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BENDROFLUMETHIAZIDE

Basic information Safety Supplier Related

BENDROFLUMETHIAZIDE Basic information

Product Name:
BENDROFLUMETHIAZIDE
Synonyms:
  • BENDROFLUMETHIAZIDE
  • BENDROFLUMETHIAZIDE-D5
  • 1,1-dioxo-3-(phenylmethyl)-6-(trifluoromethyl)-3,4-dihydro-2H-benzo[e][1,2,4]thiadiazine-7-sulfonamide
  • 3-(benzyl)-1,1-diketo-6-(trifluoromethyl)-3,4-dihydro-2H-benzo[e][1,2,4]thiadiazine-7-sulfonamide
  • rac Bendroflumethiazide
  • Bendroflumethiazide (200 mg)
  • Bendroflumethiazide (200 mg)H0C4020.994mg/mg(ai)
  • 6-trifluoromethyl-3-benzyl-7-sulfamyl-3,4-dihydro-1,2,4-benzothiadiazine,1,1
CAS:
73-48-3
MF:
C15H14F3N3O4S2
MW:
421.41
EINECS:
200-800-1
Product Categories:
  • Isotope
  • BISOLVON
  • Aromatics
  • Heterocycles
  • Intermediates & Fine Chemicals
  • Pharmaceuticals
  • Sulfur & Selenium Compounds
Mol File:
73-48-3.mol
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BENDROFLUMETHIAZIDE Chemical Properties

Melting point:
205-207°C
Boiling point:
602.1±65.0 °C(Predicted)
Density 
1.4711 (estimate)
storage temp. 
Refrigerator
solubility 
Practically insoluble in water, freely soluble in acetone, soluble in ethanol (96 per cent).
form 
neat
pka
pKa 8.53±0.05(H2O t=25 I=0.2) (Uncertain)
color 
Crystals from MeOH/CHCl3
Water Solubility 
40mg/L(room temperature)
EPA Substance Registry System
2H-1,2,4-Benzothiadiazine-7-sulfonamide, 3,4-dihydro-3-(phenylmethyl)-6-(trifluoromethyl)-, 1,1-dioxide (73-48-3)
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Safety Information

WGK Germany 
2
RTECS 
DK8225000
HS Code 
2935904000
Toxicity
LD50 oral in mouse: > 10gm/kg

MSDS

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BENDROFLUMETHIAZIDE Usage And Synthesis

Chemical Properties

White Solid

Originator

Naturetin,Squibb,US,1959

Uses

Bendroflumethiazide may be used for the same indications as the aforementioned drugs; however, it is primarily used as an adjuvant agent for relieving edema associated with cardiac insufficiency, liver cirrhosis, and edema caused by taking corticosteroids.

Uses

Diuretic; antihypertensive.

Uses

expectorant

Definition

ChEBI: A sulfonamide consisting of 7-sulfamoyl-3,4-dihydro-2H-1,2,4-benzothiadiazine 1,1-dioxide in which the hydrogen at position 6 is substituted by a trifluoromethyl group and that at position 3 is substituted by a benzyl group.

Manufacturing Process

The process is described in US Patent 3,392,168 as follows:
(A) Preparation of 5-Trifluoromethylaniline-2,4-Disulfonylchloride - 113 ml of chlorosulfonic acid is cooled in an ice bath, and to the acid is added dropwise while stirring 26.6 grams of α,α,α-trifluoro-m-toluidine. 105 grams of sodium chloride is added during 1-2 hours, where after the temperature of the reaction mixture is raised slowly to 150° - 160°C which temperature is maintained for three hours. After cooling the mixture, ice-cooled water is added, whereby 5-trifluoromethylaniline-2,4-disulfonyl chloride separates out from the mixture.
(B) Preparation of 5-Trifluoromethyl-2,4-Disulfamylaniline - The 5- trifluoromethylaniline-2,4-disulfonyl chloride obtained in step (A) is taken up in ether and the ether solution dried with magnesium sulfate. The ether is removed from the solution by distillation, the residue is cooled to 0°, and 60 ml of ice-cooled, concentrated ammonia water is added while stirring. The solution is then heated for one hour on a steam bath and evaporated in vacuo to crystallization. The crystallized product is 5-trifluoromethyl-2,4- disulfamylaniline, which is filtered off, washed with water and dried in a vacuum-desiccator over phosphorus pentoxide. After recrystallization from a mixture of 30% ethanol and 70% water, the compound has a MP of 247°- 248°C.
(C) Preparation of 3-Benzyl-6-Trifluoromethyl-7-Sulfarnyl-3,4-Dihydro-1,2,4- Benzothiadiazine-1,1-Dioxide - 6.4 grams of 5-trifluoromethyl-2,4- disulfamylaniline is dissolved in 12 ml of dioxane, 2.7 ml of phenylacetaldehyde and a catalytic amount of p-toluenesulfonic acid are added. After boiling for a short time under reflux, the reaction mixture crystallizes, and, after filtration and recrystallization from dioxane, the desired product is obtained with a MP of 224.5°-225.5°C.
(D) Alternative to (C) - 9.6 grams of 5-trifluoromethyl-2,4-disulfarnylaniline and 4.9 grams of ω-ethoxystyrene are dissolved in 35 ml of n-butanol. 0.5 grams of p-toluenesulfonic acid is added, and the mixture is heated on a steam bath while stirring. When the solution is clear, 55 ml of hexane is added, whereafter the mixture is heated further for one and a half hours. After cooling, the substance identical to that of Example (C) is filtered off and has a MP of 222°-223°C.
Sterile compositions containing Bendroflumethiazide for parenteral administration may be prepared as described in US Patent 3,265,573.

brand name

Naturetin (Apothecon).

Therapeutic Function

Diuretic, Antihypertensive

Safety Profile

Poison by intravenous route.Human systemic effects by ingestion: convulsions andsomnolence. Mutation data reported. When heated todecomposition it emits toxic fumes of F-, SOx, and NOx.

Chemical Synthesis

Bendroflumethiazide, 1,1-dioxide 3-benzyl-6-(trifluoromethyl)- 3,4-dihydro-2H-1,2,4-benzothiadiazin-7-sulfonamide (21.3.6), is synthesized by the same scheme of making the aforementioned drugs using phenylacetaldehyde or its acetale as a carbonyl component, and using 2,4-disulfonamido-5-trifluoromethylaniline (21.3.5) as an o-aminosulfonamide component.

BENDROFLUMETHIAZIDE Preparation Products And Raw materials

Raw materials

BENDROFLUMETHIAZIDESupplier

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