Ganstigmine
CHF3360 is an enantiomer || Physostigmine derivative
General
Type : Derivative of physostigmine-eserine, Carbamate, Indole
Chemical_Nomenclature : 1,2,3,3a,8,8a-Hexahydro-1,3a,8-trimethylpyrrolo[2,3-b]indol-5-ol 2-ethylphenylcarbamate N-oxide hydrochloride 3aS-cis
Canonical SMILES : CCC1=CC=CC=C1NC(=O)OC2=CC3=C(C=C2)NC4C3(CC[N+]4(C)[O-])C.Cl
InChI : InChI=1S\/C21H25N3O3.ClH\/c1-4-14-7-5-6-8-17(14)23-20(25)27-15-9-10-18-16(13-15)21(2)11-12-24(3,26)19(21)22-18\;\/h5-10,13,19,22H,4,11-12H2,1-3H3,(H,23,25)\;1H
InChIKey : CVDHRWXJJRBPFA-UHFFFAOYSA-N
Other name(s) : CHF2819 || CHF 2819 || CHF-2819 || physostigmine derivative
MW : 417.93
Formula : C22H28ClN3O3
CAS_number : 223585-99-7, 412044-92-9
PubChem : 56842812
UniChem : CVDHRWXJJRBPFA-UHFFFAOYSA-N
Target
References (10)
| Title : Structural determinants of Torpedo californica acetylcholinesterase inhibition by the novel and orally active carbamate based anti-alzheimer drug ganstigmine (CHF-2819) - Bartolucci_2006_J.Med.Chem_49_5051 |
| Author(s) : Bartolucci C , Siotto M , Ghidini E , Amari G , Bolzoni PT , Racchi M , Villetti G , Delcanale M , Lamba D |
| Ref : Journal of Medicinal Chemistry , 49 :5051 , 2006 |
| Abstract : |
| PubMedSearch : Bartolucci_2006_J.Med.Chem_49_5051 |
| PubMedID: 16913695 |
| Gene_locus related to this paper: torca-ACHE |
| Title : Ganstigmine and donepezil improve neurodegeneration in AD11 antinerve growth factor transgenic mice - Capsoni_2004_Am.J.Alzheimers.Dis.Other.Demen_19_153 |
| Author(s) : Capsoni S , Giannotta S , Stebel M , Garcia AA , De Rosa R , Villetti G , Imbimbo BP , Pietra C , Cattaneo A |
| Ref : Am J Alzheimers Dis Other Demen , 19 :153 , 2004 |
| Abstract : |
| PubMedSearch : Capsoni_2004_Am.J.Alzheimers.Dis.Other.Demen_19_153 |
| PubMedID: 15214201 |
| Title : First clinical evaluation of ganstigmine in patients with probable Alzheimer's disease - Jhee_2003_Clin.Neuropharmacol_26_164 |
| Author(s) : Jhee SS , Fabbri L , Piccinno A , Monici P , Moran S , Zarotsky V , Tan EY , Frackiewicz EJ , Shiovitz T |
| Ref : Clinical Neuropharmacology , 26 :164 , 2003 |
| Abstract : |
| PubMedSearch : Jhee_2003_Clin.Neuropharmacol_26_164 |
| PubMedID: 12782920 |
| Title : Characterization of the effect of ganstigmine (CHF2819) on amyloid precursor protein metabolism in SH-SY5Y neuroblastoma cells - Mazzucchelli_2003_J.Neural.Transm.(Vienna)_110_935 |
| Author(s) : Mazzucchelli M , Porrello E , Villetti G , Pietra C , Govoni S , Racchi M |
| Ref : J Neural Transm (Vienna) , 110 :935 , 2003 |
| Abstract : |
| PubMedSearch : Mazzucchelli_2003_J.Neural.Transm.(Vienna)_110_935 |
| PubMedID: 12898348 |
| Title : Characterization of Ganstigmine metabolites in hepatocytes by low- and high-resolution mass spectrometry coupled with liquid chromatography - Pelizzi_2003_Rapid.Commun.Mass.Spectrom_17_1691 |
| Author(s) : Pelizzi N , Puccini P , Riccardi B , Acerbi D , Catinella S |
| Ref : Rapid Commun Mass Spectrom , 17 :1691 , 2003 |
| Abstract : |
| PubMedSearch : Pelizzi_2003_Rapid.Commun.Mass.Spectrom_17_1691 |
| PubMedID: 12872272 |
| Title : The protective effect of ganstigmine against amyloid beta 25-35 neurotoxicity on chicken cortical neurons is independent from the cholinesterase inhibition - Windisch_2003_Neurosci.Lett_341_181 |
| Author(s) : Windisch M , Hutter-Paier B , Jerkovic L , Imbimbo B , Villetti G |
| Ref : Neuroscience Letters , 341 :181 , 2003 |
| Abstract : |
| PubMedSearch : Windisch_2003_Neurosci.Lett_341_181 |
| PubMedID: 12697278 |
| Title : CHF2819: pharmacological profile of a novel acetylcholinesterase inhibitor - Trabace_2002_CNS.Drug.Rev_8_53 |
| Author(s) : Trabace L , Cassano T , Loverre A , Steardo L , Cuomo V |
| Ref : CNS Drug Rev , 8 :53 , 2002 |
| Abstract : |
| PubMedSearch : Trabace_2002_CNS.Drug.Rev_8_53 |
| PubMedID: 12070526 |
| Title : Phase I metabolism of ganstigmine. Rat, dog, monkey and human liver microsomal extracts investigated by liquid chromatography electrospray tandem mass spectrometry - Catinella_2001_J.Mass.Spectrom_36_1287 |
| Author(s) : Catinella S , Pelizzi N , Puccini P , Marchetti S , Zanol M , Acerbi D , Ventura P |
| Ref : J Mass Spectrom , 36 :1287 , 2001 |
| Abstract : |
| PubMedSearch : Catinella_2001_J.Mass.Spectrom_36_1287 |
| PubMedID: 11754120 |
| Title : Effects of ENA713 and CHF2819, two anti-Alzheimer's disease drugs, on rat amino acid levels - Trabace_2001_Brain.Res_910_182 |
| Author(s) : Trabace L , Cassano T , Cagiano R , Tattoli M , Pietra C , Steardo L , Kendrick KM , Cuomo V |
| Ref : Brain Research , 910 :182 , 2001 |
| Abstract : |
| PubMedSearch : Trabace_2001_Brain.Res_910_182 |
| PubMedID: 11489269 |
| Title : Biochemical and neurobehavioral profile of CHF2819, a novel, orally active acetylcholinesterase inhibitor for Alzheimer's disease - Trabace_2000_J.Pharmacol.Exp.Ther_294_187 |
| Author(s) : Trabace L , Cassano T , Steardo L , Pietra C , Villetti G , Kendrick KM , Cuomo V |
| Ref : Journal of Pharmacology & Experimental Therapeutics , 294 :187 , 2000 |
| Abstract : |
| PubMedSearch : Trabace_2000_J.Pharmacol.Exp.Ther_294_187 |
| PubMedID: 10871311 |