chlorothiazide   

GtoPdb Ligand ID: 4835

Synonyms: Diuril®
chlorothiazide is an approved drug (FDA (1958))
Compound class: Synthetic organic
Comment: Chlorothiazide is a thiazide diuretic, similar to hydrochlorothiazide.
2D Structure

2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

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Click here for structure editor
Physico-chemical Properties

Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the CDK toolkit. All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

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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
SMILES / InChI / InChIKey

SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

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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)
InChI Key JBMKAUGHUNFTOL-UHFFFAOYSA-N
No information available.
Summary of Clinical Use
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
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.