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Details

Stereochemistry ABSOLUTE
Molecular Formula C23H29N3OS.ClH
Molecular Weight 432.022
Optical Activity UNSPECIFIED
Defined Stereocenters 1 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of APADOLINE HYDROCHLORIDE

SMILES

Cl.CCCNC(=O)C1=CC2=C(SC3=C(C=CC=C3)N2[C@H](C)CN4CCCC4)C=C1

InChI

InChIKey=VZVNQTBWGIMVRJ-UNTBIKODSA-N
InChI=1S/C23H29N3OS.ClH/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);1H/t17-;/m1./s1

HIDE SMILES / InChI
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
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

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

Unknown
149124
PubMed

PubMed

TitleDatePubMed
Novel developments with selective, non-peptidic kappa-opioid receptor agonists.
1997-10
Antinociceptive effects of the kappa-opioid receptor agonist RP 60180 compared with pentazocine in an experimental human pain model.
1997-06
Patents

Patents

EP2525830B1
2
US20120088756A1
2

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 Mon Mar 31 18:12:10 GMT 2025
Edited
by admin
on Mon Mar 31 18:12:10 GMT 2025
Record UNII
JB3J6BAJ3T
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
APADOLINE HYDROCHLORIDE
Common Name English
10H-PHENOTHIAZINE-2-CARBOXAMIDE, 10-(1-METHYL-2-(1-PYRROLIDINYL)ETHYL)-N-PROPYL-, MONOHYDROCHLORIDE, (R)-
Preferred Name English
N-PROPYL-10-(2-(1-PYRROLIDINYL)-1-METHYLETHYL)-2-PHENOTHIAZINECARBOXAMIDE HYDROCHLORIDE, D-
Common Name English
Code System Code Type Description
CAS
135092-09-0
Created by admin on Mon Mar 31 18:12:10 GMT 2025 , Edited by admin on Mon Mar 31 18:12:10 GMT 2025
PRIMARY
PUBCHEM
9867435
Created by admin on Mon Mar 31 18:12:10 GMT 2025 , Edited by admin on Mon Mar 31 18:12:10 GMT 2025
PRIMARY
FDA UNII
JB3J6BAJ3T
Created by admin on Mon Mar 31 18:12:10 GMT 2025 , Edited by admin on Mon Mar 31 18:12:10 GMT 2025
PRIMARY
Related Record Type Details
Structure of APADOLINE
PARENT -> SALT/SOLVATE
Related Record Type Details
Structure of APADOLINE
ACTIVE MOIETY
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