U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry RACEMIC
Molecular Formula C15H14F3N3O4S2
Molecular Weight 421.415
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of BENDROFLUMETHIAZIDE

SMILES

NS(=O)(=O)C1=CC2=C(NC(CC3=CC=CC=C3)NS2(=O)=O)C=C1C(F)(F)F

InChI

InChIKey=HDWIHXWEUNVBIY-UHFFFAOYSA-N
InChI=1S/C15H14F3N3O4S2/c16-15(17,18)10-7-11-13(8-12(10)26(19,22)23)27(24,25)21-14(20-11)6-9-4-2-1-3-5-9/h1-5,7-8,14,20-21H,6H2,(H2,19,22,23)

HIDE SMILES / InChI

Description

Bendroflumethiazide (INN), formerly bendrofluazide (BAN) is a thiazide diuretic used to treat hypertension. CORZIDE (Nadolol and Bendroflumethiazide Tablets) for oral administration combines two antihypertensive agents: CORGARD (nadolol), a nonselective beta-adrenergic blocking agent, and NATURETIN (bendroflumethiazide), a thiazide diuretic-antihypertensive. Bendroflumethiazide works by inhibiting sodium reabsorption at the beginning of the distal convoluted tubule (DCT). Bendroflumethiazide 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 bendroflumethiazide 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 bendroflumethiazide 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. Thiazides do not affect normal blood pressure. Onset of action of thiazides occurs in two hours and the peak effect at about four hours. Duration of action persists for approximately six to 12 hours. Thiazides are eliminated rapidly by the kidney.

Approval Year

PubMed

PubMed

TitleDatePubMed
Quinine-mediated disseminated intravascular coagulation.
1999 Jul
Effects of thiazide- and loop-diuretics, alone or in combination, on calcitropic hormones and biochemical bone markers: a randomized controlled study.
2001 Aug
Nebivolol reverses endothelial dysfunction in essential hypertension: a randomized, double-blind, crossover study.
2001 Jul 31
Determination and characterization of diuretics in human urine by liquid chromatography coupled to pneumatically assisted electrospray ionization mass spectrometry.
2001 Jun
Rationale, design, methods and baseline demography of participants of the Anglo-Scandinavian Cardiac Outcomes Trial. ASCOT investigators.
2001 Jun
Role of sodium depletion in acute antidiuretic effect of bendroflumethiazide in rats with nephrogenic diabetes insipidus.
2001 Oct
Loop diuretics alter the diurnal rhythm of endogenous parathyroid hormone secretion. A randomized-controlled study on the effects of loop- and thiazide-diuretics on the diurnal rhythms of calcitropic hormones and biochemical bone markers in postmenopausal women.
2001 Sep
Monitoring one-year compliance to antihypertension medication in the Seychelles.
2002
Double-blind, placebo-controlled crossover comparison of five classes of antihypertensive drugs.
2002 Apr
Von Willebrand factor, soluble P-selectin, and target organ damage in hypertension: a substudy of the Anglo-Scandinavian Cardiac Outcomes Trial (ASCOT).
2002 Jul
The effect of spray drying solutions of bendroflumethiazide/polyethylene glycol on the physicochemical properties of the resultant materials.
2003 Aug 27
The potential savings of using thiazides as the first choice antihypertensive drug: cost-minimisation analysis.
2003 Sep 8
Comparison of the effects of a 7-day period of non-compliance on blood pressure control using three different antihypertensive agents.
2004 Jul
Paradoxical antidiuretic effect of thiazides in diabetes insipidus: another piece in the puzzle.
2004 Nov
Ongoing clinical trials of the pleiotropic effects of statins.
2005
Physicochemical evaluation of PVP-thiazide diuretic interactions in co-spray-dried composites--analysis of glass transition composition relationships.
2005 Apr
Screening procedure for detection of diuretics and uricosurics and/or their metabolites in human urine using gas chromatography-mass spectrometry after extractive methylation.
2005 Aug
[Prevention of cardiovascular events by the antihypertensive treatment using amlodipine and perindopril in comparison with the use of atenolol and bendroflumethiazide. The ASCOT (Anglo-Scandinavian Outcomes Trail: blood pressure lowering arm) study results--multicentre, randomised, controlled trial. Landmark in the development of opinions on combination therapy in hypertension? (comment)].
2005 Dec
Aldosterone-to-renin ratio, arterial stiffness, and the response to aldosterone antagonism in essential hypertension.
2005 Jan
[Old or new antihypertensives--which are better?].
2005 Mar 31
ASCOT blood pressure-lowering arm--study of effects of two BP-lowering regimens in hypertensive patients with cardiovascular risk factors.
2005 Mar-Apr
[Cardiac arrest following treatment with non-cardiologic QT-interval-increasing medications].
2005 May 2
Prevention of cardiovascular events with an antihypertensive regimen of amlodipine adding perindopril as required versus atenolol adding bendroflumethiazide as required, in the Anglo-Scandinavian Cardiac Outcomes Trial-Blood Pressure Lowering Arm (ASCOT-BPLA): a multicentre randomised controlled trial.
2005 Sep 10-16
A review of Perindopril in the reduction of cardiovascular events.
2006
Efficacy and safety of 24 weeks of therapy with bendroflumethiazide 1.25 mg/day or 2.5 mg/day and potassium chloride compared with enalapril 10 mg/day and amlodipine 5 mg/day in patients with mild to moderate primary hypertension : a multicentre, randomised, open study.
2006
Amlodipine plus perindopril was better than atenolol plus bendroflumethiazide for reducing complications in hypertension.
2006 Apr
[The most recent study into blood pressure lowering by amlodipine: the beginning of the end for the beta-blockers].
2006 Apr 22
High-speed gas chromatography in doping control: fast-GC and fast-GC/MS determination of beta-adrenoceptor ligands and diuretics.
2006 Dec
Fracture risk and the use of a diuretic (indapamide SR) +/- perindopril: a substudy of the Hypertension in the Very Elderly Trial (HYVET).
2006 Dec 19
Carbonic anhydrase inhibitors ameliorate the symptoms of hypokalaemic periodic paralysis in rats by opening the muscular Ca2+-activated-K+ channels.
2006 Jan
Indirect laser-induced fluorescence detection of diuretics separated by capillary electrophoresis.
2006 Mar
Low-dose quadruple antihypertensive combination: more efficacious than individual agents--a preliminary report.
2007 Feb
Treatments with losartan or enalapril are equally sensitive to deterioration in renal function from cyclooxygenase inhibition.
2007 Feb
The spironolactone, amiloride, losartan, and thiazide (SALT) double-blind crossover trial in patients with low-renin hypertension and elevated aldosterone-renin ratio.
2007 Jul 17
A second corneal arcus?
2007 Mar
Flecainide cardiotoxicity precipitated by electrolyte imbalance. Caution with thiazide diuretics.
2007 May
Delayed cardiotoxicity in chronic lithium poisoning: discrepancy between serum lithium concentrations and clinical status.
2007 May
Does the aldosterone:renin ratio predict the efficacy of spironolactone over bendroflumethiazide in hypertension? A clinical trial protocol for RENALDO (RENin-ALDOsterone) study.
2007 May 9
Combined effect of solvent content, temperature and pH on the chromatographic behaviour of ionisable compounds.
2007 Sep 7
Pseudoneuropathic CPPD arthropathy: magnesium matters.
2008 Apr
Upregulation of apical sodium-chloride cotransporter and basolateral chloride channels is responsible for the maintenance of salt-sensitive hypertension.
2008 Aug
[Serious debate on unconventional treatment, thank you].
2008 Feb 25
The Sandwell Project: a controlled evaluation of a programme of targeted screening for prevention of cardiovascular disease in primary care.
2008 Feb 25
Acute angiotensin II infusions elicit pressure natriuresis in mice and reduce distal fractional sodium reabsorption.
2008 Jul
Burden and rates of treatment and control of cardiovascular disease risk factors in obesity: the Framingham Heart Study.
2008 Jul
Comparison of effects of combined ACE inhibitor and low-dose thiazide diuretic with ACE inhibitor alone on insulin action in patients with hypertension and Type 2 diabetes: a double-blind crossover study.
2008 May
Effective management of hypertension with dihydropyridine calcium channel blocker-based combination therapy in patients at high cardiovascular risk.
2008 May
Acetazolamide prevents vacuolar myopathy in skeletal muscle of K(+) -depleted rats.
2008 May
LC-high-resolution multiple stage spectrometric analysis of diuretic compounds Unusual mass fragmentation pathways.
2008 Sep 29
Patents

Patents

Sample Use Guides

In Vivo Use Guide
The initial dose of CORZIDE (Nadolol and Bendroflumethiazide Tablets) may therefore be the 40 mg/5 mg tablet once daily. When the antihypertensive response is not satisfactory, the dose may be increased by administering the 80 mg/5 mg tablet once daily. When necessary, another antihypertensive agent may be added gradually beginning with 50 percent of the usual recommended starting dose to avoid an excessive fall in blood pressure.
Route of Administration: Oral
In Vitro Use Guide
Incubation in vitro of human recombinant and erythrocyte (RBC) thiopurine methyl transferase (TPMT) with furosemide, bendroflumethiazide and trichlormethiazide demonstrated inhibition of both enzyme preparations, with IC50 values of 170 microM, 360 microM and 1 mM, respectively.
Name Type Language
BENDROFLUMETHIAZIDE
EP   HSDB   INN   JAN   MART.   MI   ORANGE BOOK   USP   USP-RS   VANDF   WHO-DD  
INN  
Official Name English
BENDROFLUMETHIAZIDE [MI]
Common Name English
BENDROFLUAZIDE
Common Name English
BENDROFLUMETHIAZIDE [HSDB]
Common Name English
BENDROFLUMETHIAZIDE [WHO-DD]
Common Name English
BENDROFLUMETHIAZIDE [VANDF]
Common Name English
BENDROFLUMETHIAZIDE [USP]
Common Name English
BENDROFLUMETHIAZIDE [INN]
Common Name English
BENDROFLUMETHIAZIDE [USP-RS]
Common Name English
BENDROFLUMETHIAZIDE [ORANGE BOOK]
Common Name English
NATURETIN
Brand Name English
BENDROFLUMETHIAZIDE COMPONENT OF CORZIDE
Common Name English
BENDROFLUMETHIAZIDE [EP]
Common Name English
BENDROFLUMETHIAZIDE [MART.]
Common Name English
2H-1,2,4-BENZOTHIADIAZINE-7-SULFONAMIDE, 3,4-DIHYDRO-3-(PHENYLMETHYL)-6-(TRIFLUOROMETHYL)-, 1,1-DIOXIDE, (+/-)-
Systematic Name English
(+/-)-3-BENZYL-3,4-DIHYDRO-6-(TRIFLUOROMETHYL)-2H-1,2,4-BENZOTHIADIAZINE-7-SULFONAMIDE 1,1-DIOXIDE
Systematic Name English
BENDROFLUMETHIAZIDE [JAN]
Common Name English
CORZIDE COMPONENT BENDROFLUMETHIAZIDE
Common Name English
Classification Tree Code System Code
NDF-RT N0000175359
Created by admin on Tue Oct 22 00:48:24 UTC 2019 , Edited by admin on Tue Oct 22 00:48:24 UTC 2019
NCI_THESAURUS C49185
Created by admin on Tue Oct 22 00:48:24 UTC 2019 , Edited by admin on Tue Oct 22 00:48:24 UTC 2019
WHO-VATC QC03EA13
Created by admin on Tue Oct 22 00:48:24 UTC 2019 , Edited by admin on Tue Oct 22 00:48:24 UTC 2019
NDF-RT N0000166469
Created by admin on Tue Oct 22 00:48:24 UTC 2019 , Edited by admin on Tue Oct 22 00:48:24 UTC 2019
WHO-ATC C03EA13
Created by admin on Tue Oct 22 00:48:24 UTC 2019 , Edited by admin on Tue Oct 22 00:48:24 UTC 2019
NDF-RT N0000175419
Created by admin on Tue Oct 22 00:48:24 UTC 2019 , Edited by admin on Tue Oct 22 00:48:24 UTC 2019
NDF-RT N0000166469
Created by admin on Tue Oct 22 00:48:24 UTC 2019 , Edited by admin on Tue Oct 22 00:48:24 UTC 2019
LIVERTOX 95
Created by admin on Tue Oct 22 00:48:24 UTC 2019 , Edited by admin on Tue Oct 22 00:48:24 UTC 2019
WHO-VATC QC03AA01
Created by admin on Tue Oct 22 00:48:24 UTC 2019 , Edited by admin on Tue Oct 22 00:48:24 UTC 2019
WHO-ATC C03AA01
Created by admin on Tue Oct 22 00:48:24 UTC 2019 , Edited by admin on Tue Oct 22 00:48:24 UTC 2019
WHO-VATC QC03AB01
Created by admin on Tue Oct 22 00:48:24 UTC 2019 , Edited by admin on Tue Oct 22 00:48:24 UTC 2019
WHO-ATC C03AB01
Created by admin on Tue Oct 22 00:48:24 UTC 2019 , Edited by admin on Tue Oct 22 00:48:24 UTC 2019
Code System Code Type Description
IUPHAR
7122
Created by admin on Tue Oct 22 00:48:24 UTC 2019 , Edited by admin on Tue Oct 22 00:48:24 UTC 2019
PRIMARY
CAS
73-48-3
Created by admin on Tue Oct 22 00:48:24 UTC 2019 , Edited by admin on Tue Oct 22 00:48:24 UTC 2019
PRIMARY
HSDB
73-48-3
Created by admin on Tue Oct 22 00:48:24 UTC 2019 , Edited by admin on Tue Oct 22 00:48:24 UTC 2019
PRIMARY
INN
994
Created by admin on Tue Oct 22 00:48:24 UTC 2019 , Edited by admin on Tue Oct 22 00:48:24 UTC 2019
PRIMARY
NCI_THESAURUS
C47410
Created by admin on Tue Oct 22 00:48:24 UTC 2019 , Edited by admin on Tue Oct 22 00:48:24 UTC 2019
PRIMARY
LactMed
73-48-3
Created by admin on Tue Oct 22 00:48:24 UTC 2019 , Edited by admin on Tue Oct 22 00:48:24 UTC 2019
PRIMARY
ECHA (EC/EINECS)
200-800-1
Created by admin on Tue Oct 22 00:48:24 UTC 2019 , Edited by admin on Tue Oct 22 00:48:24 UTC 2019
PRIMARY
EVMPD
SUB20550
Created by admin on Tue Oct 22 00:48:24 UTC 2019 , Edited by admin on Tue Oct 22 00:48:24 UTC 2019
PRIMARY
ChEMBL
CHEMBL1684
Created by admin on Tue Oct 22 00:48:24 UTC 2019 , Edited by admin on Tue Oct 22 00:48:24 UTC 2019
PRIMARY
DRUG BANK
DB00436
Created by admin on Tue Oct 22 00:48:24 UTC 2019 , Edited by admin on Tue Oct 22 00:48:24 UTC 2019
PRIMARY
MERCK INDEX
M2309
Created by admin on Tue Oct 22 00:48:24 UTC 2019 , Edited by admin on Tue Oct 22 00:48:24 UTC 2019
PRIMARY Merck Index
PUBCHEM
2315
Created by admin on Tue Oct 22 00:48:24 UTC 2019 , Edited by admin on Tue Oct 22 00:48:24 UTC 2019
PRIMARY
MESH
D001539
Created by admin on Tue Oct 22 00:48:24 UTC 2019 , Edited by admin on Tue Oct 22 00:48:24 UTC 2019
PRIMARY
WIKIPEDIA
BENDROFLUMETHIAZIDE
Created by admin on Tue Oct 22 00:48:24 UTC 2019 , Edited by admin on Tue Oct 22 00:48:24 UTC 2019
PRIMARY
EVMPD
SUB05711MIG
Created by admin on Tue Oct 22 00:48:24 UTC 2019 , Edited by admin on Tue Oct 22 00:48:24 UTC 2019
PRIMARY
RXCUI
1369
Created by admin on Tue Oct 22 00:48:24 UTC 2019 , Edited by admin on Tue Oct 22 00:48:24 UTC 2019
PRIMARY RxNorm
EPA CompTox
73-48-3
Created by admin on Tue Oct 22 00:48:24 UTC 2019 , Edited by admin on Tue Oct 22 00:48:24 UTC 2019
PRIMARY