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Compound Detail

CHEMBL1054

TRICHLORMETHIAZIDE
💊 Approved Drug
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💊 Approved Drug
NS(=O)(=O)c1cc2c(cc1Cl)NC(C(Cl)Cl)NS2(=O)=O
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL1054
Name TRICHLORMETHIAZIDE
Phase Approved
Structure Type MOL
InChI Key LMJSLTNSBFUCMU-UHFFFAOYSA-N
Therapeutic ✓ Yes

Known Names

Metahydrin Naqua NSC-61560 Trichlorex Trichlormas Trichlormethiazide Trichlormethiazide component of metatensin Trichlormethiazide component of naquival Trichloromethiazide Triclormetiazida
11
Targets
14
Activities
2
Assay Types
0
PK Parameters
20
Publications
10
Known Names
1
Indications
1
Mechanisms

Molecular Properties

380.7
MW (Da)
0.82
ALogP
5
HBA
3
HBD
118.4
PSA (Ų)
0.66
QED
0
Ro5 Violations
2
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 1960
Availability Discontinued
Chirality Racemic

Routes of Administration

Oral

Flags

Natural Product
USAN Stem -thiazide

Extended Properties

Molecular Formula C8H8Cl3N3O4S2
MW 380.66
Aromatic Rings 1
Heavy Atoms 20
NP-Likeness -1.17

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

ATC Classification

C03AA06
trichlormethiazide
Level 1: CARDIOVASCULAR SYSTEM
Level 2: DIURETICS

Activity Summary

Ki 12 meas. best 8.1
Kd 2 meas. best 5.77

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Carbonic anhydrase 7
CHEMBL2326
 Ki 8.1 8.1 7.9 1
Carbonic anhydrase 9
CHEMBL3594
 Ki 7.06 7.06 87.0 1
Carbonic anhydrase 2
CHEMBL205
 Ki 7.04 7.04 91.0 1
Carbonic anhydrase 5B, mitochondrial
CHEMBL3969
 Ki 6.87 6.87 134.0 1
Carbonic anhydrase 12
CHEMBL3242
 Ki 6.51 6.51 312.0 1
Carbonic anhydrase 1
CHEMBL261
 Ki 6.46 6.46 345.0 1
Carbonic anhydrase 4
CHEMBL3729
 Ki 6.35 6.35 449.0 1
Carbonic anhydrase 13
CHEMBL2186
 Ki 6.19 6.19 645.0 1
Carbonic anhydrase 5A, mitochondrial
CHEMBL4789
 Ki 6.12 6.12 763.0 1
Carbonic anhydrase 2
CHEMBL205
 Kd 5.77 5.675 1700.0 2
Carbonic anhydrase 6
CHEMBL3025
 Ki 5.61 5.61 2459.0 1
Carbonic anhydrase 14
CHEMBL3510
 Ki 5.46 5.46 3450.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Carbonic anhydrase 7 Ki = 7.9 nM 8.1 Inhibition of human recombinant full length CA7 by stopped-flow CO2 hydration me... 19119014
Carbonic anhydrase 9 Ki = 87.0 nM 7.06 Inhibition of human recombinant CA9 catalytic domain by stopped-flow CO2 hydrati... 19119014
Carbonic anhydrase 2 Ki = 91.0 nM 7.04 Inhibition of human recombinant full length CA2 by stopped-flow CO2 hydration me... 19119014
Carbonic anhydrase 5B, mitochondrial Ki = 134.0 nM 6.87 Inhibition of human recombinant full length CA5B by stopped-flow CO2 hydration m... 19119014
Carbonic anhydrase 12 Ki = 312.0 nM 6.51 Inhibition of human recombinant CA12 catalytic domain by stopped-flow CO2 hydrat... 19119014
Carbonic anhydrase 1 Ki = 345.0 nM 6.46 Inhibition of human recombinant full length CA1 by stopped-flow CO2 hydration me... 19119014
Carbonic anhydrase 4 Ki = 449.0 nM 6.35 Inhibition of human recombinant full length CA4 by stopped-flow CO2 hydration me... 19119014
Carbonic anhydrase 13 Ki = 645.0 nM 6.19 Inhibition of mouse recombinant full length CA13 by stopped-flow CO2 hydration m... 19119014
Carbonic anhydrase 5A, mitochondrial Ki = 763.0 nM 6.12 Inhibition of human recombinant full length CA5A by stopped-flow CO2 hydration m... 19119014
Carbonic anhydrase 2 Kd = 1700.0 nM 5.77 Binding affinity to human recombinant CA II assessed as dissociation constant 39161321
Carbonic anhydrase 6 Ki = 2459.0 nM 5.61 Inhibition of human recombinant full length CA6 by stopped-flow CO2 hydration me... 19119014
Carbonic anhydrase 2 Kd = 2600.0 nM 5.58 Displacement of dansylamide from human recombinant CA II expressed in Escherichi... 39161321
Carbonic anhydrase 14 Ki = 3450.0 nM 5.46 Inhibition of human recombinant full length CA14 by stopped-flow CO2 hydration m... 19119014

Literature References

PubMed DOI Target Context # Activities
15646539 10.1016/s0399-8320(04)95062-2 Unchecked 11
15646539 10.1016/s0399-8320(04)95062-2 NON-PROTEIN TARGET 8
- 10.6019/CHEMBL4495565 SARS-CoV-2 4
39161321 10.1021/acs.jmedchem.4c01512 Carbonic anhydrase 2 4
17540563 10.1016/j.bmcl.2007.05.045 Unchecked 3
37468498 10.1038/s41467-023-40064-9 Muscarinic acetylcholine receptor M1 2
- 10.6019/CHEMBL4808148 Histone deacetylase 6 2
39161321 10.1021/acs.jmedchem.4c01512 Carbonic anhydrase 3 2
37468498 10.1038/s41467-023-40064-9 Prostaglandin G/H synthase 1 2
- 10.6019/CHEMBL3301361 No relevant target 2
- 10.6019/CHEMBL4495564 Replicase polyprotein 1ab 2
37468498 10.1038/s41467-023-40064-9 Thromboxane A2 receptor 2
18834112 10.1021/jm800656v Amine oxidase [flavin-containing] B 2
- 10.6019/CHEMBL4651402 SARS-CoV-2 2
37468498 10.1038/s41467-023-40064-9 Alpha-1A adrenergic receptor 2
18834112 10.1021/jm800656v Amine oxidase [flavin-containing] A 2
17540563 10.1016/j.bmcl.2007.05.045 Carbonic anhydrase 12 1
17540563 10.1016/j.bmcl.2007.05.045 Carbonic anhydrase 13 1
17540563 10.1016/j.bmcl.2007.05.045 Carbonic anhydrase 5A, mitochondrial 1
17540563 10.1016/j.bmcl.2007.05.045 Carbonic anhydrase 4 1

Data from ChEMBL 36 via Core Engine