Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C19H33N5O2 |
| Molecular Weight | 363.4976 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 4 / 4 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
[H][C@@]12CC[C@H](CCC3=NN=NN3)C[C@]1([H])C[C@H](NC2)C(=O)OCC(CC)CC
InChI
InChIKey=NHYHKMQUHRGUEH-TWMKSMIVSA-N
InChI=1S/C19H33N5O2/c1-3-13(4-2)12-26-19(25)17-10-16-9-14(5-7-15(16)11-20-17)6-8-18-21-23-24-22-18/h13-17,20H,3-12H2,1-2H3,(H,21,22,23,24)/t14-,15+,16-,17+/m1/s1
| Molecular Formula | C19H33N5O2 |
| Molecular Weight | 363.4976 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ABSOLUTE |
| Additional Stereochemistry | No |
| Defined Stereocenters | 4 / 4 |
| E/Z Centers | 0 |
| Optical Activity | UNSPECIFIED |
Tezampanel, also known as LY 293558 and NGX-424, is a drug originally developed by Eli Lilly, which is a competitive antagonist of the AMPA and kainate subtypes of the ionotropic glutamate receptor family. Tezampanel was in phase II clinical trial for treatment migraine, but this study was discontinued. Also this drug has several others potential pharmacological actions, one of them is anxiety disorders
Approval Year
Cmax
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
18433 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/23042954 |
15 mg/kg single, intramuscular dose: 15 mg/kg route of administration: Intramuscular experiment type: SINGLE co-administered: |
TEZAMPANEL plasma | Rattus norvegicus population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
AUC
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
9396 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/23042954 |
15 mg/kg single, intramuscular dose: 15 mg/kg route of administration: Intramuscular experiment type: SINGLE co-administered: |
TEZAMPANEL plasma | Rattus norvegicus population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
T1/2
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
1.5 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/23042954 |
15 mg/kg single, intramuscular dose: 15 mg/kg route of administration: Intramuscular experiment type: SINGLE co-administered: |
TEZAMPANEL plasma | Rattus norvegicus population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
PubMed
| Title | Date | PubMed |
|---|---|---|
| Role of AMPA and GluR5 kainate receptors in the development and expression of amygdala kindling in the mouse. | 2001 |
|
| Differential involvement of NMDA, AMPA/kainate, and dopamine receptors in the nucleus accumbens core in the acquisition and performance of pavlovian approach behavior. | 2001 Dec 1 |
|
| Amygdala regulation of nucleus accumbens dopamine output is governed by the prefrontal cortex. | 2001 Jan 15 |
|
| Synthesis of anticonvulsive AMPA antagonists: 4-oxo-10-substituted-imidaz. | 2001 May 7 |
|
| LY293558, an AMPA glutamate receptor antagonist, prevents and reverses levodopa-induced motor alterations in Parkinsonian rats. | 2001 Oct |
|
| LY-293558. Eli Lilly & Co. | 2001 Sep |
|
| Dissociable effects of antagonism of NMDA and AMPA/KA receptors in the nucleus accumbens core and shell on cocaine-seeking behavior. | 2001 Sep |
|
| Distinct contributions of glutamate receptor subtypes to cognitive set-shifting abilities in the rat. | 2003 Nov |
|
| LY293558, a novel AMPA/GluR5 antagonist, is efficacious and well-tolerated in acute migraine. | 2004 Jul |
|
| Examining the neural targets of the AMPA receptor potentiator LY404187 in the rat brain using pharmacological magnetic resonance imaging. | 2005 Aug |
|
| Epidural tezampanel, an AMPA/kainate receptor antagonist, produces postoperative analgesia in rats. | 2007 Oct |
|
| Gateways to clinical trials. | 2008 Oct |
|
| Suppression of stretch reflex activity after spinal or systemic treatment with AMPA receptor antagonist NGX424 in rats with developed baclofen tolerance. | 2010 Nov |
Sample Use Guides
Single Administration of: TEZAMPANEL 40 mg; TEZAMPANEL 70 mg; TEZAMPANEL 100 mg
Route of Administration:
Other
LY293558 (Tezampanel) had a rank order of potency of GLU(K5) > or = GLU(K5/6) approximately GLU(A2i) approximately GLU(K2/5) approximately GLU(A1i) approximately GLU(A2o) approximately GLU(A3i) approximately GLU(A1o) > or = GLU(A3o) > or = GLU(A4i) approximately GLU(A4o) and >100 microM affinity for rat cortical GABA(A) receptors. Comparison of the blockade of AMPA- vs N-methyl-D-aspartate (NMDA)-induced inward currents demonstrated that LY293558 was five-fold more potent as an antagonist at AMPA vs NMDA receptors in vitro.
| Substance Class |
Chemical
Created
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Edited
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Sat Dec 16 10:53:42 GMT 2023
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| Record UNII |
5QE0H7SK7G
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Validated (UNII)
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1166398-55-5
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10457739
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SALT/SOLVATE -> PARENT |
