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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
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.

Approval Year

PubMed

PubMed

TitleDatePubMed
Liquid chromatography-tandem mass spectrometry method for determination of phencynonate in rat blood and urine.
2005 Dec 15
[Anticonvulsant effect of phencynonate hydrochloride on maximal electroshock seizure and the metrazol seizure threshold test in mice].
2005 Jun
Pharmacological profiles of an anticholinergic agent, phencynonate hydrochloride, and its optical isomers.
2005 May
Anticonvulsant effects of phencynonate hydrochloride and other anticholinergic drugs in soman poisoning: neurochemical mechanisms.
2005 Nov 26
Comparative study on pharmacological effects of DM-phencynonate hydrochloride and its optical isomers.
2005 Oct
Determination of thiencynonate by liquid chromatographic-mass spectrometry and its application to pharmacokinetics in rats.
2006 Sep 18
Liquid chromatography-tandem electrospray mass spectrometry method for determination of serial chiral novel anticholinergic compounds of phencynonate in rat plasma.
2007 Aug 15
Comparative pharmacokinetics and distribution kinetics in brain of phencynonate enantiomers in rats.
2008 Apr 2
Structural elucidation of in vivo metabolites of phencynonate and its analogue thiencynonate in rats by HPLC-ESI-MSn.
2010 Sep 15
Preparation and evaluation of orally disintegrating tablets of taste masked phencynonate HCl using ion-exchange resin.
2015 Jun
Simultaneous quantification of phencynonate and its active metabolite N-demethyl phencynonate in human plasma using liquid chromatography and isotope-dilution mass spectrometry.
2015 Sep
A rapid and efficient analytical method for the quantification of a novel anticholinergic compound, R-phencynonate, by stable isotope-dilution LC-MS/MS and its application to bioavailability and dose proportionality studies.
2017 May
Phencynonate mediates antidepressant response by activating sirtuin 6-SOD2/Prdx6 pathway.
2018 Nov 2
Phencynonate S-isomer as a eutomer is a novel central anticholinergic drug for anti-motion sickness.
2019 Feb 13
Comparative effects of scopolamine and phencynonate on organophosphorus nerve agent-induced seizure activity, neuropathology and lethality.
2019 Jun
Name Type Language
PHENCYNONATE HYDROCHLORIDE
Common Name English
BENZENEACETIC ACID, .ALPHA.-CYCLOPENTYL-.ALPHA.-HYDROXY-, (9-ANTI)-3-METHYL-3-AZABICYCLO(3.3.1)NON-9-YL ESTER, HYDROCHLORIDE (1:1)
Common Name English
Phencynonate hydrochloride [WHO-DD]
Common Name English
Code System Code Type Description
PUBCHEM
9821969
Created by admin on Sat Dec 16 02:31:11 GMT 2023 , Edited by admin on Sat Dec 16 02:31:11 GMT 2023
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CAS
172451-71-7
Created by admin on Sat Dec 16 02:31:11 GMT 2023 , Edited by admin on Sat Dec 16 02:31:11 GMT 2023
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EPA CompTox
DTXSID90938161
Created by admin on Sat Dec 16 02:31:11 GMT 2023 , Edited by admin on Sat Dec 16 02:31:11 GMT 2023
PRIMARY
FDA UNII
54F576E38V
Created by admin on Sat Dec 16 02:31:11 GMT 2023 , Edited by admin on Sat Dec 16 02:31:11 GMT 2023
PRIMARY