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
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
Molecular Formula | ClH |
Molecular Weight | 36.461 |
Charge | 0 |
Count |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Optical Activity | NONE |
Molecular Formula | C22H31NO3 |
Molecular Weight | 357.4864 |
Charge | 0 |
Count |
|
Stereochemistry | EPIMERIC |
Additional Stereochemistry | No |
Defined Stereocenters | 3 / 4 |
E/Z Centers | 0 |
Optical Activity | UNSPECIFIED |
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
Title | Date | PubMed |
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Liquid chromatography-tandem mass spectrometry method for determination of phencynonate in rat blood and urine. | 2005 Dec 15 |
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[Anticonvulsant effect of phencynonate hydrochloride on maximal electroshock seizure and the metrazol seizure threshold test in mice]. | 2005 Jun |
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Pharmacological profiles of an anticholinergic agent, phencynonate hydrochloride, and its optical isomers. | 2005 May |
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Anticonvulsant effects of phencynonate hydrochloride and other anticholinergic drugs in soman poisoning: neurochemical mechanisms. | 2005 Nov 26 |
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Comparative study on pharmacological effects of DM-phencynonate hydrochloride and its optical isomers. | 2005 Oct |
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Determination of thiencynonate by liquid chromatographic-mass spectrometry and its application to pharmacokinetics in rats. | 2006 Sep 18 |
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Liquid chromatography-tandem electrospray mass spectrometry method for determination of serial chiral novel anticholinergic compounds of phencynonate in rat plasma. | 2007 Aug 15 |
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Comparative pharmacokinetics and distribution kinetics in brain of phencynonate enantiomers in rats. | 2008 Apr 2 |
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Structural elucidation of in vivo metabolites of phencynonate and its analogue thiencynonate in rats by HPLC-ESI-MSn. | 2010 Sep 15 |
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Preparation and evaluation of orally disintegrating tablets of taste masked phencynonate HCl using ion-exchange resin. | 2015 Jun |
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Simultaneous quantification of phencynonate and its active metabolite N-demethyl phencynonate in human plasma using liquid chromatography and isotope-dilution mass spectrometry. | 2015 Sep |
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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 |
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Phencynonate mediates antidepressant response by activating sirtuin 6-SOD2/Prdx6 pathway. | 2018 Nov 2 |
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Phencynonate S-isomer as a eutomer is a novel central anticholinergic drug for anti-motion sickness. | 2019 Feb 13 |
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Comparative effects of scopolamine and phencynonate on organophosphorus nerve agent-induced seizure activity, neuropathology and lethality. | 2019 Jun |
Substance Class |
Chemical
Created
by
admin
on
Edited
Sat Dec 16 02:31:11 GMT 2023
by
admin
on
Sat Dec 16 02:31:11 GMT 2023
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Record UNII |
54F576E38V
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Record Status |
Validated (UNII)
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Record Version |
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172451-71-7
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DTXSID90938161
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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
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