PZM21   

GtoPdb Ligand ID: 9286

Synonyms: (S,S)-1-[2-(dimethylamino)-3-(4-hydroxyphenyl)propyl]-3-(1-thiophen-3-ylpropan-2-yl)urea | (S,S)-21 [PMID: 27533032]
Compound class: Synthetic organic
Comment: PZM21 is a potent, selective μ opioid receptor agonist with bias towards G-protein (Gi) activation over β-arrestin 2 recruitment [1]. This provides a compound with reduced propensity to produce common opioid side effects whilst retaining analgesic activity. PZM21 is being used experimentally for its analgesic activity.
This compound is not in PubChem and its SMILES string does not retrieve any patent documents from SureChembl (late August 2016).
Compare this with oliceridine, a chemically unrelated μ opioid receptor G-protein biased agonist.
2D Structure
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Physico-chemical Properties
Hydrogen bond acceptors 4
Hydrogen bond donors 3
Rotatable bonds 10
Topological polar surface area 92.84
Molecular weight 361.18
XLogP 2.42
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
Canonical SMILES CC(Cc1cscc1)NC(=O)NCC(N(C)C)Cc1ccc(cc1)O
Isomeric SMILES C[C@@H](Cc1cscc1)NC(=O)NC[C@@H](N(C)C)Cc1ccc(cc1)O
InChI InChI=1S/C19H27N3O2S/c1-14(10-16-8-9-25-13-16)21-19(24)20-12-17(22(2)3)11-15-4-6-18(23)7-5-15/h4-9,13-14,17,23H,10-12H2,1-3H3,(H2,20,21,24)/t14-,17-/m0/s1
InChI Key MEDBIJOVZJEMBI-YOEHRIQHSA-N
References
1. Manglik A, Lin H, Aryal DK, McCorvy JD, Dengler D, Corder G, Levit A, Kling RC, Bernat V, Hübner H et al.. (2016)
Structure-based discovery of opioid analgesics with reduced side effects.
Nature, 537 (7619): 185-190. [PMID:27533032]