Rasagiline mesylate

Names

[ Name ]:
Rasagiline mesylate

[Synonym ]:
acide méthanesulfonique - (1R)-N-prop-2-yn-1-yl-2,3-dihydro-1H-indén-1-amine (1:1)
Methansulfonsäure--(1R)-N-prop-2-in-1-yl-2,3-dihydro-1H-inden-1-amin(1:1)
methanesulfonic acid,(1R)-N-prop-2-ynyl-2,3-dihydro-1H-inden-1-amine
(1R)-N-(Prop-2-yn-1-yl)indan-1-amine methanesulfonate (1:1)
(1R)-N-(2-Propyn-1-yl)-1-indanamine methanesulfonate (1:1)
(1R)-N-prop-2-yn-1-yl-2,3-dihydro-1H-inden-1-amine methanesulfonate
Rasagiline mesylate
(R)-N-(Prop-2-yn-1-yl)-2,3-dihydro-1H-inden-1-amine methanesulfonate
(1R)-N-(prop-2-yn-1-yl)-2,3-dihydro-1H-inden-1-amine methanesulfonate (1:1)
1H-Inden-1-amine, 2,3-dihydro-N-2-propyn-1-yl-, (1R)-, methanesulfonate (1:1)
1H-inden-1-amine, 2,3-dihydro-N-2-propynyl-, (1R)-, methanesulfonate (1:1)
Rasagiline (mesylate)

Biological Activity

[Description]:

Rasagiline Mesylate is a new MAO-B inhibitor for the treatment of idiopathic Parkinson's disease. Target: Monoamine Oxidase (MAO)-BRasagiline (N-propargyl-1-(R)-aminoindan) is a novel, highly potent irreversible monoamine oxidase (MAO)-B inhibitor, anti-Parkinsonian drug. Rasagiline is effective as monotherapy or adjunct to L-Dopa for patients with early and late Parkinson's disease (PD) [1]. Rasagiline inhibits MAO-B more potently than selegiline and has the advantage of once-daily dosing. In several large, randomized, placebo-controlled trials, rasagiline has demonstrated efficacy as monotherapy in early PD and as adjunctive therapy in advanced PD. In addition, rasagiline has been shown to have neuroprotective effects in in vitro and in vivo studies. The recently completed delayed-start ADAGIO (Attenuation of Disease Progression with Azilect Given Once-daily) trial suggests a potential disease-modifying effect for rasagiline 1 mg/day, though the clinical import of this finding has yet to be established [2]. Rasagiline has been found to be well tolerated and effective in the treatment of early PD and as adjunctive treatment in motor fluctuations. Whether rasagiline is associated with clinically significant neuroprotection (ie, disease modification) in PD is the subject of ongoing clinical trials [3].

[Related Catalog]:

Signaling Pathways >> Autophagy >> Autophagy

Signaling Pathways >> Neuronal Signaling >> Monoamine Oxidase

Research Areas >> Neurological Disease

[References]

[1]. Weinreb, O., et al., Rasagiline: a novel anti-Parkinsonian monoamine oxidase-B inhibitor with neuroprotective activity. Prog Neurobiol, 2010. 92(3): p. 330-44.

[2]. Leegwater-Kim, J. and E. Bortan, The role of rasagiline in the treatment of Parkinson's disease. Clin Interv Aging, 2010. 5: p. 149-56.

[3]. Chen, J.J., D.M. Swope, and K. Dashtipour, Comprehensive review of rasagiline, a second-generation monoamine oxidase inhibitor, for the treatment of Parkinson's disease. Clin Ther, 2007. 29(9): p. 1825-49.

[4]. Lei D, et al. Synergistic neuroprotective effect of rasagiline and idebenone against retinal ischemia-reperfusion injury via the Lin28-let-7-Dicer pathway. Oncotarget. 2018 Jan 30;9(15):12137-12153.

[Related Small Molecules]

Chemical & Physical Properties

[ Density]:
1.05 g/cm3

[ Boiling Point ]:
305.5ºC at 760 mmHg

[ Melting Point ]:
155-158°C

[ Molecular Formula ]:
C₁₃H₁₇NO₃S

[ Molecular Weight ]:
267.344

[ Flash Point ]:
146.8ºC

[ Exact Mass ]:
267.092926

[ PSA ]:
74.78000

[ LogP ]:
2.87240

[ Vapour Pressure ]:
0.000816mmHg at 25°C

[ Storage condition ]:
-20°C Freezer

MSDS

Click to get detail MSDS

Safety Information

[ Symbol ]:

GHS07

[ Signal Word ]:
Warning

[ Hazard Statements ]:
H302

[ Hazard Codes ]:
Xi

[ Risk Phrases ]:
R36/37/38:Irritating to eyes, respiratory system and skin .

[ Safety Phrases ]:
S26-S37/39

[ RIDADR ]:
NONH for all modes of transport

[ WGK Germany ]:
3

[ HS Code ]:
2921499090

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Customs

[ HS Code ]: 2921499090

[ Summary ]:
2921499090 other aromatic monoamines and their derivatives; salts thereof VAT:17.0% Tax rebate rate:9.0% Supervision conditions:none MFN tariff:6.5% General tariff:30.0%

Articles

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.

Lancet 365(9463) , 947-54, (2005)

Rasagiline mesylate is a novel drug for Parkinson's disease with selective, irreversible monoamine oxidase B (MAO-B) inhibitor activity, and is effective as monotherapy in early disease. This study in...

Rasagiline mesylate, a new MAO-B inhibitor for the treatment of Parkinson's disease: a double-blind study as adjunctive therapy to levodopa.

Clin. Neuropharmacol. 23(6) , 324-30, (2000)

Rasagiline mesylate (TVP-1012) is a potent, selective, non-reversible MAO-B inhibitor, without the tyramine-potentiating effect and with neuroprotective activities. The benefit of rasagiline as monoth...

Increased survival of dopaminergic neurons by rasagiline, a monoamine oxidase B inhibitor.

Neuroreport 9(4) , 703-7, (1998)

Both deprenyl and rasagiline (R(+)-N-propargyl-1-aminoindane mesylate), at a concentration of 1-10 microM, increased survival in vitro of rat E14 mesencephalic dopaminergic neurons that had been prime...