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| Record Information |
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| Version | 3.6 |
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| Creation Date | 2012-09-06 15:16:52 UTC |
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| Update Date | 2016-02-11 01:33:36 UTC |
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| HMDB ID | HMDB15615 |
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| Secondary Accession Numbers | None |
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| Metabolite Identification |
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| Common Name | Rotigotine |
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| Description | 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. 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. Like other dopamine agonists, rotigotine has been shown to possess antidepressant effects and may be useful in the treatment of depression as well. 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.). 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. |
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| Structure | |
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| Synonyms | Not Available |
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| Chemical Formula | C19H25NOS |
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| Average Molecular Weight | 315.473 |
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| Monoisotopic Molecular Weight | 315.165685117 |
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| IUPAC Name | 6-{propyl[2-(thiophen-2-yl)ethyl]amino}-5,6,7,8-tetrahydronaphthalen-1-ol |
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| Traditional Name | rotigotine |
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| CAS Registry Number | 92206-54-7 |
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| SMILES | CCCN(CCC1=CC=CS1)C1CCC2=C(C1)C=CC=C2O |
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| InChI Identifier | InChI=1S/C19H25NOS/c1-2-11-20(12-10-17-6-4-13-22-17)16-8-9-18-15(14-16)5-3-7-19(18)21/h3-7,13,16,21H,2,8-12,14H2,1H3 |
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| InChI Key | InChIKey=KFQYTPMOWPVWEJ-UHFFFAOYSA-N |
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| Chemical Taxonomy |
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| Description | This compound belongs to the class of organic compounds known as tetralins. These are polycyclic aromatic compounds containing a tetralin moiety, which consists of a benzene fused to a cyclohexane. |
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| Kingdom | Organic compounds |
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| Super Class | Benzenoids |
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| Class | Tetralins |
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| Sub Class | Not Available |
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| Direct Parent | Tetralins |
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| Alternative Parents | |
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| Substituents | - Tetralin
- Aralkylamine
- Heteroaromatic compound
- Thiophene
- Tertiary aliphatic amine
- Tertiary amine
- Organoheterocyclic compound
- Hydrocarbon derivative
- Organooxygen compound
- Organonitrogen compound
- Amine
- Aromatic heteropolycyclic compound
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| Molecular Framework | Aromatic heteropolycyclic compounds |
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| External Descriptors | Not Available |
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| Ontology |
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| Status | Expected but not Quantified |
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| Origin | |
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| Biofunction | - Antidyskinetics
- Antiparkinson Agents
- Dopamine Agonists
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| Application | |
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| Cellular locations | |
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| Physical Properties |
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| State | Solid |
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| Experimental Properties | | Property | Value | Reference |
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| Melting Point | Not Available | Not Available | | Boiling Point | Not Available | Not Available | | Water Solubility | 9.04e-03 g/L | Not Available | | LogP | 4.70 | BIOBYTE STARLIST (2009) |
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| Predicted Properties | |
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| Spectra |
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| Spectra | Not Available |
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| Biological Properties |
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| Cellular Locations | |
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| Biofluid Locations | |
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| Tissue Location | Not Available |
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| Pathways | Not Available |
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| Normal Concentrations |
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| Blood | Expected but not Quantified | Not Applicable | Not Available | Not Available | Taking drug identified by DrugBank entry DB05271 | | details | | Urine | Expected but not Quantified | Not Applicable | Not Available | Not Available | Taking drug identified by DrugBank entry DB05271 | | details |
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| Abnormal Concentrations |
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| Not Available |
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| Associated Disorders and Diseases |
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| Disease References | None |
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| Associated OMIM IDs | None |
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| External Links |
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| DrugBank ID | DB05271 |
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| DrugBank Metabolite ID | Not Available |
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| Phenol Explorer Compound ID | Not Available |
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| Phenol Explorer Metabolite ID | Not Available |
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| FoodDB ID | Not Available |
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| KNApSAcK ID | Not Available |
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| Chemspider ID | 51867 |
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| KEGG Compound ID | Not Available |
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| BioCyc ID | Not Available |
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| BiGG ID | Not Available |
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| Wikipedia Link | Rotigotine |
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| NuGOwiki Link | HMDB15615 |
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| Metagene Link | HMDB15615 |
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| METLIN ID | Not Available |
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| PubChem Compound | 57537 |
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| PDB ID | Not Available |
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| ChEBI ID | Not Available |
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| References |
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| Synthesis Reference | Not Available |
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| Material Safety Data Sheet (MSDS) | Not Available |
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| General References | - Giladi N, Boroojerdi B, Korczyn AD, Burn DJ, Clarke CE, Schapira AH: Rotigotine transdermal patch in early Parkinson's disease: a randomized, double-blind, controlled study versus placebo and ropinirole. Mov Disord. 2007 Dec;22(16):2398-404. [17935234 ]
- Chen JJ, Swope DM, Dashtipour K, Lyons KE: Transdermal rotigotine: a clinically innovative dopamine-receptor agonist for the management of Parkinson's disease. Pharmacotherapy. 2009 Dec;29(12):1452-67. doi: 10.1592/phco.29.12.1452. [19947805 ]
- Perez-Lloret S, Rey MV, Ratti PL, Rascol O: Rotigotine transdermal patch for the treatment of Parkinson's Disease. Fundam Clin Pharmacol. 2013 Feb;27(1):81-95. doi: 10.1111/j.1472-8206.2012.01028.x. Epub 2012 Feb 9. [22320451 ]
- de Biase S, Merlino G, Lorenzut S, Valente M, Gigli GL: ADMET considerations for restless leg syndrome drug treatments. Expert Opin Drug Metab Toxicol. 2012 Oct;8(10):1247-61. doi: 10.1517/17425255.2012.708023. Epub 2012 Jul 18. [22808933 ]
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