Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C13H21N5O2 |
Molecular Weight | 279.3381 |
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)=O
InChI
InChIKey=ZXFRFPSZAKNPQQ-YTWAJWBKSA-N
InChI=1S/C13H21N5O2/c19-13(20)11-6-10-5-8(1-3-9(10)7-14-11)2-4-12-15-17-18-16-12/h8-11,14H,1-7H2,(H,19,20)(H,15,16,17,18)/t8-,9+,10-,11+/m1/s1
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
CNS Activity
Sources: https://www.ncbi.nlm.nih.gov/pubmed/23042954
Curator's Comment: Known to be CNS penetrant in rat. Human data not available
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
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Target ID: CHEMBL2109241 Sources: https://www.ncbi.nlm.nih.gov/pubmed/8609884 |
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Target ID: CHEMBL2096670 Sources: https://www.ncbi.nlm.nih.gov/pubmed/7760975 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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Primary | Unknown Approved UseUnknown |
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Primary | Unknown Approved UseUnknown |
Cmax
Value | Dose | Co-administered | Analyte | Population |
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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 |
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Role of AMPA and GluR5 kainate receptors in the development and expression of amygdala kindling in the mouse. | 2001 |
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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 |
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Synthesis of anticonvulsive AMPA antagonists: 4-oxo-10-substituted-imidaz. | 2001 May 7 |
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Examining the neural targets of the AMPA receptor potentiator LY404187 in the rat brain using pharmacological magnetic resonance imaging. | 2005 Aug |
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The effect of the AMPA/kainate receptor antagonist LY293558 in a rat model of postoperative pain. | 2006 Oct |
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Epidural tezampanel, an AMPA/kainate receptor antagonist, produces postoperative analgesia in rats. | 2007 Oct |
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Gateways to clinical trials. | 2008 Oct |
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Fractionating spatial memory with glutamate receptor subunit-knockout mice. | 2009 Dec |
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Suppression of stretch reflex activity after spinal or systemic treatment with AMPA receptor antagonist NGX424 in rats with developed baclofen tolerance. | 2010 Nov |
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A rat model of nerve agent exposure applicable to the pediatric population: The anticonvulsant efficacies of atropine and GluK1 antagonists. | 2015 Apr 15 |
Sample Use Guides
In Vivo Use Guide
Sources: https://clinicaltrials.gov/ct2/show/NCT00567086
Single Administration of: TEZAMPANEL 40 mg; TEZAMPANEL 70 mg; TEZAMPANEL 100 mg
Route of Administration:
Other
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/16470401
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.
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C47795
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C80379
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TEZAMPANEL
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ACTIVE MOIETY
SALT/SOLVATE (PARENT)