rotigotine   Click here for help

GtoPdb Ligand ID: 941

Synonyms: Leganto® | N-0437 | Neupro®
Approved drug PDB Ligand
rotigotine is an approved drug (EMA (2006), FDA (2007))
Compound class: Synthetic organic
Comment: Rotigotine is a non-ergoline type, dopamine receptor agonist drug. At clinical doses rotigotine acts somewhat selectively for D1-like (D1, D5) and D2-like (D2, D3, D4) receptors. α2B-adrenergic and 5-HT1A activity may also provide some clinical benefit.
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Ligand Activity Visualisation Charts

These are box plot that provide a unique visualisation, summarising all the activity data for a ligand taken from ChEMBL and GtoPdb across multiple targets and species. Click on a plot to see the median, interquartile range, low and high data points. A value of zero indicates that no data are available. A separate chart is created for each target, and where possible the algorithm tries to merge ChEMBL and GtoPdb targets by matching them on name and UniProt accession, for each available species. However, please note that inconsistency in naming of targets may lead to data for the same target being reported across multiple charts.

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View interactive charts of activity data across species

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View more information in the IUPHAR Pharmacology Education Project: rotigotine

2D Structure
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2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

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Physico-chemical Properties
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Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the CDK toolkit. All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

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Hydrogen bond acceptors 1
Hydrogen bond donors 1
Rotatable bonds 6
Topological polar surface area 51.71
Molecular weight 315.17
XLogP 3.48
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
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SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

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Canonical SMILES CCCN(C1CCc2c(C1)cccc2O)CCc1cccs1
Isomeric SMILES CCCN([C@H]1CCc2c(C1)cccc2O)CCc1cccs1
InChI 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/t16-/m0/s1
InChI Key KFQYTPMOWPVWEJ-INIZCTEOSA-N
References
1. Dijkstra D, Rodenhuis N, Vermeulen ES, Pugsley TA, Wise LD, Wikström HV. (2002)
Further characterization of structural requirements for ligands at the dopamine D(2) and D(3) receptor: exploring the thiophene moiety.
J Med Chem, 45 (14): 3022-31. [PMID:12086487]
2. Sunahara RK, Guan HC, O'Dowd BF, Seeman P, Laurier LG, Ng G, George SR, Torchia J, Van Tol HH, Niznik HB. (1991)
Cloning of the gene for a human dopamine D5 receptor with higher affinity for dopamine than D1.
Nature, 350 (6319): 614-9. [PMID:1826762]
3. van Vliet LA, Tepper PG, Dijkstra D, Damsma G, Wikström H, Pugsley TA, Akunne HC, Heffner TG, Glase SA, Wise LD. (1996)
Affinity for dopamine D2, D3, and D4 receptors of 2-aminotetralins. Relevance of D2 agonist binding for determination of receptor subtype selectivity.
J Med Chem, 39 (21): 4233-7. [PMID:8863800]