Heptylphysostigmine

Treatment of Alzheimer Disease

General

Type : Derivative of physostigmine-eserine, Carbamate, Indole

Chemical_Nomenclature : (3,4,8b-trimethyl-2,3a-dihydro-1H-pyrrolo[2,3-b]indol-7-yl) N-heptylcarbamate

Canonical SMILES : CCCCCCCNC(=O)OC1=CC2=C(C=C1)N(C3C2(CCN3C)C)C

InChI : InChI=1S\/C21H33N3O2\/c1-5-6-7-8-9-13-22-20(25)26-16-10-11-18-17(15-16)21(2)12-14-23(3)19(21)24(18)4\/h10-11,15,19H,5-9,12-14H2,1-4H3,(H,22,25)

InChIKey : RRGMXBQMCUKRLH-UHFFFAOYSA-N

Other name(s) : pyrrolo 2,3b indol-5-ol 3,3a,8,8a-hexahydro-1,3a,8-trimethylheptylcarbamate ester 3aS-cis  ||  Heptylstigmine  ||  Eptastigmine  ||  Eseroline, heptylcarbamate  ||  N-Demethyl-N-heptylphysostigmine  ||  Eseroline, heptylcarbamate(ester)  ||  MF-201  ||  MF201  ||  heptastigmine  ||  Eptastigmine, (Mediolanum)


MW : 359.506

Formula : C21H33N3O2

CAS_number : 101246-68-8

PubChem : 612747

UniChem : RRGMXBQMCUKRLH-UHFFFAOYSA-N

Target

Families : Heptylphysostigmine ligand of proteins in family
ACHE

References (29)

Title : Invited review: Cholinesterase inhibitors for Alzheimer's disease therapy: from tacrine to future applications - Giacobini_1998_Neurochem.Int_32_413
Author(s) : Giacobini E
Ref : Neurochem Int , 32 :413 , 1998
Abstract :
PubMedSearch : Giacobini_1998_Neurochem.Int_32_413
PubMedID: 9676739

Title : Inhibition of cholinesterase-associated aryl acylamidase activity by anticholinesterase agents: focus on drugs potentially effective in Alzheimer's disease - Costagli_1998_Biochem.Pharmacol_55_1733
Author(s) : Costagli C , Galli A
Ref : Biochemical Pharmacology , 55 :1733 , 1998
Abstract :
PubMedSearch : Costagli_1998_Biochem.Pharmacol_55_1733
PubMedID: 9634011

Title : Effect of the subchronic treatment with the acetylcholinesterase inhibitor heptastigmine on central cholinergic transmission and memory impairment in aged rats - Garrone_1998_Neurosci.Lett_245_53
Author(s) : Garrone B , Luparini MR , Tolu L , Magnani M , Landolfi C , Milanese C
Ref : Neuroscience Letters , 245 :53 , 1998
Abstract :
PubMedSearch : Garrone_1998_Neurosci.Lett_245_53
PubMedID: 9596354

Title : Effect of food on the absorption of eptastigmine - Bjornsson_1998_Eur.J.Clin.Pharmacol_54_243
Author(s) : Bjornsson TD , Troetel WM , Imbimbo BP
Ref : European Journal of Clinical Pharmacology , 54 :243 , 1998
Abstract :
PubMedSearch : Bjornsson_1998_Eur.J.Clin.Pharmacol_54_243
PubMedID: 9681667

Title : Maximum tolerated dose and pharmacodynamics of eptastigmine in elderly healthy volunteers - Mant_1998_J.Clin.Pharmacol_38_610
Author(s) : Mant T , Troetel WM , Imbimbo BP
Ref : Journal of Clinical Pharmacology , 38 :610 , 1998
Abstract :
PubMedSearch : Mant_1998_J.Clin.Pharmacol_38_610
PubMedID: 9702845

Title : Cholinesterase inhibition improves blood flow in the ischemic cerebral cortex - Scremin_1997_Brain.Res.Bull_42_59
Author(s) : Scremin OU , Li MG , Scremin AM , Jenden DJ
Ref : Brain Research Bulletin , 42 :59 , 1997
Abstract :
PubMedSearch : Scremin_1997_Brain.Res.Bull_42_59
PubMedID: 8978935

Title : Pharmacodynamic monitoring of eptastigmine in capillary blood [letter] -
Author(s) : Mosca A , Ghezzi A , Luzzana M , Paleari R , Imbimbo BP
Ref : European Journal of Clinical Pharmacology , 50 :425 , 1996
PubMedID: 8839668

Title : Cholinergic control of cerebral blood flow in stroke, trauma and aging - Scremin_1996_Life.Sci_58(22)_2011
Author(s) : Scremin OU , Jenden DJ
Ref : Life Sciences , 58 :2011 , 1996
Abstract :
PubMedSearch : Scremin_1996_Life.Sci_58(22)_2011
PubMedID: 8637431

Title : Eptastigmine-phosphotriesterase combination in DFP intoxication - Tuovinen_1996_Toxicol.Appl.Pharmacol_140_364
Author(s) : Tuovinen K , Kaliste-Korhonen E , Raushel FM , Hanninen O
Ref : Toxicology & Applied Pharmacology , 140 :364 , 1996
Abstract :
PubMedSearch : Tuovinen_1996_Toxicol.Appl.Pharmacol_140_364
PubMedID: 8887453

Title : Phosphotriesterase, pralidoxime-2-chloride (2-PAM) and eptastigmine treatments and their combinations in DFP intoxication - Tuovinen_1996_Toxicol.Appl.Pharmacol_141_555
Author(s) : Tuovinen K , Kaliste-Korhonen E , Raushel FM , Hanninen O
Ref : Toxicology & Applied Pharmacology , 141 :555 , 1996
Abstract :
PubMedSearch : Tuovinen_1996_Toxicol.Appl.Pharmacol_141_555
PubMedID: 8975781

Title : An inverted U-shaped curve for heptylphysostigmine on radial maze performance in rats: comparison with other cholinesterase inhibitors - Braida_1996_Eur.J.Pharmacol_302_13
Author(s) : Braida D , Paladini E , Griffini P , Lamperti M , Maggi A , Sala M
Ref : European Journal of Pharmacology , 302 :13 , 1996
Abstract :
PubMedSearch : Braida_1996_Eur.J.Pharmacol_302_13
PubMedID: 8790986

Title : A multiple-dose safety trial of eptastigmine in Alzheimer's disease, with pharmacodynamic observations of red blood cell cholinesterase - Sramek_1995_Life.Sci_56_319
Author(s) : Sramek JJ , Block GA , Reines SA , Sawin SF , Barchowsky A , Cutler NR
Ref : Life Sciences , 56 :319 , 1995
Abstract :
PubMedSearch : Sramek_1995_Life.Sci_56_319
PubMedID: 7837931

Title : The behavioral effects of heptylphysostigmine on rats lesioned in the nucleus basalis - Waite_1995_Neurosci.Research_21_251
Author(s) : Waite JJ , Thal LJ
Ref : Neuroscience Research , 21 :251 , 1995
Abstract :
PubMedSearch : Waite_1995_Neurosci.Research_21_251
PubMedID: 7753506

Title : Relationship between pharmacokinetics and pharmacodynamics of eptastigmine in young healthy volunteers - Imbimbo_1995_J.Clin.Pharmacol_35_285
Author(s) : Imbimbo BP , Licini M , Schettino M , Mosca A , Onelli E , Zecca L , Giustina A
Ref : Journal of Clinical Pharmacology , 35 :285 , 1995
Abstract :
PubMedSearch : Imbimbo_1995_J.Clin.Pharmacol_35_285
PubMedID: 7608318

Title : A patient-side technique for real-time measurement of acetylcholinesterase activity during monitoring of eptastigmine treatment - Mosca_1995_Therapeut.Drug.Monit_17_230
Author(s) : Mosca A , Onelli E , Rosti E , Paleari R , Luzzana M , Imbimbo BP
Ref : Therapeutic Drug Monitoring , 17 :230 , 1995
Abstract :
PubMedSearch : Mosca_1995_Therapeut.Drug.Monit_17_230
PubMedID: 7624918

Title : Clinical pharmacokinetics of drugs for Alzheimer's disease - Parnetti_1995_Clin.Pharmacokinet_29_110
Author(s) : Parnetti L
Ref : Clinical Pharmacokinetics , 29 :110 , 1995
Abstract :
PubMedSearch : Parnetti_1995_Clin.Pharmacokinet_29_110
PubMedID: 7586900

Title : Cholinesterase inhibitor effects on neurotransmitters in rat cortex in vivo - Cuadra_1994_J.Pharmacol.Exp.Ther_270_277
Author(s) : Cuadra G , Summers K , Giacobini E
Ref : Journal of Pharmacology & Experimental Therapeutics , 270 :277 , 1994
Abstract :
PubMedSearch : Cuadra_1994_J.Pharmacol.Exp.Ther_270_277
PubMedID: 7913496

Title : Synthesis of 2'-heptylcarbamoyloxy-2-methyl-6,7-benzomorphan: a new analogue of heptylphysostigmine (MF 201) - Brufani_1994_Farmaco_40_743
Author(s) : Brufani M , Filocamo L , Imbriani E , Lappa S , Mannina L
Ref : Farmaco , 40 :743 , 1994
Abstract :
PubMedSearch : Brufani_1994_Farmaco_40_743
PubMedID: 7832976

Title : Transdermal patch delivery of acetylcholinesterase inhibitors - Moriearty_1993_Meth.Find.Exp.Clin.Pharmacol_15_407
Author(s) : Moriearty PL , Thornton SL , Becker RE
Ref : Methods Find Exp Clin Pharmacol , 15 :407 , 1993
Abstract :
PubMedSearch : Moriearty_1993_Meth.Find.Exp.Clin.Pharmacol_15_407
PubMedID: 8231460

Title : The effects of novel cholinesterase inhibitors and selective muscarinic receptor agonists in tests of reference and working memory - Dawson_1993_Behav.Brain.Res_57_143
Author(s) : Dawson GR , Iversen SD
Ref : Behavioural Brain Research , 57 :143 , 1993
Abstract :
PubMedSearch : Dawson_1993_Behav.Brain.Res_57_143
PubMedID: 8117420

Title : Prolonged effects of cholinesterase inhibition with eptastigmine on the cerebral blood flow-metabolism ratio of normal rats - Scremin_1993_J.Cereb.Blood.Flow.Metab_13_702
Author(s) : Scremin OU , Scremin AM , Heuser D , Hudgell R , Romero E , Imbimbo BP
Ref : Journal of Cerebral Blood Flow & Metabolism , 13 :702 , 1993
Abstract :
PubMedSearch : Scremin_1993_J.Cereb.Blood.Flow.Metab_13_702
PubMedID: 8314923

Title : Cholinesterase inhibitor effects on extracellular acetylcholine in rat cortex - Messamore_1993_Neuropharmacol_32_745
Author(s) : Messamore E , Warpman U , Ogane N , Giacobini E
Ref : Neuropharmacology , 32 :745 , 1993
Abstract :
PubMedSearch : Messamore_1993_Neuropharmacol_32_745
PubMedID: 8413838

Title : Reversal of cognitive impairment by heptyl physostigmine, a long-lasting cholinesterase inhibitor, in primates - Rupniak_1992_J.Neurol.Sci_107_246
Author(s) : Rupniak NM , Tye SJ , Brazell C , Heald A , Iversen SD , Pagella PG
Ref : Journal of Neurology Sci , 107 :246 , 1992
Abstract :
PubMedSearch : Rupniak_1992_J.Neurol.Sci_107_246
PubMedID: 1564524

Title : Pharmacokinetics of heptastigmine in rats - Segre_1992_Pharmacol.Res_25_139
Author(s) : Segre G , Cerretani D , Baldi A , Urso R
Ref : Pharmacol Res , 25 :139 , 1992
Abstract :
PubMedSearch : Segre_1992_Pharmacol.Res_25_139
PubMedID: 1635892

Title : Heptyl-physostigmine enhances basal forebrain control of cortical cerebral blood flow - Linville_1992_J.Neurosci.Res_31_573
Author(s) : Linville DG , Giacobini E , Arneric SP
Ref : Journal of Neuroscience Research , 31 :573 , 1992
Abstract :
PubMedSearch : Linville_1992_J.Neurosci.Res_31_573
PubMedID: 1640506

Title : Determination of picogram levels of heptylphysostigmine in human plasma using high-performance liquid chromatography with fluorescence detection - Herold_1992_J.Chromatogr_581_227
Author(s) : Herold ML , Constanzer ML , Matuszewski BK
Ref : Journal of Chromatography , 581 :227 , 1992
Abstract :
PubMedSearch : Herold_1992_J.Chromatogr_581_227
PubMedID: 1452613

Title : Preferential inhibition of acetylcholinesterase molecular forms in rat brain - Ogane_1992_Neurochem.Res_17_489
Author(s) : Ogane N , Giacobini E , Messamore E
Ref : Neurochemical Research , 17 :489 , 1992
Abstract :
PubMedSearch : Ogane_1992_Neurochem.Res_17_489
PubMedID: 1528356

Title : Inhibition of human brain and RBC acetylcholinesterase (AChE) by heptylphysostigmine (HPTL) - Moriearty_1992_Meth.Find.Exp.Clin.Pharmacol_14_615
Author(s) : Moriearty PL , Becker RE
Ref : Methods Find Exp Clin Pharmacol , 14 :615 , 1992
Abstract :
PubMedSearch : Moriearty_1992_Meth.Find.Exp.Clin.Pharmacol_14_615
PubMedID: 1494302

Title : Kinetics of cholinesterase inhibition by eptastigmine in man [letter] -
Author(s) : Unni LK , Hutt V , Imbimbo BP , Becker RE
Ref : European Journal of Clinical Pharmacology , 41 :83 , 1991
PubMedID: 1782985