ENADOLINE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C24H32N2O3
Molecular Weight	396.5225
Optical Activity	UNSPECIFIED
Defined Stereocenters	3 / 3
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CN([C@H]1CC[C@@]2(CCCO2)C[C@@H]1N3CCCC3)C(=O)CC4=CC=CC5=C4C=CO5

InChI

InChIKey=JMBYBVLCYODBJQ-HFMPRLQTSA-N

InChI=1S/C24H32N2O3/c1-25(23(27)16-18-6-4-7-22-19(18)9-15-28-22)20-8-11-24(10-5-14-29-24)17-21(20)26-12-2-3-13-26/h4,6-7,9,15,20-21H,2-3,5,8,10-14,16-17H2,1H3/t20-,21-,24-/m0/s1

HIDE SMILES / InChI

Molecular Formula	C24H32N2O3
Molecular Weight	396.5225
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	3 / 3
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/2178014 | https://www.ncbi.nlm.nih.gov/pubmed/8889289 | https://www.ncbi.nlm.nih.gov/pubmed/15989506

Enadoline (CI-977) is a potent and selective agonist at the kappa-opioid receptor. Enadoline is a potent antinociceptive agent. Clinical use of enadoline was associated with dose-limiting neuropsychiatric adverse events. Enadoline may yet find some application against ischaemic stroke and severe head injury, presumably in comatose patients.

CNS Activity

Originator

Approval Year

PubMed

Title	Date	PubMed
CI-977, a novel and selective agonist for the kappa-opioid receptor.	1990 Sep	2178014
Radioligand-dependent discrepancy in agonist affinities enhanced by mutations in the kappa-opioid receptor.	1996 Oct	8863844
Analysis of [3H]bremazocine binding in single and combinatorial opioid receptor knockout mice.	2001 Mar 2	11239918
Design and synthesis of novel dimeric morphinan ligands for kappa and micro opioid receptors.	2003 Nov 20	14613319

Sample Use Guides

In Vivo Use Guide

20, 40, 80, and 160 microg/70 kg. The highest dose (160 microg/70 kg) was not tolerated and led to psychotomimetic effects.

Route of Administration: Intramuscular

Substance Class	Chemical Created by `admin` on `Fri Dec 15 16:12:49 GMT 2023` Edited by `admin` on `Fri Dec 15 16:12:49 GMT 2023`
Record UNII	KJL283326C
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

ENADOLINE

Official Name

English

ENADOLINE [HSDB]

Common Name

English

4-BENZOFURANACETAMIDE, N-METHYL-N-(7-(1-PYRROLIDINYL)-1-OXASPIRO(4.5)DEC-8-YL)-, (5R-(5.ALPHA.,7.ALPHA.,8.BETA.))-

Common Name

English

N-METHYL-N-((5R,7S,8S)-7-(1-PYRROLIDINYL)-1-OXASPIRO(4.5)DEC-8-YL)-4-BENZOFURANACETAMIDE

Systematic Name

English

enadoline [INN]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C67413