C9847

Sigma-Aldrich

Cyclothiazide

Synonym(s):
6-Chloro-3,4-dihydro-3-(2-norbornen-5-yl)-2H-1,2-4-benzothiadiazine-7-sulfonamide 1,1-dioxide
Empirical Formula (Hill Notation):
C14H16ClN3O4S2
CAS Number:
Molecular Weight:
389.88
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.77

Quality Level

originator

Eli Lilly

storage temp.

2-8°C

SMILES string

[H][C@@]12CC(C3Nc4cc(Cl)c(cc4S(=O)(=O)N3)S(N)(=O)=O)[C@@]([H])(C1)C=C2

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)/t7-,8+,9?,14?/m0/s1

InChI key

BOCUKUHCLICSIY-QJWLJZLASA-N

Gene Information

human ... CA1(759), CA4(762), GRIA1(2890), GRIA2(2891), GRIA3(2892), GRIA4(2893)
rat ... Gria1(50592)

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General description

Cyclothiazide is a benzothiadiazine, which has a similar structure to diazoxide.

Application

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.

Packaging

10 mg in poly bottle
25 mg in glass bottle

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.

Features and Benefits

This compound is also offered as part of Sigma′s Library of Pharmacologically Active Compounds (LOPAC®1280), a biologically annotated collection of high-quality, ready-to-screen compounds. Click here to learn more.

Legal Information

LOPAC is a registered trademark of Sigma-Aldrich Co. LLC

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

RIDADR

NONH for all modes of transport

WGK Germany

WGK 2

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Patricio Opazo et al.
Neuron, 67(2), 239-252 (2010-07-31)
The Ca(2+)/calmodulin-dependent protein kinase II (CaMKII) is critically required for the synaptic recruitment of AMPA-type glutamate receptors (AMPARs) during both development and plasticity. However, the underlying mechanism is unknown. Using single-particle tracking of AMPARs, we show that CaMKII activation and...
Lisa Grant et al.
The Journal of neuroscience : the official journal of the Society for Neuroscience, 30(12), 4210-4220 (2010-03-26)
Cochlear inner hair cells (IHCs) convert sounds into receptor potentials and via their ribbon synapses into firing rates in auditory nerve fibers. Multivesicular release at individual IHC ribbon synapses activates AMPA-mediated EPSCs with widely ranging amplitudes. The underlying mechanisms and...
Richard Piet et al.
The Journal of neuroscience : the official journal of the Society for Neuroscience, 31(46), 16591-16596 (2011-11-18)
The endocannabinoid (eCB) system and the cannabinoid CB1 receptor (CB1R) play key roles in the modulation of brain functions. Although actions of eCBs and CB1Rs are well described at the synaptic level, little is known of their modulation of neural...
Cole W Graydon et al.
The Journal of neuroscience : the official journal of the Society for Neuroscience, 34(24), 8358-8372 (2014-06-13)
Sensory processing in the auditory system requires that synapses, neurons, and circuits encode information with particularly high temporal and spectral precision. In the amphibian papillia, sound frequencies up to 1 kHz are encoded along a tonotopic array of hair cells...
Autumn M Weeks et al.
Neuropharmacology, 85, 57-66 (2014-06-01)
Positive allosteric modulators of α-amino-3-hydroxy-5-methyl-isoxazole-propionic acid (AMPA) ionotropic glutamate receptors facilitate synaptic plasticity and contribute essentially to learning and memory, properties which make AMPA receptors targets for drug discovery and development. One region at which several different classes of positive...
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