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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
Structure of DEXOXADROL

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

HIDE SMILES / InChI

Description

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

Targets

Targets

Primary TargetPharmacologyConditionPotency
104.0 nM [Ki]
19.0 nM [Ki]
Conditions
PubMed

PubMed

TitleDatePubMed
Structure-affinity relationship studies of non-competitive NMDA receptor antagonists derived from dexoxadrol and etoxadrol.
2005 Dec 15
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
Patents

Sample Use Guides

In Vivo Use Guide
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
In Vitro Use Guide
Dexoxadrol (10 uM) selectively blocked the secondary components of the synaptic response in rat hippocampal slices.
Name Type Language
DEXOXADROL
HSDB   INN  
INN  
Official Name English
DEXOXADROL [HSDB]
Common Name English
DEXOXADROL [INN]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C241
Created by admin on Tue Oct 22 06:06:27 UTC 2019 , Edited by admin on Tue Oct 22 06:06:27 UTC 2019
Code System Code Type Description
ChEMBL
CHEMBL72982
Created by admin on Tue Oct 22 06:06:27 UTC 2019 , Edited by admin on Tue Oct 22 06:06:27 UTC 2019
PRIMARY
PUBCHEM
3034023
Created by admin on Tue Oct 22 06:06:27 UTC 2019 , Edited by admin on Tue Oct 22 06:06:27 UTC 2019
PRIMARY
HSDB
4741-41-7
Created by admin on Tue Oct 22 06:06:27 UTC 2019 , Edited by admin on Tue Oct 22 06:06:27 UTC 2019
PRIMARY
NCI_THESAURUS
C65372
Created by admin on Tue Oct 22 06:06:27 UTC 2019 , Edited by admin on Tue Oct 22 06:06:27 UTC 2019
PRIMARY
WIKIPEDIA
DEXOXADROL
Created by admin on Tue Oct 22 06:06:27 UTC 2019 , Edited by admin on Tue Oct 22 06:06:27 UTC 2019
PRIMARY
CAS
4741-41-7
Created by admin on Tue Oct 22 06:06:27 UTC 2019 , Edited by admin on Tue Oct 22 06:06:27 UTC 2019
PRIMARY
INN
1504
Created by admin on Tue Oct 22 06:06:27 UTC 2019 , Edited by admin on Tue Oct 22 06:06:27 UTC 2019
PRIMARY
MESH
C005840
Created by admin on Tue Oct 22 06:06:27 UTC 2019 , Edited by admin on Tue Oct 22 06:06:27 UTC 2019
PRIMARY
EVMPD
SUB07041MIG
Created by admin on Tue Oct 22 06:06:27 UTC 2019 , Edited by admin on Tue Oct 22 06:06:27 UTC 2019
PRIMARY