OLICERIDINE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C22H30N2O2S
Molecular Weight	386.5527
Optical Activity	UNSPECIFIED
Defined Stereocenters	1 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

COc1ccsc1CNCC[C@]2(CCOC3(CCCC3)C2)c4ccccn4

InChI

InChIKey=DMNOVGJWPASQDL-OAQYLSRUSA-N

InChI=1S/C22H30N2O2S/c1-25-18-7-15-27-19(18)16-23-13-10-21(20-6-2-5-12-24-20)11-14-26-22(17-21)8-3-4-9-22/h2,5-7,12,15,23H,3-4,8-11,13-14,16-17H2,1H3/t21-/m1/s1

HIDE SMILES / InChI

Description
Sources: http://adisinsight.springer.com/drugs/800035617
Curator's Comment:: Description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/23300227

Oliceridine (TRV-130) is a potent μ-opioid receptor agonist. In cell-based assays, TRV130 elicits robust G protein signaling, with potency and efficacy similar to morphine, but with far less β-arrestin recruitment and receptor internalization. In rodents, TRV130 is potently analgesic while causing less gastrointestinal dysfunction and respiratory suppression than morphine at equianalgesic doses. Oliceridine is being developed by Trevena for the first-line treatment of moderate-to-severe acute postoperative pain. Phase III development is underway for the treatment of postoperative pain in the US. Phase II development is underway for the treatment of acute pain in the US.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Mu opioid receptor 205 Target ID: CHEMBL233 Sources: https://www.ncbi.nlm.nih.gov/pubmed/23300227 \| https://www.ncbi.nlm.nih.gov/pubmed/24063433	Agonist 2470		8.0 nM [EC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Pain 580 Sources: http://adisinsight.springer.com/drugs/800035617	Primary		Phase III 643	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
A G protein-biased ligand at the μ-opioid receptor is potently analgesic with reduced gastrointestinal and respiratory dysfunction compared with morphine.	2013 Mar	23300227
Structure-activity relationships and discovery of a G protein biased μ opioid receptor ligand, [(3-methoxythiophen-2-yl)methyl]({2-[(9R)-9-(pyridin-2-yl)-6-oxaspiro-[4.5]decan-9-yl]ethyl})amine (TRV130), for the treatment of acute severe pain.	2013 Oct 24	24063433
First clinical experience with TRV130: pharmacokinetics and pharmacodynamics in healthy volunteers.	2014 Mar	24122908
Biased agonism of the μ-opioid receptor by TRV130 increases analgesia and reduces on-target adverse effects versus morphine: A randomized, double-blind, placebo-controlled, crossover study in healthy volunteers.	2014 Sep	24954166
A randomized, phase 2 study investigating TRV130, a biased ligand of the μ-opioid receptor, for the intravenous treatment of acute pain.	2016 Jan	26683109
How Oliceridine (TRV-130) Binds and Stabilizes a μ-Opioid Receptor Conformational State That Selectively Triggers G Protein Signaling Pathways.	2016 Nov 22	27778501

Patents

Sample Use Guides

In Vivo Use Guide

Oliceridine dosed at 2mg or 3mg every 3 hours demonstrated a tolerability profile similar to morphine dosed at 4mg every 4 hours, in a randomised, double-blind, placebo-controlled, 48-hour phase IIa/b trial in patients with acute postoperative pain after bunionectomy

Route of Administration: Intravenous

In Vitro Use Guide

Unknown

Name

Type

Language

OLICERIDINE

Official Name

English

TRV130

Code

English

OLICERIDINE [INN]

Common Name

English

TRV-130

Code

English

6-OXASPIRO(4.5)DECANE-9-ETHANAMINE, N-((3-METHOXY-2-THIENYL)METHYL)-9-(2-PYRIDINYL)-, (9R)-

Systematic Name

English

OLICERIDINE [WHO-DD]

Common Name

English

OLICERIDINE [USAN]

Common Name

English

N-((3-METHOXYTHIOPHEN-2-YL)METHYL)-2-((9R)-9-(PYRIDIN-2-YL)-6-OXASPIRO(4.5)DECAN-9-YL)ETHANAMINE

Systematic Name

English

OLINVYK

Brand Name

English

Classification Tree Code System Code

DEA NO.

9245