rotigotine   Click here for help

GtoPdb Ligand ID: 941

Synonyms: Leganto® | N-0437 | Neupro®
Approved drug
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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2D Structure
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Physico-chemical Properties
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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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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]