Details
Stereochemistry | RACEMIC |
Molecular Formula | C19H20N4O3 |
Molecular Weight | 352.3871 |
Optical Activity | ( + / - ) |
Defined Stereocenters | 0 / 1 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
CNC(=O)N1N=C(C2=CC=C(N)C=C2)C3=CC4=C(OCO4)C=C3CC1C
InChI
InChIKey=SMGACXZFVXKEAX-UHFFFAOYSA-N
InChI=1S/C19H20N4O3/c1-11-7-13-8-16-17(26-10-25-16)9-15(13)18(22-23(11)19(24)21-2)12-3-5-14(20)6-4-12/h3-6,8-9,11H,7,10,20H2,1-2H3,(H,21,24)
Molecular Formula | C19H20N4O3 |
Molecular Weight | 352.3871 |
Charge | 0 |
Count |
|
Stereochemistry | RACEMIC |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 1 |
E/Z Centers | 0 |
Optical Activity | ( + / - ) |
DescriptionSources: https://www.ncbi.nlm.nih.gov/pubmed/12353057Curator's Comment: description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/25578259 | https://www.ncbi.nlm.nih.gov/pubmed/11489346
Sources: https://www.ncbi.nlm.nih.gov/pubmed/12353057
Curator's Comment: description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/25578259 | https://www.ncbi.nlm.nih.gov/pubmed/11489346
LY-300168 (GYKI-53655) is a negative allosteric AMPA modulator. It is used as a tool compound to study role of AMPA receptor in CNS functioning. Administration of LY-300168 demonstrated anxyolitic effects. GYKI-53655 produced a dose-dependent prolongation of survival time in the MgCl2 induced global ischaemia model.
CNS Activity
Originator
Sources: https://www.ncbi.nlm.nih.gov/pubmed/9274935
Curator's Comment: https://www.ncbi.nlm.nih.gov/pubmed/7679352 # Egis Pharmaceuticals; Eli Lilly
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL3753 Sources: https://www.ncbi.nlm.nih.gov/pubmed/9076748 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | Unknown Approved UseUnknown |
|||
Palliative | Unknown Approved UseUnknown |
PubMed
Title | Date | PubMed |
---|---|---|
Cyclothiazide reverses AMPA receptor antagonism of the 2,3-benzodiazepine, GYKI 53655. | 1993 Jan 15 |
|
GYKI 53665, a 2,3-benzodiazepine, non-competitively protects cultured neurones against AMPA toxicity. | 1997 Jul 16 |
|
Comparison of anticonvulsive and acute neuroprotective activity of three 2,3-benzodiazepine compounds, GYKI 52466, GYKI 53405, and GYKI 53655. | 2001 Jun |
|
Negative allosteric modulation of AMPA-preferring receptors by the selective isomer GYKI 53784 (LY303070), a specific non-competitive AMPA antagonist. | 2002 Fall |
|
Differential role of AMPA receptors in mouse tests of antidepressant and anxiolytic action. | 2015 Mar 19 |
Patents
Sample Use Guides
In Vivo Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/25578259
GYKI-53655 1.25-7.5 mg/kg free base; was dissolved in 100% DMSO, and then diluted to a concentration of 2.5% DMSO, using a solution of 10% (w/v) (2-hydroxypropyl)-p-cyclodextrin in 5% (w/v) D-(+)-glucose monohydrate heated to 35-40 °C. Drug was administered to mice intraperitoneally (i.p.) 30 min prior to testing in an injection volume of 10 mL/kg.
Route of Administration:
Intraperitoneal
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/9076748
Whole-cell voltage clamp recordings were made from single cells with use of the tight seal whole cell configuration of the patch-clamp technique. Glass fragments of coverslips with adherent cells (HEK293, expressing GluR1) were placed in a perfusion chamber and rinsed with buffer of composition 138 mM NaCl, 5 mM CaCl2, 5 mM KC1, 1 mM MgCl2, 10 mM HEPES and 10 mM glucose, pH to 7.5 with NaOH (osmolality 315 mosm/ kg). Pipette solutions contained 140 mM CsCl, 1 mM MgCl2, 14 mM diTris creatine phosphate, 50 U/ml creatine phosphokinase, 14 mM MgATP, 10 mM HEPES and 15 mM BAPTA, pH to 7.2 with CsOH (osmolality 295 mosm/kg). Experiments were performed at room temperature (20-22°C) and recorded on either a List EPC-7 or an Axopatch ID amplifier. Pipette resistances were typically 1.5-2.5 MQ. Drug application was via a series of perfusion lines to a multi-barrelled applicator (Biologic Inc.) and exchange of solutions under the present recording conditions was approximately 100 msec. LY-300168 inhibited AMPA (10uM)-mediated responses in recombinant human GluR1 receptors expressed in HEK293 cells with approximate IC50 of 5.9 uM.
Substance Class |
Chemical
Created
by
admin
on
Edited
Sat Dec 16 11:37:54 GMT 2023
by
admin
on
Sat Dec 16 11:37:54 GMT 2023
|
Record UNII |
X46FC5N190
|
Record Status |
Validated (UNII)
|
Record Version |
|
-
Download
Name | Type | Language | ||
---|---|---|---|---|
|
Common Name | English | ||
|
Systematic Name | English | ||
|
Code | English | ||
|
Code | English | ||
|
Systematic Name | English |
Code System | Code | Type | Description | ||
---|---|---|---|---|---|
|
DTXSID30276296
Created by
admin on Sat Dec 16 11:37:54 GMT 2023 , Edited by admin on Sat Dec 16 11:37:54 GMT 2023
|
PRIMARY | |||
|
143692-18-6
Created by
admin on Sat Dec 16 11:37:54 GMT 2023 , Edited by admin on Sat Dec 16 11:37:54 GMT 2023
|
PRIMARY | |||
|
X46FC5N190
Created by
admin on Sat Dec 16 11:37:54 GMT 2023 , Edited by admin on Sat Dec 16 11:37:54 GMT 2023
|
PRIMARY | |||
|
126758
Created by
admin on Sat Dec 16 11:37:54 GMT 2023 , Edited by admin on Sat Dec 16 11:37:54 GMT 2023
|
PRIMARY |