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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:49 UTC
Update Date2022-03-07 02:51:36 UTC
HMDB IDHMDB0014413
Secondary Accession Numbers
  • HMDB14413
Metabolite Identification
Common NameRopinirole
DescriptionRopinirole, also known as ropitor or requip, 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. This usually leads to constant dosage increases in an attempt to offset the symptom progression. A 52-week open label study had a mean dosage of 1.90 mg, once daily 1 to 3 hours before bedtime. Ropinirole is a drug which is used for the treatment of the signs and symptoms of parkinson's disease and for the treatment of primary moderate-severe restless legs syndrome [fda label]. Ropinirole is a very strong basic compound (based on its pKa). Ropinirole is a potentially toxic compound. In 2016 it was the 111th most prescribed medication in the United States with more than 6 million prescriptions. For Parkinson's disease, the maximum recommended dose is 24 mg per day, taken in three separate doses spread throughout the day.
Structure
Data?1582753176
Synonyms
ValueSource
RopinirolChEBI
RopinirolumChEBI
RopitorKegg
4-(2-(Di-N-propylamino)ethyl)-2(3H)-indoloneHMDB
GlaxoSmithKline brand OF ropinirole hydrochlorideHMDB
RequipHMDB
SK And F-101,468HMDB
SmithKline beecham brand OF ropinirole hydrochlorideHMDB
Ropinirole hydrochlorideHMDB
SK And F 101468HMDB
Chemical FormulaC16H24N2O
Average Molecular Weight260.3746
Monoisotopic Molecular Weight260.1888634
IUPAC Name4-[2-(dipropylamino)ethyl]-2,3-dihydro-1H-indol-2-one
Traditional Nameropinirole
CAS Registry Number91374-21-9
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 KeyUHSKFQJFRQCDBE-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.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassIndoles and derivatives
Sub ClassIndolines
Direct ParentIndolines
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 FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Disposition

Biological location

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point243 - 250 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.35 g/LNot Available
LogP2.3Not Available
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M+H]+CBM163.830932474
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.35 g/LALOGPS
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 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity81.43 m³·mol⁻¹ChemAxon
Polarizability31.19 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+161.10331661259
DarkChem[M-H]-159.06631661259
DeepCCS[M+H]+163.87630932474
DeepCCS[M-H]-161.51830932474
DeepCCS[M-2H]-194.40430932474
DeepCCS[M+Na]+169.96930932474
AllCCS[M+H]+163.532859911
AllCCS[M+H-H2O]+160.132859911
AllCCS[M+NH4]+166.632859911
AllCCS[M+Na]+167.532859911
AllCCS[M-H]-167.432859911
AllCCS[M+Na-2H]-167.832859911
AllCCS[M+HCOO]-168.332859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
RopiniroleCCCN(CCC)CCC1=C2CC(=O)NC2=CC=C13263.9Standard polar33892256
RopiniroleCCCN(CCC)CCC1=C2CC(=O)NC2=CC=C12318.1Standard non polar33892256
RopiniroleCCCN(CCC)CCC1=C2CC(=O)NC2=CC=C12339.3Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Ropinirole,1TMS,isomer #1CCCN(CCC)CCC1=CC=CC2=C1CC(=O)N2[Si](C)(C)C2125.4Semi standard non polar33892256
Ropinirole,1TMS,isomer #1CCCN(CCC)CCC1=CC=CC2=C1CC(=O)N2[Si](C)(C)C2228.8Standard non polar33892256
Ropinirole,1TMS,isomer #1CCCN(CCC)CCC1=CC=CC2=C1CC(=O)N2[Si](C)(C)C2626.6Standard polar33892256
Ropinirole,1TBDMS,isomer #1CCCN(CCC)CCC1=CC=CC2=C1CC(=O)N2[Si](C)(C)C(C)(C)C2344.3Semi standard non polar33892256
Ropinirole,1TBDMS,isomer #1CCCN(CCC)CCC1=CC=CC2=C1CC(=O)N2[Si](C)(C)C(C)(C)C2487.1Standard non polar33892256
Ropinirole,1TBDMS,isomer #1CCCN(CCC)CCC1=CC=CC2=C1CC(=O)N2[Si](C)(C)C(C)(C)C2713.1Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Ropinirole GC-MS (Non-derivatized) - 70eV, Positivesplash10-03kd-8950000000-65ad14635cd7e9f251532017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Ropinirole GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Ropinirole 50V, Positive-QTOFsplash10-001i-0900000000-fd0720d43d850f7b41122021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Ropinirole 30V, Positive-QTOFsplash10-03e9-0900000000-0cffe19378ee7388c9b32021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Ropinirole 40V, Positive-QTOFsplash10-001i-0900000000-7b58f2b7d78649e5141a2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Ropinirole 20V, Positive-QTOFsplash10-03di-0390000000-844dec8f945ae2bdddcd2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Ropinirole 10V, Positive-QTOFsplash10-03di-0090000000-8c7df92a90c013ff6e262021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ropinirole 10V, Positive-QTOFsplash10-03di-0190000000-7e072cf65f341641938c2015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ropinirole 20V, Positive-QTOFsplash10-03di-3960000000-47d2311adfeeacf4062d2015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ropinirole 40V, Positive-QTOFsplash10-0006-7900000000-0891c66db163729a53602015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ropinirole 10V, Negative-QTOFsplash10-0a4i-0090000000-88c0fa3d93090a0d06c62015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ropinirole 20V, Negative-QTOFsplash10-0pb9-3590000000-8fb5fc766313ee6bbd9e2015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ropinirole 40V, Negative-QTOFsplash10-0k96-9400000000-f1b50dacd59a9bfe90b72015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ropinirole 10V, Positive-QTOFsplash10-03di-0190000000-bfa59f1f4dd92796c2f12021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ropinirole 20V, Positive-QTOFsplash10-03di-1970000000-134d3ee14c868165c82d2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ropinirole 40V, Positive-QTOFsplash10-01pp-7900000000-2459901fcec4348b7dbc2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ropinirole 10V, Negative-QTOFsplash10-0a4i-0090000000-7c4aa654b272455d29042021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ropinirole 20V, Negative-QTOFsplash10-0a4i-0590000000-4395944c67ba02f5a73b2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ropinirole 40V, Negative-QTOFsplash10-053r-2900000000-2cb3b5572e758c0d2eb02021-09-23Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00268 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00268 details
Abnormal Concentrations
Not Available
Predicted Concentrations
BiospecimenValueOriginal ageOriginal sexOriginal conditionComments
Blood0.000 uMAdult (>18 years old)BothNormalPredicted based on drug qualities
Blood0.000 umol/mmol creatinineAdult (>18 years old)BothNormalPredicted based on drug qualities
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00268
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID4916
KEGG Compound IDC07564
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkRopinirole
METLIN IDNot Available
PubChem Compound5095
PDB IDNot Available
ChEBI ID8888
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Only showing the first 10 proteins. There are 17 proteins in total.

Enzymes

General function:
Involved in monooxygenase activity
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 performs a variety of oxidation reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4-hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Acts as a 1,8-cineole 2-exo-monooxygenase. The enzyme also hydroxylates etoposide.
Gene Name:
CYP3A4
Uniprot ID:
P08684
Molecular weight:
57255.585
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. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
General function:
Involved in monooxygenase activity
Specific function:
Responsible for the metabolism of many drugs and environmental chemicals that it oxidizes. It is involved in the metabolism of drugs such as antiarrhythmics, adrenoceptor antagonists, and tricyclic antidepressants.
Gene Name:
CYP2D6
Uniprot ID:
P10635
Molecular weight:
55768.94
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. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
General function:
Involved in monooxygenase activity
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 unrelated compounds, including steroids, fatty acids, and xenobiotics. Most active in catalyzing 2-hydroxylation. Caffeine is metabolized primarily by cytochrome CYP1A2 in the liver through an initial N3-demethylation. Also acts in the metabolism of aflatoxin B1 and acetaminophen. Participates in the bioactivation of carcinogenic aromatic and heterocyclic amines. Catalizes the N-hydroxylation of heterocyclic amines and the O-deethylation of phenacetin.
Gene Name:
CYP1A2
Uniprot ID:
P05177
Molecular weight:
58406.915
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. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
General function:
Involved in G-protein coupled receptor protein signaling pathway
Specific function:
Alpha-2 adrenergic receptors mediate the catecholamine- induced inhibition of adenylate cyclase through the action of G proteins. The rank order of potency for agonists of this receptor is oxymetazoline > clonidine > epinephrine > norepinephrine > phenylephrine > dopamine > p-synephrine > p-tyramine > serotonin = p-octopamine. For antagonists, the rank order is yohimbine > phentolamine = mianserine > chlorpromazine = spiperone = prazosin > propanolol > alprenolol = pindolol
Gene Name:
ADRA2A
Uniprot ID:
P08913
Molecular weight:
48956.3
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 ]
General function:
Involved in G-protein coupled receptor protein signaling pathway
Specific function:
Alpha-2 adrenergic receptors mediate the catecholamine- induced inhibition of adenylate cyclase through the action of G proteins. The rank order of potency for agonists of this receptor is clonidine > norepinephrine > epinephrine = oxymetazoline > dopamine > p-tyramine = phenylephrine > serotonin > p-synephrine / p-octopamine. For antagonists, the rank order is yohimbine > chlorpromazine > phentolamine > mianserine > spiperone > prazosin > alprenolol > propanolol > pindolol
Gene Name:
ADRA2B
Uniprot ID:
P18089
Molecular weight:
49953.1
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 ]
General function:
Involved in G-protein coupled receptor protein signaling pathway
Specific function:
This is one of the five types (D1 to D5) of receptors for dopamine. The activity of this receptor is mediated by G proteins which inhibit adenylyl cyclase
Gene Name:
DRD2
Uniprot ID:
P14416
Molecular weight:
50618.9
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. 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 ]
  3. 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 ]
  4. 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 ]
  5. Lam YW: Clinical pharmacology of dopamine agonists. Pharmacotherapy. 2000 Jan;20(1 Pt 2):17S-25S. [PubMed:10641988 ]
  6. 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 ]
General function:
Involved in G-protein coupled receptor protein signaling pathway
Specific function:
This is one of the several different receptors for 5- hydroxytryptamine (serotonin), a biogenic hormone that functions as a neurotransmitter, a hormone, and a mitogen. This receptor mediates its action by association with G proteins that activate a phosphatidylinositol-calcium second messenger system
Gene Name:
HTR2B
Uniprot ID:
P41595
Molecular weight:
54297.4
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 ]
General function:
Involved in G-protein coupled receptor protein signaling pathway
Specific function:
This is one of the several different receptors for 5- hydroxytryptamine (serotonin), a biogenic hormone that functions as a neurotransmitter, a hormone, and a mitogen. The activity of this receptor is mediated by G proteins that inhibit adenylate cyclase activity
Gene Name:
HTR1B
Uniprot ID:
P28222
Molecular weight:
43567.5
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 ]
General function:
Involved in G-protein coupled receptor protein signaling pathway
Specific function:
This is one of the five types (D1 to D5) of receptors for dopamine. The activity of this receptor is mediated by G proteins which inhibit adenylyl cyclase
Gene Name:
DRD4
Uniprot ID:
P21917
Molecular weight:
48359.9
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 ]
General function:
Involved in G-protein coupled receptor protein signaling pathway
Specific function:
This is one of the several different receptors for 5- hydroxytryptamine (serotonin), a biogenic hormone that functions as a neurotransmitter, a hormone, and a mitogen. The activity of this receptor is mediated by G proteins that inhibit adenylate cyclase activity
Gene Name:
HTR1A
Uniprot ID:
P08908
Molecular weight:
46106.3
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 ]

Only showing the first 10 proteins. There are 17 proteins in total.