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Details

Stereochemistry ACHIRAL
Molecular Formula C15H14ClN3O4S3
Molecular Weight 431.9411
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of BENZTHIAZIDE

SMILES

c1ccc(cc1)CSCC2=Nc3cc(c(cc3S(=O)(=O)N2)S(=O)(=O)N)Cl

InChI

InChIKey=NDTSRXAMMQDVSW-UHFFFAOYSA-N
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)

HIDE SMILES / InChI

Molecular Formula C15H14ClN3O4S3
Molecular Weight 431.9411
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description
Curator's Comment:: description was created based on several sources, including: http://www.tabletwise.com/us/exna-tablet | http://edudrugs.com/A/Aquatag/more.html | https://www.drugs.com/uk/dytide-capsules-leaflet.html | http://www.tabletwise.com/us/exna-tablet

Benzthiazide (trade names Aquatag, Dihydrex, Diucen, Edemax, Exna, Foven and others) is a thiazide diuretic used in the treatment of high blood pressure and edema. It is no longer available in the United States. 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. The following is a list of possible side effects that may occur from all constituting ingredients of Exna Tablet: vomiting, diarrhoea, photosensitivity reactions, increased in uric acid concentrations, megaloblastic anaemia, thrombocytopenia. Exna tablet may interact with the following drugs and products: ACE inhibitors, angiotensin II receptor antagonists, potassium-sparing diuretics.

Originator

Curator's Comment:: Pfizer https://www.google.ch/patents/US3440244

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
0.0167 µM [Kd]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
EXNA

Approved Use

Management of mild to moderate hypertension; treatment of edema in congestive heart failure and nephrotic syndrome

Launch Date

-2.9082239E11
Primary
EXNA

Approved Use

Management of mild to moderate hypertension; treatment of edema in congestive heart failure and nephrotic syndrome

Launch Date

-2.9082239E11
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
10 h
unknown, oral
BENZTHIAZIDE unknown
Homo sapiens
population: UNKNOWN
age: UNKNOWN
sex: UNKNOWN
food status: UNKNOWN
Funbound

Funbound

ValueDoseCo-administeredAnalytePopulation
90%
unknown, oral
BENZTHIAZIDE unknown
Homo sapiens
population: UNKNOWN
age: UNKNOWN
sex: UNKNOWN
food status: UNKNOWN
Overview

Overview

OverviewOther

Other InhibitorOther SubstrateOther Inducer





Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
inconclusive [Activation 12.5893 uM]
inconclusive [Activation 3.9811 uM]
no [Activation 12.5893 uM]
no [Activation >10 uM]
no [Activation >10 uM]
yes [Activation 12.5893 uM]
yes [IC50 5.743 uM]
yes [Inhibition 10 uM]
yes [Inhibition 10 uM]
PubMed

PubMed

TitleDatePubMed
Determination and characterization of diuretics in human urine by liquid chromatography coupled to pneumatically assisted electrospray ionization mass spectrometry.
2001 Jun
Effects of pH and the presence of micelles on the resolution of diuretics by reversed-phase liquid chromatography.
2004 Jan 2
Assessment of different protocols for the isolation and purification of gut associated lymphoid cells from the gilthead seabream (Sparus aurata L.).
2007 Nov 25
Combined effect of solvent content, temperature and pH on the chromatographic behaviour of ionisable compounds.
2007 Sep 7
Capillary electrophoresis of diuretics and probenecid in methanol.
2008 Jul 11
Expression profile of CREB knockdown in myeloid leukemia cells.
2008 Sep 18
Generic sample preparation combined with high-resolution liquid chromatography-time-of-flight mass spectrometry for unification of urine screening in doping-control laboratories.
2010 Apr
The neuropharmacology of implicit learning.
2010 Dec
Patents

Sample Use Guides

Hypertension: 50-100 mg/day; maintenance: individualize dose (maximum effective dose: 200 mg/day)
Route of Administration: Oral
Carbon dioxide protects the carbonic anhydrase from inhibition by benzthiazide. After equilibration of inhibitor with enzyme in the presence of substrate, an inhibition is observed at a drug concentration 100-fold higher than that required for a similar inhibition after equilibration in the absence of substrate.
Substance Class Chemical
Created
by admin
on Fri Jun 25 22:04:43 UTC 2021
Edited
by admin
on Fri Jun 25 22:04:43 UTC 2021
Record UNII
1TD8J48L61
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
BENZTHIAZIDE
HSDB   INN   JAN   MART.   MI   ORANGE BOOK   VANDF   WHO-DD  
INN  
Official Name English
BENZOTHIAZIDE
Common Name English
BENZTHIAZIDE [HSDB]
Common Name English
URESE
Brand Name English
EXNA
Brand Name English
BENZTHIAZIDE [WHO-DD]
Common Name English
BENZTHIAZIDE [MI]
Common Name English
BENZTHIAZIDE [MART.]
Common Name English
BENZTHIAZIDE [VANDF]
Common Name English
NSC-755902
Code English
FOVANE
Brand Name English
3-((BENZYLTHIO)METHYL)-6-CHLORO-2H-1,2,4-BENZOTHIADIAZINE-7-SULFONAMIDE 1,1-DIOXIDE
Systematic Name English
BENZTHIAZIDE [INN]
Common Name English
AQUATAG
Brand Name English
BENZTHIAZIDE [JAN]
Common Name English
2H-1,2,4-BENZOTHIADIAZINE-7-SULFONAMIDE, 6-CHLORO-3-(((PHENYLMETHYL)THIO)METHYL)-, 1,1-DIOXIDE
Systematic Name English
BENZTHIAZIDE [ORANGE BOOK]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C49185
Created by admin on Fri Jun 25 22:04:43 UTC 2021 , Edited by admin on Fri Jun 25 22:04:43 UTC 2021
Code System Code Type Description
DRUG CENTRAL
332
Created by admin on Fri Jun 25 22:04:43 UTC 2021 , Edited by admin on Fri Jun 25 22:04:43 UTC 2021
PRIMARY
FDA UNII
1TD8J48L61
Created by admin on Fri Jun 25 22:04:43 UTC 2021 , Edited by admin on Fri Jun 25 22:04:43 UTC 2021
PRIMARY
LACTMED
Benzthiazide
Created by admin on Fri Jun 25 22:04:43 UTC 2021 , Edited by admin on Fri Jun 25 22:04:43 UTC 2021
PRIMARY
EPA CompTox
91-33-8
Created by admin on Fri Jun 25 22:04:43 UTC 2021 , Edited by admin on Fri Jun 25 22:04:43 UTC 2021
PRIMARY
EVMPD
SUB05769MIG
Created by admin on Fri Jun 25 22:04:43 UTC 2021 , Edited by admin on Fri Jun 25 22:04:43 UTC 2021
PRIMARY
WIKIPEDIA
BENZTHIAZIDE
Created by admin on Fri Jun 25 22:04:43 UTC 2021 , Edited by admin on Fri Jun 25 22:04:43 UTC 2021
PRIMARY
INN
944
Created by admin on Fri Jun 25 22:04:43 UTC 2021 , Edited by admin on Fri Jun 25 22:04:43 UTC 2021
PRIMARY
PUBCHEM
2343
Created by admin on Fri Jun 25 22:04:43 UTC 2021 , Edited by admin on Fri Jun 25 22:04:43 UTC 2021
PRIMARY
HSDB
3296
Created by admin on Fri Jun 25 22:04:43 UTC 2021 , Edited by admin on Fri Jun 25 22:04:43 UTC 2021
PRIMARY
MERCK INDEX
M2393
Created by admin on Fri Jun 25 22:04:43 UTC 2021 , Edited by admin on Fri Jun 25 22:04:43 UTC 2021
PRIMARY Merck Index
ECHA (EC/EINECS)
202-061-0
Created by admin on Fri Jun 25 22:04:43 UTC 2021 , Edited by admin on Fri Jun 25 22:04:43 UTC 2021
PRIMARY
RXCUI
19008
Created by admin on Fri Jun 25 22:04:43 UTC 2021 , Edited by admin on Fri Jun 25 22:04:43 UTC 2021
PRIMARY RxNorm
MESH
C004463
Created by admin on Fri Jun 25 22:04:43 UTC 2021 , Edited by admin on Fri Jun 25 22:04:43 UTC 2021
PRIMARY
IUPHAR
7125
Created by admin on Fri Jun 25 22:04:43 UTC 2021 , Edited by admin on Fri Jun 25 22:04:43 UTC 2021
PRIMARY
NCI_THESAURUS
C65254
Created by admin on Fri Jun 25 22:04:43 UTC 2021 , Edited by admin on Fri Jun 25 22:04:43 UTC 2021
PRIMARY
DRUG BANK
DB00562
Created by admin on Fri Jun 25 22:04:43 UTC 2021 , Edited by admin on Fri Jun 25 22:04:43 UTC 2021
PRIMARY
ChEMBL
CHEMBL1201039
Created by admin on Fri Jun 25 22:04:43 UTC 2021 , Edited by admin on Fri Jun 25 22:04:43 UTC 2021
PRIMARY
CAS
91-33-8
Created by admin on Fri Jun 25 22:04:43 UTC 2021 , Edited by admin on Fri Jun 25 22:04:43 UTC 2021
PRIMARY
Related Record Type Details
ACTIVE MOIETY