Details
| Stereochemistry | ACHIRAL |
| Molecular Formula | C21H23NO3 |
| Molecular Weight | 337.4122 |
| Optical Activity | NONE |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 1 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
CC(C)(C)C1=CC=C(C=C1)\C=C\C(=O)NC2=CC=C3OCCOC3=C2
InChI
InChIKey=GZTFUVZVLYUPRG-IZZDOVSWSA-N
InChI=1S/C21H23NO3/c1-21(2,3)16-7-4-15(5-8-16)6-11-20(23)22-17-9-10-18-19(14-17)25-13-12-24-18/h4-11,14H,12-13H2,1-3H3,(H,22,23)/b11-6+
| Molecular Formula | C21H23NO3 |
| Molecular Weight | 337.4122 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 1 |
| Optical Activity | NONE |
AMG-9810, is a TRPV1 (vanilloid receptor 1) antagonist which blocks all known modes of TRPV1 activation, including heat, proton, and endogenous ligand activation. TRPV1 is a membrane-bound cation channel in peripheral sensory neurons. Inhibition of this receptor has been noted to cause anti-inflammatory effects. In murine dorsal root ganglion primary neuron studies, this compound has been shown to block capsaicin-evoked depolarization and calcitonin gene-related peptide release. Screening of AMG 9810 against a panel of G protein-coupled receptors and ion channels indicated selectivity toward TRPV1. In vivo, AMG-9810 is effective at preventing capsaicin-induced eye wiping in a dose-dependent manner, and it reverses thermal and mechanical hyperalgesia in a model of inflammatory pain induced by intraplantar injection of complete Freund's adjuvant. AMG-9810 is the first cinnamide TRPV1 antagonist reported to block capsaicin-induced eye wiping behavior and reverse hyperalgesia in an animal model of inflammatory pain.
Approval Year
PubMed
| Title | Date | PubMed |
|---|---|---|
| AMG 9810 [(E)-3-(4-t-butylphenyl)-N-(2,3-dihydrobenzo[b][1,4] dioxin-6-yl)acrylamide], a novel vanilloid receptor 1 (TRPV1) antagonist with antihyperalgesic properties. | 2005 Apr |
|
| Thermal sensitivity of isolated vagal pulmonary sensory neurons: role of transient receptor potential vanilloid receptors. | 2006 Sep |
|
| Novel vanilloid receptor-1 antagonists: 1. Conformationally restricted analogues of trans-cinnamides. | 2007 Jul 26 |
|
| TRPV1-antagonist AMG9810 promotes mouse skin tumorigenesis through EGFR/Akt signaling. | 2011 May |
Sample Use Guides
Rats: a dose-dependent decrease of capsaicin-induced
eye wipes was observed at 15 min with all AMG-9810 doses
tested (3, 10, and 30 mg/kg intraperitoneal). In animals
treated with AMG 9810, 30 min before capsaicin treatment,
statistically significant reductions of the number of eye
wipes were observed with 10 and 30 mg/kg AMG-9810.
Route of Administration:
Intraperitoneal
In Vitro Use Guide
Curator's Comment: To determine whether AMG-9810 competitively inhibits
capsaicin binding to rat TRPV1, concentration-response
curves for capsaicin were generated in the absence or presence
of AMG 9810 (0.1, 0.3, and 1.0 uM). Preincubation of rat
TRPV1-expressing CHO cells with AMG-9810 caused a rightward
shift in the concentration-response to capsaicin, with no
apparent change in maximum response in 45Ca2+ uptake.
AMG-9810 potently and concentration-dependently inhibited
capsaicin- and proton-induced 45Ca2+ uptake into CHO
cells expressing r/h chimera with IC50 values of 19.1 +/- 7.9
and 90.3 +/- 53.1 nM, respectively. IC50 values for blocking
capsaicin activation of at rat and human TRPV1 were 85.6 +/-39.4 and 24.5 +/- 15.7 nM, respectively. IC50 values
for blocking proton activation of rat and human TRPV1 were
294 +/- 192 and 92.7 +/- 72.8 nM, respectively.
| Substance Class |
Chemical
Created
by
admin
on
Edited
Sat Dec 16 08:36:55 UTC 2023
by
admin
on
Sat Dec 16 08:36:55 UTC 2023
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| Record UNII |
182HIJ2D7F
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| Record Status |
Validated (UNII)
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| Record Version |
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DTXSID40202960
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545395-94-6
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680502
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182HIJ2D7F
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AMG-9810
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admin on Sat Dec 16 08:36:55 UTC 2023 , Edited by admin on Sat Dec 16 08:36:55 UTC 2023
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