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Details

Stereochemistry ACHIRAL
Molecular Formula C15H14ClN3O4S3
Molecular Weight 431.937
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of BENZTHIAZIDE

SMILES

NS(=O)(=O)C1=CC2=C(C=C1Cl)N=C(CSCC3=CC=CC=C3)NS2(=O)=O

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 431.937
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

McManus, J. M. et al.
1
Curator's Comment: Pfizer https://www.google.ch/patents/US3440244

Approval Year

1960
107
Targets

Targets

Primary TargetPharmacologyConditionPotency
Inhibitor
8297
 0.0167 µM [Kd]
Inhibitor
8297
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Approved
8429
EXNA

Approved Use

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

Launch Date

1960
Primary
Approved
8429
EXNA

Approved Use

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

Launch Date

1960
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
10 h
REVIEW
https://pubmed.ncbi.nlm.nih.gov/3828483/
unknown, oral
 BENZTHIAZIDE unknown
Homo sapiens
population: UNKNOWN
age: UNKNOWN
sex: UNKNOWN
food status: UNKNOWN
Funbound

Funbound

ValueDoseCo-administeredAnalytePopulation
90%
REVIEW
https://pubmed.ncbi.nlm.nih.gov/3828483/
unknown, oral
 BENZTHIAZIDE unknown
Homo sapiens
population: UNKNOWN
age: UNKNOWN
sex: UNKNOWN
food status: UNKNOWN
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG
inhibitor
1587

activator
80
inhibitor
1767
inhibitor
1852

OverviewOther

Other InhibitorOther SubstrateOther Inducer
CYP1A2
1524

CYP2C19
1478

BSEP
402

OATP1B1
788

OATP1B3
706
Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
CYP2D6
1891
 inconclusive [Activation 12.5893 uM]
CYP2C9
1819
 inconclusive [Activation 3.9811 uM]
CYP3A4
1925
 no [Activation 12.5893 uM]
CYP1A2
1692
 no [Activation >10 uM]
CYP2C19
1553
 no [Activation >10 uM]
CYP3A4
1925
 yes [Activation 12.5893 uM]
BSEP
403
 yes [IC50 5.743 uM]
OATP1B1
803
 yes [Inhibition 10 uM]
OATP1B3
715
 yes [Inhibition 10 uM]
Sourcing

Sourcing

Vendor/AggregatorIDURL
ChEBI
CHEBI:3047
https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:3047
MolPort
MolPort-003-940-508
https://www.molport.com/shop/molecule-link/MolPort-003-940-508
ZINC
ZINC000003871698
http://zinc15.docking.org/substances/ZINC000003871698
eMolecules
1985676
https://www.emolecules.com/cgi-bin/more?vid=1985676
PubMed

PubMed

TitleDatePubMed
Capillary electrophoresis of diuretics and probenecid in methanol.
2008 Jul 11
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
Patents

Patents

JP2007117082A
1
JP2009095237A
1
JP2011050396A
1
JPH02276568A
1

Sample Use Guides

In Vivo Use Guide
Hypertension: 50-100 mg/day; maintenance: individualize dose (maximum effective dose: 200 mg/day)
Route of Administration: Oral
In Vitro Use Guide
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 Dec 15 15:17:38 GMT 2023
Edited
by admin
on Fri Dec 15 15:17:38 GMT 2023
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 [WHO-DD]
Common Name English
BENZTHIAZIDE [HSDB]
Common Name English
URESE
Brand Name English
EXNA
Brand 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 Dec 15 15:17:38 GMT 2023 , Edited by admin on Fri Dec 15 15:17:38 GMT 2023
Code System Code Type Description
DRUG CENTRAL
332
Created by admin on Fri Dec 15 15:17:38 GMT 2023 , Edited by admin on Fri Dec 15 15:17:38 GMT 2023
PRIMARY
FDA UNII
1TD8J48L61
Created by admin on Fri Dec 15 15:17:38 GMT 2023 , Edited by admin on Fri Dec 15 15:17:38 GMT 2023
PRIMARY
LACTMED
Benzthiazide
Created by admin on Fri Dec 15 15:17:38 GMT 2023 , Edited by admin on Fri Dec 15 15:17:38 GMT 2023
PRIMARY
NSC
755902
Created by admin on Fri Dec 15 15:17:38 GMT 2023 , Edited by admin on Fri Dec 15 15:17:38 GMT 2023
PRIMARY
EPA CompTox
DTXSID4022658
Created by admin on Fri Dec 15 15:17:38 GMT 2023 , Edited by admin on Fri Dec 15 15:17:38 GMT 2023
PRIMARY
CHEBI
3047
Created by admin on Fri Dec 15 15:17:38 GMT 2023 , Edited by admin on Fri Dec 15 15:17:38 GMT 2023
PRIMARY
EVMPD
SUB05769MIG
Created by admin on Fri Dec 15 15:17:38 GMT 2023 , Edited by admin on Fri Dec 15 15:17:38 GMT 2023
PRIMARY
SMS_ID
100000086394
Created by admin on Fri Dec 15 15:17:38 GMT 2023 , Edited by admin on Fri Dec 15 15:17:38 GMT 2023
PRIMARY
WIKIPEDIA
BENZTHIAZIDE
Created by admin on Fri Dec 15 15:17:38 GMT 2023 , Edited by admin on Fri Dec 15 15:17:38 GMT 2023
PRIMARY
INN
944
Created by admin on Fri Dec 15 15:17:38 GMT 2023 , Edited by admin on Fri Dec 15 15:17:38 GMT 2023
PRIMARY
PUBCHEM
2343
Created by admin on Fri Dec 15 15:17:38 GMT 2023 , Edited by admin on Fri Dec 15 15:17:38 GMT 2023
PRIMARY
HSDB
3296
Created by admin on Fri Dec 15 15:17:38 GMT 2023 , Edited by admin on Fri Dec 15 15:17:38 GMT 2023
PRIMARY
MERCK INDEX
m2393
Created by admin on Fri Dec 15 15:17:38 GMT 2023 , Edited by admin on Fri Dec 15 15:17:38 GMT 2023
PRIMARY Merck Index
ECHA (EC/EINECS)
202-061-0
Created by admin on Fri Dec 15 15:17:38 GMT 2023 , Edited by admin on Fri Dec 15 15:17:38 GMT 2023
PRIMARY
RXCUI
19008
Created by admin on Fri Dec 15 15:17:38 GMT 2023 , Edited by admin on Fri Dec 15 15:17:38 GMT 2023
PRIMARY RxNorm
MESH
C004463
Created by admin on Fri Dec 15 15:17:38 GMT 2023 , Edited by admin on Fri Dec 15 15:17:38 GMT 2023
PRIMARY
IUPHAR
7125
Created by admin on Fri Dec 15 15:17:38 GMT 2023 , Edited by admin on Fri Dec 15 15:17:38 GMT 2023
PRIMARY
NCI_THESAURUS
C65254
Created by admin on Fri Dec 15 15:17:38 GMT 2023 , Edited by admin on Fri Dec 15 15:17:38 GMT 2023
PRIMARY
DRUG BANK
DB00562
Created by admin on Fri Dec 15 15:17:38 GMT 2023 , Edited by admin on Fri Dec 15 15:17:38 GMT 2023
PRIMARY
ChEMBL
CHEMBL1201039
Created by admin on Fri Dec 15 15:17:38 GMT 2023 , Edited by admin on Fri Dec 15 15:17:38 GMT 2023
PRIMARY
CAS
91-33-8
Created by admin on Fri Dec 15 15:17:38 GMT 2023 , Edited by admin on Fri Dec 15 15:17:38 GMT 2023
PRIMARY
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Related Record Type Details
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ACTIVE MOIETY
NIH
NCATS
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ACCESSIBILITY
DISCLAIMER
HHS VULNERABILITY DISCLOSURE
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