Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C20H23NO2.ClH |
| Molecular Weight | 345.863 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 2 / 2 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
Cl.C1OC(O[C@H]1[C@@H]2CCCCN2)(C3=CC=CC=C3)C4=CC=CC=C4
InChI
InChIKey=GYPWNVSWCIMIHQ-GRTNUQQKSA-N
InChI=1S/C20H23NO2.ClH/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;1H/t18-,19+;/m0./s1
| Molecular Formula | C20H23NO2 |
| Molecular Weight | 309.4021 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ABSOLUTE |
| Additional Stereochemistry | No |
| Defined Stereocenters | 2 / 2 |
| E/Z Centers | 0 |
| Optical Activity | UNSPECIFIED |
| Molecular Formula | ClH |
| Molecular Weight | 36.461 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
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.
Approval Year
Doses
| Dose | Population | Adverse events |
|---|---|---|
20 mg single, oral Studied dose |
healthy, ADULT Health Status: healthy Age Group: ADULT Sex: F Food Status: UNKNOWN Sources: |
Other AEs: psychosis... |
AEs
| AE | Significance | Dose | Population |
|---|---|---|---|
| psychosis | 5 patients | 20 mg single, oral Studied dose |
healthy, ADULT Health Status: healthy Age Group: ADULT Sex: F Food Status: UNKNOWN Sources: |
PubMed
| Title | Date | PubMed |
|---|---|---|
| Synthesis and NMDA-receptor affinity of 4-oxo-dexoxadrol derivatives. | 2006-09-01 |
|
| Relationships between the structure of dexoxadrol and etoxadrol analogues and their NMDA receptor affinity. | 2006 |
|
| Structure-affinity relationship studies of non-competitive NMDA receptor antagonists derived from dexoxadrol and etoxadrol. | 2005-12-15 |
|
| Characterization of the non-competitive antagonist binding site of the NMDA receptor in dark Agouti rats. | 2004-08-06 |
|
| Synthesis and NMDA-receptor affinity of ring and side chain homologous dexoxadrol derivatives. | 2004-02 |
|
| Molecular modeling of noncompetitive antagonists of the NMDA receptor: proposal of a pharmacophore and a description of the interaction mode. | 2002-02 |
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
| Substance Class |
Chemical
Created
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admin
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Edited
Mon Mar 31 17:57:29 GMT 2025
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Mon Mar 31 17:57:29 GMT 2025
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| Record UNII |
T0C1IR71L8
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Validated (UNII)
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C245
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CHEMBL72982
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1162-15-8
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T0C1IR71L8
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C77324
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DTXSID101350576
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300000055419
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71658
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m4597
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PARENT -> SALT/SOLVATE |
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ACTIVE MOIETY |