LADOSTIGIL TARTRATE

Investigational

Details

Stereochemistry	ABSOLUTE
Molecular Formula	2C16H20N2O2.C4H6O6
Molecular Weight	694.7712
Optical Activity	UNSPECIFIED
Defined Stereocenters	4 / 4
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

O[C@H]([C@@H](O)C(O)=O)C(O)=O.CCN(C)C(=O)OC1=CC2=C(CC[C@H]2NCC#C)C=C1.CCN(C)C(=O)OC3=CC4=C(CC[C@H]4NCC#C)C=C3

InChI

InChIKey=PRLVBVAJMQZMJN-OGOSNNLPSA-N

InChI=1S/2C16H20N2O2.C4H6O6/c2*1-4-10-17-15-9-7-12-6-8-13(11-14(12)15)20-16(19)18(3)5-2;5-1(3(7)8)2(6)4(9)10/h2*1,6,8,11,15,17H,5,7,9-10H2,2-3H3;1-2,5-6H,(H,7,8)(H,9,10)/t2*15-;1-,2-/m111/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

Molecular Formula	C4H6O6
Molecular Weight	150.0868
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	2 / 2
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
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
Why do we need multifunctional neuroprotective and neurorestorative drugs for Parkinson's and Alzheimer's diseases as disease modifying agents.	2010 Jun	22110336

Substance Class	Chemical Created by `admin` on `Wed Jul 05 23:10:59 UTC 2023` Edited by `admin` on `Wed Jul 05 23:10:59 UTC 2023`
Record UNII	2J1346C51H
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

LADOSTIGIL TARTRATE

Official Name

English

TV-3326

Code

English

CARBAMIC ACID, ETHYLMETHYL, (3R)-2,3-DIHYDRO-3-(2-PROPYNYLAMINO)-1H-INDEN-5-YL ESTER,(2R,3R)-2,3-DIHYDROXYBUTANEDIOATE (2:1)

Common Name

English

LADOSTIGIL TARTRATE [USAN]

Common Name

English

(3R)-3-(Prop-2-ynylamino)-2,3-dihydro-1H-inden-5-yl ethylmethylcarbamate (2R,3R)-tartarate (2:1)

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C47792