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

Stem definition	Drug id	CAS RN
diuretics, chlorothiazide derivatives	305	73-48-3

Description:

Molecule	Description
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

Molecule

Description

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:

Dose	Unit	Route
2.50	mg	O
2.50	mg	O

ADMET properties:

Property	Value	Reference
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 µM/kg/day	Contrera JF, Matthews EJ, Kruhlak NL, Benz RD
BA (Bioavailability)	90 %	Kim MT, Sedykh A, Chakravarti SK, Saiakhov RD, Zhu H

Approvals:

Date	Agency	Company	Orphan
Dec. 7, 1959	FDA

FDA Adverse Event Reporting System (Female)

MedDRA adverse event term	Likelihood ratio	Likelihood ratio threshold	Patients taking drug having adverse event	Patients taking drug not having adverse event	Patients not taking drug having adverse event	Patients 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 term	Likelihood ratio	Likelihood ratio threshold	Patients taking drug having adverse event	Patients taking drug not having adverse event	Patients not taking drug having adverse event	Patients 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 term	Likelihood ratio	Likelihood ratio threshold	Patients taking drug having adverse event	Patients taking drug not having adverse event	Patients not taking drug having adverse event	Patients 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:

Source	Code	Description
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|

Disease	Relation	SNOMED_ID	DOID
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

🐶 Veterinary Drug Use

None

🐶 Veterinary products

None

Acid dissociation constants calculated using MoKa v3.0.0

Dissociation level	Dissociation constant	Type (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:

Target	Class	Pharos	UniProt	Action	Type	Activity value (-log[M])	Bioact source	MoA source
Solute carrier family 12 member 3	Transporter	P55017	S12A3_HUMAN	INHIBITOR	A2	8.30	WOMBAT-PK	CHEMBL
Carbonic anhydrase 2	Enzyme	P00918	CAH2_HUMAN				WOMBAT-PK
Carbonic anhydrase 1	Enzyme	P00915	CAH1_HUMAN				WOMBAT-PK
Carbonic anhydrase 4	Enzyme	P22748	CAH4_HUMAN				WOMBAT-PK
Calcium-activated potassium channel subunit alpha-1	Ion channel	Q12791	KCMA1_HUMAN				WOMBAT-PK

External reference:

ID	Source
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:

Product	Category	Ingredients	NDC	Form	Quantity	Route	Marketing	Label
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