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HomeProduct name listTrichlormethiazide

Trichlormethiazide

Synonym(s):6-Chloro-3-(dichloromethyl)-3,4-dihydro-2H-1,2,4-benzothiadiazine-7-sulfonamide 1,1-dioxide
(+/-)-;NSC 61560

  • CAS NO.:133-67-5
  • Empirical Formula: C8H8Cl3N3O4S2
  • Molecular Weight: 380.66
  • MDL number: MFCD00057315
  • EINECS: 205-118-8
  • SAFETY DATA SHEET (SDS)
  • Update Date: 2024-11-05 11:59:05
Trichlormethiazide Structural

What is Trichlormethiazide?

Toxicity

Oral Rat LD50 = 5600 mg/kg, oral Mouse LD50 = 2600 mg/kg

Chemical properties

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

Originator

Naqua,Schering,US,1960

The Uses of Trichlormethiazide

diuretic, antihypertensive

The Uses of Trichlormethiazide

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).

The Uses of Trichlormethiazide

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.

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.

Indications

Used in the treatment of oedema (including that associated with heart failure) and hypertension.

Background

A thiazide diuretic with properties similar to those of hydrochlorothiazide. (From Martindale, The Extra Pharmacopoeia, 30th ed, p830)

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

Pharmacokinetics

Trichloromethiazide is indicated as adjunctive therapy in edema associated with congestive heart failure, hepatic cirrhosis, and corticosteroid and estrogen therapy. Trichloromethiazide has also been found useful in edema due to various forms of renal dysfunction such as nephrotic syndrome, acute glomer-ulonephritis, and chronic renal failure. Trichloromethiazide is also indicated in the management of hypertension either as the sole therapeutic agent or to enhance the effectiveness of other antihypertensive drugs in the more severe forms of hypertension. Like other thiazides, Trichloromethiazide 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.

Metabolism

Not Available

Properties of Trichlormethiazide

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)

Safety information for Trichlormethiazide

Signal word Danger
Pictogram(s)
ghs
Health Hazard
GHS08
GHS Hazard Statements H317:Sensitisation, Skin
H334:Sensitisation, respiratory
Precautionary Statement Codes P261:Avoid breathing dust/fume/gas/mist/vapours/spray.
P272:Contaminated work clothing should not be allowed out of the workplace.
P280:Wear protective gloves/protective clothing/eye protection/face protection.
P284:Wear respiratory protection.
P302+P352:IF ON SKIN: wash with plenty of soap and water.

Computed Descriptors for Trichlormethiazide

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