Details
Stereochemistry | ACHIRAL |
Molecular Formula | C16H24N2O.ClH |
Molecular Weight | 296.836 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
Cl.CCCN(CCC)CCC1=CC=CC2=C1CC(=O)N2
InChI
InChIKey=XDXHAEQXIBQUEZ-UHFFFAOYSA-N
InChI=1S/C16H24N2O.ClH/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);1H
Molecular Formula | ClH |
Molecular Weight | 36.461 |
Charge | 0 |
Count |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Optical Activity | NONE |
Molecular Formula | C16H24N2O |
Molecular Weight | 260.3746 |
Charge | 0 |
Count |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Optical Activity | NONE |
DescriptionCurator's Comment: description was created based on several sources, including
http://reference.medscape.com/drug/requip-xl-ropinirole-343051 | https://www.drugs.com/cdi/ropinirole.html | https://www.drugbank.ca/drugs/DB00268
Curator's Comment: description was created based on several sources, including
http://reference.medscape.com/drug/requip-xl-ropinirole-343051 | https://www.drugs.com/cdi/ropinirole.html | https://www.drugbank.ca/drugs/DB00268
Ropinirole (INN; trade names Requip, Repreve, Ronirol, Adartrel) is a dopamine agonist of the non-ergoline class of medications, used in the treatment of Parkinson's disease and restless legs syndrome. 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 dopamine 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. Ropinirole is a nonergot dopamine agonist with high relative in vitro specificity and full intrinsic activity at the D2 subfamily of dopamine receptors, binding with higher affinity to D3 than to D2 or D4 receptor subtypes. The relevance of D3 receptor binding in Parkinson's disease is unknown. The mechanism of ropinirole-induced postural hypotension is presumed to be due to a D2 -mediated blunting of the noradrenergic response to standing and subsequent decrease in peripheral vascular resistance. Ropinirole can cause nausea, dizziness, hallucinations, orthostatic hypotension, and sudden sleep attacks during the daytime. Unusual side effects specific to D3 agonists such as ropinirole and pramipexole can include hypersexuality, punding, and compulsive gambling, even in patients without a history of these behaviors.
CNS Activity
Originator
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL217 Sources: https://www.ncbi.nlm.nih.gov/pubmed/17976986 |
83.0 nM [EC50] | ||
Target ID: CHEMBL234 Sources: https://www.ncbi.nlm.nih.gov/pubmed/20038106 |
19.2 nM [EC50] | ||
Target ID: CHEMBL2096905 Sources: https://www.ncbi.nlm.nih.gov/pubmed/4045928 |
100.0 nM [EC50] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | REQUIP Approved UseParkinson's Disease Ropinirole tablets are indicated for the treatment of the signs and symptoms of idiopathic Parkinson's disease. The effectiveness of ropinirole tablet was demonstrated in randomized, controlled trials in patients with early Parkinson's disease who were not receiving concomitant L-dopa therapy as well as in patients with advanced disease on concomitant L-dopa (see CLINICAL PHARMACOLOGY: Clinical Trials). Restless Legs Syndrome Ropinirole tablets are indicated for the treatment of moderate-to-severe primary Restless Legs Syndrome (RLS). Key diagnostic criteria for RLS are: an urge to move the legs usually accompanied or caused by uncomfortable and unpleasant leg sensations; symptoms begin or worsen during periods of rest or inactivity such as lying or sitting; symptoms are partially or totally relieved by movement such as walking or stretching at least as long as the activity continues; and symptoms are worse or occur only in the evening or night. Difficulty falling asleep may frequently be associated with moderate-to-severe RLS. Launch Date8.746272E11 |
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Primary | REQUIP Approved UseParkinson's Disease Ropinirole tablets are indicated for the treatment of the signs and symptoms of idiopathic Parkinson's disease. The effectiveness of ropinirole tablet was demonstrated in randomized, controlled trials in patients with early Parkinson's disease who were not receiving concomitant L-dopa therapy as well as in patients with advanced disease on concomitant L-dopa (see CLINICAL PHARMACOLOGY: Clinical Trials). Restless Legs Syndrome Ropinirole tablets are indicated for the treatment of moderate-to-severe primary Restless Legs Syndrome (RLS). Key diagnostic criteria for RLS are: an urge to move the legs usually accompanied or caused by uncomfortable and unpleasant leg sensations; symptoms begin or worsen during periods of rest or inactivity such as lying or sitting; symptoms are partially or totally relieved by movement such as walking or stretching at least as long as the activity continues; and symptoms are worse or occur only in the evening or night. Difficulty falling asleep may frequently be associated with moderate-to-severe RLS. Launch Date8.746272E11 |
|||
Primary | REQUIP Approved UseParkinson's Disease Ropinirole tablets are indicated for the treatment of the signs and symptoms of idiopathic Parkinson's disease. The effectiveness of ropinirole tablet was demonstrated in randomized, controlled trials in patients with early Parkinson's disease who were not receiving concomitant L-dopa therapy as well as in patients with advanced disease on concomitant L-dopa (see CLINICAL PHARMACOLOGY: Clinical Trials). Restless Legs Syndrome Ropinirole tablets are indicated for the treatment of moderate-to-severe primary Restless Legs Syndrome (RLS). Key diagnostic criteria for RLS are: an urge to move the legs usually accompanied or caused by uncomfortable and unpleasant leg sensations; symptoms begin or worsen during periods of rest or inactivity such as lying or sitting; symptoms are partially or totally relieved by movement such as walking or stretching at least as long as the activity continues; and symptoms are worse or occur only in the evening or night. Difficulty falling asleep may frequently be associated with moderate-to-severe RLS. Launch Date8.746272E11 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
5.01 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/9578193 |
2 mg 3 times / day steady-state, oral dose: 2 mg route of administration: Oral experiment type: STEADY-STATE co-administered: |
ROPINIROLE HYDROCHLORIDE plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FED |
|
6.53 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/9578193 |
2 mg 3 times / day steady-state, oral dose: 2 mg route of administration: Oral experiment type: STEADY-STATE co-administered: |
ROPINIROLE HYDROCHLORIDE plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
AUC
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
25.9 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/9578193 |
2 mg 3 times / day steady-state, oral dose: 2 mg route of administration: Oral experiment type: STEADY-STATE co-administered: |
ROPINIROLE HYDROCHLORIDE plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FED |
|
29.1 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/9578193 |
2 mg 3 times / day steady-state, oral dose: 2 mg route of administration: Oral experiment type: STEADY-STATE co-administered: |
ROPINIROLE HYDROCHLORIDE plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
6 h |
unknown, oral |
ROPINIROLE HYDROCHLORIDE plasma | Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN |
Funbound
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
60% |
unknown, oral |
ROPINIROLE HYDROCHLORIDE plasma | Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN |
Doses
Dose | Population | Adverse events |
---|---|---|
50 mg 1 times / day steady, oral Highest studied dose Dose: 50 mg, 1 times / day Route: oral Route: steady Dose: 50 mg, 1 times / day Sources: |
unhealthy n = 1 Health Status: unhealthy Condition: Parkinson's disease with severe dyskinesias Population Size: 1 Sources: |
|
435 mg 1 times / day multiple, oral Overdose Dose: 435 mg, 1 times / day Route: oral Route: multiple Dose: 435 mg, 1 times / day Sources: Page: p. 18 |
unhealthy Health Status: unhealthy Sources: Page: p. 18 |
Other AEs: Nausea, Dizziness... Other AEs: Nausea Sources: Page: p. 18Dizziness Claustrophobia Chorea Palpitations Asthenia Nightmares Hyperhidrosis Visual hallucinations |
0.5 mg 2 times / day steady, oral Recommended Dose: 0.5 mg, 2 times / day Route: oral Route: steady Dose: 0.5 mg, 2 times / day Sources: |
unhealthy n = 157 Health Status: unhealthy Condition: Parkinson’s disease Population Size: 157 Sources: |
Disc. AE: Nausea, Dizziness... AEs leading to discontinuation/dose reduction: Nausea (2%) Sources: Dizziness (2%) |
24 mg 1 times / day steady, oral Recommended Dose: 24 mg, 1 times / day Route: oral Route: steady Dose: 24 mg, 1 times / day Sources: |
unhealthy n = 61 Health Status: unhealthy Condition: Parkinson's disease Population Size: 61 Sources: |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
Asthenia | 435 mg 1 times / day multiple, oral Overdose Dose: 435 mg, 1 times / day Route: oral Route: multiple Dose: 435 mg, 1 times / day Sources: Page: p. 18 |
unhealthy Health Status: unhealthy Sources: Page: p. 18 |
|
Chorea | 435 mg 1 times / day multiple, oral Overdose Dose: 435 mg, 1 times / day Route: oral Route: multiple Dose: 435 mg, 1 times / day Sources: Page: p. 18 |
unhealthy Health Status: unhealthy Sources: Page: p. 18 |
|
Claustrophobia | 435 mg 1 times / day multiple, oral Overdose Dose: 435 mg, 1 times / day Route: oral Route: multiple Dose: 435 mg, 1 times / day Sources: Page: p. 18 |
unhealthy Health Status: unhealthy Sources: Page: p. 18 |
|
Dizziness | 435 mg 1 times / day multiple, oral Overdose Dose: 435 mg, 1 times / day Route: oral Route: multiple Dose: 435 mg, 1 times / day Sources: Page: p. 18 |
unhealthy Health Status: unhealthy Sources: Page: p. 18 |
|
Hyperhidrosis | 435 mg 1 times / day multiple, oral Overdose Dose: 435 mg, 1 times / day Route: oral Route: multiple Dose: 435 mg, 1 times / day Sources: Page: p. 18 |
unhealthy Health Status: unhealthy Sources: Page: p. 18 |
|
Nausea | 435 mg 1 times / day multiple, oral Overdose Dose: 435 mg, 1 times / day Route: oral Route: multiple Dose: 435 mg, 1 times / day Sources: Page: p. 18 |
unhealthy Health Status: unhealthy Sources: Page: p. 18 |
|
Nightmares | 435 mg 1 times / day multiple, oral Overdose Dose: 435 mg, 1 times / day Route: oral Route: multiple Dose: 435 mg, 1 times / day Sources: Page: p. 18 |
unhealthy Health Status: unhealthy Sources: Page: p. 18 |
|
Palpitations | 435 mg 1 times / day multiple, oral Overdose Dose: 435 mg, 1 times / day Route: oral Route: multiple Dose: 435 mg, 1 times / day Sources: Page: p. 18 |
unhealthy Health Status: unhealthy Sources: Page: p. 18 |
|
Visual hallucinations | 435 mg 1 times / day multiple, oral Overdose Dose: 435 mg, 1 times / day Route: oral Route: multiple Dose: 435 mg, 1 times / day Sources: Page: p. 18 |
unhealthy Health Status: unhealthy Sources: Page: p. 18 |
|
Dizziness | 2% Disc. AE |
0.5 mg 2 times / day steady, oral Recommended Dose: 0.5 mg, 2 times / day Route: oral Route: steady Dose: 0.5 mg, 2 times / day Sources: |
unhealthy n = 157 Health Status: unhealthy Condition: Parkinson’s disease Population Size: 157 Sources: |
Nausea | 2% Disc. AE |
0.5 mg 2 times / day steady, oral Recommended Dose: 0.5 mg, 2 times / day Route: oral Route: steady Dose: 0.5 mg, 2 times / day Sources: |
unhealthy n = 157 Health Status: unhealthy Condition: Parkinson’s disease Population Size: 157 Sources: |
PubMed
Title | Date | PubMed |
---|---|---|
Sleep disorders in patients with Parkinson's disease: epidemiology and management. | 2001 |
|
Ropinirole for levodopa-induced complications in Parkinson's disease. | 2001 |
|
Neostriatal muscarinic receptor subtypes involved in the generation of tremulous jaw movements in rodents implications for cholinergic involvement in parkinsonism. | 2001 Apr 27 |
|
Antiparkinsonian drugs and "sleep attacks". | 2001 Apr 3 |
|
Iontophoretic delivery of ropinirole hydrochloride: effect of current density and vehicle formulation. | 2001 Dec |
|
[Dopamine agonists situation in Parkinson disease]. | 2001 Dec 1-15 |
|
Efficacy and tolerability of dopamine agonists in a parkinsonian population. | 2001 Feb |
|
Antiparkinsonian activity and dyskinesia risk of ropinirole and L-DOPA combination therapy in drug naïve MPTP-lesioned common marmosets (Callithrix jacchus). | 2001 Jul |
|
Treatment of early onset Parkinson's disease with ropinirole. | 2001 Mar |
|
[Parkinson disease: diagnostic and therapeutic criteria]. | 2001 Mar 3 |
|
Sleep attacks and antiparkinsonian drugs: a pilot prospective pharmacoepidemiologic study. | 2001 May-Jun |
|
Randomized clinical trials with added rescue medication: some approaches to their analysis and interpretation. | 2001 Oct 30 |
|
Sleep disorders in Parkinson's disease: epidemiology and management. | 2002 |
|
DA agonists -- non-ergot derivatives: ropinirole: management of Parkinson's disease. | 2002 |
|
Clinical pharmacokinetic and pharmacodynamic properties of drugs used in the treatment of Parkinson's disease. | 2002 |
|
A six-month multicentre, double-blind, bromocriptine-controlled study of the safety and efficacy of ropinirole in the treatment of patients with Parkinson's disease not optimally controlled by L-dopa. | 2002 Apr |
|
Two advances in the management of Parkinson disease. | 2002 Aug |
|
[The usefulness of dopaminergic drugs in traumatic brain injury]. | 2002 Aug 16-31 |
|
Behavioral and neurochemical effects of dopaminergic drugs in models of brain injury. | 2002 Jun |
|
Alopecia induced by dopamine agonists. | 2002 Mar 12 |
|
Ropinirole for the treatment of tremor in early Parkinson's disease. | 2002 May |
|
Do dopamine agonists or levodopa modify Parkinson's disease progression? | 2002 Nov |
|
Dopamine agonist monotherapy in Parkinson's disease. | 2002 Nov 30 |
|
An evidence-based review of dopamine receptor agonists in the treatment of Parkinson's disease. | 2002 Oct |
|
Do dopaminergic agents increase the daytime sleep propensity? Article reviewed: Effect of ropinirole on sleep onset. A randomized, placebo-controlled study in healthy volunteers. | 2002 Sep |
|
Cabergoline, pramipexole and ropinirole used as monotherapy in early Parkinson's disease: an evidence-based comparison. | 2003 |
|
Comparison of the risk of adverse events with pramipexole and ropinirole in patients with Parkinson's disease: a meta-analysis. | 2003 |
|
[Sexual delinquency and Parkinson's disease]. | 2003 Apr |
|
Ropinirole as an adjunct to levodopa in the treatment of Parkinson's disease: a 16-week bromocriptine controlled study. | 2003 Jan |
|
Slower progression of Parkinson's disease with ropinirole versus levodopa: The REAL-PET study. | 2003 Jul |
|
The initial drug treatment of older patients with Parkinson's disease - consider an agonist, but don't demonise dopa. | 2003 May |
|
High-dose ropinirole in advanced Parkinson's disease with severe dyskinesias. | 2003 May-Jun |
|
Current treatment options for restless legs syndrome. | 2003 Oct |
Patents
Sample Use Guides
Parkinson Disease: 0.25 mg PO q8hr for 1 week initially, then increased weekly by 0.25 mg q8hr; if necessary, after week 4, may be increased weekly by 1.5 mg/day up to 9 mg/day, then increased weekly by 3 mg/day up to 24 mg/day
Restless Leg Syndrome: 0.25 mg/day PO 1-3 hr before bedtime; after day 2, may be increased to 0.5 mg/day PO; at end of week 1, increased to 1 mg/day, then increased weekly by 0.5 mg/day up to 4 mg/day
Route of Administration:
Oral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/14637109
Human SH-SY5Y neuroblastoma cells were grown to confluence in Dulbecco’s Modified Eagle’s media (DMEM) supplemented with 10% fetal calf serum, 100 mkg/mL penicillin, 100 mkg/mL streptomycin, 0.25 mkg/mL amphotericin B, and 0.01 mkM non-essential amino acids (Gibco Grand Island, NY, USA) and then sub-cultured for differentiation in 48 well Costar culture plates. For differentiation, the cells were grown in same media containing 10 mkM retinoic acid for 3 days; then the media was removed and replaced with media containing 160 nM of the phorbol ester 12-O-tetradecanoyl-phorbol-13-acetate (TPA) for 3 days of differentiation. The cells were then administered a range doses of pramipexole, ropinirole and S32504 (10 nM to 1 mM) in DMEM for three days prior to addition of 1 mM MPP+. Following transfer of MPP+ to the media cells were tested every 24 h for 72 h for the cytotoxicity of MPP+ as measured by the MTT and LDH assays which accurately measure different aspects of apoptosis. In addition, we tested for the neuroprotective effects of a fixed dose of each drug (50 mkM) and a range of doses of S32504 on MPP+ induced apoptosis, and the effects of ropinirole alone (1 mM) as measured by DNA laddering.
Substance Class |
Chemical
Created
by
admin
on
Edited
Fri Dec 16 18:24:54 UTC 2022
by
admin
on
Fri Dec 16 18:24:54 UTC 2022
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Record UNII |
D7ZD41RZI9
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Record Status |
Validated (UNII)
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Record Version |
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C38149
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68727
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EE-30
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SUB15144MIG
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1605205
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CHEMBL589
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M9658
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C47710
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DTXSID50238533
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236553
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BASIS OF STRENGTH->SUBSTANCE |
ASSAY (HPLC)
USP
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PARENT -> SALT/SOLVATE |
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
Ph.Eur.; USP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
Ph.Eur.; USP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
Ph.Eur.; USP
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ACTIVE MOIETY |