A potentiator of AMPA receptors
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Product Type

Small Molecule Modulators
Ion Channel Modulators

Research Area

Neuroscience

Cyclothiazide

Item No. 16335

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
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
CAS Number
2259-96-3
Synonyms
  • Doburil
Molecular Formula
C14H16ClN3O4S2
Formula Weight
389.9
Purity
≥95%
Formulation
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 10 mg/mlDMF:PBS(pH 7.2)(1:1): 0.5 mg/mlDMSO: 10 mg/mlEthanol: 2 mg/ml
λmax
226, 271, 317 nm
SMILES
ClC1=C(S(N)(=O)=O)C=C(S(NC(C2C3C=CC(C3)C2)N4)(=O)=O)C4=C1
InChi Code
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)
InChi Key
BOCUKUHCLICSIY-UHFFFAOYSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    Product Description

    Receptors for AMPA are ionotropic glutamate receptors with critical roles in neurological development and function.1,2,3 Cyclothiazide is a benzothiadiazide that acts as a potentiator of AMPA receptors, positively modulating its response to glutamic acid (EC50 = 3.8 µM).4,5,6 It blocks the rapid agonist-induced desensitization of AMPA receptors, resulting in enhanced excitatory activity.6 Cyclothiazide is also a negative modulator of GABAA receptors, reversibly inhibiting both evoked and spontaneous inhibitory postsynaptic currents (IC50 = 58 µM).7,8

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Gouaux, E. Structure and function of AMPA receptors. J. Physiol. 554(2), 249-253 (2004).

    2. Schoepp, D.D. Unveiling the functions of presynaptic metabotropic glutamate receptors in the central nervous system. J. Pharmacol. Exp. Ther. 299(1), 12-20 (2001).

    3. Scannevin, R.H., and Huganir, R.L. Postsynaptic organization and regulation of excitatory synapses. Nat. Rev. Neurosci. 1(2), 133-141 (2000).

    4. Partin, K.M., Patneau, D.K., Winters, C.A., et al. Selective modulation of desensitization at AMPA versus kainate receptors by cyclothiazide and concanavalin A. Neuron 11(6), 1069-1082 (1993).

    5. Ornstein, P.L., Zimmerman, D.M., Arnold, M.B., et al. Biarylpropylsulfonamides as novel, potent potentiators of 2-amino-3-(5-methyl-3-hydroxyisoxazol-4-yl)-propanoic acid (AMPA) receptors. J. Med. Chem. 43(23), 4354-4358 (2000).

    6. Bräuner-Osborne, H., Egebjerg, J., Nielsen, E.O., et al. Ligands for glutamate receptors: Design and therapeutic prospects. J. Med. Chem. 43(14), 2609-2645 (2000).

    7. Deng, L., and Chen, G. Cyclothiazide potently inhibits γ-aminobutyric acid type A receptors in addition to enhancing glutamate responses. Proc. Natl. Acad. Sci. USA 100(200), 13025-13029 (2003).

    8. Johnston, G.A.R., Chebib, M., Hanrahan, J.R., et al. Neurochemicals for the investigation of GABAC receptors. Neurochem. Res. 35(12), 1970-1977 (2010).