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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
$126
Updated
2025/07/31
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
$83
Updated
2025/07/31
TCI Chemical
Product number
C3392
Product name
Cyclothiazide (mixture of isomers)
Purity
>95.0%(HPLC)
Packaging
100mg
Price
$247
Updated
2025/07/31
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] 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

Preparation Products

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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:


  • 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