bendroflumethiazide Indications/Contra | FAERs-F | FAERs-M | Orange Bk | BioActivity |

Stem definitionDrug idCAS RN
diuretics, chlorothiazide derivatives 305 73-48-3

Description:

MoleculeDescription

Molfile Inchi Smiles

Synonyms:

  • bendroflumethiazide
  • bendrofluazide
  • benzhydroflumethiazide
  • benzidroflumetiazide
  • benzydroflumethiazide
  • benzylhydroflumethiazide
  • benzylrodiuran
A thiazide diuretic with actions and uses similar to those of HYDROCHLOROTHIAZIDE. It has been used in the treatment of familial hyperkalemia, hypertension, edema, and urinary tract disorders. (From Martindale, The Extra Pharmacopoeia, 30th ed, p810)
  • Molecular weight: 421.41
  • Formula: C15H14F3N3O4S2
  • CLOGP: 1.73
  • LIPINSKI: 0
  • HAC: 7
  • HDO: 3
  • TPSA: 118.36
  • ALOGS: -3.29
  • ROTB: 4

  • Status: OFP

  • Legend:
    OFP - off patent
    OFM - off market
    ONP - on patent

Drug dosage:

DoseUnitRoute
2.50 mg O
2.50 mg O

ADMET properties:

PropertyValueReference
BDDCS (Biopharmaceutical Drug Disposition Classification System) 3 Benet LZ, Broccatelli F, Oprea TI
S (Water solubility) 0.11 mg/mL Benet LZ, Broccatelli F, Oprea TI
EoM (Fraction excreted unchanged in urine) 21 % Benet LZ, Broccatelli F, Oprea TI
MRTD (Maximum Recommended Therapeutic Daily Dose) 0.79 ┬ÁM/kg/day Contrera JF, Matthews EJ, Kruhlak NL, Benz RD
BA (Bioavailability) 90 % Kim MT, Sedykh A, Chakravarti SK, Saiakhov RD, Zhu H

Approvals:

DateAgencyCompanyOrphan
Dec. 7, 1959 FDA

FDA Adverse Event Reporting System (Female)

MedDRA adverse event termLikelihood ratioLikelihood ratio thresholdPatients taking drug having adverse eventPatients taking drug not having adverse eventPatients not taking drug having adverse eventPatients not taking drug not having adverse event
Hyponatraemia 639.42 78.02 117 178 13208 2344582
Acute kidney injury 167.59 78.02 46 249 28076 2329714
Hypokalaemia 145.70 78.02 34 261 10620 2347170
Confusional state 126.91 78.02 36 259 24308 2333482
Hypotension 112.42 78.02 35 260 32401 2325389
Vomiting 110.32 78.02 42 253 71560 2286230
Diarrhoea 104.01 78.02 42 253 83522 2274268
Fall 103.49 78.02 36 259 47063 2310727
Hypomagnesaemia 90.76 78.02 18 277 2546 2355244
Orthostatic hypotension 88.68 78.02 18 277 2861 2354929
Seizure 82.71 78.02 26 269 24440 2333350

FDA Adverse Event Reporting System (Male)

MedDRA adverse event termLikelihood ratioLikelihood ratio thresholdPatients taking drug having adverse eventPatients taking drug not having adverse eventPatients not taking drug having adverse eventPatients not taking drug not having adverse event
Hyponatraemia 326.77 66.72 69 223 8931 1737558
Acute kidney injury 168.28 66.72 54 238 34890 1711599
Confusional state 140.08 66.72 42 250 21236 1725253
Hypophagia 97.88 66.72 22 270 3475 1743014
Dehydration 94.97 66.72 30 262 17628 1728861

Pharmacologic Action:

SourceCodeDescription
ATC C03AA01 CARDIOVASCULAR SYSTEM
DIURETICS
LOW-CEILING DIURETICS, THIAZIDES
Thiazides, plain
ATC C03AB01 CARDIOVASCULAR SYSTEM
DIURETICS
LOW-CEILING DIURETICS, THIAZIDES
Thiazides and potassium in combination
ATC C03EA13 CARDIOVASCULAR SYSTEM
DIURETICS
DIURETICS AND POTASSIUM-SPARING AGENTS IN COMBINATION
Low-ceiling diuretics and potassium-sparing agents
FDA PE N0000175359 Increased Diuresis
FDA EPC N0000175419 Thiazide Diuretic
FDA Chemical/Ingredient N0000166469 Thiazides
MeSH PA D000959 Antihypertensive Agents
MeSH PA D002317 Cardiovascular Agents
MeSH PA D004232 Diuretics
MeSH PA D049990 Membrane Transport Modulators
MeSH PA D045283 Natriuretic Agents
CHEBI has role CHEBI:35498 diuretic
CHEBI has role CHEBI:35674 antihypertensive agent
MeSH PA D049993 Sodium Chloride Symporter Inhibitors

Drug Use (View source of the data)

DiseaseRelationSNOMED_IDDOID
Hypertensive disorder indication 38341003 DOID:10763
Anuria contraindication 2472002 DOID:2983
Bronchospasm contraindication 4386001
Hypercholesterolemia contraindication 13644009
Complete atrioventricular block contraindication 27885002
Depressive disorder contraindication 35489007
Hyperuricemia contraindication 35885006 DOID:1920
Anaphylaxis contraindication 39579001
Hypokalemia contraindication 43339004
Sinus bradycardia contraindication 49710005
Systemic lupus erythematosus contraindication 55464009 DOID:9074
Sympathectomy contraindication 57071006
Acute nephropathy contraindication 58574008
Hypercalcemia contraindication 66931009 DOID:12678
Hyperparathyroidism contraindication 66999008 DOID:13543
Hepatic coma contraindication 72836002 DOID:12550
Diabetes mellitus contraindication 73211009 DOID:9351
Oliguria contraindication 83128009
Pulmonary emphysema contraindication 87433001
Cardiogenic shock contraindication 89138009
Hyponatremia contraindication 89627008
Gout contraindication 90560007 DOID:13189
Kidney disease contraindication 90708001 DOID:557
Myasthenia gravis contraindication 91637004 DOID:437
Hypomagnesemia contraindication 190855004
Partial atrioventricular block contraindication 195039008
Decompensated cardiac failure contraindication 195111005
Acute pancreatitis contraindication 197456007 DOID:2913
Disease of liver contraindication 235856003 DOID:409
Raynaud's phenomenon contraindication 266261006
Neonatal hyperbilirubinemia contraindication 281610001
Pregnancy, function contraindication 289908002
Severe chronic obstructive pulmonary disease contraindication 313299006
Right ventricular failure contraindication 367363000

Acid dissociation constants calculated using MoKa v3.0.0

Dissociation levelDissociation constantType (acidic/basic)
pKa1 8.79 acidic
pKa2 10.52 acidic
pKa3 1.03 Basic

Orange Book patent data (new drug applications)

None

Orange Book exclusivity data (new drug applications)

None

Bioactivity Summary:

TargetClassPharosUniProtActionTypeActivity value
(-log[M])
Mechanism
action
Bioact sourceMoA source
Solute carrier family 12 member 3 Transporter INHIBITOR A2 8.30 WOMBAT-PK CHEMBL
Calcium-activated potassium channel subunit alpha-1 Ion channel WOMBAT-PK
Carbonic anhydrase 4 Enzyme WOMBAT-PK
Carbonic anhydrase 1 Enzyme WOMBAT-PK
Carbonic anhydrase 2 Enzyme WOMBAT-PK

External reference:

IDSource
D001539 MESH_DESCRIPTOR_UI
4017612 VUID
N0000145992 NUI
C0004975 UMLSCUI
D00650 KEGG_DRUG
5Q52X6ICJI UNII
994 INN_ID
91135008 SNOMEDCT_US
4017612 VANDF
3020 MMSL
1369 RXNORM
387520007 SNOMEDCT_US
4252 MMSL
d00641 MMSL
002297 NDDF
DB00436 DRUGBANK_ID
CHEMBL1684 ChEMBL_ID
CHEBI:3013 CHEBI
7122 IUPHAR_LIGAND_ID
2315 PUBCHEM_CID

Pharmaceutical products:

ProductCategoryIngredientsNDCFormQuantityRouteMarketingLabel
Nadolol and Bendroflumethiazide HUMAN PRESCRIPTION DRUG LABEL 2 0115-5311 TABLET 5 mg ORAL ANDA 12 sections
Nadolol and Bendroflumethiazide HUMAN PRESCRIPTION DRUG LABEL 2 0115-5322 TABLET 5 mg ORAL ANDA 12 sections