XORPHANOL

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C23H31NO
Molecular Weight	337.4983
Optical Activity	UNSPECIFIED
Defined Stereocenters	4 / 4
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

C[C@H]1CC(=C)C[C@]23CCN(CC4CCC4)[C@H](CC5=CC=C(O)C=C25)[C@H]13

InChI

InChIKey=AZJPPZHRNFQRRE-AZIXLERZSA-N

InChI=1S/C23H31NO/c1-15-10-16(2)22-21-11-18-6-7-19(25)12-20(18)23(22,13-15)8-9-24(21)14-17-4-3-5-17/h6-7,12,16-17,21-22,25H,1,3-5,8-11,13-14H2,2H3/t16-,21+,22-,23+/m0/s1

HIDE SMILES / InChI

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/4039650 | https://www.ncbi.nlm.nih.gov/pubmed/6135994 | https://adisinsight.springer.com/drugs/800003663

Xorphanol (also known as TR5379M) is a full κ-opioid receptor agonist and is a partial agonist at μ opioid receptor. Clinically, xorphanol was studied as an orally active analgesic that provided effective pain relief but showed low physical dependence liability. Further development of this drug was discontinued.

Originator

Approval Year

PubMed

Title	Date	PubMed
Pharmacological profiles of opioid ligands at kappa opioid receptors.	2006-01-25	16433932
Activity of opioid ligands in cells expressing cloned mu opioid receptors.	2003-01-04	12513698
Activation profiles of opioid ligands in HEK cells expressing delta opioid receptors.	2002-11-18	12437765

Sample Use Guides

In Vivo Use Guide

Unknown

Route of Administration: Oral

Name

Type

Language

XORPHANOL

Official Name

English

TR 5379

Preferred Name

English

xorphanol [INN]

Common Name

English

17-(CYCLOBUTYLMETHYL)-8.BETA.-METHYL-6-METHYLENEMORPHINAN-3-OL

Systematic Name

English

Classification Tree Code System Code

NCI_THESAURUS

C241