bendroflumethiazide

Trade name: naturetin

Small moleculeapproved

Approved

Dec 7, 1959

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. — NCATS

Clinical trial activity

5 trials · 6 clinical orgs · 5 marketing orgs

Phase 1
2
Phase 2
0
Phase 3
0
Phase 4
1

Earliest trial started Dec 1, 1997 (NCT02235402)

Timeline

1950s

  1. Dec 7, 1959

    Apothecon — Earliest FDA Approval

  2. Dec 7, 1959

    Apothecon — NDA Secondary Org

  3. Dec 7, 1959

    Apothecon — NDA Organization

1980s

  1. May 25, 1983

    King Pharmaceuticals — Marketing Organization

  2. May 25, 1983

    King Pharmaceuticals — NDA Secondary Org

2000s

  1. Jan 1, 2006

    Mylan — Earliest Phase 1 Sponsor(trial)

  2. Mar 30, 2007

    Impax Laboratories — Marketing Organization

  3. Feb 15, 2008

    Natco Pharma — Marketing Organization

  4. Feb 15, 2008

    Mylan — Marketing Organization

Indications

Approved for

Mechanism of action

Combination products

Approval history

  • approvedDec 7, 1959

Chemistry & pharmacology

Loading structure…

SMILES

NS(=O)(=O)C1=CC2=C(NC(CC3=CC=CC=C3)NS2(=O)=O)C=C1C(F)(F)F
Mol. weight
421.415 g/mol
Lipinski Ro5
Pass
Rule of 3
No
Chirality
Racemic Mixture
Inorganic
No
Polymer
No
Delivery
Oral
Availability
Discontinued

Oral

Yes

Parenteral

No

Topical

No

Sources

Also known as

  • +--3-benzyl-3,4-dihydro-6-(trifluoromethyl)-2h-1,2,4-benzothiadiazine-7-sulfonamide 1,1-dioxide
  • +--3-benzyl-3,4-dihydro-6-(trifluoromethyl)-2h-1,2,4-benzothiadiazine-7-sulfonamide 1,1-dioxide
  • 6-trifluoromethyl-3-benzyl-7-sulfamyl-3,4-dihydro-1,2,4-benzothiadiazine 1,1-dioxide
  • 6-trifluoromethyl-3-benzyl-7-sulfamyl-3,4-dihydro-1,2,4-benzothiadiazine 1,1-dioxide
  • aprinox
  • aprinox
  • bendrofluazide
  • bendrofluazide
  • bendrofluazide
  • bendrofluazide
  • bendrofluazide
  • bendroflumethiazid
  • bendroflumethiazid
  • bendroflumethiazide
  • bendroflumethiazide
  • bendroflumethiazide
  • bendroflumethiazide
  • bendroflumethiazide
  • bendroflumethiazide
  • bendroflumethiazide
  • bendroflumethiazide
  • bendroflumethiazide
  • bendroflumethiazide
  • bendroflumethiazide
  • bendrofluméthiazide
  • bendrofluméthiazide
  • bendroflumethiazidum
  • bendroflumethiazidum
  • bendroflumetiazida
  • bendroflumetiazida
  • benzhydroflumethiazide
  • benzhydroflumethiazide
  • benzhydroflumethiazide
  • benzidroflumetiazide
  • benzydroflumethiazide
  • benzydroflumethiazide
  • benzydroflumethiazide
  • benzylhydroflumethiazide
  • benzylrodiuran
  • berkozide
  • berkozide
  • centyl
  • centyl
  • nadolol/bendroflumethiazide
  • naturetin
  • naturetin
  • naturetin
  • naturetin-10
  • naturetin-10
  • naturetin-2.5
  • naturetin-2.5
  • naturetin-5
  • naturetin-5
  • neo-bendromax 2.5
  • neo-bendromax 5
  • neo-naclex
  • neo-naclex
  • urizide

Clinical trials

NCT IDPhaseStart dateSponsor(s)
NCT00429897N/AAug 1, 2006British Heart Foundation, University of Cambridge
NCT00648297Phase 1Aug 1, 2006Mylan, PRACS
NCT00647660Phase 1Jul 1, 2006Mylan, PRACS
NCT00518479N/ASep 1, 2003University of Leeds
NCT02235402Phase 4Dec 1, 1997Boehringer Ingelheim
Showing 5 of 5 trials
Page 1 / 1

Organizations

Research & Development (6)

OrganizationOrg typeTrialsAs lead sponsorPhasesEarliest year
MylanFor profit2212006
PRACSFor profit2012006
Boehringer IngelheimFor profit1111997
British Heart FoundationAcademic/Hospital1012006
University of CambridgeAcademic/Hospital1112006
University of LeedsAcademic/Hospital1112003
6 organizations
Page 1 / 1

Marketing (7)

OrganizationOrg typeRelationshipDate
ApotheconFor profitNDA2Dec 7, 1959
ApotheconFor profitNDADec 7, 1959
Impax LaboratoriesFor profitMKTGMar 30, 2007
King PharmaceuticalsFor profitMKTGMay 25, 1983
King PharmaceuticalsFor profitNDA2May 25, 1983
MylanFor profitMKTGFeb 15, 2008
Natco PharmaFor profitMKTGFeb 15, 2008