ropinirole Indications/Contra | FAERs-F | FAERs-M | Orange Bk | BioActivity |

Stem definitionDrug idCAS RN
2402 91374-21-9

Description:

MoleculeDescription

Molfile Inchi Smiles

Synonyms:

  • ropinirol
  • requip
  • ropinirole
  • ropinirole hydrochloride
  • ropinirole HCl
Ropinirole is a non-ergoline dopamine agonist. The precise mechanism of action of ropinirole as a treatment for Parkinson’s disease is unknown, although it is thought to be related to its ability to stimulate dopamine D2 receptors within the caudate-putamen in the brain.
  • Molecular weight: 260.38
  • Formula: C16H24N2O
  • CLOGP: 2.80
  • LIPINSKI: 0
  • HAC: 3
  • HDO: 1
  • TPSA: 32.34
  • ALOGS: -2.87
  • ROTB: 7

  • Status: OFP

  • Legend:
    OFP - off patent
    OFM - off market
    ONP - on patent

Drug dosage:

DoseUnitRoute
6 mg O

ADMET properties:

PropertyValueReference
BDDCS (Biopharmaceutical Drug Disposition Classification System) 1 Benet LZ, Broccatelli F, Oprea TI
S (Water solubility) 133 mg/mL Benet LZ, Broccatelli F, Oprea TI
EoM (Fraction excreted unchanged in urine) 5 % Benet LZ, Broccatelli F, Oprea TI
MRTD (Maximum Recommended Therapeutic Daily Dose) 1.32 µM/kg/day Contrera JF, Matthews EJ, Kruhlak NL, Benz RD
BA (Bioavailability) 55 % Kim MT, Sedykh A, Chakravarti SK, Saiakhov RD, Zhu H
Vd (Volume of distribution) 7.70 L/kg Lombardo F, Berellini G, Obach RS
CL (Clearance) 30 mL/min/kg Lombardo F, Berellini G, Obach RS
fu (Fraction unbound in plasma) 0.60 % Lombardo F, Berellini G, Obach RS
t_half (Half-life) 6 hours Lombardo F, Berellini G, Obach RS

Approvals:

DateAgencyCompanyOrphan
Sept. 19, 1997 FDA GLAXOSMITHKLINE LLC
Sept. 20, 2019 PMDA Hisamitsu Pharmaceutical Co., Inc.

FDA Adverse Event Reporting System (Female)

MedDRA adverse event termLikelihood ratioLikelihood ratio thresholdPatients taking drug having adverse eventPatients taking drug not having adverse eventPatients not taking drug having adverse eventPatients not taking drug not having adverse event
Hallucination 312.32 36.40 78 1067 8070 2348870
Parkinson's disease 300.02 36.40 55 1090 1271 2355669
Compulsive shopping 295.76 36.40 41 1104 128 2356812
Sudden onset of sleep 285.70 36.40 41 1104 175 2356765
Impulse-control disorder 241.84 36.40 35 1110 160 2356780
Gambling disorder 240.27 36.40 36 1109 218 2356722
Dyskinesia 229.61 36.40 55 1090 4734 2352206
Hallucination, visual 221.95 36.40 49 1096 2930 2354010
Restless legs syndrome 212.10 36.40 45 1100 2226 2354714
Somnolence 195.53 36.40 69 1076 23416 2333524
Drug ineffective 187.87 36.40 103 1042 101521 2255419
Dopamine dysregulation syndrome 169.92 36.40 22 1123 32 2356908
Drug hypersensitivity 134.07 36.40 64 1081 46579 2310361
Condition aggravated 120.37 36.40 53 1092 31926 2325014
Anxiety 108.29 36.40 48 1097 29311 2327629
On and off phenomenon 108.21 36.40 17 1128 145 2356795
Insomnia 104.28 36.40 45 1100 25742 2331198
Tremor 93.23 36.40 39 1106 20622 2336318
Nausea 88.71 36.40 67 1078 112122 2244818
Gambling 87.93 36.40 13 1132 70 2356870
Fall 86.74 36.40 48 1097 47051 2309889
Delusion 84.82 36.40 21 1124 2044 2354896
Confusional state 80.71 36.40 37 1108 24307 2332633
Drug interaction 80.34 36.40 39 1106 29124 2327816
Oedema peripheral 75.27 36.40 35 1110 23728 2333212
Dizziness 74.41 36.40 47 1098 58618 2298322
Illusion 73.66 36.40 13 1132 236 2356704
Completed suicide 72.94 36.40 33 1112 21001 2335939
Weight increased 71.04 36.40 33 1112 22304 2334636
Binge eating 68.14 36.40 11 1134 113 2356827
Bradykinesia 67.82 36.40 14 1131 597 2356343
Psychotic disorder 67.81 36.40 21 1124 4658 2352282
Stereotypy 67.71 36.40 11 1134 118 2356822
Gait disturbance 67.65 36.40 32 1113 22513 2334427
Syncope 66.58 36.40 29 1116 16846 2340094
Obsessive-compulsive disorder 66.58 36.40 14 1131 654 2356286
Hypersexuality 66.27 36.40 11 1134 136 2356804
Agitation 60.48 36.40 24 1121 11027 2345913
Abnormal behaviour 59.14 36.40 19 1126 4741 2352199
Jealous delusion 57.59 36.40 8 1137 25 2356915
Paranoia 50.59 36.40 14 1131 2093 2354847
Malaise 49.88 36.40 36 1109 55549 2301391
Delirium 49.50 36.40 17 1128 5206 2351734
Hyperhidrosis 46.53 36.40 22 1123 15400 2341540
Drug withdrawal syndrome 45.07 36.40 17 1128 6804 2350136
Withdrawal syndrome 44.24 36.40 14 1131 3323 2353617
Mental impairment 44.13 36.40 13 1132 2427 2354513
Movement disorder 42.24 36.40 13 1132 2815 2354125
Parkinsonism hyperpyrexia syndrome 41.83 36.40 6 1139 25 2356915
Muscular weakness 41.12 36.40 20 1125 14877 2342063
Camptocormia 40.31 36.40 6 1139 34 2356906
Major depression 39.78 36.40 10 1135 1031 2355909
Dementia 38.67 36.40 12 1133 2669 2354271
Muscle rigidity 38.64 36.40 11 1134 1820 2355120
Psychotic symptom 36.68 36.40 7 1138 198 2356742

FDA Adverse Event Reporting System (Male)

MedDRA adverse event termLikelihood ratioLikelihood ratio thresholdPatients taking drug having adverse eventPatients taking drug not having adverse eventPatients not taking drug having adverse eventPatients not taking drug not having adverse event
Hypersexuality 526.27 46.67 80 1117 286 1745298
Gambling disorder 450.26 46.67 71 1126 339 1745245
Hallucination 343.00 46.67 94 1103 8076 1737508
Hallucination, visual 303.06 46.67 68 1129 2524 1743060
Parkinson's disease 300.79 46.67 63 1134 1679 1743905
Impulse-control disorder 287.69 46.67 47 1150 288 1745296
Sudden onset of sleep 279.53 46.67 42 1155 133 1745451
Dyskinesia 241.57 46.67 61 1136 3758 1741826
Dopamine dysregulation syndrome 238.51 46.67 35 1162 89 1745495
Somnolence 188.68 46.67 71 1126 16668 1728916
Confusional state 148.57 46.67 64 1133 21214 1724370
Abnormal behaviour 129.43 46.67 42 1155 6300 1739284
Gambling 128.30 46.67 20 1177 85 1745499
Obsessive-compulsive disorder 125.71 46.67 27 1170 801 1744783
Compulsive shopping 121.45 46.67 19 1178 83 1745501
Insomnia 120.14 46.67 51 1146 16225 1729359
Stereotypy 117.75 46.67 19 1178 105 1745479
Jealous delusion 111.54 46.67 17 1180 60 1745524
Aggression 107.88 46.67 39 1158 8076 1737508
Serotonin syndrome 106.67 46.67 30 1167 2758 1742826
Psychotic disorder 105.18 46.67 34 1163 5022 1740562
Libido increased 96.71 46.67 18 1179 250 1745334
Delirium 86.07 46.67 31 1166 6331 1739253
Paranoia 85.81 46.67 24 1173 2157 1743427
Muscle rigidity 85.02 46.67 23 1174 1825 1743759
Depression 83.82 46.67 40 1157 16629 1728955
On and off phenomenon 83.66 46.67 16 1181 259 1745325
Drug withdrawal syndrome 80.27 46.67 27 1170 4498 1741086
Orthostatic hypotension 75.07 46.67 24 1173 3407 1742177
Fall 70.59 46.67 42 1155 27172 1718412
Parkinson's disease psychosis 70.02 46.67 9 1188 3 1745581
Freezing phenomenon 68.46 46.67 13 1184 202 1745382
Impulsive behaviour 67.82 46.67 15 1182 509 1745075
Agitation 66.35 46.67 30 1167 10996 1734588
Dropped head syndrome 66.10 46.67 10 1187 33 1745551
Drug ineffective 65.85 46.67 56 1141 63745 1681839
Restless legs syndrome 62.82 46.67 16 1181 1001 1744583
Sleep attacks 62.13 46.67 10 1187 54 1745530
Nausea 61.24 46.67 49 1148 51147 1694437
Hyperkinesia 60.57 46.67 12 1185 235 1745349
Anticholinergic syndrome 57.67 46.67 11 1186 175 1745409
Asthenia 56.54 46.67 40 1157 34630 1710954
Tremor 55.40 46.67 28 1169 13103 1732481
Product dispensing error 55.00 46.67 16 1181 1650 1743934
Parkinsonism hyperpyrexia syndrome 54.81 46.67 8 1189 19 1745565
Suicidal ideation 53.83 46.67 24 1173 8494 1737090
Compulsions 53.54 46.67 9 1188 66 1745518
Psychomotor hyperactivity 52.98 46.67 16 1181 1877 1743707
Dependence 51.62 46.67 11 1186 312 1745272
Stress cardiomyopathy 50.40 46.67 11 1186 350 1745234
Delusion 50.39 46.67 16 1181 2215 1743369
Memory impairment 49.34 46.67 21 1176 6642 1738942
Loss of consciousness 49.31 46.67 27 1170 14848 1730736
Balance disorder 48.68 46.67 20 1177 5792 1739792
Hyperhidrosis 47.95 46.67 25 1172 12463 1733121
Syncope 47.74 46.67 26 1171 14143 1731441

Pharmacologic Action:

SourceCodeDescription
ATC N04BC04 NERVOUS SYSTEM
ANTI-PARKINSON DRUGS
DOPAMINERGIC AGENTS
Dopamine agonists
FDA EPC N0000175768 Nonergot Dopamine Agonist
CHEBI has role CHEBI:51065 dopamine agonist
CHEBI has role CHEBI:35470 central nervous system drug
CHEBI has role CHEBI:66956 antidyskinesia agent
CHEBI has role CHEBI:48407 antiparkinson drug
MeSH PA D018726 Anti-Dyskinesia Agents
MeSH PA D000978 Antiparkinson Agents
MeSH PA D002491 Central Nervous System Agents
MeSH PA D015259 Dopamine Agents
MeSH PA D018491 Dopamine Agonists
MeSH PA D018377 Neurotransmitter Agents

Drug Use (View source of the data)

DiseaseRelationSNOMED_IDDOID
Restless legs indication 32914008 DOID:0050425
Parkinson's disease indication 49049000 DOID:14330
Hallucinations contraindication 7011001
Dyskinesia contraindication 9748009
Orthostatic hypotension contraindication 28651003
Low blood pressure contraindication 45007003
Bradycardia contraindication 48867003
Acute nephropathy contraindication 58574008
Hepatic failure contraindication 59927004
Psychotic disorder contraindication 69322001
Syncope contraindication 271594007
Drowsy contraindication 271782001
Central nervous system depression contraindication 418072004
Smokes tobacco daily contraindication 449868002

Acid dissociation constants calculated using MoKa v3.0.0

Dissociation levelDissociation constantType (acidic/basic)
pKa1 10.82 acidic
pKa2 9.18 Basic

Orange Book patent data (new drug applications)

Formulation strengthTrade nameApplicantApplication numberApproval dateTypeDose formRoutePatent numberPatent expiration datePatent use
EQ 12MG BASE REQUIP XL GLAXOSMITHKLINE LLC N022008 Oct. 31, 2008 RX TABLET, EXTENDED RELEASE ORAL 7927624 Dec. 2, 2021 A PROCESS FOR TREATING A PATIENT SUFFERING FROM PARKINSON'S SYNDROME AND IN NEED OF TREATMENT
EQ 2MG BASE REQUIP XL GLAXOSMITHKLINE LLC N022008 June 13, 2008 RX TABLET, EXTENDED RELEASE ORAL 7927624 Dec. 2, 2021 A PROCESS FOR TREATING A PATIENT SUFFERING FROM PARKINSON'S SYNDROME AND IN NEED OF TREATMENT
EQ 3MG BASE **Federal Register determination that product was not discontinued or withdrawn for safety or efficacy reasons** REQUIP XL GLAXOSMITHKLINE LLC N022008 June 13, 2008 DISCN TABLET, EXTENDED RELEASE ORAL 7927624 Dec. 2, 2021 A PROCESS FOR TREATING A PATIENT SUFFERING FROM PARKINSON'S SYNDROME AND IN NEED OF TREATMENT
EQ 4MG BASE REQUIP XL GLAXOSMITHKLINE LLC N022008 June 13, 2008 DISCN TABLET, EXTENDED RELEASE ORAL 7927624 Dec. 2, 2021 A PROCESS FOR TREATING A PATIENT SUFFERING FROM PARKINSON'S SYNDROME AND IN NEED OF TREATMENT
EQ 6MG BASE REQUIP XL GLAXOSMITHKLINE LLC N022008 April 10, 2009 RX TABLET, EXTENDED RELEASE ORAL 7927624 Dec. 2, 2021 A PROCESS FOR TREATING A PATIENT SUFFERING FROM PARKINSON'S SYNDROME AND IN NEED OF TREATMENT
EQ 8MG BASE REQUIP XL GLAXOSMITHKLINE LLC N022008 June 13, 2008 DISCN TABLET, EXTENDED RELEASE ORAL 7927624 Dec. 2, 2021 A PROCESS FOR TREATING A PATIENT SUFFERING FROM PARKINSON'S SYNDROME AND IN NEED OF TREATMENT

Orange Book exclusivity data (new drug applications)

Formulation strengthTrade nameApplicantApplication numberApproval dateTypeDose formRouteExclusivity dateDescription
EQ 12MG BASE REQUIP XL GLAXOSMITHKLINE LLC N022008 Oct. 31, 2008 RX TABLET, EXTENDED RELEASE ORAL March 23, 2020 PROVIDES FOR REVISIONS TO THE PACKAGE INSERT TO REFLECT RESULTS OF TWO POSTMARKETING REQUIREMENT STUDIES ROP111662 AND ROP111569
EQ 2MG BASE REQUIP XL GLAXOSMITHKLINE LLC N022008 June 13, 2008 RX TABLET, EXTENDED RELEASE ORAL March 23, 2020 PROVIDES FOR REVISIONS TO THE PACKAGE INSERT TO REFLECT RESULTS OF TWO POSTMARKETING REQUIREMENT STUDIES ROP111662 AND ROP111569
EQ 3MG BASE **Federal Register determination that product was not discontinued or withdrawn for safety or efficacy reasons** REQUIP XL GLAXOSMITHKLINE LLC N022008 June 13, 2008 DISCN TABLET, EXTENDED RELEASE ORAL March 23, 2020 PROVIDES FOR REVISIONS TO THE PACKAGE INSERT TO REFLECT RESULTS OF TWO POSTMARKETING REQUIREMENT STUDIES ROP111662 AND ROP111569
EQ 4MG BASE REQUIP XL GLAXOSMITHKLINE LLC N022008 June 13, 2008 DISCN TABLET, EXTENDED RELEASE ORAL March 23, 2020 PROVIDES FOR REVISIONS TO THE PACKAGE INSERT TO REFLECT RESULTS OF TWO POSTMARKETING REQUIREMENT STUDIES ROP111662 AND ROP111569
EQ 6MG BASE REQUIP XL GLAXOSMITHKLINE LLC N022008 April 10, 2009 RX TABLET, EXTENDED RELEASE ORAL March 23, 2020 PROVIDES FOR REVISIONS TO THE PACKAGE INSERT TO REFLECT RESULTS OF TWO POSTMARKETING REQUIREMENT STUDIES ROP111662 AND ROP111569
EQ 8MG BASE REQUIP XL GLAXOSMITHKLINE LLC N022008 June 13, 2008 DISCN TABLET, EXTENDED RELEASE ORAL March 23, 2020 PROVIDES FOR REVISIONS TO THE PACKAGE INSERT TO REFLECT RESULTS OF TWO POSTMARKETING REQUIREMENT STUDIES ROP111662 AND ROP111569

Bioactivity Summary:

TargetClassPharosUniProtActionTypeActivity value
(-log[M])
Mechanism
action
Bioact sourceMoA source
D(2) dopamine receptor GPCR AGONIST Ki 8.14 IUPHAR IUPHAR
D(3) dopamine receptor GPCR AGONIST Ki 7.43 WOMBAT-PK
5-hydroxytryptamine receptor 2B GPCR Ki 5.42 PDSP
5-hydroxytryptamine receptor 7 GPCR Ki 5.82 PDSP
5-hydroxytryptamine receptor 1D GPCR Ki 5.86 PDSP
Alpha-2C adrenergic receptor GPCR Ki 5.92 PDSP
Alpha-2A adrenergic receptor GPCR Ki 5.73 PDSP
D(4) dopamine receptor GPCR AGONIST Ki 6.07 WOMBAT-PK
Alpha-2B adrenergic receptor GPCR Ki 6.12 WOMBAT-PK
5-hydroxytryptamine receptor 1A GPCR Ki 6.54 WOMBAT-PK
D(1A) dopamine receptor GPCR Ki 4.49 CHEMBL
D(1B) dopamine receptor GPCR Ki 4.38 CHEMBL
D(2) dopamine receptor GPCR IC50 5.17 CHEMBL
D(3) dopamine receptor GPCR Ki 7.53 CHEMBL
D(2) dopamine receptor GPCR Ki 5.57 CHEMBL

External reference:

IDSource
4024081 VUID
N0000022086 NUI
C0244821 UMLSCUI
D00784 KEGG_DRUG
030PYR8953 UNII
6436 INN_ID
108473005 SNOMEDCT_US
4024081 VANDF
72302 RXNORM
d04215 MMSL
006273 NDDF
372499000 SNOMEDCT_US
91374-20-8 SECONDARY_CAS_RN
CHEBI:8888 CHEBI
CHEMBL589 ChEMBL_ID
DB00268 DRUGBANK_ID
CHEMBL1200411 ChEMBL_ID
5095 PUBCHEM_CID
7295 IUPHAR_LIGAND_ID
C046649 MESH_SUPPLEMENTAL_RECORD_UI

Pharmaceutical products:

ProductCategoryIngredientsNDCFormQuantityRouteMarketingLabel
REQUIP HUMAN PRESCRIPTION DRUG LABEL 1 0007-4882 TABLET, FILM COATED, EXTENDED RELEASE 12 mg ORAL NDA 18 sections
REQUIP HUMAN PRESCRIPTION DRUG LABEL 1 0007-4883 TABLET, FILM COATED, EXTENDED RELEASE 6 mg ORAL NDA 18 sections
REQUIP HUMAN PRESCRIPTION DRUG LABEL 1 0007-4885 TABLET, FILM COATED, EXTENDED RELEASE 2 mg ORAL NDA 18 sections
REQUIP HUMAN PRESCRIPTION DRUG LABEL 1 0007-4887 TABLET, FILM COATED, EXTENDED RELEASE 4 mg ORAL NDA 18 sections
REQUIP HUMAN PRESCRIPTION DRUG LABEL 1 0007-4888 TABLET, FILM COATED, EXTENDED RELEASE 8 mg ORAL NDA 18 sections
Ropinirole HUMAN PRESCRIPTION DRUG LABEL 1 0054-0116 TABLET 0.25 mg ORAL ANDA 18 sections
Ropinirole HUMAN PRESCRIPTION DRUG LABEL 1 0054-0117 TABLET 0.50 mg ORAL ANDA 18 sections
Ropinirole HUMAN PRESCRIPTION DRUG LABEL 1 0054-0118 TABLET 1 mg ORAL ANDA 18 sections
Ropinirole HUMAN PRESCRIPTION DRUG LABEL 1 0054-0119 TABLET 2 mg ORAL ANDA 18 sections
Ropinirole HUMAN PRESCRIPTION DRUG LABEL 1 0054-0120 TABLET 3 mg ORAL ANDA 18 sections
Ropinirole HUMAN PRESCRIPTION DRUG LABEL 1 0054-0121 TABLET 4 mg ORAL ANDA 18 sections
Ropinirole HUMAN PRESCRIPTION DRUG LABEL 1 0054-0122 TABLET 5 mg ORAL ANDA 18 sections
Ropinirole HUMAN PRESCRIPTION DRUG LABEL 1 0228-3640 TABLET, FILM COATED, EXTENDED RELEASE 6 mg ORAL ANDA 17 sections
Ropinirole HUMAN PRESCRIPTION DRUG LABEL 1 0228-3658 TABLET, FILM COATED, EXTENDED RELEASE 2 mg ORAL ANDA 17 sections
Ropinirole HUMAN PRESCRIPTION DRUG LABEL 1 0228-3659 TABLET, FILM COATED, EXTENDED RELEASE 4 mg ORAL ANDA 17 sections
Ropinirole HUMAN PRESCRIPTION DRUG LABEL 1 0228-3660 TABLET, FILM COATED, EXTENDED RELEASE 8 mg ORAL ANDA 17 sections
Ropinirole HUMAN PRESCRIPTION DRUG LABEL 1 0228-3661 TABLET, FILM COATED, EXTENDED RELEASE 12 mg ORAL ANDA 17 sections
Ropinirole Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0378-5501 TABLET 1 mg ORAL ANDA 18 sections
Ropinirole Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0378-5502 TABLET 2 mg ORAL ANDA 18 sections
Ropinirole Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0378-5503 TABLET 3 mg ORAL ANDA 18 sections
Ropinirole Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0378-5504 TABLET 4 mg ORAL ANDA 18 sections
Ropinirole Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0378-5505 TABLET 5 mg ORAL ANDA 18 sections
Ropinirole Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0378-5525 TABLET 0.25 mg ORAL ANDA 18 sections
Ropinirole Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0378-5550 TABLET 0.50 mg ORAL ANDA 18 sections
Ropinirole Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0615-7536 TABLET 0.25 mg ORAL ANDA 13 sections
Ropinirole Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0615-7537 TABLET 0.50 mg ORAL ANDA 13 sections
Ropinirole Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0615-7538 TABLET 1 mg ORAL ANDA 13 sections
Ropinirole Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0615-7539 TABLET 2 mg ORAL ANDA 13 sections
Ropinirole Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0615-7567 TABLET 3 mg ORAL ANDA 13 sections
ROPINIROLE HYDROCHLORIDE HUMAN PRESCRIPTION DRUG LABEL 1 0615-8188 TABLET, FILM COATED 0.25 mg ORAL ANDA 17 sections