CYCLOTHIAZIDE CAS 2259-96-3
Introduction：Basic information about CYCLOTHIAZIDE CAS 2259-96-3, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.
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 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. |
| pka | pKa 9.1(30% EtOH) (Uncertain) |
| color | Off-white |
| λmax | 273nm(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. |
| InChI | 1S/C14H16ClN3O4S2/c15-10-5-11-13(6-12(10)23(16,19)20)24(21,22)18-14(17-11)9-4-7-1-2-8(9)3-7/h1-2,5-9,14,17-18H,3-4H2,(H2,16,19,20) |
| InChIKey | BOCUKUHCLICSIY-UHFFFAOYSA-N |
| 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) |
Safety Information
| Hazard Codes | Xi |
| Risk Statements | 36/37/38 |
| Safety Statements | 26-36 |
| WGK Germany | 2 |
| RTECS | DK9610000 |
| HS Code | 2935904000 |
| Storage Class | 11 - Combustible Solids |
| Hazardous Substances Data | 2259-96-3(Hazardous Substances Data) |
| Toxicity | LD50 oral in rat: > 5gm/kg |
| Description | 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 |
| Uses | Diuretic; antihypertensive. A subunit-specific inhibitor of GABAC receptors. |
| Uses | 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 ad 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 washeated for 2 hours at 100°C. During this time the major portion of the initiallyundissolved crystals went into solution; thereafter, the reaction mixture wasallowed to stand for 14 hours at room temperature, during which theremaining undissolved crystals also went into solution. The reddish, clearsolution thus obtained was admixed with 50 cc of chloroform. The greyishwhite precipitate formed thereby was separated by vacuum filtration, washedwith a small amount of chloroform, dried and recrystallized from aqueousmethanol. 7.5 g of white crystalline needles having a melting point of 229° to230°C were obtained. |
| Brand name | Anhydron (Lilly). |
| Therapeutic Function | Diuretic, Antihypertensive |
| General Description | Cyclothiazide is a benzothiadiazine, which has a similar structure to diazoxide. |
| 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™ . |
| 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. |
| storage | Room temperature |
| References | [1] S.D DONEVAN M. A R. Allosteric regulation of α-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[J]. Neuroscience, 1998, 87 3: Pages 615-629. DOI:10.1016/s0306-4522(98)00109-2 [2] M A DESAI. 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]. Journal of Pharmacology and Experimental Therapeutics, 1995, 272 1: 38-43. [3] XAVIER JEUNEMAITRE MD. Long-term metabolic effects of spironolactone and thiazides combined with potassium-sparing agents for treatment of essential hypertension[J]. American Journal of Cardiology, 1988, 62 16: Pages 1072-1077. DOI:10.1016/0002-9149(88)90551-6 [4] JINSHUN QI. Cyclothiazide induces robust epileptiform activity in rat hippocampal neurons both in vitro and in vivo[J]. Journal of Physiology-London, 2006, 571 3: 605-618. DOI:10.1113/jphysiol.2005.103812 [5] SHUZHEN KONG . Cyclothiazide induces seizure behavior in freely moving rats[J]. Brain Research, 2010, 1355: Pages 207-213. DOI:10.1016/j.brainres.2010.07.088 |
CYCLOTHIAZIDE Preparation Products And Raw materials
| Raw materials | 4-Amino-6-chlorobenzene-1,3-disulfonamide |
