DEXOXADROL HYDROCHLORIDE

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

Structure Search

SMILES

Cl.[H][C@@]1(COC(O1)(C2=CC=CC=C2)C3=CC=CC=C3)[C@]4([H])CCCCN4

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

HIDE SMILES / InChI

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

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/3253423 | https://www.ncbi.nlm.nih.gov/pubmed/16719812

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

Primary Target	Pharmacology	Condition	Potency
Glutamate NMDA receptor 46 Target ID: CHEMBL1907608 Sources: https://www.ncbi.nlm.nih.gov/pubmed/2747847 \| https://www.ncbi.nlm.nih.gov/pubmed/16169732	Antagonist 2778		104.0 nM [Ki]
Glutamate NMDA receptor; GRIN1/GRIN2A 3 Target ID: CHEMBL1907604 Sources: https://www.ncbi.nlm.nih.gov/pubmed/26430967	Antagonist 2778		19.0 nM [Ki]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Alcoholism 19 Sources: https://www.ncbi.nlm.nih.gov/pubmed/5441096	Primary		Phase I 428	Unknown Approved Use Unknown
Pain 614 Sources: https://www.ncbi.nlm.nih.gov/pubmed/4187619 https://www.ncbi.nlm.nih.gov/pubmed/14270339	Primary		Phase I 428	Unknown Approved Use Unknown

Doses

Dose	Population	Adverse events
20 mg single, oral (unknown) Studied dose Dose: 20 mg Route: oral Route: single Dose: 20 mg Sources: https://pubmed.ncbi.nlm.nih.gov/14270339	healthy, ADULT n = 74 Health Status: healthy Age Group: ADULT Sex: F Food Status: UNKNOWN Population Size: 74 Sources: https://pubmed.ncbi.nlm.nih.gov/14270339	Other AEs: psychosis... Other AEs: psychosis (5 patients) Sources: https://pubmed.ncbi.nlm.nih.gov/14270339

AEs

AE	Significance	Dose	Population
psychosis	5 patients	20 mg single, oral (unknown) Studied dose Dose: 20 mg Route: oral Route: single Dose: 20 mg Sources: https://pubmed.ncbi.nlm.nih.gov/14270339	healthy, ADULT n = 74 Health Status: healthy Age Group: ADULT Sex: F Food Status: UNKNOWN Population Size: 74 Sources: https://pubmed.ncbi.nlm.nih.gov/14270339

Sourcing

Vendor/Aggregator	ID	URL
AK Scientific	SYN5508	https://aksci.com/item_detail.php?cat=SYN5508
AOBIOUS INC	AOB5315	http://aobious.com/aobious/search?search_query=AOB5315
Alfa Chemistry	162111	http://www.alfa-chemistry.com/search.aspx?q=162111
Alfa Chemistry	ACM4792181	http://www.alfa-chemistry.com/search.aspx?q=ACM4792181
Hairui	HR149457	http://www.hairuichem.com/en/product/search.do?q=HR149457
Hairui	HR149520	http://www.hairuichem.com/en/product/search.do?q=HR149520
KeyOrganics	AS-16845	http://www.keyorganicsinc.com/bionet/catalogsearch/result?q=AS-16845
MolPort	MolPort-044-181-434	https://www.molport.com/shop/molecule-link/MolPort-044-181-434
MuseChem	I006462	https://www.musechem.com/product/I006462.html
MuseChem	I012683	https://www.musechem.com/product/I012683.html
TimTec	ST50556819	http://www.echemstore.com/catalogsearch/result/?q=ST50556819
eMolecules	85147611	https://orderbb.emolecules.com/search/#?query=85147611
mcule	MCULE-3791881888	https://mcule.com/MCULE-3791881888/
mcule	MCULE-4804227183	https://mcule.com/MCULE-4804227183/
mcule	MCULE-9801028073	https://mcule.com/MCULE-9801028073/

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	12032600
Structure-affinity relationship studies of non-competitive NMDA receptor antagonists derived from dexoxadrol and etoxadrol.	2005 Dec 15	16169732

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.

Substance Class	Chemical Created by `admin` on `Fri Dec 15 15:25:50 GMT 2023` Edited by `admin` on `Fri Dec 15 15:25:50 GMT 2023`
Record UNII	T0C1IR71L8
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

DEXOXADROL HYDROCHLORIDE

Official Name

English

D-DIOXADROL HYDROCHLORIDE

Common Name

English

CL-911C

Code

English

U-22559A

Code

English

DIOXADROL HYDROCHLORIDE, (+)-

Common Name

English

DEXOXADROL HYDROCHLORIDE [USAN]

Common Name

English

U-22,559A

Code

English

DEXOXADROL HCL

Common Name

English

NIH-10375

Code

English

PIPERIDINE, 2-((4S)-2,2-DIPHENYL-1,3-DIOXOLAN-4-YL)-, HYDROCHLORIDE, (2S)-

Systematic Name

English

RELANE

Brand Name

English

(+)-2-(2,2-DIPHENYL-1,3-DIOXOLAN-4-YL)PIPERIDINE HYDROCHLORIDE

Systematic Name

English

DIOXADROL D-FORM HYDROCHLORIDE [MI]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C245