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Details

Stereochemistry RACEMIC
Molecular Formula C22H31NO3
Molecular Weight 357.4864
Optical Activity ( + / - )
Defined Stereocenters 3 / 4
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of PHENCYNONATE

SMILES

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

InChI

InChIKey=ROZOEEGFKDFEFP-UHFFFAOYSA-N
InChI=1S/C22H31NO3/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

HIDE SMILES / InChI

Molecular Formula C22H31NO3
Molecular Weight 357.4864
Charge 0
Count
Stereochemistry MIXED
Additional Stereochemistry No
Defined Stereocenters 2 / 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.

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
Comparative pharmacokinetics and distribution kinetics in brain of phencynonate enantiomers in rats.
2008 Apr 2
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
Phencynonate S-isomer as a eutomer is a novel central anticholinergic drug for anti-motion sickness.
2019 Feb 13
Substance Class Chemical
Created
by admin
on Sat Dec 16 02:31:11 GMT 2023
Edited
by admin
on Sat Dec 16 02:31:11 GMT 2023
Record UNII
H84F112WBJ
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
PHENCYNONATE
Common Name English
.ALPHA.-BENCYNONATINE
Common Name English
BENZENEACETIC ACID, .ALPHA.-CYCLOPENTYL-.ALPHA.-HYDROXY-, (9-ANTI)-3-METHYL-3-AZABICYCLO(3.3.1)NON-9-YL ESTER
Common Name English
Phencynonate [WHO-DD]
Common Name English
Code System Code Type Description
FDA UNII
H84F112WBJ
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
CAS
256511-89-4
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
PUBCHEM
9821970
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
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SALT/SOLVATE -> PARENT
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ACTIVE MOIETY