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.
General
Type : Derivative of physostigmine-eserine,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)-
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
Other name(s) : (-)-Phenserine,(-)-Eseroline phenylcarbamate,N-phenylcarbamoyl eseroline
MW : 337.42
Formula : C20H23N3O2
CAS_number : 101246-66-6
PubChem : 192706
UniChem : PBHFNBQPZCRWQP-QUCCMNQESA-N
IUPHAR :
Wikipedia :
Target
References (19)
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| Ref : Front Neurosci , 15 :635483 , 2021 |
| Abstract : Ghiam_2021_Front.Neurosci_15_635483 |
| ESTHER : Ghiam_2021_Front.Neurosci_15_635483 |
| PubMedSearch : Ghiam_2021_Front.Neurosci_15_635483 |
| PubMedID: 33833663 |
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| Abstract : Hsueh_2019_Cell.Transplant__963689719854693 |
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| PubMedSearch : Hsueh_2019_Cell.Transplant__963689719854693 |
| PubMedID: 31177840 |
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| PubMedSearch : Thatte_2005_Curr.Opin.Investig.Drugs_6_729 |
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| PubMedSearch : Greig_2005_Curr.Alzheimer.Res_2_281 |
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| Abstract : Shaw_2001_Proc.Natl.Acad.Sci.U.S.A_98_7605 |
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| PubMedSearch : Shaw_2001_Proc.Natl.Acad.Sci.U.S.A_98_7605 |
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| ESTHER : Greig_2000_Acta.Neurol.Scand.Suppl_176_74 |
| PubMedSearch : Greig_2000_Acta.Neurol.Scand.Suppl_176_74 |
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| ESTHER : Yu_1999_J.Med.Chem_42_1855 |
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| Title : Phenserine, a novel acetylcholinesterase inhibitor, attenuates impaired learning of rats in a 14-unit T-maze induced by blockade of the N- methyl-D-aspartate receptor - Patel_1998_Neuroreport_9_171 |
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| ESTHER : Patel_1998_Neuroreport_9_171 |
| PubMedSearch : Patel_1998_Neuroreport_9_171 |
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| Abstract : al-Jafari_1998_Biochem.Biophys.Res.Commun_248_180 |
| ESTHER : al-Jafari_1998_Biochem.Biophys.Res.Commun_248_180 |
| PubMedSearch : al-Jafari_1998_Biochem.Biophys.Res.Commun_248_180 |
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| Title : Syntheses and anticholinesterase activities of (3aS)-N1, N8- bisnorphenserine, (3aS)-N1,N8-bisnorphysostigmine, their antipodal isomers, and other potential metabolites of phenserine - Yu_1998_J.Med.Chem_41_2371 |
| Author(s) : Yu Q , Greig NH , Holloway HW , Brossi A |
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| Abstract : Yu_1998_J.Med.Chem_41_2371 |
| ESTHER : Yu_1998_J.Med.Chem_41_2371 |
| PubMedSearch : Yu_1998_J.Med.Chem_41_2371 |
| PubMedID: 9632370 |
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| Abstract : Yu_1997_J.Med.Chem_40_2895 |
| ESTHER : Yu_1997_J.Med.Chem_40_2895 |
| PubMedSearch : Yu_1997_J.Med.Chem_40_2895 |
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| Abstract : Ikari_1995_Neuroreport_6_481 |
| ESTHER : Ikari_1995_Neuroreport_6_481 |
| PubMedSearch : Ikari_1995_Neuroreport_6_481 |
| PubMedID: 7766848 |
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| ESTHER : Iijima_1993_Psychopharmacology_112_415 |
| PubMedSearch : Iijima_1993_Psychopharmacology_112_415 |
| PubMedID: 7871051 |