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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 of LADOSTIGIL TARTRATE

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

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.

Approval Year

PubMed

PubMed

TitleDatePubMed
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
Inactivation of purified human recombinant monoamine oxidases A and B by rasagiline and its analogues.
2004 Mar 25
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
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
Rasagiline: neurodegeneration, neuroprotection, and mitochondrial permeability transition.
2005 Jan 1-15
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
Ladostigil, a novel multifunctional drug for the treatment of dementia co-morbid with depression.
2006
Implications of co-morbidity for etiology and treatment of neurodegenerative diseases with multifunctional neuroprotective-neurorescue drugs; ladostigil.
2006 Dec
The path from anti Parkinson drug selegiline and rasagiline to multifunctional neuroprotective anti Alzheimer drugs ladostigil and m30.
2006 Dec
A multifunctional, neuroprotective drug, ladostigil (TV3326), regulates holo-APP translation and processing.
2006 Oct
Chronic brain cytochrome oxidase inhibition selectively alters hippocampal cholinergic innervation and impairs memory: prevention by ladostigil.
2007 Aug
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
The application of proteomics and genomics to the study of age-related neurodegeneration and neuroprotection.
2007 Feb
Ladostigil prevents gliosis, oxidative-nitrative stress and memory deficits induced by intracerebroventricular injection of streptozotocin in rats.
2007 Mar
Aminoindan and hydroxyaminoindan, metabolites of rasagiline and ladostigil, respectively, exert neuroprotective properties in vitro.
2007 Oct
The effects of rivastigmine plus selegiline on brain acetylcholinesterase, (Na, K)-, Mg-ATPase activities, antioxidant status, and learning performance of aged rats.
2008 Aug
The neuroprotective mechanism of action of the multimodal drug ladostigil.
2008 May 1
The neuroprotective effect of ladostigil against hydrogen peroxide-mediated cytotoxicity.
2008 Sep 25
The neurotrophic and neuroprotective effects of psychotropic agents.
2009
Pharmacological Treatment of Alzheimer's Disease: Is it Progressing Adequately?
2009 Apr 2
Activation of mGlu3 receptors stimulates the production of GDNF in striatal neurons.
2009 Aug 12
Interaction between environmental and genetic factors modulates schizophrenic endophenotypes in the Snap-25 mouse mutant blind-drunk.
2009 Dec 1
The novel cholinesterase-monoamine oxidase inhibitor and antioxidant, ladostigil, confers neuroprotection in neuroblastoma cells and aged rats.
2009 Feb
Multifunctional neuroprotective derivatives of rasagiline as anti-Alzheimer's disease drugs.
2009 Jan
The New Inhibitor of Monoamine Oxidase, M30, has a Neuroprotective Effect Against Dexamethasone-Induced Brain Cell Apoptosis.
2010
Why do we need multifunctional neuroprotective and neurorestorative drugs for Parkinson's and Alzheimer's diseases as disease modifying agents.
2010 Jun
The role of rasagiline in the treatment of Parkinson's disease.
2010 May 25
Substance Class Chemical
Created
by admin
on Fri Dec 15 15:42:04 GMT 2023
Edited
by admin
on Fri Dec 15 15:42:04 GMT 2023
Record UNII
2J1346C51H
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
LADOSTIGIL TARTRATE
USAN  
USAN  
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
Created by admin on Fri Dec 15 15:42:04 GMT 2023 , Edited by admin on Fri Dec 15 15:42:04 GMT 2023
NCI_THESAURUS C667
Created by admin on Fri Dec 15 15:42:04 GMT 2023 , Edited by admin on Fri Dec 15 15:42:04 GMT 2023
Code System Code Type Description
SMS_ID
300000044446
Created by admin on Fri Dec 15 15:42:04 GMT 2023 , Edited by admin on Fri Dec 15 15:42:04 GMT 2023
PRIMARY
ChEMBL
CHEMBL255231
Created by admin on Fri Dec 15 15:42:04 GMT 2023 , Edited by admin on Fri Dec 15 15:42:04 GMT 2023
PRIMARY
CAS
209394-46-7
Created by admin on Fri Dec 15 15:42:04 GMT 2023 , Edited by admin on Fri Dec 15 15:42:04 GMT 2023
PRIMARY
NCI_THESAURUS
C76072
Created by admin on Fri Dec 15 15:42:04 GMT 2023 , Edited by admin on Fri Dec 15 15:42:04 GMT 2023
PRIMARY
USAN
QQ-52
Created by admin on Fri Dec 15 15:42:04 GMT 2023 , Edited by admin on Fri Dec 15 15:42:04 GMT 2023
PRIMARY
FDA UNII
2J1346C51H
Created by admin on Fri Dec 15 15:42:04 GMT 2023 , Edited by admin on Fri Dec 15 15:42:04 GMT 2023
PRIMARY
PUBCHEM
11607225
Created by admin on Fri Dec 15 15:42:04 GMT 2023 , Edited by admin on Fri Dec 15 15:42:04 GMT 2023
PRIMARY
EPA CompTox
DTXSID60175107
Created by admin on Fri Dec 15 15:42:04 GMT 2023 , Edited by admin on Fri Dec 15 15:42:04 GMT 2023
PRIMARY
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ACTIVE MOIETY