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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

11 - Combustible Solids

wgk_germany

WGK 2

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

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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Martin Loynaz Prieto et al.
The Journal of neuroscience : the official journal of the Society for Neuroscience, 30(12), 4449-4459 (2010-03-26)
AMPA receptors are ligand-gated ion channels that show multiple conductance levels, indicating that gating of individual AMPA subunits is to some extent independent of the other subunits. To study AMPAR subunit interactions during activation gating, we recorded from single channels
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
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
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
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
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