Cyclothiazid

Bezeichnung:Cyclothiazid

CAS-Nr2259-96-3

Englisch Name:CYCLOTHIAZIDE

CBNumberCB6123851

SummenformelC14H16ClN3O4S2

Molgewicht389.88

MOL-Datei2259-96-3.mol

Synonyma

Cyclothiazid

Cyclothiazid physikalisch-chemischer Eigenschaften

Schmelzpunkt	234°
Dichte	1.3781 (rough estimate)
Brechungsindex	1.6100 (estimate)
storage temp.	2-8°C
Löslichkeit	Soluble in DMSO (up to 35 mg/ml) or in Ethanol (up to 9 mg/ml)
pka	pKa 9.1(30% EtOH) (Uncertain)
Aggregatzustand	White to off-white solid.
Farbe	Off-white
maximale Wellenlänge (λmax)	273nm(lit.)
Merck	14,2754
Stabilität	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 chemische Informationen	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)

Sicherheit

Kennzeichnung gefährlicher	Xi
R-Sätze:	36/37/38
S-Sätze:	26-36
WGK Germany	2
RTECS-Nr.	DK9610000
HS Code	2935904000
Giftige Stoffe Daten	2259-96-3(Hazardous Substances Data)
Toxizität	LD50 oral in rat: > 5gm/kg

Gefahreninformationscode (GHS)

CYCLOTHIAZIDE Chemische Eigenschaften,Einsatz,Produktion Methoden

R-Sätze Betriebsanweisung:
R36/37/38:Reizt die Augen, die Atmungsorgane und die Haut.
S-Sätze Betriebsanweisung:
S26:Bei Berührung mit den Augen sofort gründlich mit Wasser abspülen und Arzt konsultieren.
S36:DE: Bei der Arbeit geeignete Schutzkleidung tragen.
Beschreibung
Cyclothiazide (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
Originator
Anhydron,Lilly,US,1963
Verwenden
Diuretic; antihypertensive. A subunit-specific inhibitor of GABAC receptors.
Verwenden
Cyclothiazide 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.
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.
Trademarks
Anhydron (Lilly).
Therapeutic Function
Diuretic, Antihypertensive
Allgemeine Beschreibung
Cyclothiazide is a benzothiadiazine, which has a similar structure to diazoxide.
Biologische Aktivität
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™ .
Biochem/physiol Actions
Blocks the rapid desensitization of the AMPA glutamate receptors and markedly prolongs the decay time of the evoked excitatory post-synaptic current.
Lager
Room temperature
Einzelnachweise
1) 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 Upstream-Materialien And Downstream Produkte

Cyclothiazid Anbieter Lieferant Produzent Hersteller Vertrieb Händler.

2259-96-3, CYCLOTHIAZIDE Verwandte Suche:

Send Inquriy