Benzthiazide (CHEM002221)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesTargets (7)XML
Record Information
Version1.0
Creation Date2009-07-21 20:27:09 UTC
Update Date2026-03-26 20:22:41 UTC
Accession NumberCHEM002221
Identification
Common NameBenzthiazide
ClassSmall Molecule
DescriptionBenzthiazide 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.
Contaminant Sources
  • HMDB Contaminants - Urine
  • STOFF IDENT Compounds
  • T3DB toxins
  • ToxCast & Tox21 Chemicals
Contaminant Type
  • Amide
  • Amine
  • Antihypertensive Agent
  • Diuretic
  • Drug
  • Ether
  • Metabolite
  • Organic Compound
  • Organochloride
  • Stimulant
  • Synthetic Compound
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
3-((Benzylthio)methyl)-6-chloro-7-sulfamoyl-2H-benzo-1,2,4-thiadiazine 1,1-dioxideChEBI
3-Benzylthiomethyl-6-chloro-2H-1,2,4-benzothiadiazine-7-sulfonamide 1,1-dioxideChEBI
3-Benzylthiomethyl-6-chloro-7-sulfamoyl-1,2,4-benzothiadiazine 1,1-dioxideChEBI
6-Chloro-1,1-dioxo-3-(phenylmethylsulfanylmethyl)-4H-benzo[e][1,2,4]thiadiazine-7-sulfonamideChEBI
6-Chloro-7-sulfamoyl-3-benzylthiomethyl-2H-1,2,4-benzothiadiazine 1,1-dioxideChEBI
BenzothiazideChEBI
BenzotiazidaChEBI
BenzthiazidumChEBI
ExnaKegg
3-((Benzylthio)methyl)-6-chloro-7-sulphamoyl-2H-benzo-1,2,4-thiadiazine 1,1-dioxideGenerator
3-Benzylthiomethyl-6-chloro-2H-1,2,4-benzothiadiazine-7-sulphonamide 1,1-dioxideGenerator
3-Benzylthiomethyl-6-chloro-7-sulphamoyl-1,2,4-benzothiadiazine 1,1-dioxideGenerator
6-Chloro-1,1-dioxo-3-(phenylmethylsulphanylmethyl)-4H-benzo[e][1,2,4]thiadiazine-7-sulphonamideGenerator
6-Chloro-7-sulphamoyl-3-benzylthiomethyl-2H-1,2,4-benzothiadiazine 1,1-dioxideGenerator
Chemical FormulaC15H14ClN3O4S3
Average Molecular Mass431.937 g/mol
Monoisotopic Mass430.983 g/mol
CAS Registry Number91-33-8
IUPAC Name3-[(benzylsulfanyl)methyl]-6-chloro-1,1-dioxo-4H-1λ⁶,2,4-benzothiadiazine-7-sulfonamide
Traditional Nameregulon
SMILESNS(=O)(=O)C1=C(Cl)C=C2NC(CSCC3=CC=CC=C3)=NS(=O)(=O)C2=C1
InChI IdentifierInChI=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)
InChI KeyNDTSRXAMMQDVSW-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as 1,2,4-benzothiadiazine-1,1-dioxides. These are aromatic heterocyclic compounds containing a 1,2,4-benzothiadiazine ring system with two S=O bonds at the 1-position.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassThiadiazines
Sub ClassBenzothiadiazines
Direct Parent1,2,4-benzothiadiazine-1,1-dioxides
Alternative Parents
Substituents
  • 1,2,4-benzothiadiazine-1,1-dioxide
  • Aryl chloride
  • Aryl halide
  • Monocyclic benzene moiety
  • Organosulfonic acid amide
  • Imidolactam
  • Benzenoid
  • Organic sulfonic acid or derivatives
  • Organosulfonic acid or derivatives
  • Sulfonyl
  • Aminosulfonyl compound
  • Amidine
  • Azacycle
  • Dialkylthioether
  • Thioether
  • Sulfenyl compound
  • Organic oxide
  • Organosulfur compound
  • Organonitrogen compound
  • Organochloride
  • Organohalogen compound
  • Hydrocarbon derivative
  • Organic nitrogen compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
Applications
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateSolid
AppearanceWhite powder.
Experimental Properties
PropertyValue
Melting Point210-211°C
Boiling PointNot Available
Solubility8.91 mg/L
Predicted Properties
PropertyValueSource
Water Solubility0.013 g/LALOGPS
logP2.26ALOGPS
logP1.84ChemAxon
logS-4.5ALOGPS
pKa (Strongest Acidic)8.77ChemAxon
pKa (Strongest Basic)1.25ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area118.69 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity104.14 m³·mol⁻¹ChemAxon
Polarizability41.5 ųChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9242000000-15561d025e3aa0c75308Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001l-6202900000-2a70b9803c4b86c5dd1fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00ko-9567100000-99dca328e8d7361a3afcSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-01vo-9551000000-d1e207308294a5deee08Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0iki-2069300000-96a7d5e7dc1269a42044Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004r-9128100000-4954efc1704bdde45009Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9010000000-d24b3facbec316c46e12Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0009000000-ef28da9b71b01c96fb7aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-0009000000-8007d10d85565090d549Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0fb9-9520000000-542b3b8a75568a776f6aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-0001900000-e655f017360118b76da1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001i-3101900000-f89180b83227d57566b2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9000000000-688382bcfe309825184bSpectrum
MSMass Spectrum (Electron Ionization)splash10-06r6-9624000000-532194fb14045a87f8deSpectrum
Toxicity Profile
Route of ExposureAbsorbed in the digestive tract.
Mechanism of ToxicityAs 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.
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Uses/SourcesFor the treatment of high blood pressure and management of edema.
Minimum Risk LevelNot Available
Health EffectsUsing 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.
SymptomsSymptoms of overdose include nausea, vomiting, fatigue, urinary problems and drowsiness.
TreatmentNot Available
Concentrations
Not Available
DrugBank IDDB00562
HMDB IDHMDB0014702
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkBenzthiazide
Chemspider ID2253
ChEBI ID3047
PubChem Compound ID2343
Kegg Compound IDC07759
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis Reference

Samuel M. Fainberg, Porfirio F. Perez, “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.” U.S. Patent US4022894, issued May 10, 1977.

MSDSNot Available
General ReferencesNot Available