Phenserine
Derivative of Physostigmine (Eserine) || Phenserine is under development by Axonyx, a US biopharmaceutical company that focuses on treatments for dementia. Phenserine is a next generation acetylcholinesterase (AChE) inhibitor indicated for the treatment of AD. Unlike currently marketed AChE inhibitors, it has a dual mechanism of action that also includes anti-amyloid activity, which may confer disease-modifying effects in patients with AD. If this is substantiated in an ongoing clinical trial then phenserine may open the door to an entirely new type of treatment for AD. Axonyx announced on 20 September 2005 that phenserine was ineffective in two curtailed phase 3 trials. || Phenyl carbamoyl analogues of physostigmine-esrine were developed to provide longer acting and better tolerated Alzheimer's disease treatment. Posiphen (enantiomer of phenserine: ANVS401 (+)-phenserine) is under investigation in clinical trial NCT02925650 (Early Alzheimer's Disease) Posiphen does not inhibit AChE or BChE, but its major and minor metabolites (+)-N1-norPosiphen and (+)-N1,N8-bisnorPosiphen, respectively, possessed modest AChE inhibitory activity.
General
Type : Derivative of physostigmine-eserine, Stigmine, Carbamate, Drug, Indole
Chemical_Nomenclature : Pyrrolo(2,3-b)indol-5-ol, 1,2,3,3a,8,8a-hexahydro-1,3a,8-trimethyl-, phenylcarbamate (ester), (3aS-cis)- || [(3aS,8bR)-3,4,8b-trimethyl-2,3a-dihydro-1H-pyrrolo[2,3-b]indol-7-yl] N-phenylcarbamate
Canonical SMILES : CC12CCN(C1N(C3=C2C=C(C=C3)OC(=O)NC4=CC=CC=C4)C)C
InChI : InChI=1S\/C20H23N3O2\/c1-20-11-12-22(2)18(20)23(3)17-10-9-15(13-16(17)20)25-19(24)21-14-7-5-4-6-8-14\/h4-10,13,18H,11-12H2,1-3H3,(H,21,24)\/t18-,20+\/m1\/s1
InChIKey : PBHFNBQPZCRWQP-QUCCMNQESA-N || PBHFNBQPZCRWQP-AZUAARDMSA-N
Other name(s) : (-)-Phenserine || (-)-Eseroline phenylcarbamate || N-phenylcarbamoyl eseroline || Posiphen || (+)-phenserine || (+)-Posiphen || Phenserine, (+)- || Buntanetap || R-Phenserine || DB15317 || CHEMBL4297417 || SCHEMBL23874278
MW : 337.42 || 337.4
Formula : C20H23N3O2
CAS_number : 101246-66-6, 116839-68-0
UniChem : PBHFNBQPZCRWQP-QUCCMNQESA-N, PBHFNBQPZCRWQP-AZUAARDMSA-N
Target
Families : Phenserine ligand of proteins in family
ACHE
References (31)
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