Phenserine (original) (raw)
Phenserine (also known as (-)-phenserine or (-)-eseroline phenylcarbamate) is a synthetic drug which has been investigated as a medication to treat Alzheimer's disease (AD), as the drug exhibits neuroprotective and neurotrophic effects. Phenserine was introduced as an inhibitor of acetylcholinesterase (AChE) and demonstrated significant alleviation in numerous neuropathological manifestations, improving cognitive functions of the brain. The ameliorative mechanism involves both cholinergic and non-cholinergic pathways.
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| dbo:abstract | Phenserine (also known as (-)-phenserine or (-)-eseroline phenylcarbamate) is a synthetic drug which has been investigated as a medication to treat Alzheimer's disease (AD), as the drug exhibits neuroprotective and neurotrophic effects. The research of phenserine, initially patented by the National Institute on Aging (NIA), has been suspended since phase III of clinical trials in 2006, conducted right after the drug licenses were issued. The abandonment of the clinical trials led to disapproval by FDA. The retrospective meta-analysis of the phenserine research proposed that its clinical invalidation was arisen from methodological issues that were not impeccably settled before proceeding to the subsequent clinical phases. Phenserine was introduced as an inhibitor of acetylcholinesterase (AChE) and demonstrated significant alleviation in numerous neuropathological manifestations, improving cognitive functions of the brain. The ameliorative mechanism involves both cholinergic and non-cholinergic pathways. The clinical translatable doses of phenserine show relatively high tolerability and rarely manifest severe adverse effects. With respect to overdosing of the drug (20 mg/kg), a few cholinergic adverse effects were reported, including nausea and tremor which are not life-threatening. An administration form of phenserine, (-)-phenserine tartrate, which exhibits high bioavailability and solubility, is taken by mouth. Phenserine and its metabolites can readily access the brain with high permeability across the blood-brain barrier and sustain to act for a long duration with the relatively short half-life. Posiphen ((+)-phenserine), the enantiomer of (-)-phenserine, is also a potential drug by itself or synergically with (-)-phenserine, to mitigate the progression of neurological diseases, mainly Alzheimer's disease. (en) |
| dbo:casNumber | 101246-66-6 |
| dbo:chEMBL | 74926 |
| dbo:drugbank | DB04892 |
| dbo:fdaUniiCode | SUE285UG3S |
| dbo:pubchem | 192706 |
| dbo:thumbnail | wiki-commons:Special:FilePath/Phenserine.svg?width=300 |
| dbo:wikiPageID | 63481932 (xsd:integer) |
| dbo:wikiPageLength | 32476 (xsd:nonNegativeInteger) |
| dbo:wikiPageRevisionID | 1093210520 (xsd:integer) |
| dbo:wikiPageWikiLink | dbr:Bcl-2 dbr:Enantiomer dbr:National_Institute_on_Aging dbr:MMP9 dbr:Meta-analysis dbr:Metabolite dbr:Bradycardia dbr:Dementia dbr:Allograft_inflammatory_factor_1 dbr:Beta-secretase_1 dbr:Daewoong_Pharmaceutical dbr:Investigational_New_Drug dbr:Neurotransmitter dbr:Neurodegeneration dbr:Concussion dbr:Amyloid_beta dbr:Chemical_synapse dbr:Neuropathology dbr:Oral_administration dbr:Cognitive_functions dbr:Brain-derived_neurotrophic_factor dbr:Cortex_(anatomy) dbr:Apoptosis dbr:Calibration dbr:Cholinergic dbr:Statistical_significance dbr:Stem_cell dbr:Programmed_cell_death dbr:Microdialysis dbr:Traumatic_brain_injury dbr:Tremor dbr:Tumor_necrosis_factor_alpha dbr:Acetylcholinesterase dbr:Amyloid_precursor_protein dbr:Amyotrophic_lateral_sclerosis dbc:Neuroprotective_agents dbr:Alpha-synuclein dbr:Alzheimer's_disease dbc:Alzheimer's_disease_research dbr:Food_and_Drug_Administration dbr:Parkinson's_disease dbr:Diffuse_axonal_injury dbr:Glia dbr:Glial_fibrillary_acidic_protein dbr:Protocol_(science) dbr:Ischemia dbr:Hypoxia_(medical) dbr:Acetylcholinesterase_inhibitor dbr:Cholinergic_crisis dbr:Bioavailability dbr:Blood–brain_barrier dbr:Tacrine dbr:Effective_dose_(pharmacology) dbr:Donepezil dbc:Neurotrophic_factors dbr:Physostigmine dbr:Positron_emission_tomography dbr:Metrifonate dbr:National_Institutes_of_Health dbr:Caspase_3 dbr:Neuroinflammation dbr:Neurological_disorder dbr:Neuroprotection dbr:Neurotrophic_factors dbr:Placebo-controlled_study dbr:Striatum dbr:Oxidative_stress dbr:Methodological dbr:Protein_misfolding dbr:Oral_drug dbr:Double_blinded dbr:Hydrolyzed dbr:File:AChE_Mechanism_of_Action_and_How_phenserine_inhibits_it.png dbr:File:Amyloid-plaque_formation-big.jpg |
| dbp:bioavailability | ~100% (en) |
| dbp:c | 20 (xsd:integer) |
| dbp:casNumber | 101246 (xsd:integer) |
| dbp:chembl | 74926 (xsd:integer) |
| dbp:chemspiderid | 167225 (xsd:integer) |
| dbp:drugName | Phenserine (en) |
| dbp:drugbank | DB04892 (en) |
| dbp:durationOfAction | 29700.0 |
| dbp:eliminationHalfLife | 756.0 |
| dbp:excretion | renal or hepatic clearance (en) |
| dbp:footer | Comparison of the chemical structures of phenserine and posiphen (en) |
| dbp:h | 23 (xsd:integer) |
| dbp:image | Phenserine.svg (en) Posiphen.svg (en) |
| dbp:iupacName | -13 (xsd:integer) |
| dbp:legalStatus | Investigational (en) |
| dbp:meltingPoint | 150 (xsd:integer) |
| dbp:metabolism | liver (en) |
| dbp:metabolites | -N1-norphenserine, -N8-norphenserine, -N1,N8-bisnorphenserine (en) |
| dbp:molecularWeight | 337.415500 (xsd:double) |
| dbp:n | 3 (xsd:integer) |
| dbp:o | 2 (xsd:integer) |
| dbp:pubchem | 192706 (xsd:integer) |
| dbp:routesOfAdministration | dbr:Oral_administration |
| dbp:smiles | [H][C@]12NCC[C@@]1C1=CN2C (en) |
| dbp:stdinchi | InChI=1S/C20H23N3O2/c1-20-11-12-22182317-10-9-1525-1921-14-7-5-4-6-8-14/h4-10,13,18H,11-12H2,1-3H3,/t18-,20+/m1/s1 (en) |
| dbp:stdinchikey | PBHFNBQPZCRWQP-QUCCMNQESA-N (en) |
| dbp:synonyms | -Phenserine, -Eseroline phenylcarbamate, N-phenylcarbamoyleseroline, N-phenylcarbamoyl eseroline (en) |
| dbp:unii | SUE285UG3S (en) |
| dbp:width | 150 (xsd:integer) |
| dbp:wikiPageUsesTemplate | dbt:Infobox_drug dbt:Multiple_image dbt:Reflist |
| dcterms:subject | dbc:Neuroprotective_agents dbc:Alzheimer's_disease_research dbc:Neurotrophic_factors |
| rdf:type | owl:Thing dul:ChemicalObject dbo:ChemicalSubstance wikidata:Q8386 dbo:Drug |
| rdfs:comment | Phenserine (also known as (-)-phenserine or (-)-eseroline phenylcarbamate) is a synthetic drug which has been investigated as a medication to treat Alzheimer's disease (AD), as the drug exhibits neuroprotective and neurotrophic effects. Phenserine was introduced as an inhibitor of acetylcholinesterase (AChE) and demonstrated significant alleviation in numerous neuropathological manifestations, improving cognitive functions of the brain. The ameliorative mechanism involves both cholinergic and non-cholinergic pathways. (en) |
| rdfs:label | Phenserine (en) |
| owl:sameAs | wikidata:Phenserine https://global.dbpedia.org/id/2XpDS |
| prov:wasDerivedFrom | wikipedia-en:Phenserine?oldid=1093210520&ns=0 |
| foaf:depiction | wiki-commons:Special:FilePath/AChE_Mechanism_of_Action_and_How_phenserine_inhibits_it.png wiki-commons:Special:FilePath/Amyloid-plaque_formation-big.jpg wiki-commons:Special:FilePath/Phenserine.svg wiki-commons:Special:FilePath/Posiphen.svg |
| foaf:isPrimaryTopicOf | wikipedia-en:Phenserine |
| foaf:name | Phenserine (en) |
| is dbo:wikiPageWikiLink of | dbr:Cholinesterase_inhibitor |
| is foaf:primaryTopic of | wikipedia-en:Phenserine |
