chlorothiazide   Click here for help

GtoPdb Ligand ID: 4835

Synonyms: Diuril®
Approved drug
chlorothiazide is an approved drug (FDA (1958))
Compound class: Synthetic organic
Comment: Chlorothiazide is a thiazide diuretic, similar to hydrochlorothiazide.
2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 7
Hydrogen bond donors 2
Rotatable bonds 1
Topological polar surface area 135.45
Molecular weight 294.95
XLogP 0.16
No. Lipinski's rules broken 0
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Canonical SMILES Clc1cc2NC=NS(=O)(=O)c2cc1S(=O)(=O)N
Isomeric SMILES Clc1cc2NC=NS(=O)(=O)c2cc1S(=O)(=O)N
InChI InChI=1S/C7H6ClN3O4S2/c8-4-1-5-7(2-6(4)16(9,12)13)17(14,15)11-3-10-5/h1-3H,(H,10,11)(H2,9,12,13)
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Summary of Clinical Use Click here for help
Diuretic and anti-hypertensive drug used as an adjunctive therapy in edema associated with congestive heart failure, cirrhosis of the liver and corticosteroid and estrogen therapy. Chlorothiazide is used in the treatment of hypertension either alone or as an adjuvant to other drugs in the treatment of severe forms of the condition.
Mechanism Of Action and Pharmacodynamic Effects Click here for help
Chlorothiazide inhibits the thiazide-sensitive sodium-chloride cotransporter (Na-Cl symporter, SLC12A3). The main action of chlorothiazide is inhibition of active chloride reabsorption in the early distal tubule of the kidney, via the Na-Cl symporter, resulting in an increase in the excretion of sodium, chloride, and water. This activity may also result in increased potassium excretion via the sodium-potassium exchange mechanism.