Identification

Name
Ropinirole
Accession Number
DB00268
Description

Ropinirole, also known as ReQuip, is a non-ergoline dopamine agonist used in Parkinson's disease and restless legs syndrome Label, 3. It is manufactured by GlaxoSmithKline Pharmaceuticals. Ropinirole was initially approved in 1997 by the FDA Label for the management of Parkinson's disease. In 2005, it was the first drug approved in the US for the management of primary moderate to severe restless legs syndrome 3.

In 2008, the extended-release capsules of ropinirole were approved, allowing for less frequent dosing, therefore increased compliance, and offering a similar side effect profile and efficacy to previous formulations of ropinirole 4.

Type
Small Molecule
Groups
Approved, Investigational
Structure
Thumb
Weight
Average: 260.3746
Monoisotopic: 260.1888634
Chemical Formula
C16H24N2O
Synonyms
  • Ropinirol
  • Ropinirole
  • Ropinirolum
External IDs
  • SK&F 101468
  • SK&F-101468

Pharmacology

Indication

For the treatment of the signs and symptoms of Parkinson's disease and for the treatment of primary moderate-severe restless legs syndrome Label.

Associated Conditions
Contraindications & Blackbox Warnings
Learn about our commercial Contraindications & Blackbox Warnings data.
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Pharmacodynamics

Effects on Parkinson's and restless leg syndrome

This drug promotes the relief or improvement of symptoms of Parkinson's or restless leg syndrome by stimulatory actions on dopamine receptors, which regulate movement.

Effects on blood pressure

Clinical experience with dopamine agonists, including ropinirole, suggests an association with impaired abilities in regulating blood pressure with resulting orthostatic hypotension, especially with patients undergoing dose escalation. In some patients in clinical studies, blood pressure changes were associated with orthostatic symptoms, bradycardia, and, in one case in a healthy volunteer, transient sinus arrest accompanied by syncope Label. The mechanism of orthostatic hypotension caused by ropinirole is assumed to be due to a D2-mediated blunting of noradrenergic response to a standing position, followed by a decrease in peripheral vascular resistance. Nausea is also a frequent symptom which accompanies orthostatic signs and symptoms Label.

Effects on prolactin

At oral doses as low as 0.2 mg, ropinirole suppressed serum prolactin concentrations in healthy male volunteers. Ropinirole had no dose-related effect on ECG wave form and rhythm in young, healthy, male volunteers in the range of 0.01 to 2.5 mg Label.

Effects on QT interval

Ropinirole had no dose- or exposure-related effect on average QT intervals in healthy male and female volunteers at doses up to 4 mg/day. The effect of ropinirole on QTc intervals at higher exposures reached either due to drug interactions, hepatic dysfunction, or at higher doses has not been adequately evaluated Label.

Mechanism of action

Ropinirole is a non-ergoline dopamine agonist. Ropinirole has the highest affinity at the D3 receptors, which are concentrated in the limbic areas of the brain and may be responsible for some of the neuropsychiatric effects 4. The exact mechanism of action of ropinirole as a treatment for Parkinson’s disease is unknown, however, it is believed to be related to its ability to selectively stimulate dopamine D2 receptors within the caudate-putamen system in the brain. This system affects body movement. Negligible affinity is seen for ropinirole at α2 adrenoreceptors in the periphery and 5HT-1 receptor. Ropinirole has no affinity at the D1-like receptors, benzodiazepine or GABA receptors 4.

The precise mechanism of action of ropinirole as a treatment for Restless Legs Syndrome is unknown, however, it is believed to be related to its ability to stimulate dopamine receptors Label.

TargetActionsOrganism
ADopamine D3 receptor
agonist
Humans
UDopamine D4 receptor
agonist
Humans
UAlpha adrenergic receptor
antagonist
Humans
ADopamine D2 receptor
agonist
Humans
Absorption

Ropinirole is rapidly absorbed after oral administration, reaching peak concentration in approximately 1 to 2 hours Label, 5.

Absolute bioavailability was 45% to 55%, suggesting approximately 50% hepatic first-pass effect Label. The bioavailability of ropinirole prolonged release compared to the immediate release tablets is about 100% 2.

Ingestion of food does not affect the absorption of ropinirole, although its Tmax was increased by 2.5 hours and its Cmax was reduced by approximately 25% when the drug is taken with a high-fat meal Label.

Volume of distribution

Ropinirole is found to be widely distributed throughout the body, with an apparent volume of distribution of 7.5 L/kg Label.

Protein binding

40% bound to plasma proteins with a blood-to-plasma ratio of 1:1 Label.

Metabolism

Ropinirole is heavily metabolized by the liver. The most important metabolic pathways are N­ despropylation and hydroxylation to form the N-despropyl metabolite and hydroxy metabolites Label, both of which are inactive 4.

The N-despropyl metabolite is then converted to carbamyl glucuronide, carboxylic acid, and N-despropyl hydroxy metabolites. Following this process, the hydroxy metabolite of ropinirole is glucuronidated at a rapid rate Label.

In vitro studies show that the major cytochrome P450 enzyme involved in the metabolism of ropinirole is CYP1A2 Label, 5.

Hover over products below to view reaction partners

Route of elimination

The majority of the absorbed dose is cleared by the liver 4.

In clinical trials, more than 88% of a radiolabeled dose was recovered in urine Label. Less than 10% of the administered dose is excreted as unchanged drug in urine. N-despropyl ropinirole is the major metabolite found in the urine (40%), followed by the carboxylic acid metabolite (10%), and the glucuronide of the hydroxy metabolite (10%) Label.

Half-life

Approximately 6 hours Label, 5.

Clearance

The clearance of ropinirole after oral administration is 47 L/h Label.

Adverse Effects
Learn about our commercial Adverse Effects data.
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Toxicity

Overdose

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 Label.

Carcinogenicity

Two-year carcinogenicity studies of ropinirole were performed on animal models at oral doses of 5, 15, and 50 mg/kg/day and in rats at oral doses of 1.5, 15, and 50 mg/kg/day. There was an increase in testicular Leydig cell adenomas at all doses tested in rats. The hormonal mechanisms thought to be involved in the development of these tumors in rats are not considered relevant to humans. In mice, there was an increase in benign uterine endometrial polyps at a dose of 50 mg/kg/day. The highest dose not associated with this observation (15 mg/kg/day) is three times the maximum recommended human dose on a mg/m2 basis Label.

Mutagenesis

Ropinirole was not found to be mutagenic or clastogenic during in vitro assays, or in the in vivo mouse micronucleus test Label.

Effects on reproduction

When given to female rats prior to and during mating and throughout pregnancy, ropinirole led to disruption of implantation at oral doses of 20 mg/kg/day (8 times the MRHD on a mg/m2 basis) or higher. This effect in rats is believed to be due to the prolactin-lowering effects of ropinirole.

Use in Pregnancy

Pregnancy Category C. There are no sufficient and well-controlled studies done in pregnant women. In animal reproduction studies, ropinirole has demonstrated adverse effects on embryo-fetal development, including teratogenicity Label.

Affected organisms
  • Humans and other mammals
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
AbametapirThe serum concentration of Ropinirole can be increased when it is combined with Abametapir.
AbataceptThe metabolism of Ropinirole can be increased when combined with Abatacept.
AbirateroneThe risk or severity of adverse effects can be increased when Abiraterone is combined with Ropinirole.
AcebutololThe risk or severity of adverse effects can be increased when Ropinirole is combined with Acebutolol.
AcenocoumarolThe risk or severity of adverse effects can be increased when Ropinirole is combined with Acenocoumarol.
AcetazolamideAcetazolamide may increase the sedative activities of Ropinirole.
AcetophenazineThe therapeutic efficacy of Ropinirole can be decreased when used in combination with Acetophenazine.
AclidiniumRopinirole may increase the central nervous system depressant (CNS depressant) activities of Aclidinium.
AdalimumabThe metabolism of Ropinirole can be increased when combined with Adalimumab.
AgomelatineAgomelatine may increase the sedative activities of Ropinirole.
Additional Data Available
  • Extended Description
    Extended Description

    Extended description of the mechanism of action and particular properties of each drug interaction.

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  • Severity
    Severity

    A severity rating for each drug interaction, from minor to major.

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  • Evidence Level
    Evidence Level

    A rating for the strength of the evidence supporting each drug interaction.

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  • Action
    Action

    An effect category for each drug interaction. Know how this interaction affects the subject drug.

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Food Interactions
  • Take with or without food. May take with food to reduce nausea.

Products

Product Ingredients
IngredientUNIICASInChI Key
Ropinirole HydrochlorideD7ZD41RZI991374-20-8XDXHAEQXIBQUEZ-UHFFFAOYSA-N
Product Images
International/Other Brands
Adartrel / ReQuip CR (GlaxoSmithKline) / Ronirol
Brand Name Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
RequipTablet, film coated2 mg/1OralPhysicians Total Care, Inc.2006-01-302008-12-31US flag
RequipTablet, film coated3 mg/1OralGlaxo Wellcome SA2001-06-192018-10-31US flag
RequipTablet5 mgOralGlaxosmithkline Inc1997-09-252018-03-01Canada flag
RequipTablet, film coated3 mg/1OralGlaxoSmithKline LLC2001-06-192019-10-31US flag00007 4895 20 nlmimage10 d218e947
RequipTablet, film coated3 mg/1OralPhysicians Total Care, Inc.2006-02-202008-12-31US flag
RequipTablet0.25 mgOralGlaxosmithkline Inc1997-09-292017-10-31Canada flag
RequipTablet, film coated0.25 mg/1OralPhysicians Total Care, Inc.2007-10-182008-12-31US flag
RequipTablet, film coated0.5 mg/1OralGlaxoSmithKline LLC1997-10-102019-11-30US flag00007 4891 20 nlmimage10 cd18e6d7
RequipTablet, film coated1 mg/1OralGlaxo Wellcome SA1997-10-012019-07-31US flag
RequipTablet, film coated5 mg/1OralGlaxo Wellcome SA1997-10-102019-03-31US flag
Additional Data Available
  • Application Number
    Application Number

    A unique ID assigned by the FDA when a product is submitted for approval by the labeller.

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  • Product Code
    Product Code

    A governmentally-recognized ID which uniquely identifies the product within its regulatory market.

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Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
Apo-ropiniroleTabletOralApotex CorporationNot applicableNot applicableCanada flag
Apo-ropiniroleTabletOralApotex CorporationNot applicableNot applicableCanada flag
Apo-ropiniroleTabletOralApotex CorporationNot applicableNot applicableCanada flag
Apo-ropiniroleTabletOralApotex CorporationNot applicableNot applicableCanada flag
Apo-ropiniroleTabletOralApotex CorporationNot applicableNot applicableCanada flag
Apo-ropiniroleTabletOralApotex CorporationNot applicableNot applicableCanada flag
Apo-ropiniroleTabletOralApotex CorporationNot applicableNot applicableCanada flag
Dom-ropiniroleTabletOralDominion PharmacalNot applicableNot applicableCanada flag
Dom-ropiniroleTabletOralDominion PharmacalNot applicableNot applicableCanada flag
Dom-ropiniroleTabletOralDominion PharmacalNot applicableNot applicableCanada flag
Additional Data Available
  • Application Number
    Application Number

    A unique ID assigned by the FDA when a product is submitted for approval by the labeller.

    Learn more
  • Product Code
    Product Code

    A governmentally-recognized ID which uniquely identifies the product within its regulatory market.

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Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
RequipRopinirole Hydrochloride + Ropinirole Hydrochloride + Ropinirole HydrochlorideTablet, film coatedOralGlaxoSmithKline2006-10-062006-10-06US flag
RequipRopinirole Hydrochloride + Ropinirole Hydrochloride + Ropinirole HydrochlorideTablet, film coatedOralGlaxoSmithKline2006-10-062006-10-06US flag
RequipRopinirole Hydrochloride + Ropinirole Hydrochloride + Ropinirole HydrochlorideTablet, film coatedOralGlaxoSmithKline2006-10-062006-10-06US flag

Categories

ATC Codes
N04BC04 — Ropinirole
Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as indolines. These 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
Phenethylamines / Aralkylamines / Trialkylamines / Secondary carboxylic acid amides / Lactams / Amino acids and derivatives / Azacyclic compounds / Organopnictogen compounds / Organic oxides / Hydrocarbon derivatives
show 1 more
Substituents
Amine / Amino acid or derivatives / Aralkylamine / Aromatic heteropolycyclic compound / Azacycle / Benzenoid / Carbonyl group / Carboxamide group / Carboxylic acid derivative / Dihydroindole
show 12 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
tertiary amine, indolones (CHEBI:8888)

Chemical Identifiers

UNII
030PYR8953
CAS number
91374-21-9
InChI Key
UHSKFQJFRQCDBE-UHFFFAOYSA-N
InChI
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)
IUPAC Name
4-[2-(dipropylamino)ethyl]-2,3-dihydro-1H-indol-2-one
SMILES
CCCN(CCC)CCC1=C2CC(=O)NC2=CC=C1

References

Synthesis Reference
US4452808
General References
  1. Matheson AJ, Spencer CM: Ropinirole: a review of its use in the management of Parkinson's disease. Drugs. 2000 Jul;60(1):115-37. doi: 10.2165/00003495-200060010-00007. [PubMed:10929932]
  2. Nashatizadeh MM, Lyons KE, Pahwa R: A review of ropinirole prolonged release in Parkinson's disease. Clin Interv Aging. 2009;4:179-86. Epub 2009 May 14. [PubMed:19503779]
  3. Kushida CA: Ropinirole for the treatment of restless legs syndrome. Neuropsychiatr Dis Treat. 2006 Dec;2(4):407-19. [PubMed:19412490]
  4. Shill HA, Stacy M: Update on ropinirole in the treatment of Parkinson's disease. Neuropsychiatr Dis Treat. 2009;5:33-6. Epub 2009 Apr 8. [PubMed:19557097]
  5. Kaye CM, Nicholls B: Clinical pharmacokinetics of ropinirole. Clin Pharmacokinet. 2000 Oct;39(4):243-54. doi: 10.2165/00003088-200039040-00001. [PubMed:11069211]
  6. Drug Approval Package, FDA [Link]
  7. Ropinirole extended release FDA label [File]
  8. UK labeling, Ropinirole [File]
Human Metabolome Database
HMDB0014413
KEGG Drug
D08489
KEGG Compound
C07564
PubChem Compound
5095
PubChem Substance
46507918
ChemSpider
4916
BindingDB
50020680
RxNav
72302
ChEBI
8888
ChEMBL
CHEMBL589
ZINC
ZINC000000002041
Therapeutic Targets Database
DAP001515
PharmGKB
PA164749035
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
PDRhealth
PDRhealth Drug Page
Wikipedia
Ropinirole
AHFS Codes
  • 28:36.20.08 — Nonergot-derivative Dopamine Receptor Agonists
FDA label
Download (796 KB)
MSDS
Download (29.6 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
4CompletedDiagnosticParkinson's Disease (PD)1
4CompletedTreatmentBipolar Disorder (BD)1
4CompletedTreatmentParkinson's Disease (PD)4
4CompletedTreatmentRestless Legs Syndrome (RLS)2
4CompletedTreatmentSexual Dysfunctions1
4Enrolling by InvitationSupportive CareLiver Cirrhosis / Muscle Cramps1
4Unknown StatusTreatmentBipolar Disorder (BD) / Major Depressive Disorder (MDD)1
3CompletedTreatmentDyskinesia / Parkinson's Disease (PD)1
3CompletedTreatmentIdiopathic Parkinson's Disease2
3CompletedTreatmentModerate to Severe Idiopathic Restless Legs Syndrome (RLS) / Restless Legs Syndrome (RLS)1

Pharmacoeconomics

Manufacturers
  • Smithkline beecham corp dba glaxosmithkline
  • Glaxosmithkline
  • Alembic ltd
  • Corepharma llc
  • Glenmark generics ltd
  • Huahai us inc
  • Mylan pharmaceuticals inc
  • Roxane laboratories inc
  • Teva pharmaceuticals usa inc
  • Wockhardt ltd
  • Zydus pharmaceuticals usa inc
Packagers
  • Amerisource Health Services Corp.
  • A-S Medication Solutions LLC
  • Atlantic Biologicals Corporation
  • Bryant Ranch Prepack
  • Cadila Healthcare Ltd.
  • Cardinal Health
  • Corepharma LLC
  • GlaxoSmithKline Inc.
  • Glenmark Generics Ltd.
  • Heartland Repack Services LLC
  • Heritage Pharmaceuticals
  • Innoviant Pharmacy Inc.
  • Kaiser Foundation Hospital
  • Lake Erie Medical and Surgical Supply
  • Major Pharmaceuticals
  • Mckesson Corp.
  • Murfreesboro Pharmaceutical Nursing Supply
  • Mylan
  • Nucare Pharmaceuticals Inc.
  • PD-Rx Pharmaceuticals Inc.
  • Physicians Total Care Inc.
  • Rebel Distributors Corp.
  • Resource Optimization and Innovation LLC
  • Roxane Labs
  • Stat Rx Usa
  • Teva Pharmaceutical Industries Ltd.
  • Vangard Labs Inc.
  • Wockhardt Ltd.
  • Zydus Pharmaceuticals
Dosage Forms
FormRouteStrength
Tablet, film coatedOral0.25 MG
Tablet, film coatedOral0.5 MG
Tablet, film coatedOral2 MG
Tablet, extended releaseOral2 MG
Tablet, extended releaseOral4 MG
Tablet, extended releaseOral8 MG
TabletOral
TabletOral0.25 MG
TabletOral0.5 MG
TabletOral1 MG
TabletOral2 MG
TabletOral5 MG
Tablet, extended release2 MG
Tablet, extended release3 MG
Tablet, extended release4 MG
Tablet, extended release8 MG
Tablet, film coatedOral
Tablet, film coatedOral0.25 mg/1
Tablet, film coatedOral0.5 mg/1
Tablet, film coatedOral1 mg/1
Tablet, film coatedOral2 mg/1
Tablet, film coatedOral3 mg/1
Tablet, film coatedOral4 mg/1
Tablet, film coatedOral1.0 MG
Tablet, film coatedOral2.0 MG
Tablet, film coatedOral5.0 MG
Tablet
Tablet, film coated, extended releaseOral2 mg/1
Tablet, film coatedOral5 MG
Tablet, film coatedOral1 MG
Tablet, film coatedOral3 MG
Tablet, film coatedOral4 MG
Tablet, extended releaseOral3 MG
TabletOral4 mg/1
TabletOral0.25 mg/1
TabletOral0.5 mg/1
TabletOral1 mg/1
TabletOral2 mg/1
TabletOral3 mg/1
TabletOral5 mg/1
Tablet, coatedOral0.25 mg/1
Tablet, coatedOral0.5 mg/1
Tablet, coatedOral1 mg/1
Tablet, coatedOral2 mg/1
Tablet, coatedOral3 mg/1
Tablet, coatedOral4 mg/1
Tablet, coatedOral5 mg/1
Tablet, film coatedOral5 mg/1
Tablet, film coated, extended releaseOral12 mg/1
Tablet, film coated, extended releaseOral3 mg/1
Tablet, film coated, extended releaseOral4 mg/1
Tablet, film coated, extended releaseOral6 mg/1
Tablet, film coated, extended releaseOral8 mg/1
Tablet, coatedOral0.25 MG
Tablet, coatedOral0.5 MG
Tablet, coatedOral1 MG
Tablet, coatedOral2 MG
Tablet, coatedOral5 MG
Prices
Unit descriptionCostUnit
Requip XL 12 mg 24 Hour tablet14.92USD tablet
Requip xl 12 mg tablet14.35USD tablet
Requip XL 8 mg 24 Hour tablet8.96USD tablet
Requip xl 6 mg tablet8.61USD tablet
Requip xl 8 mg tablet8.61USD tablet
Requip XL 4 mg 24 Hour tablet5.97USD tablet
Requip xl 4 mg tablet5.74USD tablet
Requip 5 mg Tablet3.87USD tablet
Requip 3 mg tablet3.41USD tablet
Requip 4 mg tablet3.41USD tablet
Requip 5 mg tablet3.41USD tablet
Requip 0.25 mg tablet3.29USD tablet
Requip 0.5 mg tablet3.29USD tablet
Requip 1 mg tablet3.29USD tablet
Requip 2 mg tablet3.29USD tablet
Requip xl 2 mg tablet2.87USD tablet
Ropinirole hcl 3 mg tablet2.65USD tablet
Ropinirole hcl 4 mg tablet2.65USD tablet
Ropinirole hcl 5 mg tablet2.65USD tablet
Ropinirole hcl 0.25 mg tablet2.55USD tablet
Ropinirole hcl 0.5 mg tablet2.55USD tablet
Ropinirole hcl 1 mg tablet2.55USD tablet
Ropinirole hcl 2 mg tablet2.55USD tablet
Co Ropinirole 5 mg Tablet1.8USD tablet
Pms-Ropinirole 5 mg Tablet1.8USD tablet
Ran-Ropinirole 5 mg Tablet1.8USD tablet
Ropinirole 5 mg Tablet1.8USD tablet
Requip 2 mg Tablet1.41USD tablet
Requip 1 mg Tablet1.28USD tablet
Co Ropinirole 2 mg Tablet0.65USD tablet
Pms-Ropinirole 2 mg Tablet0.65USD tablet
Ran-Ropinirole 2 mg Tablet0.65USD tablet
Ropinirole 2 mg Tablet0.65USD tablet
Co Ropinirole 1 mg Tablet0.59USD tablet
Pms-Ropinirole 1 mg Tablet0.59USD tablet
Ran-Ropinirole 1 mg Tablet0.59USD tablet
Ropinirole 1 mg Tablet0.59USD tablet
Requip 0.25 mg Tablet0.32USD tablet
Co Ropinirole 0.25 mg Tablet0.15USD tablet
Pms-Ropinirole 0.25 mg Tablet0.15USD tablet
Ran-Ropinirole 0.25 mg Tablet0.15USD tablet
Ropinirole 0.25 mg Tablet0.15USD tablet
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)Region
US5422123No1995-06-062012-06-06US flag
US7927624No2011-04-192021-12-02US flag
US8303986No2012-11-062021-04-12US flag
Additional Data Available
  • Filed On
    Filed On

    The date on which a patent was filed with the relevant government.

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Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)243-250 °CFDA label
boiling point (°C)410.5±45.0 °C at 760 mmHghttp://www.chemspider.com/Chemical-Structure.4916.html
water solubility133 mg/mLFDA label
logP3.06http://www.t3db.ca/toxins/T3D2731
logS-2.9http://www.t3db.ca/toxins/T3D2731
pKa10.17http://www.t3db.ca/toxins/T3D2731
Predicted Properties
PropertyValueSource
Water Solubility0.353 mg/mLALOGPS
logP3.16ALOGPS
logP3.06ChemAxon
logS-2.9ALOGPS
pKa (Strongest Acidic)13.24ChemAxon
pKa (Strongest Basic)10.17ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area32.34 Å2ChemAxon
Rotatable Bond Count7ChemAxon
Refractivity81.43 m3·mol-1ChemAxon
Polarizability31.19 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+1.0
Blood Brain Barrier+0.9971
Caco-2 permeable+0.6087
P-glycoprotein substrateSubstrate0.7604
P-glycoprotein inhibitor IInhibitor0.5458
P-glycoprotein inhibitor IINon-inhibitor0.8641
Renal organic cation transporterNon-inhibitor0.602
CYP450 2C9 substrateNon-substrate0.8593
CYP450 2D6 substrateNon-substrate0.9116
CYP450 3A4 substrateSubstrate0.6903
CYP450 1A2 substrateNon-inhibitor0.9045
CYP450 2C9 inhibitorNon-inhibitor0.9071
CYP450 2D6 inhibitorInhibitor0.8932
CYP450 2C19 inhibitorNon-inhibitor0.9025
CYP450 3A4 inhibitorNon-inhibitor0.8309
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.6959
Ames testNon AMES toxic0.7302
CarcinogenicityNon-carcinogens0.905
BiodegradationNot ready biodegradable0.9966
Rat acute toxicity2.6400 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.8959
hERG inhibition (predictor II)Non-inhibitor0.7066
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-03di-0190000000-7e072cf65f341641938c
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-03di-3960000000-47d2311adfeeacf4062d
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0006-7900000000-0891c66db163729a5360
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0a4i-0090000000-88c0fa3d93090a0d06c6
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0pb9-3590000000-8fb5fc766313ee6bbd9e
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0k96-9400000000-f1b50dacd59a9bfe90b7

Targets

Details
1. Dopamine D3 receptor
Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Agonist
General Function
G-protein coupled amine receptor activity
Specific Function
Dopamine receptor whose activity is mediated by G proteins which inhibit adenylyl cyclase. Promotes cell proliferation.
Gene Name
DRD3
Uniprot ID
P35462
Uniprot Name
D(3) dopamine receptor
Molecular Weight
44224.335 Da
References
  1. Kvernmo T, Houben J, Sylte I: Receptor-binding and pharmacokinetic properties of dopaminergic agonists. Curr Top Med Chem. 2008;8(12):1049-67. [PubMed:18691132]
  2. Lam YW: Clinical pharmacology of dopamine agonists. Pharmacotherapy. 2000 Jan;20(1 Pt 2):17S-25S. [PubMed:10641988]
  3. Nashatizadeh MM, Lyons KE, Pahwa R: A review of ropinirole prolonged release in Parkinson's disease. Clin Interv Aging. 2009;4:179-86. Epub 2009 May 14. [PubMed:19503779]
  4. Shill HA, Stacy M: Update on ropinirole in the treatment of Parkinson's disease. Neuropsychiatr Dis Treat. 2009;5:33-6. Epub 2009 Apr 8. [PubMed:19557097]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Agonist
General Function
Sh3 domain binding
Specific Function
Dopamine receptor responsible for neuronal signaling in the mesolimbic system of the brain, an area of the brain that regulates emotion and complex behavior. Its activity is mediated by G proteins ...
Gene Name
DRD4
Uniprot ID
P21917
Uniprot Name
D(4) dopamine receptor
Molecular Weight
48359.86 Da
References
  1. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352]
  2. Kvernmo T, Houben J, Sylte I: Receptor-binding and pharmacokinetic properties of dopaminergic agonists. Curr Top Med Chem. 2008;8(12):1049-67. [PubMed:18691132]
  3. Shill HA, Stacy M: Update on ropinirole in the treatment of Parkinson's disease. Neuropsychiatr Dis Treat. 2009;5:33-6. Epub 2009 Apr 8. [PubMed:19557097]
Kind
Protein group
Organism
Humans
Pharmacological action
Unknown
Actions
Antagonist
General Function
Protein heterodimerization activity
Specific Function
This alpha-adrenergic receptor mediates its action by association with G proteins that activate a phosphatidylinositol-calcium second messenger system. Its effect is mediated by G(q) and G(11) prot...

Components:
References
  1. Shill HA, Stacy M: Update on ropinirole in the treatment of Parkinson's disease. Neuropsychiatr Dis Treat. 2009;5:33-6. Epub 2009 Apr 8. [PubMed:19557097]
  2. Kvernmo T, Houben J, Sylte I: Receptor-binding and pharmacokinetic properties of dopaminergic agonists. Curr Top Med Chem. 2008;8(12):1049-67. [PubMed:18691132]
Details
4. Dopamine D2 receptor
Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Agonist
General Function
Potassium channel regulator activity
Specific Function
Dopamine receptor whose activity is mediated by G proteins which inhibit adenylyl cyclase.
Gene Name
DRD2
Uniprot ID
P14416
Uniprot Name
D(2) dopamine receptor
Molecular Weight
50618.91 Da
References
  1. de Mey C, Enterling D, Meineke I, Yeulet S: Interactions between domperidone and ropinirole, a novel dopamine D2-receptor agonist. Br J Clin Pharmacol. 1991 Oct;32(4):483-8. [PubMed:1683559]
  2. Iida M, Miyazaki I, Tanaka K, Kabuto H, Iwata-Ichikawa E, Ogawa N: Dopamine D2 receptor-mediated antioxidant and neuroprotective effects of ropinirole, a dopamine agonist. Brain Res. 1999 Aug 14;838(1-2):51-9. [PubMed:10446316]
  3. Kvernmo T, Houben J, Sylte I: Receptor-binding and pharmacokinetic properties of dopaminergic agonists. Curr Top Med Chem. 2008;8(12):1049-67. [PubMed:18691132]
  4. Lam YW: Clinical pharmacology of dopamine agonists. Pharmacotherapy. 2000 Jan;20(1 Pt 2):17S-25S. [PubMed:10641988]
  5. Matsukawa N, Maki M, Yasuhara T, Hara K, Yu G, Xu L, Kim KM, Morgan JC, Sethi KD, Borlongan CV: Overexpression of D2/D3 receptors increases efficacy of ropinirole in chronically 6-OHDA-lesioned Parkinsonian rats. Brain Res. 2007 Jul 30;1160:113-23. Epub 2007 May 26. [PubMed:17573046]
  6. Shill HA, Stacy M: Update on ropinirole in the treatment of Parkinson's disease. Neuropsychiatr Dis Treat. 2009;5:33-6. Epub 2009 Apr 8. [PubMed:19557097]
  7. Requip FDA label [File]

Enzymes

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Oxidoreductase activity, acting on paired donors, with incorporation or reduction of molecular oxygen, reduced flavin or flavoprotein as one donor, and incorporation of one atom of oxygen
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name
CYP1A2
Uniprot ID
P05177
Uniprot Name
Cytochrome P450 1A2
Molecular Weight
58293.76 Da
References
  1. Kvernmo T, Houben J, Sylte I: Receptor-binding and pharmacokinetic properties of dopaminergic agonists. Curr Top Med Chem. 2008;8(12):1049-67. [PubMed:18691132]
  2. Wynalda MA, Wienkers LC: Assessment of potential interactions between dopamine receptor agonists and various human cytochrome P450 enzymes using a simple in vitro inhibition screen. Drug Metab Dispos. 1997 Oct;25(10):1211-4. [PubMed:9321526]
  3. Kaye CM, Nicholls B: Clinical pharmacokinetics of ropinirole. Clin Pharmacokinet. 2000 Oct;39(4):243-54. doi: 10.2165/00003088-200039040-00001. [PubMed:11069211]
  4. Kushida CA: Ropinirole for the treatment of restless legs syndrome. Neuropsychiatr Dis Treat. 2006 Dec;2(4):407-19. [PubMed:19412490]
  5. Ropinrole FDA label [File]

Drug created on June 13, 2005 07:24 / Updated on September 27, 2020 08:17

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