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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 of OLICERIDINE

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

Molecular Formula C22H30N2O2S
Molecular Weight 386.5527
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 1 / 1
E/Z Centers 0
Optical Activity UNSPECIFIED

Description
Curator's Comment:: 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.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
8 nM [EC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
PubMed

PubMed

TitleDatePubMed
A G protein-biased ligand at the μ-opioid receptor is potently analgesic with reduced gastrointestinal and respiratory dysfunction compared with morphine.
2013 Mar
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
First clinical experience with TRV130: pharmacokinetics and pharmacodynamics in healthy volunteers.
2014 Mar
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
A randomized, phase 2 study investigating TRV130, a biased ligand of the μ-opioid receptor, for the intravenous treatment of acute pain.
2016 Jan
How Oliceridine (TRV-130) Binds and Stabilizes a μ-Opioid Receptor Conformational State That Selectively Triggers G Protein Signaling Pathways.
2016 Nov 22
Patents

Patents

Sample Use Guides

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
Substance Class Chemical
Created
by admin
on Sat Jun 26 14:09:30 UTC 2021
Edited
by admin
on Sat Jun 26 14:09:30 UTC 2021
Record UNII
MCN858TCP0
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
OLICERIDINE
INN   USAN   WHO-DD  
INN   USAN  
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
Created by admin on Sat Jun 26 14:09:31 UTC 2021 , Edited by admin on Sat Jun 26 14:09:31 UTC 2021
Code System Code Type Description
CAS
1401028-24-7
Created by admin on Sat Jun 26 14:09:31 UTC 2021 , Edited by admin on Sat Jun 26 14:09:31 UTC 2021
PRIMARY
DRUG BANK
DB14881
Created by admin on Sat Jun 26 14:09:31 UTC 2021 , Edited by admin on Sat Jun 26 14:09:31 UTC 2021
PRIMARY
INN
10250
Created by admin on Sat Jun 26 14:09:31 UTC 2021 , Edited by admin on Sat Jun 26 14:09:31 UTC 2021
PRIMARY
NCI_THESAURUS
C174704
Created by admin on Sat Jun 26 14:09:31 UTC 2021 , Edited by admin on Sat Jun 26 14:09:31 UTC 2021
PRIMARY
WIKIPEDIA
Oliceridine
Created by admin on Sat Jun 26 14:09:31 UTC 2021 , Edited by admin on Sat Jun 26 14:09:31 UTC 2021
PRIMARY
PUBCHEM
66553195
Created by admin on Sat Jun 26 14:09:31 UTC 2021 , Edited by admin on Sat Jun 26 14:09:31 UTC 2021
PRIMARY
FDA UNII
MCN858TCP0
Created by admin on Sat Jun 26 14:09:31 UTC 2021 , Edited by admin on Sat Jun 26 14:09:31 UTC 2021
PRIMARY
RXCUI
2392230
Created by admin on Sat Jun 26 14:09:31 UTC 2021 , Edited by admin on Sat Jun 26 14:09:31 UTC 2021
PRIMARY
ChEMBL
CHEMBL2443262
Created by admin on Sat Jun 26 14:09:31 UTC 2021 , Edited by admin on Sat Jun 26 14:09:31 UTC 2021
PRIMARY
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METABOLIC ENZYME -> SUBSTRATE
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TARGET -> AGONIST
METABOLIC ENZYME -> SUBSTRATE
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EXCRETED UNCHANGED
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ACTIVE MOIETY
Name Property Type Amount Referenced Substance Defining Parameters References
Volume of Distribution PHARMACOKINETIC AT STEADY-STATE

Tmax PHARMACOKINETIC SINGLE DOSE

INTRAVENOUS ADMINISTRATION

Biological Half-life PHARMACOKINETIC INTRAVENOUS ADMINISTRATION

SINGLE DOSE