CYCLOTHIAZIDE

Product Name: CYCLOTHIAZIDE
CAS No.: 2259-96-3
Chemical Name: CYCLOTHIAZIDE
Synonyms: Lil;35483;mdi193;Aquador;Aquirel;Doburil;Fluidil;MDi 193;Valmiran;Renazide
CBNumber: CB6123851
Molecular Formula: C14H16ClN3O4S2
Formula Weight: 389.88
MOL File: 2259-96-3.mol

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CYCLOTHIAZIDE Property

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)
pka: pKa 9.1(30% EtOH) (Uncertain)
form: White to off-white solid.
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.
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

Hazard Codes: Xi
Risk Statements: 36/37/38
Safety Statements: 26-36
WGK Germany: 2
RTECS: DK9610000
HS Code: 2935904000
Hazardous Substances Data: 2259-96-3(Hazardous Substances Data)
Toxicity: LD50 oral in rat: > 5gm/kg

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Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P302+P352IF ON SKIN: wash with plenty of soap and water.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

P321Specific treatment (see … on this label).

P332+P313IF SKIN irritation occurs: Get medical advice/attention.

P362Take off contaminated clothing and wash before reuse.

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N-Bromosuccinimide Price

Sigma-Aldrich

Product number: C9847
Product name: Cyclothiazide
Packaging: 10mg
Price: $123
Updated: 2024/03/01

Sigma-Aldrich

Product number: 1159008
Product name: Cyclothiazide
Purity: United States Pharmacopeia (USP) Reference Standard
Packaging: 200mg
Price: $377
Updated: 2022/05/15

TCI Chemical

Product number: C3392
Product name: Cyclothiazide (mixture of isomers)
Purity: >95.0%(HPLC)
Packaging: 25mg
Price: $85
Updated: 2024/03/01

TCI Chemical

Product number: C3392
Product name: Cyclothiazide (mixture of isomers)
Purity: >95.0%(HPLC)
Packaging: 100mg
Price: $254
Updated: 2024/03/01

Cayman Chemical

Product number: 16335
Product name: Cyclothiazide
Purity: ≥95%
Packaging: 10mg
Price: $44
Updated: 2024/03/01

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CYCLOTHIAZIDE Chemical Properties,Usage,Production

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 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

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) 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 materials

Preparation Products

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CYCLOTHIAZIDE Suppliers

Americas 1 Canada 1 China 57 Europe 1 Germany 3 India 4 Japan 2 South Korea 1 Switzerland 2 United Kingdom 7 United States 21 USA 1 Global 101

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View Lastest Price from CYCLOTHIAZIDE manufacturers

Career Henan Chemical Co

Product: CYCLOTHIAZIDE 2259-96-3
Price: US $1.00/g
Min. Order: 1g
Purity: 99%
Supply Ability: 200kg
Release date: 2019-12-30

2259-96-3, CYCLOTHIAZIDERelated Search:

(RS)-AMPA Comphene Chlorothiazide Camphene Aminomethylcyclopentane hydrochloride Hydrochlorothiazide butizide mebutizide CYCLOTHIAZIDE CLOFENAMIDE 2-amino-N-propylbenzenesulfonamide 4-Amino-6-chlorobenzene-1,3-disulfonamide ethiazide 2-AMINO-N-METHYLBENZENESULFONAMIDE N-(5-NORBORNENE-2-METHYL)-METHANESULFONAMIDE 2-AMINO-N-BUTYLBENZENESULFONAMIDE 4-CHLORO-1,3-BENZENEDITHIOL Benzenesulfonamide, 2-(methylamino)- (9CI)

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

Renazide

Valmiran

CYCLOTHIAZIDE

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

6-CHLORO-3,4-DIHYDRO-3-(5-NORBORNEN-2-YL)-2H-1,2,4-BENZOTHIAZIDIAZINE-7-SULFONAMIDE-1,1-DIOXIDE

6-CHLORO-3,4-DIHYDRO-3-(NORBORNER-5-YL)-2H-1,2,4-BENZOTHIADIAZINE

6-CHLORO-3,4-DIHYDRO-3-(NORBORNER-5-YL)-2H-1,2,4-BENZOTHIADIAZINE-7-SULPHONAMIDE-1,1-DIOXIDE

6-chloro-3,4-dihydro-3-(8,9,10-trinorborn-5-en-2-yl)-2H-1,2,4-benzothiadiazine-7-sulphonamide 1,1-dioxide

Anhydrom

Aquador

3-(6-bicyclo[2.2.1]hept-2-enyl)-6-chloro-1,1-diketo-3,4-dihydro-2H-benzo[e][1,2,4]thiadiazine-7-sulfonamide

3-(6-bicyclo[2.2.1]hept-2-enyl)-6-chloro-1,1-dioxo-3,4-dihydro-2H-benzo[e][1,2,4]thiadiazine-7-sulfonamide

4-benzothiadiazine-7-sulfonamide,6-chloro-3,4-dihydro-3-(5-norbornen-2-2h-2

6-chloro-3-(2-norbornen-5-yl)-7-sulfamyl-3,4-dihydro-1,2,4-benzothiadiazine1,1

6-chloro-3,4-dihydro-3-(2-norbornen-5-yl)-2h-1,2,4-benzothiadiazine-7-sulfonam

6-chloro-3,4-dihydro-3-(2-norbornen-5-yl)-7-sulfamoyl-1,2,4-benzothiadiazine1,

6-Chloro-3,4-dihydro-3-(5-norbornen-2-yl)-2H-1,2,4-benzothiadiazine-7-sulfonamide 1,1-dioxide

7-sulfonamide1,1-dioxide

Anhydron

Aquirel

Doburil

Fluidil

Lilly 35483

lilly35,483

MDi 193

Cyclothiazide (200 mg) (AS)

Lil

3-((1S,4S)-bicyclo[2.2.1]hept-5-en-2-yl)-6-chloro-3,4-dihydro-2H-benzo[e][1,2,4]thiadiazine-7-sulfonaMide 1,1-dioxide

Cyclothiazide (mixture of isomers)

CYCLOTHIAZIDE USP/EP/BP

Cyclothiazide (AS) (1159008)

Inhibitor,neurones,iGluR,AMPA receptor desensitization,current potentiation,Cyclothiazide,Ionotropic glutamate receptors,positive allosteric modulator,inhibit

Cyclothiazide (200 mg) (AS) (DISCONTINUED)

Cyclothiazide, AMPA receptor desensitisation inhibitor

Cyclothiazide, 10 mM in DMSO

2259-96-3

C14H16ClN3O4S2

C14H16N3O4S2Cl

Cell Signaling and Neuroscience

Cell Biology

BioChemical

Ligand-Gated Ion Channels

Ionotropic Glutamate Receptor Modulators

Ion Channels

Glutamate

Glutamate receptor

Amines

Heterocycles

Inhibitors