Chemistry:Bendroflumethiazide

Short description: Chemical compound

Bendroflumethiazide

Clinical data
AHFS/Drugs.com	Consumer Drug Information
Pregnancy category	Risk neonatal thrombocytopenia in 3rd trimester
Routes of administration	Oral
ATC code	C03AA01 (WHO)
Legal status
Legal status	UK: POM (Prescription only)
Pharmacokinetic data
Bioavailability	100%
Protein binding	96%
Metabolism	extensive
Elimination half-life	3-4 hours
Identifiers
IUPAC name 3-Benzyl-1,1-dioxo-6-(trifluoromethyl)-3,4-dihydro-2H-1,2,4- benzothiadiazine-7-sulfonamide
CAS Number	73-48-3 Y
PubChem CID	2315
IUPHAR/BPS	7122
DrugBank	DB00436 Y
ChemSpider	2225 Y
UNII	5Q52X6ICJI
KEGG	D00650 Y
ChEBI	CHEBI:3013 Y
ChEMBL	ChEMBL1684 Y
Chemical and physical data
Formula	C15H14F3N3O4S2
Molar mass	421.41 g·mol−1
3D model (JSmol)	Interactive image
SMILES FC(F)(F)c3c(cc1c(NC(NS1(=O)=O)Cc2ccccc2)c3)S(=O)(=O)N
InChI 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) Y Key:HDWIHXWEUNVBIY-UHFFFAOYSA-N Y
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Bendroflumethiazide, formerly bendrofluazide, trade name Aprinox, is a thiazide diuretic used to treat hypertension.

Bendroflumethiazide is a thiazide diuretic which works by inhibiting sodium reabsorption at the beginning of the distal convoluted tubule (DCT). Water is lost as a result of more sodium reaching the collecting ducts. Bendroflumethiazide has a role in the treatment of mild heart failure although loop diuretics are better for reducing overload. The main use of bendroflumethiazide currently is in hypertension (part of the effect is due to vasodilation).

It was patented in 1958 and approved for medical use in 1960.

Adverse effects

Common adverse effects:

• feeling dizzy due to orthostatic hypotension
• dry mouth or feeling thirsty
• nausea
• stomach ache
• fatigue
• diarrhea or constipation
• joint pain due to gout

Rare adverse effects:

• thrombocytopenia
• agranulocytosis
• photosensitivity rash
• pancreatitis
• chronic kidney disease

Alcohol

Bendroflumethiazide is known to have an adverse interaction with alcohol. It is advised that those using this diuretic should abstain from alcohol consumption during use, as it is possible to experience a sudden drop in blood pressure, especially if standing up (an effect known as orthostatic hypotension).

Other considerations

Bendroflumethiazide should not be used by pregnant women, or women who have just given birth. Due to the nature of the medication, it is possible for it to pass into the breast milk and consequently to the child. It is also known that bendroflumethiazide suppresses the production of breast milk. Pregnant or lactating women with hypertension may need to discuss with their prescriber as to which alternative treatment may be more suitable. Bendroflumethiazide may also impair the user's motor skills, therefore it is important to be aware of its effects and to take caution when operating machinery of driving.