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Chlorothiazide

CAS No.
58-94-6
Chemical Name:
Chlorothiazide
Synonyms
Diuril;Flumen;Minzil;Urinex;Alurene;Diupres;Diurite;Diutrid;Salisan;Salunil
CBNumber:
CB6756754
Molecular Formula:
C7H6ClN3O4S2
Molecular Weight:
295.72
MDL Number:
MFCD00058576
MOL File:
58-94-6.mol
MSDS File:
SDS
Last updated:2023-09-01 18:47:01

Chlorothiazide Properties

Melting point 342-343°C
Boiling point 608.8±65.0 °C(Predicted)
Density 1.7303 (rough estimate)
refractive index 1.6100 (estimate)
storage temp. 2-8°C
solubility DMSO (Slightly), Methanol (Very Slightly, Heated)
pka 6.85, 9.45(at 25℃)
color White to Off-White
Water Solubility <0.1 g/100 mL at 19.5 ºC
Merck 14,2168
BCS Class 4
Stability Stable. Incompatible with strong oxidizing agents.
LogP -0.240
CAS DataBase Reference 58-94-6(CAS DataBase Reference)
EWG's Food Scores 1
FDA UNII 77W477J15H
NIST Chemistry Reference Chlorothiazide(58-94-6)
ATC code C03AA04,C03AH01
EPA Substance Registry System Chlorothiazide (58-94-6)

SAFETY

Risk and Safety Statements

Symbol(GHS)  GHS hazard pictograms
GHS08
Signal word  Danger
Hazard statements  H317-H334
Precautionary statements  P261-P272-P280-P284-P302+P352-P304+P340+P312
Hazard Codes  Xn
Risk Statements  42/43-20/21/22
Safety Statements  36
WGK Germany  2
RTECS  DK9450000
HS Code  2935904000

Chlorothiazide price More Price(29)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich C4911 Chlorothiazide thiazide diuretic 58-94-6 50g $152.4 2024-03-01 Buy
Sigma-Aldrich 1121005 Chlorothiazide United States Pharmacopeia (USP) Reference Standard 58-94-6 200mg $436 2024-03-01 Buy
Sigma-Aldrich BP076 Chlorothiazide British Pharmacopoeia (BP) Reference Standard 58-94-6 100MG $243 2022-05-15 Buy
Cayman Chemical 17909 Chlorothiazide ≥95% 58-94-6 1g $32 2024-03-01 Buy
Cayman Chemical 17909 Chlorothiazide ≥95% 58-94-6 5g $86 2024-03-01 Buy
Product number Packaging Price Buy
C4911 50g $152.4 Buy
1121005 200mg $436 Buy
BP076 100MG $243 Buy
17909 1g $32 Buy
17909 5g $86 Buy

Chlorothiazide Chemical Properties,Uses,Production

Description

Chlorothiazide is a first-in-class thiazide diuretic initially discovered from its ability to inhibit carbonic anhydrase in vitro. As an antihypertensive agent, this thiazide increases renal excretion of sodium, potassium, chloride, and bicarbonate ions by inhibiting tubular reabsorptive mechanisms.

Chemical Properties

Off-White Solid

Originator

Diuril,Merck Sharp and,US,1957

Uses

Chlorthiazide is a diuretic that causes the body to excrete excess fluid. This drug exhibits strong diuretic action during both acidosis and alkalosis. It is used for arterial hypertension, in edematous syndromes of various genesis, congestive effects in cardiovascular insufficiency, nephrosis and nephritis, and toxicosis. It is especially recommended for hypertonic illnesses. It lowers intraocular pressure in a number of cases.

Definition

ChEBI: Chlorothiazide is 4H-1,2,4-benzothiadiazine 1,1-dioxide in which the hydrogen at position is substituted by chlorine and that at position 7 is substituted by a sulfonamide group. A diuretic, it is used for treatment of oedema and hypertension. It has a role as a diuretic and an antihypertensive agent.

Manufacturing Process

(A) m-Chloroaniline (64 g, 0.5 mol) was added dropwise with stirring to 375 ml of chlorosulfonic acid in a 3-liter round bottom, 3-necked flask cooled in an ice bath. Sodium chloride (350 g) was added portionwise over a period of 1 to2 hours and the mixture then heated gradually in an oil bath to 150°C. After 3 hours at 150° to 160°C, the flask was cooled thoroughly in an ice bath and the contents treated with a liter of cold water. The product was extracted with ether and the extract washed with water and dried over sodium sulfate.
After removal of ether on the steam bath, the residual 5-chloroaniline-2,4- disulfonyl chloride, which may be crystallized from benzene-hexane MP 130° to 132°C, was cooled in an ice bath and treated with 150 ml of 28% ammonium hydroxide in a 2-liter Erlenmeyer flask. The mixture was heated on the steam bath for 1 hour, cooled and the product collected on the filter, washed with water and dried. Upon crystallization from dilute alcohol 5- chloro-2,4-disulfamylaniline was obtained as colorless needles, MP 251° to 252°C.
(B) A solution of 88 g of 5-chloro-2,4-disulfamylaniline in 1.1 liters of 88% formic acid was heated under reflux for 2 hours. After removal of 200 ml of solvent by distillation, one liter of water was added and the product collected, washed with water and dried. Crystallization from dilute alcohol afforded 6- chloro-7-sulfamyl-1,2,4-benzothiadiazine-1,1-dioxide as colorless needles, MP 342.5° to 343°C, as described in US Patent 2,809,194.

brand name

Diuril (Ovation).

General Description

Crystals; white powder.

Air & Water Reactions

Insoluble in water.

Reactivity Profile

Alkaline aqueous solutions will decompose on standing or heating .

Fire Hazard

Flash point data for Chlorothiazide are not available; however, Chlorothiazide is probably combustible.

Mechanism of action

The mechanism of action of Chlorothiazide is an interference with the renal tubular mechanism of electrolyte reabsorption. The diuretic action of chlorothiazide, like other drugs of this series, is caused by reduced absorption of sodium and chloride ions by the kidneys during their simultaneous, intense excretion from the organism.

Safety Profile

Moderately_toxic by intraperitoneal and intravenous routes. Mddly toxic by ingestion. Experimental reproductive effects. Has been implicated in aplastic anemia. When heated to decomposition it emits very toxic fumes of SOx NOx and Cl-.

Synthesis

Chlorothiazide, 1,1-dioxide 6-chloro-2H-1,2,4-benzothiadiazin-7-sulfonamide (21.3.3) is synthesized in the exact same manner, is all thiazide diuretics. 3- Chloroaniline (or 3-trifluoromethylaniline) undergoes sulfoylchlorination by chlorosulfonic acid, forming 4,6-sulfonochloride-3-chloroaniline (21.3.1), the reaction of which with ammonia gives 4,6-sulfonylamido-3-chloroaniline (21.3.2). Heating this with formamide leads to formation of chlorothiazide (21.3.3).

Synthesis_58-94-6

Veterinary Drugs and Treatments

In veterinary medicine, furosemide has largely supplanted the use of thiazides as a general diuretic (edema treatment). Thiazides are still used for the treatment of systemic hypertension, nephrogenic diabetes insipidus, and to help prevent the recurrence of calcium oxalate uroliths in dogs.
Chlorothiazide is approved for use in dairy cattle for the treatment of post parturient udder edema, but the veterinary labeled product has been discontinued in the USA.

121-30-2
64-18-6
58-94-6
Synthesis of Chlorothiazide from 4-Amino-6-chlorobenzene-1,3-disulfonamide and Formic acid

Chlorothiazide Preparation Products And Raw materials

Global( 231)Suppliers
Supplier Tel Email Country ProdList Advantage
Henan Tianfu Chemical Co.,Ltd.
+86-0371-55170693 +86-19937530512 info@tianfuchem.com China 21700 55
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008657128800458; +8615858145714 fandachem@gmail.com China 9354 55
Shanghai Zheyan Biotech Co., Ltd.
18017610038 zheyansh@163.com CHINA 3620 58
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+86-0371-86658258 sales@coreychem.com China 29914 58
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+8615902132654 ivy.zhuang@univarsolutions.com China 654 58
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0551-65418671 sales@tnjchem.com China 34572 58
Qiuxian Baitai New Material Co., LTD
+8618330912755 sale2@hbyalin.com China 1677 58

View Lastest Price from Chlorothiazide manufacturers

Image Update time Product Price Min. Order Purity Supply Ability Manufacturer
Chlorothiazide pictures 2023-02-13 Chlorothiazide
58-94-6
US $0.00 / kg 1kg 99% 20MT Hebei baicao biology science and technology co., ltd
Chlorothiazide pictures 2021-11-27 Chlorothiazide
58-94-6
US $1.30 / g 100g 99.99% 5ton/Month Qiuxian Baitai New Material Co., LTD
Chlorothiazide pictures 2021-09-29 Chlorothiazide
58-94-6
US $0.00 / Kg/Bag 1KG 98%-102%;EP 500kgs WUHAN FORTUNA CHEMICAL CO., LTD
  • Chlorothiazide pictures
  • Chlorothiazide
    58-94-6
  • US $0.00 / kg
  • 99%
  • Hebei baicao biology science and technology co., ltd
  • Chlorothiazide pictures
  • Chlorothiazide
    58-94-6
  • US $1.30 / g
  • 99.99%
  • Qiuxian Baitai New Material Co., LTD
  • Chlorothiazide pictures
  • Chlorothiazide
    58-94-6
  • US $0.00 / Kg/Bag
  • 98%-102%;EP
  • WUHAN FORTUNA CHEMICAL CO., LTD
2H-1,2,4-Benzothiadiazine-7-sulfonamide, 6-chloro-, 1,1-dioxide 2h-1,2,4-benzothiadiazine-7-sulfonamide,6-chloro-,1,1-dioxide Aldoclor Alurene Chloriazid Chlorosal Chlorothiazid Chlorthiazide Chlortiazid Chlorurit Chlotride Chlrosal Clotride component of Aldoclor component of Diupres Diupres Diuresal Diuril Diuril Boluses Diuril lyovac [as sodium salt] Diurilix Diurite Diutrid Flumen Lyovac diuril [as sodium salt] Minzil Neo-Dema Salisan Salunil Saluretil Saluric Sk-chlorothiazide Thiazide Urinex Warduzide Yadalan CHLOROTHIAZIDE 6-chloro-7-sulfamoyl-2h-1,2,4-benzothiadiazine 1,1-dioxide 6-CHLORO-2H-1,2,4-BENZOTHIADIAZINE-7-SULFONAMIDE 1,1-DIOXIDE 2-chloro-1,2,4-benzothiadiazine-7-sulphonamide 1,1-dioxide Chlorothiazide USP25 CHLOROTHIAZIDE CARBONIC ANHYDRASE IN Chlorothizide CHLOROTHIAZIDE CRUDE 6-chloro-1,1-diketo-4H-benzo[e][1,2,4]thiadiazine-7-sulfonamide 6-chloro-1,1-dioxo-4H-benzo[e][1,2,4]thiadiazine-7-sulfonamide Chlorothiazide,6-Chloro-2H-1,2,4-benzothiadiazine-7-sulfonamide 1,1-dioxide Chlorothiazide (200 mg) Chlorothiazide(Diuril, Chlotride) Hydrochlorothiazide IMpurity-A(EP) 6-chloro-2H-benzo[e][1,2,4]thiadiazine-7-sulfonaMide 1,1-dioxide 6-chloro-1,1-dioxide-2H-1,2,4-benzothiadiazine-7-sulfonamide Hydrochlorothiazide EP Impurity A Hydrochlorothiazide Impurity A Hydrochlorothiazide Impurity B Hydrochlorothiazide impurity A -C (EP) Chlorothiazide, 100ppm Chlorothiazide CRS