target Context # Activities
- 10.6019/CHEMBL3885881 Rattus norvegicus 320
1433206 10.1021/jm00100a001 Rattus norvegicus 48
7086830 10.1021/jm00343a022 Rattus norvegicus 29
7966129 10.1021/jm00048a005 Rattus norvegicus 25
32453565 10.1021/acs.jnatprod.0c00274 Rattus norvegicus 23
2724291 10.1021/jm00126a003 Rattus norvegicus 22
7452697 10.1021/jm00186a024 Rattus norvegicus 19
16472241 10.2174/1570163043334794 Hepatotoxicity 18
22194678 10.1371/journal.pcbi.1002310 Hepatotoxicity 14
36796127 10.1016/j.bmc.2023.117203 No relevant target 13
7205867 10.1021/jm00133a024 Rattus norvegicus 13
7452697 10.1021/jm00186a024 Canis familiaris 13
3681899 10.1021/jm00395a020 Rattus norvegicus 13
6737427 10.1021/jm00373a005 Rattus norvegicus 12
3735318 10.1021/jm00158a030 ADMET 12
15646539 10.1016/s0399-8320(04)95062-2 Unchecked 11
7966129 10.1021/jm00048a005 Canis familiaris 10
6737427 10.1021/jm00373a005 Pan troglodytes 10
3735318 10.1021/jm00158a030 Rattus norvegicus 9
8093626 10.1021/jm00053a020 Rattus norvegicus 9

Data from ChEMBL 36 via Core Engine