APADOLINE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C23H29N3OS
Molecular Weight	395.561
Optical Activity	UNSPECIFIED
Defined Stereocenters	1 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CCCNC(=O)C1=CC2=C(SC3=CC=CC=C3N2[C@H](C)CN4CCCC4)C=C1

InChI

InChIKey=KXMAIWXPZGQNCR-QGZVFWFLSA-N

InChI=1S/C23H29N3OS/c1-3-12-24-23(27)18-10-11-22-20(15-18)26(17(2)16-25-13-6-7-14-25)19-8-4-5-9-21(19)28-22/h4-5,8-11,15,17H,3,6-7,12-14,16H2,1-2H3,(H,24,27)/t17-/m1/s1

HIDE SMILES / InChI

Molecular Formula	C23H29N3OS
Molecular Weight	395.561
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	1 / 1
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://adisinsight.springer.com/drugs/800003488 | https://www.ncbi.nlm.nih.gov/pubmed/15989506

Apadoline [RP 60180, RP 60180A, RPR 60180] is a κ-opioid receptor agonist which was undergoing phase II clinical trials with Aventis Pharma for the treatment of pain.

Originator

Approval Year

PubMed

Title	Date	PubMed
Antinociceptive effects of the kappa-opioid receptor agonist RP 60180 compared with pentazocine in an experimental human pain model.	1997 Jun	9197945
Novel developments with selective, non-peptidic kappa-opioid receptor agonists.	1997 Oct	15989506

Patents

Sample Use Guides

In Vivo Use Guide

Pain: Twenty healthy male volunteers participated in a placebo-controlled, randomized, double-blind, five-way cross-over study. Single peroral doses of Apadoline (0.1, 0.5, and 1.0 mg), pentazocine (50 mg), and placebo were administered. Maximum antinociceptive effects were observed 2 h after the administration of 1.0 mg of Apadoline and 50 mg of pentazocine.

Route of Administration: Oral

Substance Class	Chemical Created by `admin` on `Fri Dec 15 16:17:20 GMT 2023` Edited by `admin` on `Fri Dec 15 16:17:20 GMT 2023`
Record UNII	5Q36UVB8YA
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

APADOLINE

Official Name

English

apadoline [INN]

Common Name

English

(+)-10-((1R)-METHYL-2-(1-PYRROLIDINYL)ETHYL)-N-PROPYLPHENOTHIAZINE-2-CARBOXAMIDE

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C241