LADOSTIGIL

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C16H20N2O2
Molecular Weight	272.3422
Optical Activity	UNSPECIFIED
Defined Stereocenters	1 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CCN(C)C(=O)OC1=CC2=C(CC[C@H]2NCC#C)C=C1

InChI

InChIKey=LHXOCOHMBFOVJS-OAHLLOKOSA-N

InChI=1S/C16H20N2O2/c1-4-10-17-15-9-7-12-6-8-13(11-14(12)15)20-16(19)18(3)5-2/h1,6,8,11,15,17H,5,7,9-10H2,2-3H3/t15-/m1/s1

HIDE SMILES / InChI

Molecular Formula	C16H20N2O2
Molecular Weight	272.3422
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	1 / 1
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://www.ncbi.nlm.nih.gov/mesh/67423264 | https://www.ncbi.nlm.nih.gov/pubmed/11205137 | https://www.ncbi.nlm.nih.gov/pubmed/22280345

LADOSTIGIL, a rasagiline derivative, is a reversible acetylcholinesterase and butyrylcholinesterase inhibitor with neuroprotective properties. It also acts as an irreversible brain monoamine oxidases inhibitor. It is under development for the treatment of neurodegenerative disorders like dementia and Alzheimer's disease.

CNS Activity

Originator

Approval Year

PubMed

Title	Date	PubMed
Protein 4.1N is required for translocation of inositol 1,4,5-trisphosphate receptor type 1 to the basolateral membrane domain in polarized Madin-Darby canine kidney cells.	2003 Feb 7	12444087
Inactivation of purified human recombinant monoamine oxidases A and B by rasagiline and its analogues.	2004 Mar 25	15027867
Effect of chronic treatment with ladostigil (TV-3326) on anxiogenic and depressive-like behaviour and on activity of the hypothalamic-pituitary-adrenal axis in male and female prenatally stressed rats.	2005 Aug	15830235
Bifunctional drug derivatives of MAO-B inhibitor rasagiline and iron chelator VK-28 as a more effective approach to treatment of brain ageing and ageing neurodegenerative diseases.	2005 Feb	15621213
Rasagiline: neurodegeneration, neuroprotection, and mitochondrial permeability transition.	2005 Jan 1-15	15573406
The neurochemical and behavioral effects of the novel cholinesterase-monoamine oxidase inhibitor, ladostigil, in response to L-dopa and L-tryptophan, in rats.	2005 Oct	16086033
Ladostigil, a novel multifunctional drug for the treatment of dementia co-morbid with depression.	2006	17017566
Implications of co-morbidity for etiology and treatment of neurodegenerative diseases with multifunctional neuroprotective-neurorescue drugs; ladostigil.	2006 Dec	17197368
The path from anti Parkinson drug selegiline and rasagiline to multifunctional neuroprotective anti Alzheimer drugs ladostigil and m30.	2006 Dec	17168653
A multifunctional, neuroprotective drug, ladostigil (TV3326), regulates holo-APP translation and processing.	2006 Oct	16935943
Chronic brain cytochrome oxidase inhibition selectively alters hippocampal cholinergic innervation and impairs memory: prevention by ladostigil.	2007 Aug	17580085
Induction of neurotrophic factors GDNF and BDNF associated with the mechanism of neurorescue action of rasagiline and ladostigil: new insights and implications for therapy.	2007 Dec	18077571
The application of proteomics and genomics to the study of age-related neurodegeneration and neuroprotection.	2007 Feb	17115941
Ladostigil prevents gliosis, oxidative-nitrative stress and memory deficits induced by intracerebroventricular injection of streptozotocin in rats.	2007 Mar	17123555
Aminoindan and hydroxyaminoindan, metabolites of rasagiline and ladostigil, respectively, exert neuroprotective properties in vitro.	2007 Oct	17635668
The effects of rivastigmine plus selegiline on brain acetylcholinesterase, (Na, K)-, Mg-ATPase activities, antioxidant status, and learning performance of aged rats.	2008 Aug	19043511
The neuroprotective mechanism of action of the multimodal drug ladostigil.	2008 May 1	18508575
The neuroprotective effect of ladostigil against hydrogen peroxide-mediated cytotoxicity.	2008 Sep 25	18598687
The neurotrophic and neuroprotective effects of psychotropic agents.	2009	19877500
Pharmacological Treatment of Alzheimer's Disease: Is it Progressing Adequately?	2009 Apr 2	19461897
Activation of mGlu3 receptors stimulates the production of GDNF in striatal neurons.	2009 Aug 12	19672295
Interaction between environmental and genetic factors modulates schizophrenic endophenotypes in the Snap-25 mouse mutant blind-drunk.	2009 Dec 1	19729413
The novel cholinesterase-monoamine oxidase inhibitor and antioxidant, ladostigil, confers neuroprotection in neuroblastoma cells and aged rats.	2009 Feb	18751929
Multifunctional neuroprotective derivatives of rasagiline as anti-Alzheimer's disease drugs.	2009 Jan	19110207
The New Inhibitor of Monoamine Oxidase, M30, has a Neuroprotective Effect Against Dexamethasone-Induced Brain Cell Apoptosis.	2010	21103012
Why do we need multifunctional neuroprotective and neurorestorative drugs for Parkinson's and Alzheimer's diseases as disease modifying agents.	2010 Jun	22110336
The role of rasagiline in the treatment of Parkinson's disease.	2010 May 25	20517484

Substance Class	Chemical Created by `admin` on `Sat Dec 16 17:45:17 GMT 2023` Edited by `admin` on `Sat Dec 16 17:45:17 GMT 2023`
Record UNII	SW3H1USR4Q
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

LADOSTIGIL

Official Name

English

ladostigil [INN]

Common Name

English

TV-3326 FREE BASE

Code

English

(3R)-3-(PROP-2-YN-1-YLAMINO)-2,3-DIHYDRO-1H-INDEN-5-YL ETHYL(METHYL)CARBAMATE

Systematic Name

English

CARBAMIC ACID, ETHYL(METHYL)-, (3R)-2,3-DIHYDRO-3-(2-PROPYNYLAMINO)-1H-INDEN-5-YL ESTER

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C667