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
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
| 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 |
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.
Originator
Approval Year
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 |
|
| 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 |
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| First clinical experience with TRV130: pharmacokinetics and pharmacodynamics in healthy volunteers. | 2014 Mar |
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| 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
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
Edited
Sat Jun 26 14:09:30 UTC 2021
by
admin
on
Sat Jun 26 14:09:30 UTC 2021
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| Record UNII |
MCN858TCP0
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| Record Status |
Validated (UNII)
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DEA NO. |
9245
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1401028-24-7
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DB14881
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10250
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C174704
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Oliceridine
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66553195
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MCN858TCP0
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2392230
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CHEMBL2443262
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METABOLIC ENZYME -> SUBSTRATE |
MINOR
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BINDER->LIGAND |
BINDING
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SALT/SOLVATE -> PARENT | |||
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METABOLIC ENZYME -> SUBSTRATE |
MAJOR
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TARGET -> AGONIST | |||
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METABOLIC ENZYME -> SUBSTRATE |
MINOR
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METABOLIC ENZYME -> SUBSTRATE |
MAJOR
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EXCRETED UNCHANGED |
URINE
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| Related Record | Type | Details | ||
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METABOLITE -> PARENT |
PLASMA
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METABOLITE -> PARENT |
URINE
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ACTIVE MOIETY |
| Name | Property Type | Amount | Referenced Substance | Defining | Parameters | References |
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| Volume of Distribution | PHARMACOKINETIC |
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AT STEADY-STATE |
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| Tmax | PHARMACOKINETIC |
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SINGLE DOSE |
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| Biological Half-life | PHARMACOKINETIC |
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INTRAVENOUS ADMINISTRATION |
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