bendroflumethiazide ๐Ÿถ Veterinary Use | 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: OFM

  • 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 ยตM/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 240.68 22.42 164 7944 95975 50501041
Confusional state 91.95 22.42 130 7978 185798 50411218
Lip swelling 85.96 22.42 52 8056 24684 50572332
Drug ineffective 84.58 22.42 15 8093 819318 49777698
Acute kidney injury 75.95 22.42 133 7975 227925 50369091
Mouth swelling 75.24 22.42 27 8081 3889 50593127
Disturbance in social behaviour 71.22 22.42 24 8084 2870 50594146
Hypokalaemia 59.71 22.42 72 8036 87920 50509096
Paranoia 55.69 22.42 29 8079 10319 50586697
Superinfection 50.39 22.42 17 8091 2039 50594977
Orthostatic hypotension 50.25 22.42 40 8068 29441 50567575
Ejection fraction decreased 49.52 22.42 33 8075 18487 50578529
Malaise 45.35 22.42 137 7971 335395 50261621
Agitation 45.18 22.42 49 8059 53335 50543681
Cellulitis 44.88 22.42 56 8052 70742 50526274
Pulmonary pain 44.62 22.42 16 8092 2299 50594717
Vomiting 42.87 22.42 166 7942 460592 50136424
Nail dystrophy 42.45 22.42 12 8096 799 50596217
Lethargy 41.18 22.42 45 8063 49387 50547629
Monoclonal B-cell lymphocytosis 40.85 22.42 7 8101 40 50596976
Femoral neck fracture 40.33 22.42 21 8087 7469 50589547
Disorientation 39.94 22.42 38 8070 35446 50561570
Hypersensitivity vasculitis 39.32 22.42 17 8091 3998 50593018
Duodenal ulcer repair 39.03 22.42 7 8101 54 50596962
Swelling face 38.90 22.42 45 8063 52550 50544466
Abnormal behaviour 36.37 22.42 28 8080 19630 50577386
Lower respiratory tract infection 36.18 22.42 59 8049 95142 50501874
Hallucination 34.63 22.42 40 8068 46617 50550399
Hypomagnesaemia 34.38 22.42 29 8079 23127 50573889
Myalgia 30.74 22.42 64 8044 124255 50472761
Neutropenic sepsis 30.29 22.42 22 8086 14125 50582891
Pustule 29.89 22.42 10 8098 1168 50595848
Cardiac ventricular thrombosis 29.14 22.42 8 8100 478 50596538
Pain 29.14 22.42 30 8078 578873 50018143
Emotional distress 27.25 22.42 28 8080 28635 50568381
Abnormal loss of weight 26.70 22.42 14 8094 5050 50591966
Fall 26.55 22.42 115 7993 334817 50262199
Hallucinations, mixed 26.46 22.42 13 8095 4090 50592926
Death 25.73 22.42 10 8098 325369 50271647
Blood magnesium decreased 25.37 22.42 18 8090 11142 50585874
Onychomadesis 25.21 22.42 12 8096 3524 50593492
Hypocalcaemia 25.13 22.42 26 8082 26790 50570226
Paraesthesia oral 23.91 22.42 18 8090 12203 50584813
Palpitations 23.76 22.42 49 8059 94457 50502559
Acute psychosis 23.72 22.42 10 8098 2210 50594806

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
Lip swelling 103.39 24.87 44 3793 12366 29558324
Hyponatraemia 88.85 24.87 72 3765 67561 29503129
Neutropenic sepsis 70.19 24.87 33 3804 11694 29558996
Acute kidney injury 61.49 24.87 117 3720 265150 29305540
Lethargy 43.00 24.87 37 3800 37543 29533147
Orthostatic hypotension 42.76 24.87 30 3807 22599 29548091
Confusional state 40.66 24.87 65 3772 127812 29442878
Liver function test abnormal 36.21 24.87 30 3807 28888 29541802
Daydreaming 35.80 24.87 9 3828 473 29570217
Drug dispensed to wrong patient 35.35 24.87 8 3829 267 29570423
Mixed dementia 35.29 24.87 8 3829 269 29570421
Wheezing 34.55 24.87 31 3806 33209 29537481
Diabetic ketoacidosis 31.97 24.87 22 3815 16051 29554639
Hallucination 26.84 24.87 31 3806 44681 29526009
Abnormal sleep-related event 26.48 24.87 7 3830 449 29570241
Jaundice 25.95 24.87 25 3812 29271 29541419
Faeces discoloured 25.91 24.87 18 3819 13333 29557357
Rash pruritic 25.52 24.87 22 3815 22341 29548349

FDA Adverse Event Reporting System (Geriatric)

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 355.75 20.65 262 11830 148077 64338563
Lip swelling 176.78 20.65 96 11996 31811 64454829
Confusional state 135.66 20.65 203 11889 260941 64225699
Acute kidney injury 118.59 20.65 260 11832 448980 64037660
Neutropenic sepsis 88.85 20.65 55 12037 23217 64463423
Lethargy 84.53 20.65 85 12007 72509 64414131
Orthostatic hypotension 80.24 20.65 68 12024 46670 64439970
Drug ineffective 76.80 20.65 31 12061 840216 63646424
Malaise 70.04 20.65 197 11895 396050 64090590
Mouth swelling 67.51 20.65 28 12064 5079 64481561
Disturbance in social behaviour 60.62 20.65 24 12068 3863 64482777
Swelling face 59.38 20.65 64 12028 59102 64427538
Hypokalaemia 57.79 20.65 91 12001 121812 64364828
Agitation 56.49 20.65 76 12016 88291 64398349
Hallucination 54.98 20.65 68 12024 72720 64413920
Pulmonary pain 51.21 20.65 19 12073 2565 64484075
Lower respiratory tract infection 51.01 20.65 75 12017 94539 64392101
Paranoia 43.82 20.65 31 12061 16321 64470319
Liver function test abnormal 42.47 20.65 54 12038 59347 64427293
Nail dystrophy 40.55 20.65 12 12080 801 64485839
Cellulitis 40.38 20.65 67 12025 93590 64393050
Vomiting 37.84 20.65 203 11889 550914 63935726
Death 37.58 20.65 22 12070 482683 64003957
Superinfection 37.29 20.65 17 12075 3869 64482771
Lid lag 36.97 20.65 7 12085 63 64486577
Duodenal ulcer repair 36.04 20.65 7 12085 73 64486567
Femoral neck fracture 34.26 20.65 21 12071 8703 64477937
Blood magnesium decreased 34.15 20.65 25 12067 13880 64472760
Wheezing 33.87 20.65 57 12035 80522 64406118
Atrioventricular block first degree 32.65 20.65 22 12070 10712 64475928
Ejection fraction decreased 32.26 20.65 33 12059 28674 64457966
Myalgia 32.05 20.65 83 12009 158534 64328106
Mixed dementia 31.99 20.65 8 12084 282 64486358
Giant cell arteritis 31.70 20.65 13 12079 2290 64484350
Acute psychosis 31.61 20.65 15 12077 3737 64482903
Pustule 30.63 20.65 11 12081 1354 64485286
Drug dispensed to wrong patient 29.91 20.65 8 12084 369 64486271
Abnormal loss of weight 29.53 20.65 18 12074 7382 64479258
Diabetic ketoacidosis 29.43 20.65 32 12060 29813 64456827
Weight increased 29.28 20.65 3 12089 213345 64273295
Hypersensitivity vasculitis 28.41 20.65 17 12075 6744 64479896
Hypomagnesaemia 28.33 20.65 35 12057 37341 64449299
Syncope 28.33 20.65 79 12013 157556 64329084
Fall 28.18 20.65 153 11939 416673 64069967
Daydreaming 27.89 20.65 9 12083 801 64485839
Swollen tongue 26.93 20.65 33 12059 34921 64451719
Disorientation 26.87 20.65 42 12050 55786 64430854
Paraesthesia oral 26.49 20.65 21 12071 13110 64473530
Completed suicide 26.48 20.65 5 12087 224409 64262231
Onychomadesis 25.74 20.65 12 12080 2872 64483768
Amnesia 25.61 20.65 38 12054 48231 64438409
Facial paralysis 25.40 20.65 24 12068 18942 64467698
Pain 24.86 20.65 41 12051 553470 63933170
Dyspnoea 24.42 20.65 223 11869 718451 63768189
Palpitations 23.53 20.65 57 12035 104431 64382209
Thirst 23.08 20.65 20 12072 14117 64472523
Toxicity to various agents 22.52 20.65 21 12071 363492 64123148
Groin pain 22.51 20.65 18 12074 11375 64475265
Gynaecomastia 22.40 20.65 14 12078 6002 64480638
Dizziness 22.08 20.65 147 11945 430016 64056624
Faeces discoloured 20.97 20.65 25 12067 25704 64460936
Hypocalcaemia 20.91 20.65 32 12060 41721 64444919
Rheumatoid arthritis 20.85 20.65 3 12089 164291 64322349

FDA Adverse Event Reporting System (Pediatric)

None

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 CS M0471776 Thiazides
FDA PE N0000175359 Increased Diuresis
FDA EPC N0000175419 Thiazide Diuretic
CHEBI has role CHEBI:35498 diuretics
CHEBI has role CHEBI:35674 antihypertensive drugs
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
MeSH PA D049993 Sodium Chloride Symporter Inhibitors

Drug Use | Suggest Off label Use Form| |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




๐Ÿถ Veterinary Drug Use

None

๐Ÿถ Veterinary products

None

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
Carbonic anhydrase 2 Enzyme WOMBAT-PK
Carbonic anhydrase 1 Enzyme WOMBAT-PK
Carbonic anhydrase 4 Enzyme WOMBAT-PK
Calcium-activated potassium channel subunit alpha-1 Ion channel WOMBAT-PK

External reference:

IDSource
4017612 VUID
N0000145992 NUI
D00650 KEGG_DRUG
1369 RXNORM
C0004975 UMLSCUI
CHEBI:59243 CHEBI
CHEMBL1684 ChEMBL_ID
D001539 MESH_DESCRIPTOR_UI
DB00436 DRUGBANK_ID
2315 PUBCHEM_CID
7122 IUPHAR_LIGAND_ID
994 INN_ID
5Q52X6ICJI UNII
3020 MMSL
4252 MMSL
d00641 MMSL
002297 NDDF
4017612 VANDF
387520007 SNOMEDCT_US
91135008 SNOMEDCT_US

Pharmaceutical products:

ProductCategoryIngredientsNDCFormQuantityRouteMarketingLabel
Nadolol and Bendroflumethiazide HUMAN PRESCRIPTION DRUG LABEL 2 0115-5311 TABLET 5 mg ORAL ANDA 25 sections
Nadolol and Bendroflumethiazide HUMAN PRESCRIPTION DRUG LABEL 2 0115-5322 TABLET 5 mg ORAL ANDA 25 sections