Bendroflumethiazide | CAS#73-48-3 | Diuretic

MedKoo Cat#: 317311 | Name: Bendroflumethiazide

Featured

Description:

WARNING: This product is for research use only, not for human or veterinary use.

Bendroflumethiazide is a thiazide diuretic used to treat hypertension. Bendroflumethiazide works by inhibiting sodium reabsorption at the beginning of the distal convoluted tubule and may play an important role in the treatment of mild heart failure.

Chemical Structure

Bendroflumethiazide

CAS#73-48-3

Theoretical Analysis

MedKoo Cat#: 317311

Name: Bendroflumethiazide

CAS#: 73-48-3

Chemical Formula: C15H14F3N3O4S2

Exact Mass: 421.0378

Molecular Weight: 421.41

Elemental Analysis: C, 42.75; H, 3.35; F, 13.52; N, 9.97; O, 15.19; S, 15.22

Price and Availability

Size	Price	Availability
100mg	USD 350.00	2 weeks
250mg	USD 650.00	2 weeks
1g	USD 950.00	2 Weeks

Bulk Inquiry

Buy Now

Add to Cart

Related CAS #

No Data

Synonym

Bendroflumethiazide; Aprinox; Be 724A; Bendrofluazide; Bentride; Benuron; Benzy-Rodiuran; Berkozide; Bristuron;Centyl;FT 81;Livesan; Naigaril; Naturetin; Neo-Rontyl; Niagaril; Orsile; Pluryl; Pluryle; Poliuron; Rauzide; Relan Beta; Salural; Sinesalin; Sodiuretic; Urlea;

IUPAC/Chemical Name

3-Benzyl-1,1-dioxo-6-(trifluoromethyl)-3,4-dihydro-2H-1,2,4- benzothiadiazine-7-sulfonamide

InChi Key

HDWIHXWEUNVBIY-UHFFFAOYSA-N

InChi Code

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)

SMILES Code

C1=CC=C(C=C1)CC2NC3=C(C=C(C(=C3)C(F)(F)F)S(=O)(=O)N)S(=O)(=O)N2

Appearance

Solid powder

Purity

>98% (or refer to the Certificate of Analysis)

Shipping Condition

Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition

Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility

Soluble in DMSO, not in water

Shelf Life

>2 years if stored properly

Drug Formulation

This drug may be formulated in DMSO

Stock Solution Storage

0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code

2934.99.9001

More Info

Product Data

Product Data

Instruction

View handling instruction

Biological target:

Bendroflumethiazide is a diuretic which inhibits sodium reabsorption at the beginning of the distal convoluted tubule.

In vitro activity:

Simultaneous specific and nonspecific binding of bendroflumethiazide (BFZ) to human serum albumin (HSA) and concentration profile of BFZ in HSA buffer (pH 7.40) solution were investigated by ¹⁹F nuclear magnetic resonance (NMR) method. The ¹⁹F NMR spectrum of BFZ (200 μM) in a buffer solution showed a sharp signal of its CF₃ group at 17.8 ppm from the reference trifluoroethanol. Addition of 0.60mM HSA to the sample solution caused the CF(3) signal splitting into three broadened peaks at 18.4 (A), 17.9 (B) and 17.4 ppm (C). By its chemical shift and spectral behavior, B was assigned to unbound BFZ. Competition experiments with Site I and II ligands lead to C being assigned to Site II bound BFZ. However, the peak intensity (areas) of A was not reduced by these ligands, suggesting that A arises from nonspecific binding. Using the peak intensities at several total concentrations of BFZ, Scatchard plot was performed. The plot for A provided a straight line parallel to the x-axis confirming nonspecific binding and that for C was consistent with specific binding. The binding constants for nonspecific and specific Site II binding were 1.02 and 1.00 × 10⁴ (M⁻¹) (n=1.1), respectively. The presence of 0.10 M Cl⁻ in the sample solution affected the binding constant of Site II binding, but not that of nonspecific binding. The concentration profile of BFZ calculated using the binding constants revealed that nonspecific binding is more effective than Site II binding for the binding of BFZ to HSA. It was also confirmed that considerable amounts of BFZ liberated from Site II by the Site II ligands or Cl⁻ ions bind again nonspecifically. Reference: Eur J Pharm Sci. 2012 Jan 23;45(1-2):195-200. https://www.sciencedirect.com/science/article/abs/pii/S0928098711004155?via%3Dihub

In vivo activity:

Whether the direct and indirect actions of bendroflumethiazide (BFTZ) simultaneously cooperated and also whether the renal nerves were involved in inducing long-term antidiuresis in nephrogenic diabetes insipidus (NDI) was investigated. BFTZ or vehicle was gavaged into bilateral renal denervated and innervated rats with lithium-induced NDI for 10 days, constituting four groups. At one day before (D0) and one, five and ten days after starting administration of BFTZ or vehicle, rats were placed in metabolic cages to collect urine for 6 hours. BFTZ-treatment in both renal innervated and denervated rats caused equivalent reductions in urine-flow, creatinine clearance, lithium clearance and free-water clearance, but rises in urine-osmolality, fractional proximal reabsorption and fractional distal reabsorption at all days compared to D0, as well as to those of their relevant vehicle-received group. Therefore, the chronic antidiuretic response to BFTZ in conscious NDI rats was exerted through a concomitant cooperation of its direct distal effect of stimulating water-reabsorption and its indirect effect of reducing distal fluid-delivery by activating volume-homeostatic mechanisms, which appeared independent of the renal nerves. Reference: Acta Physiol Hung. 2014 Mar;101(1):88-102. https://pubmed.ncbi.nlm.nih.gov/24631797/

	Solvent	mg/mL	mM
Solubility
	DMF	10.0	23.73
	DMF:PBS (pH 7.2) (1:1)	0.5	1.19
	DMSO	10.0	23.73
	Ethanol	2.0	4.74

Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 421.41 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

Formulation protocol:

1. Kitamura K, Niinobu M, Omran AA, Takegami S, Kitade T. Binding of diuretic antihypertensive bendroflumethiazide to human serum albumin studied by ¹⁹F nuclear magnetic resonance method. Eur J Pharm Sci. 2012 Jan 23;45(1-2):195-200. doi: 10.1016/j.ejps.2011.11.010. Epub 2011 Nov 17. PMID: 22115868. 2. Moosavi SM, Karimi Z. Cooperative mechanisms involved in chronic antidiuretic response to bendroflumethiazide in rats with lithium-induced nephrogenic diabetes insipidus. Acta Physiol Hung. 2014 Mar;101(1):88-102. doi: 10.1556/APhysiol.101.2014.1.10. PMID: 24631797.

In vitro protocol:

In vivo protocol:

1. Moosavi SM, Karimi Z. Cooperative mechanisms involved in chronic antidiuretic response to bendroflumethiazide in rats with lithium-induced nephrogenic diabetes insipidus. Acta Physiol Hung. 2014 Mar;101(1):88-102. doi: 10.1556/APhysiol.101.2014.1.10. PMID: 24631797.

1: Jensen JM, Mose FH, Kulik AE, Bech JN, Fenton RA, Pedersen EB. Changes in urinary excretion of water and sodium transporters during amiloride and bendroflumethiazide treatment. World J Nephrol. 2015 Jul 6;4(3):423-37. doi: 10.5527/wjn.v4.i3.423. PubMed PMID: 26167467; PubMed Central PMCID: PMC4491934. 2: Moosavi SM, Karimi Z. Cooperative mechanisms involved in chronic antidiuretic response to bendroflumethiazide in rats with lithium-induced nephrogenic diabetes insipidus. Acta Physiol Hung. 2014 Mar;101(1):88-102. doi: 10.1556/APhysiol.101.2014.1.10. PubMed PMID: 24631797. 3: Peterzan MA, Hardy R, Chaturvedi N, Hughes AD. Meta-analysis of dose-response relationships for hydrochlorothiazide, chlorthalidone, and bendroflumethiazide on blood pressure, serum potassium, and urate. Hypertension. 2012 Jun;59(6):1104-9. doi: 10.1161/HYPERTENSIONAHA.111.190637. Epub 2012 Apr 30. PubMed PMID: 22547443. 4: Kitamura K, Niinobu M, Omran AA, Takegami S, Kitade T. Binding of diuretic antihypertensive bendroflumethiazide to human serum albumin studied by ¹⁹F nuclear magnetic resonance method. Eur J Pharm Sci. 2012 Jan 23;45(1-2):195-200. doi: 10.1016/j.ejps.2011.11.010. Epub 2011 Nov 17. PubMed PMID: 22115868. 5: Moosavi SM, Haghani M. Cooperative mechanisms of acute antidiuretic response to bendroflumethiazide in rats with lithium-induced nephrogenic diabetes insipidus. Can J Physiol Pharmacol. 2010 Dec;88(12):1191-201. doi: 10.1139/Y10-098. Erratum in: Can J Physiol Pharmacol. 2011 Jan;89(1):77. PubMed PMID: 21164566. 6: Healy AM, McDonald BF, Tajber L, Corrigan OI. Characterisation of excipient-free nanoporous microparticles (NPMPs) of bendroflumethiazide. Eur J Pharm Biopharm. 2008 Aug;69(3):1182-6. doi: 10.1016/j.ejpb.2008.04.020. Epub 2008 Apr 30. PubMed PMID: 18595674. 7: Fabbiani FP, Leech CK, Shankland K, Johnston A, Fernandes P, Florence AJ, Shankland N. Hirshfeld surface analysis of two bendroflumethiazide solvates. Acta Crystallogr C. 2007 Nov;63(Pt 11):o659-63. Epub 2007 Oct 24. PubMed PMID: 17989490. 8: Parthasarathy HK, Alhashmi K, McMahon AD, Struthers AD, Connell JM, McInnes GT, Ford I, MacDonald TM. Does the aldosterone:renin ratio predict the efficacy of spironolactone over bendroflumethiazide in hypertension? A clinical trial protocol for RENALDO (RENin-ALDOsterone) study. BMC Cardiovasc Disord. 2007 May 9;7:14. PubMed PMID: 17490489; PubMed Central PMCID: PMC1877813. 9: Zarnke KB. Amlodipine plus perindopril was better than atenolol plus bendroflumethiazide for reducing complications in hypertension. Evid Based Med. 2006 Apr;11(2):42. PubMed PMID: 17213072. 10: Rasmussen S, Borrild N, Vang Andersen J. 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. Clin Drug Investig. 2006;26(2):91-101. PubMed PMID: 17163239. 11: Zarnke KB. Amlodipine plus perindopril was better than atenolol plus bendroflumethiazide for reducing complications in hypertension. ACP J Club. 2006 Mar-Apr;144(2):32. PubMed PMID: 16539347. 12: Widimský J Jr. [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)]. Vnitr Lek. 2005 Dec;51(12):1394-6, 1398-9. Czech. PubMed PMID: 16430107. 13: Dahlöf B, Sever PS, Poulter NR, Wedel H, Beevers DG, Caulfield M, Collins R, Kjeldsen SE, Kristinsson A, McInnes GT, Mehlsen J, Nieminen M, O'Brien E, Ostergren J; ASCOT Investigators. 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. Lancet. 2005 Sep 10-16;366(9489):895-906. PubMed PMID: 16154016. 14: Pang YH, Yang LL, Shuang SM, Dong C, Thompson M. Interaction of human serum albumin with bendroflumethiazide studied by fluorescence spectroscopy. J Photochem Photobiol B. 2005 Aug 1;80(2):139-44. PubMed PMID: 15916901. 15: Nederfors T, Nauntofte B, Twetman S. Effects of furosemide and bendroflumethiazide on saliva flow rate and composition. Arch Oral Biol. 2004 Jul;49(7):507-13. PubMed PMID: 15126132. 16: Corrigan DO, Healy AM, Corrigan OI. The effect of spray drying solutions of bendroflumethiazide/polyethylene glycol on the physicochemical properties of the resultant materials. Int J Pharm. 2003 Aug 27;262(1-2):125-37. PubMed PMID: 12927394. 17: Janjua NR, Jonassen TE, Langhoff S, Thomsen K, Christensen S. Role of sodium depletion in acute antidiuretic effect of bendroflumethiazide in rats with nephrogenic diabetes insipidus. J Pharmacol Exp Ther. 2001 Oct;299(1):307-13. PubMed PMID: 11561093. 18: Kristensen KS, Wiinberg N, Høegholm A, Kornerup HJ, Svendsen TL, Mølby L, Pindborg T, Nielsen PE. Benazepril versus felodipine as supplement to bendroflumethiazide: evaluation by office and ambulatory blood pressure. Blood Press Monit. 1998 Apr;3(2):115-120. PubMed PMID: 10212340. 19: Grønbeck L, Marples D, Nielsen S, Christensen S. Mechanism of antidiuresis caused by bendroflumethiazide in conscious rats with diabetes insipidus. Br J Pharmacol. 1998 Feb;123(4):737-45. PubMed PMID: 9517394; PubMed Central PMCID: PMC1565211. 20: Spannow J, Thomsen K, Petersen JS, Haugan K, Christensen S. Influence of renal nerves and sodium balance on the acute antidiuretic effect of bendroflumethiazide in rats with diabetes insipidus. J Pharmacol Exp Ther. 1997 Sep;282(3):1155-62. PubMed PMID: 9316821.