ContaminantDB: Rotigotine

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-05-22 05:56:30 UTC

Update Date

2016-11-09 01:15:57 UTC

Accession Number

CHEM019240

Identification

Common Name

Rotigotine

Class

Small 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

Not Available

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
Neupro	Kegg
N 0437, (-)-Isomer	MeSH
Rotigotine	MeSH
Rotigotine CDS	MeSH
N 0437, (R)-Isomer	MeSH
N 0437, Hydrochloride, (S)-isomer	MeSH
N 0437, (+-)-Isomer	MeSH
N 0437, Hydrochloride, (R)-isomer	MeSH
2-(N-N-Propyl-N-2-thienylethylamino)-5-hydroxytetralin	MeSH

Chemical Formula

C₁₉H₂₅NOS

Average Molecular Mass

315.480 g/mol

Monoisotopic Mass

315.166 g/mol

CAS Registry Number

99755-59-6

IUPAC Name

(6S)-6-{propyl[2-(thiophen-2-yl)ethyl]amino}-5,6,7,8-tetrahydronaphthalen-1-ol

Traditional Name

neupro

SMILES

CCCN(CCC1=CC=CS1)[C@H]1CCC2=C(O)C=CC=C2C1

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/t16-/m0/s1

InChI Key

KFQYTPMOWPVWEJ-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.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Tetralins

Sub Class

Not Available

Direct Parent

Tetralins

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 Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Biological Properties

Status

Detected and Not Quantified

Origin

Not Available

Cellular Locations

Not Available

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Physical Properties

State

Not Available

Appearance

Not Available

Experimental Properties

Property	Value
Melting Point	Not Available
Boiling Point	Not Available
Solubility	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	0.009 g/L	ALOGPS
logP	5.01	ALOGPS
logP	4.34	ChemAxon
logS	-4.5	ALOGPS
pKa (Strongest Acidic)	10.03	ChemAxon
pKa (Strongest Basic)	10.97	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	23.47 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	94.56 m³·mol⁻¹	ChemAxon
Polarizability	36.56 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-014i-1219000000-e9b0374e911f9ab493c2	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-03xv-2943000000-8ea808fc385a827db1e5	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-01ox-9710000000-c3f5bedd56fe6e66dfb7	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-03di-1019000000-965637dbc06a384d5399	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0ik9-1297000000-f1e7edc18a1314a9e104	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4i-9420000000-18f86c9374468cd168a8	Spectrum

Toxicity Profile

Route of Exposure

Not Available

Mechanism of Toxicity

Not Available

Metabolism

Not Available

Toxicity Values

Not Available

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

Not Available

Uses/Sources

Not Available

Minimum Risk Level

Not Available

Health Effects

Not Available

Symptoms

Not Available

Treatment

Not Available

Concentrations

Not Available

External Links

DrugBank ID

DB05271

HMDB ID

Not Available

FooDB ID

Not Available

Phenol Explorer ID

Not Available

KNApSAcK ID

Not Available

BiGG ID

Not Available

BioCyc ID

Not Available

METLIN ID

Not Available

PDB ID

Not Available

Wikipedia Link

Rotigotine

Chemspider ID

Not Available

ChEBI ID

Not Available

PubChem Compound ID

59227

Kegg Compound ID

Not Available

YMDB ID

Not Available

ECMDB ID

Not Available

References

Synthesis Reference

Not Available

MSDS

Not Available

General References

Not Available

Rotigotine (CHEM019240)

Structure for CHEM019240: Rotigotine