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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 of APADOLINE

SMILES

CCCNC(=O)C1=CC2=C(SC3=C(C=CC=C3)N2[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
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 1 / 1
E/Z Centers 0
Optical Activity UNSPECIFIED

Description

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

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
Record UNII
5Q36UVB8YA
Record Status Validated (UNII)
Record Version