ContaminantDB: Ropinirole

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References Targets (18)XML

Record Information

Version

1.0

Creation Date

2009-07-21 20:26:26 UTC

Update Date

2016-11-09 01:08:41 UTC

Accession Number

CHEM002156

Identification

Common Name

Ropinirole

Class

Small Molecule

Description

Ropinirole is a non-ergoline dopamine agonist, manufactured by GlaxoSmithKline. It is used in the treatment of Parkinson's disease, and is also one of two medications in the United States with an FDA-approved indication for the treatment of restless legs syndrome (the other being Pramipexole).

Contaminant Sources

HMDB Contaminants - Urine
STOFF IDENT Compounds
T3DB toxins
ToxCast & Tox21 Chemicals

Contaminant Type

Amide
Amine
Antidyskinetic
Antiparkinson Agent
Central Nervous System Agent
Dopamine Agonist
Drug
Metabolite
Organic Compound
Synthetic Compound

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
Ropinirol	ChEBI
Ropinirolum	ChEBI
Ropitor	Kegg
4-(2-(Di-N-propylamino)ethyl)-2(3H)-indolone	HMDB
GlaxoSmithKline brand OF ropinirole hydrochloride	HMDB
Requip	HMDB
SK And F-101,468	HMDB
SmithKline beecham brand OF ropinirole hydrochloride	HMDB
Ropinirole hydrochloride	HMDB
SK And F 101468	HMDB

Chemical Formula

C₁₆H₂₄N₂O

Average Molecular Mass

260.375 g/mol

Monoisotopic Mass

260.189 g/mol

CAS Registry Number

91374-21-9

IUPAC Name

4-[2-(dipropylamino)ethyl]-2,3-dihydro-1H-indol-2-one

Traditional Name

ropinirole

SMILES

CCCN(CCC)CCC1=C2CC(O)=NC2=CC=C1

InChI Identifier

InChI=1S/C16H24N2O/c1-3-9-18(10-4-2)11-8-13-6-5-7-15-14(13)12-16(19)17-15/h5-7H,3-4,8-12H2,1-2H3,(H,17,19)

InChI Key

InChIKey=UHSKFQJFRQCDBE-UHFFFAOYSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as indolines. Indolines are compounds containing an indole moiety, which consists of pyrrolidine ring fused to benzene to form 2,3-dihydroindole.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Indoles and derivatives

Sub Class

Indolines

Direct Parent

Indolines

Alternative Parents

Substituents

Dihydroindole
Phenethylamine
Aralkylamine
Benzenoid
Amino acid or derivatives
Carboxamide group
Lactam
Secondary carboxylic acid amide
Tertiary aliphatic amine
Tertiary amine
Carboxylic acid derivative
Azacycle
Organooxygen compound
Organonitrogen compound
Organic oxide
Organopnictogen compound
Amine
Organic oxygen compound
Carbonyl group
Hydrocarbon derivative
Organic nitrogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

tertiary amine (CHEBI:8888 )
indolones (CHEBI:8888 )

Biological Properties

Status

Detected and Not Quantified

Origin

Exogenous

Cellular Locations

Cytoplasm
Extracellular
Membrane

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Applications

Biological Roles

dopamine agonist

Chemical Roles

Not Available

Physical Properties

State

Solid

Appearance

White powder.

Experimental Properties

Property	Value
Melting Point	243-250°C
Boiling Point	Not Available
Solubility	133 mg/mL

Predicted Properties

Property	Value	Source
Water Solubility	0.35 g/L	ALOGPS
logP	3.16	ALOGPS
logP	3.06	ChemAxon
logS	-2.9	ALOGPS
pKa (Strongest Acidic)	13.24	ChemAxon
pKa (Strongest Basic)	10.17	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	32.34 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	81.43 m³·mol⁻¹	ChemAxon
Polarizability	31.19 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-03kd-8950000000-65ad14635cd7e9f25153	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 50V, Positive	splash10-001i-0900000000-fd0720d43d850f7b4112	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 30V, Positive	splash10-03e9-0900000000-0cffe19378ee7388c9b3	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 40V, Positive	splash10-001i-0900000000-7b58f2b7d78649e5141a	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-03di-0390000000-844dec8f945ae2bdddcd	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-03di-0090000000-8c7df92a90c013ff6e26	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-03di-0190000000-7e072cf65f341641938c	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-03di-3960000000-47d2311adfeeacf4062d	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0006-7900000000-0891c66db163729a5360	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0a4i-0090000000-88c0fa3d93090a0d06c6	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0pb9-3590000000-8fb5fc766313ee6bbd9e	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0k96-9400000000-f1b50dacd59a9bfe90b7	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-03di-0190000000-bfa59f1f4dd92796c2f1	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-03di-1970000000-134d3ee14c868165c82d	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-01pp-7900000000-2459901fcec4348b7dbc	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0a4i-0090000000-7c4aa654b272455d2904	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0a4i-0590000000-4395944c67ba02f5a73b	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-053r-2900000000-2cb3b5572e758c0d2eb0	Spectrum

Toxicity Profile

Route of Exposure

Oral. Absolute bioavailability is 55%, indicating a first pass effect. Food does not affect the extent of absorption.

Mechanism of Toxicity

Ropinirole binds the dopamine receptors D₃ and D₂. Although the precise mechanism of action of ropinirole as a treatment for Parkinson's disease is unknown, it is believed to be related to its ability to stimulate these receptors in the striatum. This conclusion is supported by electrophysiologic studies in animals that have demonstrated that ropinirole influences striatal neuronal firing rates via activation of dopamine receptors in the striatum and the substantia nigra, the site of neurons that send projections to the striatum.

Metabolism

Hepatic. Ropinirole is extensively metabolized to inactive metabolites via N -despropylation and hydroxylation pathways, largely by the P450 isoenzyme CYP1A2. N-despropyl ropinirole is the predominant metabolite found in urine (40%), followed by the carboxylic acid metabolite (10%), and the glucuronide of the hydroxy metabolite (10%). Route of Elimination: Ropinirole is extensively metabolized by the liver to inactive metabolites, and less than 10% of the administered dose is excreted as unchanged drug in urine. Half Life: 6 hours

Toxicity Values

Not Available

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

No indication of carcinogenicity to humans (not listed by IARC).

Uses/Sources

For the treatment of the signs and symptoms of idiopathic Parkinson's disease. Also used for the treatment of restless legs syndrome.

Minimum Risk Level

Not Available

Health Effects

Not Available

Symptoms

Symptoms of overdose include agitation, chest pain, confusion, drowsiness, facial muscle movements, grogginess, increased jerkiness of movement, symptoms of low blood pressure (dizziness, light-headedness)upon standing, nausea, and vomiting.

Treatment

General supportive measures are recommended. Vital signs should be maintained, if necessary. Removal of any unabsorbed material (e.g., by gastric lavage) should be considered. (2)

Concentrations

Not Available

External Links

DrugBank ID

DB00268

HMDB ID

HMDB0014413

FooDB ID

Not Available

Phenol Explorer ID

Not Available

KNApSAcK ID