Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C20H23NO2 |
| Molecular Weight | 309.4021 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 2 / 2 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
C1OC(O[C@H]1[C@@H]2CCCCN2)(C3=CC=CC=C3)C4=CC=CC=C4
InChI
InChIKey=HGKAMARNFGKMLC-RBUKOAKNSA-N
InChI=1S/C20H23NO2/c1-3-9-16(10-4-1)20(17-11-5-2-6-12-17)22-15-19(23-20)18-13-7-8-14-21-18/h1-6,9-12,18-19,21H,7-8,13-15H2/t18-,19+/m0/s1
Dexoxadrol is a sigma receptor agonist. Dexoxadrol, the D-isomer of dioxodrol, which produces PCP-like behavioural effects and displaces bound [3H]PCP, was a potent blocker of the PCP-sensitive, voltage-gated K+ channel. Dexoxadrol was developed as analgesics for use in humans, however, severe side effects including psychotomimetic effects, unpleasant dreams and aberrations stopped the clinical evaluation of dexoxadrol. Dexoxadrol is a NMDA receptor antagonist, which possesses high affinity to the phencyclidine binding site within the NMDA receptor associated ion channel.
CNS Activity
Approval Year
PubMed
| Title | Date | PubMed |
|---|---|---|
| Molecular modeling of noncompetitive antagonists of the NMDA receptor: proposal of a pharmacophore and a description of the interaction mode. | 2002 Feb |
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| Characterization of the non-competitive antagonist binding site of the NMDA receptor in dark Agouti rats. | 2004 Aug 6 |
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| Synthesis and NMDA-receptor affinity of ring and side chain homologous dexoxadrol derivatives. | 2004 Feb |
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| Structure-affinity relationship studies of non-competitive NMDA receptor antagonists derived from dexoxadrol and etoxadrol. | 2005 Dec 15 |
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| Relationships between the structure of dexoxadrol and etoxadrol analogues and their NMDA receptor affinity. | 2006 |
|
| Synthesis and NMDA-receptor affinity of 4-oxo-dexoxadrol derivatives. | 2006 Sep 1 |
Sample Use Guides
In hospitalized cancer and arthritic patients dexoxadrol at 10 mg or 20 mg dosage in combination with 600 mg of acetylsalicylic acid has analgesic properties significantly superior to either acetylsalicylic acid (600 mg) or codeine (60 mg) alone. Administration of dexoxadrol (20 mg, orally, twice daily) to 128 patients with severe pain gave complete relief to 50 % and partial relief to 28 % of the patients.
Route of Administration:
Oral
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NCI_THESAURUS |
C241
Created by
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| Code System | Code | Type | Description | ||
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CHEMBL72982
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3034023
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4741-41-7
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C65372
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DEXOXADROL
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4741-41-7
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1504
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C005840
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SUB07041MIG
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PRIMARY |
ACTIVE MOIETY
SALT/SOLVATE (PARENT)
