CYCLOTHIAZIDE

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
CYCLOTHIAZIDE Structure
CYCLOTHIAZIDE Chemical Properties
Melting point 234°
density 1.3781 (rough estimate)
refractive index 1.6100 (estimate)
storage temp. 2-8°C
solubility Soluble in DMSO (up to 35 mg/ml) or in Ethanol (up to 9 mg/ml)
form White to off-white solid.
pkapKa 9.1(30% EtOH) (Uncertain)
color Off-white
λmax273nm(lit.)
Merck 14,2754
Stability:Stable for 1 year from date of purchase as supplied. Solutions in DMSO or ethanol may be stored at -20°C for up to 3 months.
EPA Substance Registry System2H-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)
Safety Information
Hazard Codes Xi
Risk Statements 36/37/38
Safety Statements 26-36
WGK Germany 2
RTECS DK9610000
HS Code 2935904000
Hazardous Substances Data2259-96-3(Hazardous Substances Data)
ToxicityLD50 oral in rat: > 5gm/kg
MSDS Information
ProviderLanguage
SigmaAldrich English
CYCLOTHIAZIDE Usage And Synthesis
DescriptionCyclothiazide (2259-96-3) is a positive allosteric modulator of AMPA receptors acting at a site distinct from that of 2,3-benzodiazepines.1,2 Clinically useful diuretic and antihypertensive agent.3 Induces robust epileptiform activity, inducing seizures but without neuronal death.4,5 Can be used to produce a new animal model for epilepsy.5
OriginatorAnhydron,Lilly,US,1963
UsesDiuretic; antihypertensive. A subunit-specific inhibitor of GABAC receptors.
UsesCyclothiazide has been used as a α-amino-3-hydroxy-5-methyl-4-isoxazolepropionic acid receptor (AMPAR) desensitization blocker to study the effects of γ2 on receptor desensitization.
DefinitionChEBI: 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 ProcessA 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 nameAnhydron (Lilly).
Therapeutic FunctionDiuretic, Antihypertensive
General DescriptionCyclothiazide is a benzothiadiazine, which has a similar structure to diazoxide.
Biological ActivityPositive 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™ .
Biochem/physiol ActionsBlocks the rapid desensitization of the AMPA glutamate receptors and markedly prolongs the decay time of the evoked excitatory post-synaptic current.
storageRoom temperature
References1) Donevan and Rogawski (1998), Allosteric regulation of alpha-amino-3-hydroxy-5-methyl-4-isoxazole-propionate receptors by thiocyanate and cyclothiazide at a common modulatory site distinct from that of 2,3-benzodiazepines; Neuroscience 87 615 2) Desai et al. (1995), Cyclothiazide acts at a site on the alpha-amino-3-hydroxy-5-methyl-4-isoxazole propionic acid receptor complex that does not recognize competitive or noncompetitive AMPA receptor antagonists; J. Pharmacol. Exp. Ther. 272 38 3) Jeunemaitre et al. (1988), Long-term metabolic effects of spironolactone and thiazides combined with potassium-sparing agents for treatment of essential hypertension; Am. J. Cardiol. 62 1072 4) Qi et al. (2006), Cyclothiazide induces robust epileptiform activity in rat hippocampal neurons both in vitro and in vivo; J. Physiol. 571 605 5) Kong et al. (2010), Cyclothiazide induces seizure behavior in freely moving rats; Brain Res. 1355 207
CYCLOTHIAZIDE Preparation Products And Raw materials
Raw materials4-Amino-6-chlorobenzene-1,3-disulfonamide
(RS)-AMPA mebutizide Benzenesulfonamide, 2-(methylamino)- (9CI) 2-AMINO-N-METHYLBENZENESULFONAMIDE butizide 4-CHLORO-1,3-BENZENEDITHIOL CLOFENAMIDE Hydrochlorothiazide N-(5-NORBORNENE-2-METHYL)-METHANESULFONAMIDE CYCLOTHIAZIDE 2-AMINO-N-BUTYLBENZENESULFONAMIDE Comphene Chlorothiazide ethiazide 2-amino-N-propylbenzenesulfonamide 4-Amino-6-chlorobenzene-1,3-disulfonamide Aminomethylcyclopentane hydrochloride Camphene

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