RASAGILINE TARTRATE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	2C12H13N.C4H6O6
Molecular Weight	492.5635
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.C#CCN[C@@H]1CCC2=CC=CC=C12.C#CCN[C@@H]3CCC4=CC=CC=C34

InChI

InChIKey=YGKHOZXCTLKSLJ-KHAGDFGNSA-N

InChI=1S/2C12H13N.C4H6O6/c2*1-2-9-13-12-8-7-10-5-3-4-6-11(10)12;5-1(3(7)8)2(6)4(9)10/h2*1,3-6,12-13H,7-9H2;1-2,5-6H,(H,7,8)(H,9,10)/t2*12-;1-,2-/m111/s1

HIDE SMILES / InChI

Molecular Formula	C12H13N
Molecular Weight	171.2383
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	1 / 1
E/Z Centers	0
Optical Activity	( + )

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.accessdata.fda.gov/drugsatfda_docs/label/2006/021641lbl.pdf | https://www.ncbi.nlm.nih.gov/pubmed/18488080

Rasagiline (N-propargyl-1-(R)-aminoindan) is a selective, irreversible monoamine oxidase B (MAO B) inhibitor, which has been developed as an anti-Parkinson drug and was sold as a mesylate salt under brand name AZILECT. AZILECT is indicated for the treatment of the signs and symptoms of idiopathic Parkinson’s disease (PD) as initial monotherapy and as adjunct therapy to levodopa. The effectiveness of AZILECT was demonstrated in patients with early Parkinson’s disease who were receiving AZILECT as monotherapy and who were not receiving any concomitant dopaminergic therapy. The effectiveness of AZILECT as adjunct therapy was demonstrated in patients with Parkinson’s disease who were treated with levodopa. PD is a progressive neurodegenerative, dopamine deficiency disorder. The main therapeutic strategies for PD treatment relies on dopamine precursors (levodopa), inhibition of dopamine metabolism (monoamine oxidase [MAO] B and catechol-O-methyl transferase inhibitors), and dopamine receptor agonists. In contrast to selegiline, rasagiline is not metabolized to potentially toxic amphetamine metabolites. The precise mechanisms of action of rasagiline is unknown. One mechanism is believed to be related to its MAO-B inhibitory activity, which causes an increase in extracellular levels of dopamine in the striatum.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Monoamine oxidase B 75 Target ID: CHEMBL2039 Sources: https://www.ncbi.nlm.nih.gov/pubmed/19673610	Inhibitor 8504

Conditions

Condition	Modality	Targets	Highest Phase	Product
Idiopathic Parkinson's disease 19 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2006/021641lbl.pdf	Primary		Approved 8583	AZILECT Approved Use AZILECT (rasagiline tablets) is indicated for the treatment of Parkinson’s disease (PD). AZILECT, a monoamine oxidase (MAO)-B inhibitor (MAOI), is indicated for the treatment of Parkinson’s disease (1) Launch Date 2006

C_max

Value	Dose	Co-administered	Analyte	Population
56.13 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/15628826	10 mg 1 times / day multiple, oral dose: 10 mg route of administration: Oral experiment type: MULTIPLE co-administered:		RASAGILINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED

AUC

Value	Dose	Co-administered	Analyte	Population
53.53 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/15628826	10 mg 1 times / day multiple, oral dose: 10 mg route of administration: Oral experiment type: MULTIPLE co-administered:		RASAGILINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED

T_1/2

Value	Dose	Co-administered	Analyte	Population
3.17 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/15628826	10 mg 1 times / day multiple, oral dose: 10 mg route of administration: Oral experiment type: MULTIPLE co-administered:		RASAGILINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
inhibitor 2252	inhibitor 2438	inhibitor 2507	inhibitor 2217

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
CYP1A2 2153 CYP2A6 879 CYP2C19 2057 CYP2E1 1060 CYP4A 20	CYP1A2 1197 P-gp 2052 CYP2A6 626

Drug as perpetrator

Target	Modality	Activity
CYP1A2 2333	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2006/021641s000_Azilect_ClinPharmR.pdf Page: 57, 95	no
CYP2A6 911	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2006/021641s000_Azilect_ClinPharmR.pdf Page: 57, 95	no
CYP2C19 2141	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2006/021641s000_Azilect_ClinPharmR.pdf Page: 57, 95	no
CYP2C9 2497	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2006/021641s000_Azilect_ClinPharmR.pdf Page: 57, 95	no
CYP2D6 2546	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2006/021641s000_Azilect_ClinPharmR.pdf Page: 57, 95	no
CYP2E1 1146	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2006/021641s000_Azilect_ClinPharmR.pdf Page: 57, 95	no
CYP3A4 2633	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2006/021641s000_Azilect_ClinPharmR.pdf Page: 57, 95	no
CYP4A 34	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2006/021641s000_Azilect_ClinPharmR.pdf Page: 57, 95	no

Drug as victim

Target	Modality	Activity	Clinical evidence
CYP1A2 1197	substrate 4014 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2006/021641s000_Azilect_ClinPharmR.pdf Page: 56, 57, 69	major	yes (co-administration study) Comment: ciprofloxacin increased rasagiline AUC by 83% Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2006/021641s000_Azilect_ClinPharmR.pdf Page: 56, 57, 69
CYP2A6 626	substrate 4014 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2006/021641s000_Azilect_ClinPharmR.pdf Page: 97.0	no
P-gp 2052	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/26530401/	no	no (co-administration study) Comment: hesperetin and narigenin enhanced the systemic exposure of rasagiline not through P-gp Sources: https://pubmed.ncbi.nlm.nih.gov/26530401/

Tox targets

Target	Modality	Activity	Metabolite	Clinical evidence
hERG 2263	inhibitor 2237 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2006/021641s000_Azilect_PharmR.pdf Page: 265.0

Sourcing

Vendor/Aggregator	ID	URL
ChEBI	CHEBI:63620	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:63620
ChemicalBook	CB2459598	https://www.chemicalbook.com/ChemicalProductProperty_EN_CB2459598
eMolecules	2727012	https://www.emolecules.com/cgi-bin/more?vid=2727012
MolPort	MolPort-003-850-132	https://www.molport.com/shop/molecule-link/MolPort-003-850-132
ZINC	ZINC000019875504	http://zinc15.docking.org/substances/ZINC000019875504

PubMed

Title	Date	PubMed
Rationale for considering that propargylamines might be neuroprotective in Parkinson's disease.	2006-05-23	16717254
Rasagiline: A second-generation monoamine oxidase type-B inhibitor for the treatment of Parkinson's disease.	2006-05-15	16675649
Safety of rasagiline in elderly patients with Parkinson disease.	2006-05-09	16682679
Rasagiline improves quality of life in patients with early Parkinson's disease.	2006-05	16450340
Practice Parameter: treatment of Parkinson disease with motor fluctuations and dyskinesia (an evidence-based review): report of the Quality Standards Subcommittee of the American Academy of Neurology.	2006-04-11	16606909
Cost-utility model of rasagiline in the treatment of advanced Parkinson's disease in Finland.	2006-04	16569799
Rasagiline: defining the role of a novel therapy in the treatment of Parkinson's disease.	2006-02	16451296
Rasagiline -- is there a place for this drug in managing Parkinson's disease?	2006-02	16451281
Drugs in development for Parkinson's disease: an update.	2006-01	16425668
Monoamine oxidase: isoforms and inhibitors in Parkinson's disease and depressive illness.	2006-01	16402116
N-Propargylamine protects SH-SY5Y cells from apoptosis induced by an endogenous neurotoxin, N-methyl(R)salsolinol, through stabilization of mitochondrial membrane and induction of anti-apoptotic Bcl-2.	2006-01	15843867
Binding of rasagiline-related inhibitors to human monoamine oxidases: a kinetic and crystallographic analysis.	2005-12-29	16366596
Novel potential neuroprotective agents with both iron chelating and amino acid-based derivatives targeting central nervous system neurons.	2005-11-25	16226724
Recent advances in Parkinson's disease therapy: use of monoamine oxidase inhibitors.	2005-11	16274338
Present and future drug treatment for Parkinson's disease.	2005-11	16227533
Regulation of Bcl-2 family proteins, neurotrophic factors, and APP processing in the neurorescue activity of propargylamine.	2005-11	16148027
In vivo measurement of brain monoamine oxidase B occupancy by rasagiline, using (11)C-l-deprenyl and PET.	2005-10	16204711
Rasagiline in the pharmacotherapy of Parkinson's disease--a review.	2005-10	16197359
Novel multifunctional neuroprotective iron chelator-monoamine oxidase inhibitor drugs for neurodegenerative diseases: in vitro studies on antioxidant activity, prevention of lipid peroxide formation and monoamine oxidase inhibition.	2005-10	16181413
The neurochemical and behavioral effects of the novel cholinesterase-monoamine oxidase inhibitor, ladostigil, in response to L-dopa and L-tryptophan, in rats.	2005-10	16086033
[Rasagiline in motor fluctuations].	2005-09	16217881
Novel neuroprotective mechanism of action of rasagiline is associated with its propargyl moiety: interaction of Bcl-2 family members with PKC pathway.	2005-08	16179541
Rasagiline.	2005-08	16106586
Reexamination of the TEMPO Study.	2005-08	16087778
Clinical pharmacology of rasagiline: a novel, second-generation propargylamine for the treatment of Parkinson disease.	2005-08	16027398
Neuroprotective effect of rasagiline, a monoamine oxidase-B inhibitor, on spontaneous cell degeneration in a rat model.	2005-08	15765264
[Rasagiline. A new monoamine oxidase b inhibitor for Parkinson treatment].	2005-07	16038119
Parkinson's disease. Diagnosis and the initiation of therapy.	2005-06	16175158
Neuropharmacological, neuroprotective and amyloid precursor processing properties of selective MAO-B inhibitor antiparkinsonian drug, rasagiline.	2005-06	16110345
Evidence-based medical review update: pharmacological and surgical treatments of Parkinson's disease: 2001 to 2004.	2005-05	15818599
Novel pharmacological strategies for motor complications in Parkinson's disease.	2005-04	15882115
Mechanism of neuroprotective action of the anti-Parkinson drug rasagiline and its derivatives.	2005-04	15850677
Rasagiline as an adjunct to levodopa in patients with Parkinson's disease and motor fluctuations (LARGO, Lasting effect in Adjunct therapy with Rasagiline Given Once daily, study): a randomised, double-blind, parallel-group trial.	2005-03-16	15766996
Rasagiline for motor complications in Parkinson's disease.	2005-03-16	15766976
Characterization of the neuroprotective activity of rasagiline in cerebellar granule cells.	2005-03	15721173
A randomized placebo-controlled trial of rasagiline in levodopa-treated patients with Parkinson disease and motor fluctuations: the PRESTO study.	2005-02	15710852
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.	2005-02	15621213
Movement disorders: understanding clinical trials.	2005-01	15620847
[The early therapy challenge].	2005	16515310
Alternatives to levodopa in the initial treatment of early Parkinson's disease.	2005	16156677
Neuroprotection by rasagiline: a new therapeutic approach to Parkinson's disease?	2005	16007239
Neuroprotective therapy in Parkinson's disease and motor complications: a search for a pathogenesis-targeted, disease-modifying strategy.	2005	15822111
Rasagiline.	2005	15663351
Rasagiline: neurodegeneration, neuroprotection, and mitochondrial permeability transition.	2004-12-02	15573406
[Are there innovations in the treatment of Parkinson's disease?].	2004-11-03	15571301
Clinical trials of neuroprotection for Parkinson's disease.	2004-10-12	15477583
Preclinical evidence for neuroprotection with monoamine oxidase-B inhibitors in Parkinson's disease.	2004-10-12	15477581
Tolerability, safety, pharmacodynamics, and pharmacokinetics of rasagiline: a potent, selective, and irreversible monoamine oxidase type B inhibitor.	2004-10	15628826
Novel bifunctional drugs targeting monoamine oxidase inhibition and iron chelation as an approach to neuroprotection in Parkinson's disease and other neurodegenerative diseases.	2004-10	15480846
Recent approaches to novel anti-Alzheimer therapy.	2004	15544506

Patents

Sample Use Guides

In Vivo Use Guide

Monotherapy: the recommended AZILECT (RASAGILINE MESYLATE) dose for the treatment of Parkinson’s disease patients is 1 mg administered once daily. Adjunctive Therapy: the recommended initial dose is 0.5 mg administered once daily. If a sufficient clinical response is not achieved, the dose may be increased to 1 mg administered once daily. Change of levodopa dose in adjunct therapy: When AZILECT is used in combination with levodopa, a reduction of the levodopa dosage may be considered based upon individual response. During the controlled trials of AZILECT as adjunct therapy to levodopa, levodopa dosage was reduced in some patients. In clinical studies, dosage reduction of levodopa was allowed within the first 6 weeks if dopaminergic side effects, including dyskinesia and hallucinations, emerged.

Route of Administration: Oral

In Vitro Use Guide

The present series of in vitro experiments using the rat hippocampal slice preparation deals with effects of rasagiline and its metabolite R-(-)-aminoindan on the pyramidal cell response after electric stimulation of the Schaffer Collaterals in comparison to selegiline, another MAO B inhibitor. During the first series, this response was attenuated in the presence of rasagiline and aminoindan-to a lesser degree of selegiline-in a concentration dependent manner (5-50 μM) after single stimuli as well as under theta burst stimulation (TBS). The presence of rasagiline and aminoindan, but rarely the presence of selegiline, prevented this break down. Following glutamate receptor mediated enhancements of neuronal transmission in a second series of experiments very clear differences could be observed in comparison to the action of selegiline: NMDA receptor, AMPA receptor as well as metabotropic glutamate receptor mediated increases of transmission were concentration dependently (0,3 - 2 μM) antagonized by rasagiline and aminoindan, but not by selegiline. On the opposite, only selegiline attenuated kainate receptor mediated increases of excitability. Thus, both monoamino oxidase (MAO) B inhibitors show attenuation of glutamatergic transmission in the hippocampus but interfere with different receptor mediated excitatory modulations at low concentrations.

Substance Class	Chemical Created by `admin` on `Mon Mar 31 19:09:54 GMT 2025` Edited by `admin` on `Mon Mar 31 19:09:54 GMT 2025`
Record UNII	B9A329CN07
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

1-H-INDEN-1-AMINE, 2,3-DIHYDRO-N-2-PROPYN-1-YL-, 1(R)-, (2R,3R)-2,3-DIHYDROXYBUTANEDIOATE (2:1)

Preferred Name

English

RASAGILINE TARTRATE

Common Name

English

Rasagiline tartrate [WHO-DD]

Common Name

English

RASAGILINE HEMITARTRATE

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C667