BENZTHIAZIDE
- CAS NO.:91-33-8
- Empirical Formula: C15H14ClN3O4S3
- Molecular Weight: 431.94
- MDL number: MFCD00078969
- EINECS: 202-061-0
- SAFETY DATA SHEET (SDS)
- Update Date: 2024-11-19 20:33:22
What is BENZTHIAZIDE?
Absorption
Absorbed in the digestive tract.
Toxicity
Symptoms of overdose include nausea, vomiting, fatigue, urinary problems and drowsiness.
Originator
Exna,Robins,US,1960
The Uses of BENZTHIAZIDE
Benzthiazide is a diuretic, antihypertensive agent.
Background
Benzthiazide is used to treat hypertension and edema. Like other thiazides, benzthiazide promotes water loss from the body (diuretics). They inhibit Na+/Cl- reabsorption from the distal convoluted tubules in the kidneys. Thiazides also cause loss of potassium and an increase in serum uric acid. Thiazides are often used to treat hypertension, but their hypotensive effects are not necessarily due to their diuretic activity. Thiazides have been shown to prevent hypertension-related morbidity and mortality although the mechanism is not fully understood. Thiazides cause vasodilation by activating calcium-activated potassium channels (large conductance) in vascular smooth muscles and inhibiting various carbonic anhydrases in vascular tissue.
Indications
For the treatment of high blood pressure and management of edema.
Definition
ChEBI: 7-Sulfamoyl-1,2,4-benzothiadiazine 1,1-dioxide in which the hydrogen at position 6 is substituted by chlorine and that at position 3 is substituted by a benzylsulfanylmethyl group. A diuretic, it is used to treat hypertension and edema.
What are the applications of Application
Benzthiazide is a diuretic and antihypertensive compound
Manufacturing Process
The preparation of the dihydro analog is as follows:
(A) Preparation of 3-Chloromethyl-6-Chloro-7-Sulfamyl-3,4-DihydroBenzothiadizine-1,1-Dioxide - To 8 ml of 40-50% chloroacetaldehyde aqueous
solution and 7 ml of dimethylformamide are added 10 grams of 2,4-
disulfamyl-5-chloroaniline. The mixture is heated on a steam bath for 2 hours
after which it is concentrated at reduced pressure. The residue is triturated
with water. The solid material is recrystallized from methanol-ether after
treatment with activated carbon to give 7.2 grams of product, MP 229°-
230°C.
(B) Preparation of Benzylthiomethyl-6-Chloro-7-Sulfamyl-3,4-
Dihydrobenzothiadiazine-1,1-Dioxide - A mixture of 3-(chloromethyl)-6-chloro-
7-sulfamyl-3,4-dihydrobenzothiadiazine-1,1-dioxide (0.02 mol) and
benzylmercaptan (0.024 mol) in 20 ml of 10% sodium hydroxide and 20 ml of
dimethylformamide is stirred at room temperature for 6 hours. After heating
for 10 minutes on a steam bath, the mixture is cooled and acidified with 6 N
HCl. The product, after recrystallization from acetone, melts at 210°-211°C.
brand name
Aquatag (Solvay Pharmaceuticals); Fovane (Pfizer).
Therapeutic Function
Diuretic, Antihypertensive
Pharmacokinetics
Benzthiazide is used to treat hypertension and edema. Like other thiazides, benzthiazide promotes water loss from the body (diuretics). They inhibit Na+/Cl- reabsorption from the distal convoluted tubules in the kidneys. Thiazides also cause loss of potassium and an increase in serum uric acid. Thiazides are often used to treat hypertension, but their hypotensive effects are not necessarily due to their diuretic activity. Thiazides have been shown to prevent hypertension-related morbidity and mortality although the mechanism is not fully understood. Thiazides cause vasodilation by activating calcium-activated potassium channels (large conductance) in vascular smooth muscles and inhibiting various carbonic anhydrases in vascular tissue.
Safety Profile
Poison by intravenous route. Adiuretic and antihypertensive agent. When heated todecomposition it emits very toxic fumes of SOx, NOx, andCl-.
Metabolism
Not Available
Properties of BENZTHIAZIDE
Melting point: | 231-232° (U.S. patent); mp 238-239° (P'an) |
Boiling point: | 680.6±65.0 °C(Predicted) |
Density | 1.4176 (rough estimate) |
refractive index | 1.6100 (estimate) |
storage temp. | Refrigerator |
solubility | DMSO (Slightly), Methanol (Slightly) |
pka | 9.57±0.20(Predicted) |
form | Solid |
color | White to Off-White |
Water Solubility | 2.8mg/L(room temperature) |
EPA Substance Registry System | 2H-1,2,4-Benzothiadiazine-7-sulfonamide, 6-chloro-3-[[(phenylmethyl)thio]methyl]-, 1,1-dioxide (91-33-8) |
Safety information for BENZTHIAZIDE
Signal word | Danger |
Pictogram(s) |
Health Hazard GHS08 |
GHS Hazard Statements |
H317:Sensitisation, Skin H334:Sensitisation, respiratory |
Precautionary Statement Codes |
P261:Avoid breathing dust/fume/gas/mist/vapours/spray. P280:Wear protective gloves/protective clothing/eye protection/face protection. P342+P311:IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician. |
Computed Descriptors for BENZTHIAZIDE
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