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Details

Stereochemistry RACEMIC
Molecular Formula C22H31NO3.ClH
Molecular Weight 393.947
Optical Activity ( + / - )
Defined Stereocenters 2 / 4
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of PHENCYNONATE HYDROCHLORIDE

SMILES

Cl.CN1C[C@@H]2CCC[C@H](C1)[C@@H]2OC(=O)C(O)(C3CCCC3)C4=CC=CC=C4

InChI

InChIKey=AUKYHFFECJXLHI-UHFFFAOYSA-N
InChI=1S/C22H31NO3.ClH/c1-23-14-16-8-7-9-17(15-23)20(16)26-21(24)22(25,19-12-5-6-13-19)18-10-3-2-4-11-18;/h2-4,10-11,16-17,19-20,25H,5-9,12-15H2,1H3;1H

HIDE SMILES / InChI

Description

Phencynonate (PHH) is a novel anticholinergic compound. It is structurally similar to scopolamine, possesses both muscarinic and nicotinic antagonistic properties as well as anti-NMDA properties. It has been developed as a safe and effective drug for the prevention of motion sickness in tablet form, it also demonstrates clear anticonvulsant effectiveness after soman poisoning in a rat model. S-isomer was more effective against motion sickness and had not anxiogenic action at therapeutic doses. S-isomer has the higher affinity and activity for mAChR in cerebral cortex and acted as a competitive mAChR antagonist. PHH was able to suppress chronic unpredictable mild stress (CUMS)-induced oxidative stress and enhance the antioxidant capacity and antioxidant proteins activity, such as superoxide dismutase 2 (SOD2) and peroxiredoxin 6 (Prdx6). PHH ameliorated CUMS-induced depressive phenotypes by up-regulating SIRT6 deacetylation activity. PHH-mediating SIRT6 pathway is required for antidepressant response and PHH can be used as a novel therapeutic to effectively treat depression. Phencynonate is in phase III clinical trials for the treatment of vertigo.

Originator

Approval Year

PubMed