oliceridine   

GtoPdb Ligand ID: 7334

Synonyms: TRV130 | TRV130A
Compound class: Synthetic organic
Comment: Oliceridine (TRV130) is an opioid compound. This compound has been developed to exhibit biased-signalling (specifically bias towards G protein signalling), with the aim of reducing the adverse effects associated with use of other opioid drugs [1-2].
2D Structure
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Physico-chemical Properties
Hydrogen bond acceptors 3
Hydrogen bond donors 1
Rotatable bonds 7
Topological polar surface area 71.62
Molecular weight 386.2
XLogP 3.12
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
Canonical SMILES COc1ccsc1CNCCC1(CCOC2(C1)CCCC2)c1ccccn1
Isomeric SMILES COc1ccsc1CNCC[C@]1(CCOC2(C1)CCCC2)c1ccccn1
InChI 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
InChI Key DMNOVGJWPASQDL-OAQYLSRUSA-N
References
1. Chen XT, Pitis P, Liu G, Yuan C, Gotchev D, Cowan CL, Rominger DH, Koblish M, Dewire SM, Crombie AL et al.. (2013)
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.
J. Med. Chem., 56 (20): 8019-31. [PMID:24063433]
2. DeWire SM, Yamashita DS, Rominger DH, Liu G, Cowan CL, Graczyk TM, Chen XT, Pitis PM, Gotchev D, Yuan C et al.. (2013)
A G protein-biased ligand at the μ-opioid receptor is potently analgesic with reduced gastrointestinal and respiratory dysfunction compared with morphine.
J. Pharmacol. Exp. Ther., 344 (3): 708-17. [PMID:23300227]
3. Soergel DG, Ann Subach R, Sadler B, Connell J, Marion AS, Cowan CL, Violin JD, Lark MW. (2014)
First Clinical Experience With TRV130: Pharmacokinetics and Pharmacodynamics in Healthy Volunteers.
J Clin Pharmacol, 54 (3): 351-7. [PMID:24122908]