ChemFOnt: Showing chemical card for Benzthiazide (CFc000009054)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:56:04 UTC

Chemfont ID

CFc000009054

Molecule Identification

Common Name

Benzthiazide

Definition

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.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
3-((Benzylthio)methyl)-6-chloro-7-sulfamoyl-2H-benzo-1,2,4-thiadiazine 1,1-dioxide	ChEBI
3-Benzylthiomethyl-6-chloro-2H-1,2,4-benzothiadiazine-7-sulfonamide 1,1-dioxide	ChEBI
3-Benzylthiomethyl-6-chloro-7-sulfamoyl-1,2,4-benzothiadiazine 1,1-dioxide	ChEBI
6-Chloro-1,1-dioxo-3-(phenylmethylsulfanylmethyl)-4H-benzo[e][1,2,4]thiadiazine-7-sulfonamide	ChEBI
6-Chloro-7-sulfamoyl-3-benzylthiomethyl-2H-1,2,4-benzothiadiazine 1,1-dioxide	ChEBI
Benzothiazide	ChEBI
Benzotiazida	ChEBI
Benzthiazidum	ChEBI
Exna	Kegg
3-((Benzylthio)methyl)-6-chloro-7-sulphamoyl-2H-benzo-1,2,4-thiadiazine 1,1-dioxide	Generator
3-Benzylthiomethyl-6-chloro-2H-1,2,4-benzothiadiazine-7-sulphonamide 1,1-dioxide	Generator
3-Benzylthiomethyl-6-chloro-7-sulphamoyl-1,2,4-benzothiadiazine 1,1-dioxide	Generator
6-Chloro-1,1-dioxo-3-(phenylmethylsulphanylmethyl)-4H-benzo[e][1,2,4]thiadiazine-7-sulphonamide	Generator
6-Chloro-7-sulphamoyl-3-benzylthiomethyl-2H-1,2,4-benzothiadiazine 1,1-dioxide	Generator

Chemical Formula

C₁₅H₁₄ClN₃O₄S₃

Average Molecular Weight

431.937

Monoisotopic Molecular Weight

430.983495728

IUPAC Name

3-[(benzylsulfanyl)methyl]-6-chloro-1,1-dioxo-4H-1λ⁶,2,4-benzothiadiazine-7-sulfonamide

Traditional Name

regulon

CAS Registry Number

91-33-8

SMILES

NS(=O)(=O)C1=C(Cl)C=C2NC(CSCC3=CC=CC=C3)=NS(=O)(=O)C2=C1

InChI Identifier

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)

InChI Key

NDTSRXAMMQDVSW-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.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Thiadiazines

Sub Class

Benzothiadiazines

Direct Parent

1,2,4-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 Framework

Aromatic heteropolycyclic compounds

External Descriptors

sulfonamide (CHEBI:3047 )
benzothiadiazine (CHEBI:3047 )

Functional Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 21059682)

Excreta

Biofluid or Excreta

Urine (PMID: 21059682)

Cellular substructure

Source

Exogenous

Exogenous (HMDB: HMDB0014702)

Process

Not Available

Role

Industrial application

Antihypertensive agent (HMDB: HMDB0014702)

Manufacturing industry

Material processing agent

Coloring agent

Fluorescent agent

Diuretic (HMDB: HMDB0014702)

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.013 g/L	ALOGPS
logP	2.26	ALOGPS
logP	1.84	ChemAxon
logS	-4.5	ALOGPS
pKa (Strongest Acidic)	8.77	ChemAxon
pKa (Strongest Basic)	1.25	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	118.69 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	104.14 m³·mol⁻¹	ChemAxon
Polarizability	41.5 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon