<?xml version="1.0" encoding="UTF-8"?>
<compound>
  <id type="integer">2867</id>
  <title>T3D2825</title>
  <common-name>Benzthiazide</common-name>
  <description>Benzthiazide is used to treat hypertension and edema. Like other thiazides, benzthiazide promotes water loss from the body (diuretics). They inhibit Na+/Cl- reabsorption from the distal convoluted tubules in the kidneys. Thiazides also cause loss of potassium and an increase in serum uric acid. Thiazides are often used to treat hypertension, but their hypotensive effects are not necessarily due to their diuretic activity. Thiazides have been shown to prevent hypertension-related morbidity and mortality although the mechanism is not fully understood. Thiazides cause vasodilation by activating calcium-activated potassium channels (large conductance) in vascular smooth muscles and inhibiting various carbonic anhydrases in vascular tissue.</description>
  <cas>91-33-8</cas>
  <pubchem-id>2343</pubchem-id>
  <chemical-formula>C15H14ClN3O4S3</chemical-formula>
  <weight>430.983500</weight>
  <appearance>White powder.</appearance>
  <melting-point>210-211°C</melting-point>
  <boiling-point nil="true"/>
  <density nil="true"/>
  <solubility>8.91 mg/L</solubility>
  <specific-gravity nil="true"/>
  <flash-point nil="true"/>
  <vapour-pressure nil="true"/>
  <route-of-exposure>Absorbed in the digestive tract.</route-of-exposure>
  <target nil="true"/>
  <mechanism-of-toxicity>As a diuretic, benzthiazide inhibits active chloride reabsorption at the early distal tubule via the Na-Cl cotransporter, resulting in an increase in the excretion of sodium, chloride, and water. Thiazides like benzthiazide also inhibit sodium ion transport across the renal tubular epithelium through binding to the thiazide sensitive sodium-chloride transporter. This results in an increase in potassium excretion via the sodium-potassium exchange mechanism. The antihypertensive mechanism of benzthiazide is less well understood although it may be mediated through its action on carbonic anhydrases in the smooth muscle or through its action on the large-conductance calcium-activated potassium (KCa) channel, also found in the smooth muscle.</mechanism-of-toxicity>
  <metabolism></metabolism>
  <toxicity nil="true"/>
  <lethaldose nil="true"/>
  <carcinogenicity>No indication of carcinogenicity to humans (not listed by IARC).</carcinogenicity>
  <use-source>For the treatment of high blood pressure and management of edema.</use-source>
  <min-risk-level nil="true"/>
  <health-effects>Using large amounts of these drugs can result in a condition known as amphetamine psychosis -- which can result in auditory, visual and tactile hallucinations, intense paranoia, irrational thoughts and beliefs, delusions, and mental confusion.</health-effects>
  <symptoms>Symptoms of overdose include nausea, vomiting, fatigue, urinary problems and drowsiness.</symptoms>
  <treatment nil="true"/>
  <created-at type="dateTime">2009-07-21T20:27:09Z</created-at>
  <updated-at type="dateTime">2026-03-26T20:22:41Z</updated-at>
  <interacting-proteins nil="true"/>
  <wikipedia nil="true"/>
  <uniprot-id></uniprot-id>
  <kegg-compound-id>C07759</kegg-compound-id>
  <omim-id></omim-id>
  <chebi-id>3047</chebi-id>
  <biocyc-id></biocyc-id>
  <ctd-id nil="true"/>
  <stitch-id>Benzthiazide</stitch-id>
  <drugbank-id>DB00562</drugbank-id>
  <pdb-id></pdb-id>
  <actor-id nil="true"/>
  <organism nil="true"/>
  <export type="boolean">true</export>
  <metabolizing-proteins nil="true"/>
  <transporting-proteins nil="true"/>
  <moldb-smiles>NS(=O)(=O)C1=C(Cl)C=C2NC(CSCC3=CC=CC=C3)=NS(=O)(=O)C2=C1</moldb-smiles>
  <moldb-formula>C15H14ClN3O4S3</moldb-formula>
  <moldb-inchi>InChI=1S/C15H14ClN3O4S3/c16-11-6-12-14(7-13(11)25(17,20)21)26(22,23)19-15(18-12)9-24-8-10-4-2-1-3-5-10/h1-7H,8-9H2,(H,18,19)(H2,17,20,21)</moldb-inchi>
  <moldb-inchikey>NDTSRXAMMQDVSW-UHFFFAOYSA-N</moldb-inchikey>
  <moldb-average-mass type="decimal">431.937</moldb-average-mass>
  <moldb-mono-mass type="decimal">430.983495728</moldb-mono-mass>
  <origin>Exogenous</origin>
  <state>Solid</state>
  <logp>1.73</logp>
  <hmdb-id>HMDB14702</hmdb-id>
  <chembl-id>CHEMBL1201039</chembl-id>
  <chemspider-id>2253</chemspider-id>
  <structure-image-file-name nil="true"/>
  <structure-image-content-type nil="true"/>
  <structure-image-file-size type="integer" nil="true"/>
  <structure-image-updated-at type="dateTime" nil="true"/>
  <biodb-id nil="true"/>
  <synthesis-reference>&lt;p&gt;Samuel M. Fainberg, Porfirio F. Perez, &amp;#8220;Stable solution of benzthiazide (3-[benzythiol methyl]-6-chloro-2H-1,2,4-benzothiadiazine-7-sulfonamide 1,1-dioxide) suitable for parenteral administration and process of preparation.&amp;#8221; U.S. Patent US4022894, issued May 10, 1977.&lt;/p&gt;</synthesis-reference>
  <structure-image-caption nil="true"/>
  <chemdb-id>CHEM002221</chemdb-id>
  <dsstox-id>DTXSID4022658</dsstox-id>
  <toxcast-id nil="true"/>
  <stoff-ident-origin nil="true"/>
  <stoff-ident-id nil="true"/>
  <susdat-id>NS00002522</susdat-id>
  <iupac>3-[(benzylsulfanyl)methyl]-6-chloro-1,1-dioxo-4H-1λ⁶,2,4-benzothiadiazine-7-sulfonamide</iupac>
</compound>
