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CYCLOTHIAZIDE

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CYCLOTHIAZIDE Basic information

Product Name:
CYCLOTHIAZIDE
Synonyms:
  • 2,4-benzothiadiazine-3-bicyclo[2.2.1]hept-5-en-2-yl-6-chloro-4-dihydro-2h-1
  • 2H-1,2,4-Benzothiadiazine-7-sulfonamide, 3,4-dihydro-6-chloro-3-(5-norbornen-2-yl)-,1,1-dioxide
  • 2H-1,2,4-Benzothiadiazine-7-sulfonamide, 3-bicyclo[2.2.1]hept-5-en-2-yl-6-chloro-3,4-dihydro-, 1,1-dioxide
  • 2h-1,2,4-benzothiadiazine-7-sulfonamide,3-bicyclo(2.2.1)hept-5-en-2-yl-6-chlor
  • 35483
  • 4-benzothiadiazine-7-sulfonamide,3,4-dihydro-6-chloro-3-(5-norbornen-2-2h-2
  • mdi193
  • o-3,4-dihydro-,1,1-dioxide
CAS:
2259-96-3
MF:
C14H16ClN3O4S2
MW:
389.88
EINECS:
218-859-7
Product Categories:
  • Glutamate
  • Glutamate receptor
  • Amines
  • Heterocycles
  • Inhibitors
  • Intermediates & Fine Chemicals
  • Pharmaceuticals
  • Sulfur & Selenium Compounds
Mol File:
2259-96-3.mol
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CYCLOTHIAZIDE Chemical Properties

Melting point:
234°
Density 
1.3781 (rough estimate)
refractive index 
1.6100 (estimate)
storage temp. 
2-8°C
form 
White to off-white solid.
pka
pKa 9.1(30% EtOH) (Uncertain)
λmax
273nm(lit.)
Merck 
14,2754
EPA Substance Registry System
2H-1,2,4-Benzothiadiazine-7-sulfonamide, 3-bicyclo[2.2.1]hept-5-en-2-yl-6-chloro-3,4-dihydro-, 1,1-dioxide (2259-96-3)
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Safety Information

Hazard Codes 
Xi
Risk Statements 
36/37/38
Safety Statements 
26-36
WGK Germany 
2
RTECS 
DK9610000
HS Code 
2935904000
Toxicity
LD50 oral in rat: > 5gm/kg

MSDS

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CYCLOTHIAZIDE Usage And Synthesis

Originator

Anhydron,Lilly,US,1963

Uses

Diuretic; antihypertensive. A subunit-specific inhibitor of GABAC receptors

Definition

ChEBI: 3,4-Dihydro-2H-1,2,4-benzothiadiazine 1,1-dioxide substituted at positions 3, 5 and 6 by a 2-norbornen-5-yl group, chlorine, and a sulfonamide group, respectively. A thiazide diuretic, it has been used in the management of hypertension a d oedema.

Manufacturing Process

A mixture of 8.5 g (0.03 mol) of 6-chloro-4-amino-benzene-1,3- disulfonamide, 4.0 g (0.033 mol) of 2,5-endomethylene-δ3- tetrahydrobenzaldehyde and 25 cc of diethyleneglycol-dimethyl ether was heated for 2 hours at 100°C. During this time the major portion of the initially undissolved crystals went into solution; thereafter, the reaction mixture was allowed to stand for 14 hours at room temperature, during which the remaining undissolved crystals also went into solution. The reddish, clear solution thus obtained was admixed with 50 cc of chloroform. The greyishwhite precipitate formed thereby was separated by vacuum filtration, washed with a small amount of chloroform, dried and recrystallized from aqueous methanol. 7.5 g of white crystalline needles having a melting point of 229° to 230°C were obtained.

brand name

Anhydron (Lilly).

Therapeutic Function

Diuretic, Antihypertensive

Biological Activity

Positive allosteric modulator of AMPA receptors that potently inhibits AMPA receptor desensitization. Selective for the flip variant of each of the four receptor subunits. Also available as part of the AMPA Receptor Tocriset™ .

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