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Submit ReviewCyclothiazide
Description: Positive allosteric modulator of AMPA receptors; inhibits AMPA desensitization
Chemical Name: 6-Chloro-3,4-dihydro-3-(5-norbornen-2-yl)-2H-1,2,4-benzothiazidiazine-7-sulfonamide-1,1-dioxide
Purity: ≥98% (HPLC)
Biological Activity for Cyclothiazide
Cyclothiazide is a positive allosteric modulator of AMPA receptors that potently inhibits AMPA receptor desensitization. Selective for the flip variant of each of the four receptor subunits.
Compound Libraries for Cyclothiazide
Cyclothiazide is also offered as part of the Tocriscreen 2.0 Max and Tocriscreen FDA-Approved Drugs. Find out more about compound libraries available from Tocris.
Technical Data for Cyclothiazide
| M. Wt | 389.87 |
| Formula | C14H16ClN3O4S2 |
| Storage | Store at RT |
| Purity | ≥98% (HPLC) |
| CAS Number | 2259-96-3 |
| PubChem ID | 2910 |
| InChI Key | BOCUKUHCLICSIY-UHFFFAOYSA-N |
| Smiles | NS(=O)(=O)C1=C(Cl)C=C2NC(NS(=O)(=O)C2=C1)C1CC2CC1C=C2 |
The technical data provided above is for guidance only. For batch specific data refer to the Certificate of Analysis.
Tocris products are intended for laboratory research use only, unless stated otherwise.
Solubility Data for Cyclothiazide
| Solvent | Max Conc. mg/mL | Max Conc. mM | |
|---|---|---|---|
| Solubility | |||
| DMSO | 38.99 | 100 | |
| ethanol | 9.75 | 25 |
Preparing Stock Solutions for Cyclothiazide
The following data is based on the product molecular weight 389.87. Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.
| Concentration / Solvent Volume / Mass | 1 mg | 5 mg | 10 mg |
|---|---|---|---|
| 1 mM | 2.56 mL | 12.82 mL | 25.65 mL |
| 5 mM | 0.51 mL | 2.56 mL | 5.13 mL |
| 10 mM | 0.26 mL | 1.28 mL | 2.56 mL |
| 50 mM | 0.05 mL | 0.26 mL | 0.51 mL |
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Product Datasheets for Cyclothiazide
References for Cyclothiazide
References are publications that support the biological activity of the product.
Desai et al (1995) Cyclothiazide acts at a site on the α-amino-3-hydroxy-5-methyl-4-isoxazole propionic acid receptor complex that does not recognise competitive or noncompetitive AMPA receptor antagonists. J.Pharmacol.Exp.Ther. 272 38 PMID: 7529311
Donevan and Rogawski (1998) Allosteric regulation of a-amino-3-hydroxy-5-methyl-4-isoxazole propionic acid receptors by thiocyanate and cyclothiazide at a common modulatory site distinct from that of 2,3-benzodiazepines. Neuroscience 87 615 PMID: 9758228
Kessler et al (2000) The norbornenyl moiety of cyclothiazide determines the preference for flip-flop variants of AMPA receptor subunits. Neurosci.Lett. 287 161 PMID: 10854736
If you know of a relevant reference for Cyclothiazide, please let us know.
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Keywords: Cyclothiazide, Cyclothiazide supplier, AMPA, selective, desensitization, desensitisation, inhibitors, inhibits, Glutamate, Receptors, iGluR, Ionotropic, positive, allosteric, modulators, PAM, 0713, Tocris Bioscience
21 Citations for Cyclothiazide
Citations are publications that use Tocris products. Selected citations for Cyclothiazide include:
Seebohm et al (2014) Structural basis of PI(4,5)P2-dependent regulation of GluA1 by phosphatidylinositol-5-phosphate 4-kinase, type II, alpha (PIP5K2A). Pflugers Arch 466 1885 PMID: 24389605
Bretin et al (2017) Pharmacological characterisation of S 47445, a novel positive allosteric modulator of AMPA receptors. PLoS One 12 e0184429 PMID: 28886144
Falgairolle and O'Donovan (2015) Pharmacological Investigation of Fluoro-Gold Entry into Spinal Neurons. PLoS One 10 e0131430 PMID: 26102354
Maguire et al (2014) Extrasynaptic glycine receptors of rodent dorsal raphe serotonergic neurons: a sensitive target for ethanol. PLoS One 39 1232 PMID: 24264816
Menuz et al (2009) Critical role for TARPs in early development despite broad functional redundancy. Neuropharmacology 56 22 PMID: 18634809
Soto et al (2009) Selective regulation of long-form calcium-permeable AMPA receptors by an atypical TARP, gamma-5. Nat Neurosci 12 277 PMID: 19234459
Lee et al (2012) Actin-dependent rapid recruitment of reluctant synaptic vesicles into a fast-releasing vesicle pool. Proc Natl Acad Sci U S A 109 E765 PMID: 22393020
McGee et al (2015) Auxiliary Subunit GSG1L Acts to Suppress Calcium-Permeable AMPA Receptor Function. Front Cell Neurosci 35 16171 PMID: 26658868
Angelantonio et al (2015) Basal adenosine modulates the functional properties of AMPA receptors in mouse hippocampal neurons through the activation of A1R A2AR and A3R. Neuropsychopharmacology 9 409 PMID: 26528137
Harms et al (2013) Functional analysis of a novel positive allosteric modulator of AMPA receptors derived from a structure-based drug design strategy. Neuropharmacology 64 45 PMID: 22735771
Kong et al (2010) Cyclothiazide induces seizure behavior in freely moving rats. Brain Res 1355 207 PMID: 20678492
Fan et al (2018) All-optical synaptic electrophysiology probes mechanism of ketamine-induced disinhibition. Nat Methods 15 823 PMID: 30275587
Imlach et al (2016) Glycinergic dysfunction in a subpopulation of dorsal horn interneurons in a rat model of neuropathic pain Scientific Reports 6 37104 PMID: 27841371
Smejkalova and Woolley (2010) OE acutely potentiates hippocampal excitatory synaptic transmission through a presynaptic mechanism. J Neurosci 30 16137 PMID: 21123560
Oh et al (2012) Overexpression of calcium-permeable glutamate receptors in glioblastoma derived brain tumor initiating cells. PLoS One 7 e47846 PMID: 23110111
Chen et al (2013) The Munc13 proteins differentially regulate readily releasable pool dynamics and calcium-dependent recovery at a central synapse. J Neurosci 33 8336 PMID: 23658173
Kopach et al (2011) Inflammation alters trafficking of extrasynaptic AMPA receptors in tonically firing lamina II neurons of the rat spinal dorsal horn. Pain 152 912 PMID: 21282008
Bender et al (2006) Two coincidence detectors for spike timing-dependent plasticity in somatosensory cortex. J Neurosci 26 4166 PMID: 16624937
Pieri et al (2005) AMPA receptors are modulated by tachykinins in rat cerebellum neurons. J Neurophysiol 94 2484 PMID: 16160091
Takayasu et al (2006) Glial glutamate transporters maintain one-to-one relationship at the climbing fiber-Purkinje cell synapse by preventing glutamate spillover. J Neurosci 26 6563 PMID: 16775144
Bagnall et al (2008) Frequency-independent synaptic transmission supports a linear vestibular behavior. Neuron 60 343 PMID: 18957225
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Reviews for Cyclothiazide
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Modulation of AMPA-receptor kinetics.
By
Sergiy Sylantyev on 12/22/2020
Assay Type: In Vitro
Species: Rat
Cell Line/Tissue: Hippocampus
Cyclothiazide was used to prevent desensitization of AMPA-receptors in hippocampal pyramidal neurons. The compound prolonged the decay time of multi-synaptic evoked excitatory currents in cell somata. No difference between effects at 22-25 C and 33-36 C was detected. Illustration, grey trace: control response normalized to response amplitude under cyclothiazide.
Preparation of 10 mM ethanol stock requires sonication.
effectively blocks desensitization of AMPA receptors.
By
Karthik krishnamurthy on 11/02/2018
Assay Type: In Vitro
Species: Rat
Cell Line/Tissue: motor neurons
Used to prevent desensitization AMPA receptors in motor neurons. Used at concentration of 200 micromolar to measure whole cell current in motor neurons upon AMPA application.
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