Cyclothiazide

Names

[ Name ]:
Cyclothiazide

[Synonym ]:
cyclothiazidum [INN_la]
Cyclothiazide
3-(5-bicyclo[2.2.1]hept-2-enyl)-6-chloro-1,1-dioxo-3,4-dihydro-2H-1λ<sup>6</sup>,2,4-benzothiadiazine-7-sulfonamide
UNII:P71U09G5BW
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
3-(Bicyclo[2.2.1]hept-5-en-2-yl)-6-chloro-3,4-dihydro-2H-1,2,4-benzothiadiazine-7-sulfonamide 1,1-dioxide
6-Chloro-3,4-dihydro-3-(2-norbornen-5-yl)-2H-1,2-4-benzothiadiazine-7-sulfonamide 1,1-dioxide
MFCD00210192

Biological Activity

[Description]:

Cyclothiazide, a positive allosteric modulator of AMPA receptors, is used frequently to block the desensitization of both native and heterologously expressed AMPA receptors. Cyclothiazide is known to produce a fast inhibition of AMPA receptor desensitization and a much slower potentiation of the AMPA current[1].

[Related Catalog]:

Signaling Pathways >> Neuronal Signaling >> iGluR

Research Areas >> Neurological Disease

Signaling Pathways >> Membrane Transporter/Ion Channel >> iGluR

[References]

[1]. Fucile S, et al. Effects of cyclothiazide on GluR1/AMPA receptors. Proc Natl Acad Sci U S A. 2006;103(8):2943-2947.

Chemical & Physical Properties

[ Density]:
1.6±0.1 g/cm3

[ Boiling Point ]:
627.3±65.0 °C at 760 mmHg

[ Melting Point ]:
234ºC

[ Molecular Formula ]:
C₁₄H₁₆ClN₃O₄S₂

[ Molecular Weight ]:
389.878

[ Flash Point ]:
333.2±34.3 °C

[ Exact Mass ]:
389.027069

[ PSA ]:
135.12000

[ LogP ]:
1.15

[ Vapour Pressure ]:
0.0±1.8 mmHg at 25°C

[ Index of Refraction ]:
1.654

[ Storage condition ]:
2-8°C

MSDS

Click to get detail MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: DK9610000

CHEMICAL NAME :: 2H-1,2,4-Benzothiadiazine-7-sulfonamide, 3,4-dihydro-6-chloro-3-(5-norbornen-2-yl)-, 1,1-dioxide

CAS REGISTRY NUMBER :: 2259-96-3

LAST UPDATED :: 199612

DATA ITEMS CITED :: 5

MOLECULAR FORMULA :: C14-H16-Cl-N3-O4-S2

MOLECULAR WEIGHT :: 389.90

WISWESSER LINE NOTATION :: T66 BSWM EM DHJ HG ISZW D- FL55 A CUTJ

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: >5 gm/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: BCFAAI Bollettino Chimico Farmaceutico. (Societa Editoriale Farmaceutica, Via Ausonio 12, 20123 Milan, Italy) V.33- 1894- Volume(issue)/page/year: 101,929,1962

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 1500 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: BCFAAI Bollettino Chimico Farmaceutico. (Societa Editoriale Farmaceutica, Via Ausonio 12, 20123 Milan, Italy) V.33- 1894- Volume(issue)/page/year: 101,929,1962

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: >5 gm/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: NIIRDN Drugs in Japan (Ethical Drugs). (Yakugyo Jiho Co., Ltd., Tokyo, Japan) Volume(issue)/page/year: 6,460,1982

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 1500 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: ARZNAD Arzneimittel-Forschung. Drug Research. (Editio Cantor Verlag, Postfach 1255, W-7960 Aulendorf, Fed. Rep. Ger.) V.1- 1951- Volume(issue)/page/year: 18,487,1968 *** NIOSH STANDARDS DEVELOPMENT AND SURVEILLANCE DATA *** NIOSH OCCUPATIONAL EXPOSURE SURVEY DATA : NOHS - National Occupational Hazard Survey (1974) NOHS Hazard Code - A1012 No. of Facilities: 24 (estimated) No. of Industries: 1 No. of Occupations: 2 No. of Employees: 141 (estimated)

Safety Information

[ Symbol ]:

GHS07

[ Signal Word ]:
Warning

[ Hazard Statements ]:
H315-H319-H335

[ Precautionary Statements ]:
P305 + P351 + P338

[ Personal Protective Equipment ]:
dust mask type N95 (US);Eyeshields;Gloves

[ Hazard Codes ]:
Xi: Irritant;

[ Risk Phrases ]:
R36/37/38

[ Safety Phrases ]:
26-36

[ RIDADR ]:
NONH for all modes of transport

[ WGK Germany ]:
2

[ RTECS ]:
DK9610000

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Articles

Nicotinic receptors modulate the function of presynaptic AMPA receptors on glutamatergic nerve terminals in the trigeminal caudal nucleus.

Neurochem. Int. 90 , 166-72, (2015)

In this study, we demonstrate the existence on trigeminal caudal nucleus (TCN) glutamatergic terminals of α4β2 nicotinic receptors (nAChRs) capable of enhancing the terminals' spontaneous release of [...

AMPA receptor desensitization is the determinant of AMPA receptor mediated excitotoxicity in purified retinal ganglion cells.

Exp. Eye Res. 132 , 136-50, (2015)

The ionotropic glutamate receptors (iGLuR) have been hypothesized to play a role in neuronal pathogenesis by mediating excitotoxic death. Previous studies on iGluR in the retina have focused on two br...

Molecular mechanisms contributing to TARP regulation of channel conductance and polyamine block of calcium-permeable AMPA receptors.

J. Neurosci. 34(35) , 11673-83, (2014)

Many properties of fast synaptic transmission in the brain are influenced by transmembrane AMPAR regulatory proteins (TARPs) that modulate the pharmacology and gating of AMPA-type glutamate receptors ...