Rotigotine (CHEM019240)

Record Information
Version1.0
Creation Date2016-05-22 05:56:30 UTC
Update Date2026-08-20 03:58:52 UTC
Accession NumberCHEM019240
Identification
Common NameRotigotine
ClassSmall Molecule
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 to Schwarz Pharma of Germany. It was approved by the European Medicines Agency in 2006 and by the FDA in 2007. However, all Rotigotine patches in the United States and some of Europe were recalled in 2008 due to delivery mechanism issues. Rotigotine has been authorized as a treatment for RLS since August 2008.
Contaminant Sources
  • HMDB Contaminants - Urine
  • STOFF IDENT Compounds
  • ToxCast & Tox21 Chemicals
Contaminant Type
  • Human Neurotoxin
Chemical Structure
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
NeuproKegg
N 0437, (-)-IsomerMeSH
RotigotineMeSH
Rotigotine CDSMeSH
N 0437, (R)-IsomerMeSH
N 0437, Hydrochloride, (S)-isomerMeSH
N 0437, (+-)-IsomerMeSH
N 0437, Hydrochloride, (R)-isomerMeSH
2-(N-N-Propyl-N-2-thienylethylamino)-5-hydroxytetralinMeSH
Chemical FormulaC19H25NOS
Average Molecular Mass315.480 g/mol
Monoisotopic Mass315.166 g/mol
CAS Registry Number99755-59-6
IUPAC Name(6S)-6-{propyl[2-(thiophen-2-yl)ethyl]amino}-5,6,7,8-tetrahydronaphthalen-1-ol
Traditional Nameneupro
SMILESCCCN(CCC1=CC=CS1)[C@H]1CCC2=C(O)C=CC=C2C1
InChI IdentifierInChI=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 KeyKFQYTPMOWPVWEJ-INIZCTEOSA-N
Chemical Taxonomy
Description 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.
KingdomOrganic compounds
Super ClassBenzenoids
ClassTetralins
Sub ClassNot Available
Direct ParentTetralins
Alternative Parents
Substituents
  • Tetralin
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Aralkylamine
  • Thiophene
  • Heteroaromatic compound
  • Tertiary amine
  • Tertiary aliphatic amine
  • Organoheterocyclic compound
  • Hydrocarbon derivative
  • Organopnictogen compound
  • Organic oxygen compound
  • Organic nitrogen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Amine
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.009 g/LALOGPS
logP5.01ALOGPS
logP4.34ChemAxon
logS-4.5ALOGPS
pKa (Strongest Acidic)10.03ChemAxon
pKa (Strongest Basic)10.97ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area23.47 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity94.56 m³·mol⁻¹ChemAxon
Polarizability36.56 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
External Links
DrugBank IDDB05271
HMDB IDNot Available
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkRotigotine
Chemspider IDNot Available
ChEBI IDNot Available
PubChem Compound ID59227
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References