Rotigotine

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Cat Number

API99755596

CAS Number

99755-59-6

For research use only. We do not supply to patients.

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CAS Number

99755-59-6

EINECS

619-458-3

Storage

Store at 2-8°C

Synonyms

Neupro; Leganto; SPM-962; Rotigotina; DTXSID5046772

Molecular Formula

C19H25NOS

Molecular Weight

315.5

Smiles

CCCN(CCC1=CC=CS1)[C@H]2CCC3=C(C2)C=CC=C3O

Appearance

White to off-white solid powder

Melting Point

78°C

Boiling Point

470.1±45.0°C at 760 mmHg (Predicted)

Relative Density

1.15±0.1 (Predicted)

General Description

Rotigotine is a synthetic aminotetralin derivative, a non-ergoline dopamine receptor agonist with a thiophene ring. Its chemical structure is (S)-6-propyl-2-(2-thienyl)aminotetralin. Rotigotine is a white to off-white powder, practically insoluble in water but soluble in organic solvents. The molecule is a potent D2 and D3 receptor agonist with high affinity for dopamine receptors.

Mechanism of Action

Rotigotine acts as a full agonist at dopamine D2 and D3 receptors, and to a lesser extent at D1 and D4 receptors, in the basal ganglia and other brain regions. It mimics the action of endogenous dopamine, compensating for the dopaminergic deficit in Parkinson's disease. The drug also has weak agonistic activity at 5-HT1A and α2-adrenergic receptors, contributing to its overall profile.

Application

Rotigotine is indicated for the treatment of Parkinson's disease and for the management of moderate to severe restless legs syndrome (RLS). It is effective in reducing the symptoms of bradykinesia, rigidity, and tremor, and in improving sleep quality. The drug is also used for the treatment of dopaminergic dysregulation syndrome.

This review summarizes the evidence for rotigotine transdermal patch in Parkinson’s disease, with a focus on non-motor symptoms (NMS). Rotigotine addresses motor symptoms and a wide range of NMS, including non-motor fluctuations, improving health-related QoL. The patch offers advantages when oral therapy is not feasible (e.g., emergencies, pre/post-surgery).

Fig. 1 The aminotetralin structure of rotigotine is similar to that of dopamine but more rigid. (Raeder V, et al., 2021)

References

Raeder V, et al. Rotigotine Transdermal Patch for Motor and Non-motor Parkinson's Disease: A Review of 12 Years' Clinical Experience. CNS Drugs. 2021;35(2):215-231.

Rotigotine, a dopamine agonist for Parkinson’s disease, was found to suppress ox-LDL-induced endothelial damage in HUVECs. It reduced LDL-R, PCSK-9, and SREBP-2 expression; inhibited cholesterol accumulation, monocyte adhesion, ROS generation, and VCAM-1/ICAM-1 expression; and suppressed pro-inflammatory cytokines by blocking NF-κB p65 nuclear translocation. These findings suggest rotigotine may have therapeutic potential in cardiovascular diseases beyond its approved indication.

Fig. 2 Treatment with Rotigotine reduced ox-LDL-induced expressions of PCSK-9, SREBP-2, and LDL-R in HUVECs. (Kang H, et al., 2021)

References

Kang H, et al. Rotigotine protects against oxidized low-density lipoprotein(ox-LDL)-induced damages in human umbilical vein endothelial cells(HUVECs). Bioengineered. 2021;12(2):10568-10579.

Does Rotigotine require refrigerated storage as a dopamine agonist?

Yes, it should be stored at 2-8°C. At room temperature, oxidation and degradation of the aminotetralin ring occur, reducing potency.

Is Rotigotine sensitive to light and oxygen during handling?

Yes, it is highly sensitive to light and oxygen. Store in light-resistant, airtight containers under inert gas (nitrogen). Handle under subdued light.

Is Rotigotine stable in transdermal patch formulations?

Patches are stable when packaged in foil pouches with oxygen absorbers and stored under refrigeration.

How is the impurity rotigotine N-oxide (an oxidative degradation product) monitored?

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