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Rotigotine chemical structure
Rotigotine

(S)-6-[propyl(2-thiophen-2-ylethyl)amino]-5,6,7,8- tetrahydronaphthalen-1-ol
IUPAC name
CAS number
92206-54-7
ATC code

N04BC09

PubChem
57537
DrugBank
DB05271
Chemical formula {{{chemical_formula}}}
Molecular weight 315.474 g/mol
Bioavailability 37% (transdermal)
Metabolism Hepatic (CYP-mediated)
Elimination half-life 5–7 hours
Excretion Urine (71%), Fecal (23%)
Pregnancy category C
Legal status Rx-only
Routes of administration Transdermal patch


Rotigotine (Neupro) is a non-ergoline dopamine agonist indicated for the treatment of Parkinson's disease (PD) and restless legs syndrome (RLS) in Europe and the United States.[1][2] It is formulated as a once-daily transdermal patch which provides a slow and constant supply of the drug over the course of 24 hours.[1][1]

Like other dopamine agonists, rotigotine has been shown to possess antidepressant effects and may be useful in the treatment of depression as well.[3]

History[]

Rotigotine was developed by Aderis Pharmaceuticals. In 1998, Aderis licensed worldwide development and commercialization rights for rotigotine to the German pharmaceutical company Schwarz Pharma (today a subsidiary of the Belgian company UCB S.A.).[4]

The drug has been approved by the EMEA for use in Europe in 2006 and is today being sold in several European countries. In 2007, the Neupro patch was approved by the Food and Drug Administration (FDA) as the first transdermal treatment of Parkinson's disease in the United States. However, as of 2008, Schwarz Pharma has recalled all Neupro patches in the United States and some in Europe because of problems with the delivery mechanism.

Rotigotine has been authorized as a treatment for RLS since August 2008.[2]

Chemistry[]

Rotigotine is analogous to 7-OH-DPAT and UH-232, all three of which are aminotetralin derivatives. These compounds are similar in structure to dopamine, likely underlying their pharmacology.

File:Rotigotine synth.png

Cusack, N. J.; Peck, J. V.; Drugs Future 1993, 18, 1005.

Pharmacology[]

Rotigotine possesses the following in vitro receptor binding profile:[5]

  • D1 receptor (Ki = 83 nM)
  • D2 receptor (Ki = 13.5 nM)
  • D3 receptor (Ki = 0.71 nM)
  • D4.2 receptor (Ki = 3.9 nM)
  • D4.4 receptor (Ki = 15 nM)
  • D4.7 receptor (Ki = 5.9 nM)
  • D5 receptor (Ki = 5.4 nM)

  • α1A-adrenergic receptor (Ki = 176 nM)
  • α1B-adrenergic receptor (Ki = 273 nM)
  • α2A-adrenergic receptor (Ki = 338 nM)
  • α2B-adrenergic receptor (Ki = 27 nM)
  • α2C-adrenergic receptor (Ki = 135 nM)

All affinities listed were assayed using human materials except that for α2B-adrenergic which was done with NG 108–15 cells. Rotigotine behaves as a partial or full agonist (depending on the assay) at all dopamine receptors listed, as an antagonist at the α2B-adrenergic receptor, and as a partial agonist at the 5-HT1A receptor.[5] Though it has affinity for a large number of sites as shown above, at clinical doses rotigotine behaves mostly as a selective D2-like (D2, D3, D4) and D5 receptor agonist, with its α2B-adrenergic and 5-HT1A activity also possibly having some low relevance.

Side effects[]

General side effects for rotigotine may include constipation, dyskinesia, nausea, vomiting, dizziness, fatigue, insomnia, somnolence, confusion, and hallucinations.[6][7] More serious complications can include psychosis and impulse control disorders like hypersexuality, punding, and pathological gambling.[8] Mild adverse skin reactions at the patch application site may also occur.[1][7]

See also[]

References[]

  1. 1.0 1.1 1.2 1.3 Chen JJ, Swope DM, Dashtipour K, Lyons KE (December 2009). Transdermal rotigotine: a clinically innovative dopamine-receptor agonist for the management of Parkinson's disease. Pharmacotherapy 29 (12): 1452–67.
  2. 2.0 2.1 Davies S (September 2009). Rotigotine for restless legs syndrome. Drugs of Today (Barcelona, Spain : 1998) 45 (9): 663–8.
  3. Bertaina-Anglade V, La Rochelle CD, Scheller DK (October 2006). Antidepressant properties of rotigotine in experimental models of depression. European Journal of Pharmacology 548 (1-3): 106–14.
  4. Development & Commercialization of rotigotine by Aderis (Aderis Pharmaceuticals making a reference for the commercialization of rotigotine)
  5. 5.0 5.1 Scheller D, Ullmer C, Berkels R, Gwarek M, Lübbert H (January 2009). The in vitro receptor profile of rotigotine: a new agent for the treatment of Parkinson's disease. Naunyn-Schmiedeberg's Archives of Pharmacology 379 (1): 73–86.
  6. Kulisevsky J, Pagonabarraga J (2010). Tolerability and safety of ropinirole versus other dopamine agonists and levodopa in the treatment of Parkinson's disease: meta-analysis of randomized controlled trials. Drug Safety : an International Journal of Medical Toxicology and Drug Experience 33 (2): 147–61.
  7. 7.0 7.1 (December 2003)A controlled trial of rotigotine monotherapy in early Parkinson's disease. Archives of Neurology 60 (12): 1721–8.
  8. Wingo TS, Evatt M, Scott B, Freeman A, Stacy M (2009). Impulse control disorders arising in 3 patients treated with rotigotine. Clinical Neuropharmacology 32 (2): 59–62.

External links[]


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