chlorthalidone   Click here for help

GtoPdb Ligand ID: 7147

Synonyms: G-33182 | Hygroton®
Approved drug
chlorthalidone is an approved drug (FDA (1960), UK (1998))
Compound class: Synthetic organic
Comment: Chlorthalidone is a thiazide-like diuretic. It has a longer duration of action than other thiazide drugs.
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 6
Hydrogen bond donors 3
Rotatable bonds 2
Topological polar surface area 121.36
Molecular weight 338.01
XLogP 1.87
No. Lipinski's rules broken 0
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Canonical SMILES Clc1ccc(cc1S(=O)(=O)N)C1(O)N=C(c2c1cccc2)O
Isomeric SMILES Clc1ccc(cc1S(=O)(=O)N)C1(O)N=C(c2c1cccc2)O
InChI InChI=1S/C14H11ClN2O4S/c15-11-6-5-8(7-12(11)22(16,20)21)14(19)10-4-2-1-3-9(10)13(18)17-14/h1-7,19H,(H,17,18)(H2,16,20,21)
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Summary of Clinical Use Click here for help
This is predominantly used as anti-hypertensive drug with diuretic action. It may be used alone or in combination with other anti-hypertensives. This drug may also be used to reduce oedema with specific aetiologies. There is no information regarding approval for clinical use of this drug on the US FDA website. Other national approval agencies may have granted marketing authorisation.
Mechanism Of Action and Pharmacodynamic Effects Click here for help
Reduces water retention by inhibiting Na+/Cl- reabsorption from the distal convoluted tubules in the kidneys by inhibiting the Na-Cl symporter, SLC12A3. This helps to reduce blood pressure. This mechanism of action tallies with the ChEMBL target for this drug. However, published interaction data indicates that this drug also appears to be an active inhibitor of several isoforms of carbonic anhydrases, with Kis ranging from 2.8-11000 nM [1].
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