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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

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About This Item

Empirical Formula (Hill Notation):
C14H16ClN3O4S2
CAS Number:
2259-96-3
Molecular Weight:
389.88
EC Number:
218-859-7
MDL number:
MFCD00210192
UNSPSC Code:
12352125
PubChem Substance ID:
24278350
NACRES:
NA.77

form

powder

Quality Level

200

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.

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 a featured product for Neuroscience research. Click here to discover more featured Neuroscience products. Learn more about bioactive small molecules for other areas of research at sigma.com/discover-bsm.
This compound is featured on the Glutamate Receptors (Ion Channel Family) page of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.
This compound was developed by Eli Lilly. To browse the list of other pharma-developed compounds and Approved Drugs/Drug Candidates, click here.

Storage Class Code

11 - Combustible Solids

WGK

WGK 2

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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
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
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
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
H Schmidhammer et al.
Journal of medicinal chemistry, 32(2), 418-421 (1989-02-01)
(-)-N-(Cyclopropylmethyl)-4,14-dimethoxymorphinan-6-one (2) was synthesized with 4,14-dimethoxy-N-methylmorphinan-6-one (1) as starting material. In vivo and in vitro experiments show 2 (cyprodime) to be a pure opioid receptor antagonist. Some of these tests (opioid receptor binding assays, guinea pig ileal longitudinal muscle preparation
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