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Trichlormethiazide

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Trichlormethiazide Basic information

Product Name:
Trichlormethiazide
Synonyms:
  • 6-CHLORO-3-DICHLOROMETHYL-3,4-DIHYDRO-2H-1,2,4-BENZOTHIADIAZINE-7-SULFONAMIDE 1,1-DIOXIDE
  • 6-chloro-3-(dichloromethyl)-3,4-dihydro-2h-1,2,4-benzothiadiazine-7-sulfonamid
  • 6-Chloro-3-(dichloromethyl)-3,4-dihydro-2H-1,2,4-thiadiazine-7-sulfonamide1,1-dioxide
  • 6-Chloro-3-(dichloromethyl)3,4-dihydro-7-sulfamoyl-1,2,4-benzothiadiazine-1,1-dioxide
  • 6-chloro-3-(dichloromethyl)3,4-dihydro-7-sulfamyl-1,2,4-benzothiadiazine-1,1
  • 6-Chloro-3-(dichloromethyl)3,4-dihydro-7-sulfamyl-1,2,4-benzothiadiazine-1,1-dioxide
  • 6-chloro-3-dichloromethyl-7-sulfamyl-3,4-dihydro-1,2,4-benzothiadiazine1,1-dio
  • Achletin
CAS:
133-67-5
MF:
C8H8Cl3N3O4S2
MW:
380.66
EINECS:
205-118-8
Product Categories:
  • METAHYDRIN
Mol File:
133-67-5.mol
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Trichlormethiazide Chemical Properties

Melting point:
248-250℃
Boiling point:
631.3±65.0 °C(Predicted)
Density 
1.748
refractive index 
1.6000 (estimate)
storage temp. 
Keep in dark place,Inert atmosphere,Room temperature
solubility 
DMSO (Slightly), Methanol (Slightly)
form 
Solid
pka
pKa 6.9(acetone/H2O) (Uncertain)
color 
White to Off-White
Merck 
14,9624
CAS DataBase Reference
133-67-5(CAS DataBase Reference)
EPA Substance Registry System
Trichlormethiazide (133-67-5)
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Safety Information

Hazard Codes 
Xn
Risk Statements 
42/43
Safety Statements 
36
WGK Germany 
2
RTECS 
DK8925000
HS Code 
2935904000
Hazardous Substances Data
133-67-5(Hazardous Substances Data)
Toxicity
LD50 orally in rats: >20000 mg/kg (Goldenthal)

MSDS

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Trichlormethiazide Usage And Synthesis

Chemical Properties

Trichlormethiazide occurs as a white or practically white, crystalline powder and may have a slight characteristic odor.

Originator

Naqua,Schering,US,1960

Uses

diuretic, antihypertensive

Uses

Trichlormethiazide, is a diuretic, having similar properties as Hydrochlorothiazide (H714560). It is used for the treatment of oedema (including that which is associated with heart failure, hepatic cirrhosis and corticosteroid therapy) and hypertension.

Uses

Trichlormethiazide is a diuretic and anti-hypertensive agent from the benzothiadiazide class which is used in veterinary medicine in cattle, sheep, goats, pigs and horses, at the following therapeutic regimen: a single intramuscular dose of 0.4 mg/kg bw followed by two oral doses of 0.8 mg/kg bw given 12 and 36 hours after the first administration.
Trichlormethiazide is also used in humans in the United States as a diuretic and anti-hypertensive substance but not in the European Union. The usual dose is 2 to 4 mg twice a day (i.e. approximately 0.033 to 0.066 mg/kg bw/day).

Definition

ChEBI: Trichlormethiazide is a benzothiadiazine, hydrogenated at positions 2, 3 and 4 and substituted with an aminosulfonyl group at C-7, a chloro substituent at C-6 and a dichloromethyl group at C-3 and with S-1 as an S,S-dioxide. A sulfonamide antibiotic, it is used as a diuretic to treat oedema (including that associated with heart failure) and hypertension. It has a role as a diuretic and an antihypertensive agent. It is a benzothiadiazine and a sulfonamide antibiotic.

Manufacturing Process

A mixture of 5.7 grams (0.02 mol) of 5-chloro-2,4-disulfamylaniline and 4.9 grams (0.04 mol) of dichloroacetaldehyde in 25 ml of dimethyl formamide was heated at the boiling temperature and under reflux for 30 minutes. The reaction mixture was thereafter poured into a mixture of ice and water to precipitate the desired 6-chloro-7-sulfamyl-3-dichloromethyl-3,4-dihydro- 1,2,4-benzothiadiazine-1,1-dioxide as a crystalline solid melting at 250° to 270°C with decomposition.

Therapeutic Function

Diuretic

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