Rasagiline Mesylate

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Cat Number

API161735791

CAS Number

161735-79-1

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CAS Number

161735-79-1

EINECS

694-423-3

Storage

Store at room temperature

Synonyms

Azilect; Rasagiline mesilate; TVP-1012; Agilect; Rasagiline methanesulfonate; Rasagline ratiopharm; DTXSID8047848

Molecular Formula

C13H17NO3S

Molecular Weight

267.35

Smiles

CS(=O)(=O)O.C#CCN[C@@H]1CCC2=CC=CC=C12

Appearance

White to off-white powder

Melting Point

155-158°C

Boiling Point

305.5°C at 760 mmHg

Relative Density

1.05

General Description

Rasagiline mesylate is a second-generation, selective, irreversible monoamine oxidase type B (MAO-B) inhibitor. Its chemical structure is a propargylamine derivative, specifically (R)-N-2-propynyl-1-indanamine, formulated as the mesylate salt to improve aqueous solubility. The indan ring provides lipophilicity for blood-brain barrier penetration, while the propargyl group covalently binds to the flavin adenine dinucleotide (FAD) cofactor of MAO-B.

Mechanism of Action

Rasagiline irreversibly binds to MAO-B, the enzyme predominantly responsible for dopamine catabolism in the brain. By blocking MAO-B, it prevents the oxidative deamination of dopamine, raising striatal dopamine levels. Unlike non-selective MAO inhibitors, rasagiline has little effect on MAO-A at therapeutic doses, thus avoiding the “cheese effect” (tyramine-induced hypertensive crisis).

Application

Rasagiline is indicated as monotherapy for early Parkinson’s disease and as adjunctive therapy to levodopa in moderate-to-advanced stages. It provides symptomatic improvement in motor features and has been suggested to possess potential disease-modifying properties, though this remains debated. Unlike entacapone, it does not affect peripheral levodopa metabolism. The drug is also studied off-label for multiple system atrophy and restless legs syndrome.

In a rat model of myocardial infarction (permanent coronary ligation), rasagiline mesylate (2 mg/kg/day intraperitoneal for 28 days) significantly improved left ventricular function, reducing end‑systolic and end‑diastolic dimensions and preserving fractional shortening (31.6 vs. 19.6, P<0.0001). It also reduced interstitial fibrosis, decreased apoptotic myocytes in the border zone by 65%, lowered caspase‑3 levels, and reduced oxidative stress (malondialdehyde). Rasagiline attenuates post‑infarction cardiac remodeling.

Fig. 1 Rasagiline mesylate (RG) improves cardiac dysfunction at 14 and 28 days post‐MI induction, without altering infarct size. (Varela A, et al., 2017)

References

Varela A, et al. The neuroprotective agent Rasagiline mesylate attenuates cardiac remodeling after experimental myocardial infarction. ESC Heart Fail. 2017;4(3):331-340.

A microsphere‑gel in situ forming implant (MS‑Gel ISFI) was developed for rasagiline mesylate to treat Parkinson’s disease. The system showed no initial burst release and sustained drug release for 60 days in vitro. In rats, it significantly reduced initial peak plasma concentration compared with single microspheres or in situ gel alone (P<0.01). Pharmacodynamic studies showed reduced contralateral rotation and increased striatal dopamine levels after 28 days. This injectable depot system is promising for sustained delivery of hydrophilic small molecules.

Fig. 2 Effect of chronic treatment with RM–microsphere–Gel in situ forming implant on 6-hydroxydopamine-lesioned rats. (Jiang Y, et al., 2018)

References

Jiang Y, et al. Preparation and evaluation of injectable Rasagiline mesylate dual-controlled drug delivery system for the treatment of Parkinson's disease. Drug Deliv. 2018;25(1):143-152.

Does Rasagiline Mesylate require protection from light during long-term storage?

Yes, it is photosensitive. UV exposure can cause photodegradation and formation of aminoindan impurity. Store in light-resistant containers, preferably amber glass.

What is the recommended storage temperature for Rasagiline Mesylate?

Store at controlled room temperature (15-25°C). Avoid excessive heat above 30°C, which can accelerate oxidative degradation of the propargyl group.

Is Rasagiline Mesylate hygroscopic, and how is this managed?

It is slightly hygroscopic. Under high humidity (>70% RH), it may absorb moisture and clump. Storage in tightly sealed containers with desiccant is recommended.

How is the impurity aminoindan (despropargyl rasagiline) monitored during stability?

This primary degradation product is specifically quantified using a stability-indicating HPLC method, ensuring it remains within ICH qualification thresholds.