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

Stem definitionDrug idCAS RN
dopamine receptor agonists, ergoline derivatives 2407 99755-59-6

Description:

MoleculeDescription

Molfile Inchi Smiles

Synonyms:

  • rotigotine
  • neupro
  • leganto
  • (S)-(-)-Rotigotine
Rotigotine is a non-ergoline dopamine agonist. The precise mechanism of action of rotigotine as a treatment for Parkinson's disease is unknown, although it is thought to be related to its ability to stimulate dopamine receptors within the caudate-putamen in the brain. The precise mechanism of action of rotigotine as a treatment for Restless Legs Syndrome is unknown but is thought to be related to its ability to stimulate dopamine receptors.
  • Molecular weight: 315.48
  • Formula: C19H25NOS
  • CLOGP: 4.54
  • LIPINSKI: 0
  • HAC: 2
  • HDO: 1
  • TPSA: 23.47
  • ALOGS: -4.54
  • ROTB: 6

  • Status: OFP

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

Drug dosage:

DoseUnitRoute
6 mg TD patch

ADMET properties:

PropertyValueReference
BDDCS (Biopharmaceutical Drug Disposition Classification System) 1 Benet LZ, Broccatelli F, Oprea TI
S (Water solubility) 5.60 mg/mL Benet LZ, Broccatelli F, Oprea TI
EoM (Fraction excreted unchanged in urine) 0 % Benet LZ, Broccatelli F, Oprea TI
MRTD (Maximum Recommended Therapeutic Daily Dose) 0.36 ┬ÁM/kg/day Contrera JF, Matthews EJ, Kruhlak NL, Benz RD
Vd (Volume of distribution) 5.70 L/kg Lombardo F, Berellini G, Obach RS
CL (Clearance) 37 mL/min/kg Lombardo F, Berellini G, Obach RS
fu (Fraction unbound in plasma) 0.08 % Lombardo F, Berellini G, Obach RS
t_half (Half-life) 4 hours Lombardo F, Berellini G, Obach RS

Approvals:

DateAgencyCompanyOrphan
May 9, 2007 FDA UCB 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
Fall 171.63 37.61 67 677 47032 2310309
Application site erythema 140.52 37.61 27 717 1253 2356088
Application site pruritus 137.33 37.61 25 719 861 2356480
Loss of consciousness 133.52 37.61 44 700 18723 2338618
Parkinson's disease 133.40 37.61 26 718 1300 2356041
Anxiety 117.88 37.61 45 699 29314 2328027
Choking 111.74 37.61 23 721 1515 2355826
Micturition urgency 104.33 37.61 21 723 1235 2356106
Dysphagia 102.97 37.61 33 711 12772 2344569
Nocturia 99.00 37.61 19 725 871 2356470
Decreased interest 96.77 37.61 17 727 474 2356867
Disturbance in attention 91.06 37.61 25 719 5660 2351681
Depressed mood 83.89 37.61 23 721 5175 2352166
Nightmare 81.77 37.61 21 723 3676 2353665
Dyskinesia 81.04 37.61 22 722 4767 2352574
Anosmia 80.92 37.61 16 728 856 2356485
Tremor 76.71 37.61 30 714 20631 2336710
Gastrointestinal motility disorder 75.44 37.61 14 730 533 2356808
Middle insomnia 72.52 37.61 16 728 1461 2355880
Hallucination, visual 71.15 37.61 18 726 2961 2354380
Dizziness 70.80 37.61 39 705 58626 2298715
Somnolence 69.59 37.61 29 715 23456 2333885
Product adhesion issue 69.48 37.61 15 729 1237 2356104
Sexual dysfunction 68.78 37.61 12 732 320 2357021
Drug ineffective 67.36 37.61 46 698 101578 2255763
Memory impairment 67.03 37.61 24 720 12899 2344442
Drooling 65.32 37.61 13 731 718 2356623
Dopamine dysregulation syndrome 65.32 37.61 9 735 45 2357296
Constipation 65.04 37.61 27 717 21602 2335739
Stress 64.44 37.61 20 724 6918 2350423
Off label use 62.58 37.61 39 705 73559 2283782
Ageusia 62.50 37.61 15 729 1983 2355358
Vomiting 61.00 37.61 38 706 71564 2285777
Nausea 58.69 37.61 44 700 112145 2245196
Application site reaction 55.16 37.61 10 734 333 2357008
Compulsive shopping 55.05 37.61 9 735 160 2357181
Sensory disturbance 53.53 37.61 14 730 2618 2354723
Oromandibular dystonia 52.43 37.61 8 736 89 2357252
Dropped head syndrome 51.13 37.61 7 737 33 2357308
Restless legs syndrome 50.65 37.61 13 731 2258 2355083
Weight abnormal 49.27 37.61 8 736 136 2357205
Confusional state 49.18 37.61 23 721 24321 2333020
Hyperhidrosis 48.82 37.61 20 724 15402 2341939
Sleep talking 47.66 37.61 8 736 168 2357173
Poor quality sleep 47.50 37.61 12 732 1955 2355386
Impulse-control disorder 46.84 37.61 8 736 187 2357154
Application site vesicles 46.78 37.61 9 735 415 2356926
Balance disorder 46.36 37.61 17 727 9730 2347611
Hallucination, auditory 46.21 37.61 12 732 2180 2355161
Hallucination 45.48 37.61 16 728 8132 2349209
Panic disorder 45.13 37.61 9 735 501 2356840
Gait disturbance 44.60 37.61 21 723 22524 2334817
Drug dose titration not performed 43.99 37.61 7 737 104 2357237
Malaise 43.44 37.61 28 716 55557 2301784
Application site rash 43.39 37.61 9 735 610 2356731
Pruritus 41.87 37.61 25 719 43315 2314026
Speech disorder 41.12 37.61 14 730 6450 2350891
Pain 40.71 37.61 28 716 61829 2295512
Panic attack 39.20 37.61 12 732 3944 2353397
Antidiuretic hormone abnormality 38.06 37.61 5 739 16 2357325

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
Parkinson's disease 166.44 43.38 36 757 1706 1744282
Choking 130.92 43.38 27 766 1009 1744979
Impulse-control disorder 126.90 43.38 22 771 313 1745675
Application site erythema 125.26 43.38 24 769 610 1745378
Hallucination 123.70 43.38 39 754 8131 1737857
Micturition urgency 114.86 43.38 23 770 738 1745250
Dysphagia 111.36 43.38 38 755 10130 1735858
Application site pruritus 106.72 43.38 19 774 317 1745671
Anxiety 106.32 43.38 41 752 15486 1730502
Poor quality sleep 104.61 43.38 23 770 1167 1744821
Restless legs syndrome 96.87 43.38 21 772 996 1744992
Stress 95.99 43.38 25 768 2616 1743372
Application site reaction 95.79 43.38 16 777 179 1745809
Anosmia 94.01 43.38 18 775 454 1745534
Gastrointestinal motility disorder 92.36 43.38 17 776 344 1745644
Hallucination, visual 91.61 43.38 24 769 2568 1743420
Sleep talking 91.60 43.38 15 778 147 1745841
Middle insomnia 88.42 43.38 19 774 863 1745125
Fall 84.16 43.38 41 752 27173 1718815
Depressed mood 83.36 43.38 23 770 2993 1742995
Nocturia 83.22 43.38 19 774 1142 1744846
Libido decreased 80.72 43.38 19 774 1306 1744682
Hypersexuality 79.39 43.38 15 778 351 1745637
Tremor 76.83 43.38 31 762 13100 1732888
Dyskinesia 69.30 43.38 21 772 3798 1742190
Memory impairment 69.26 43.38 24 769 6639 1739349
Ageusia 67.42 43.38 17 776 1557 1744431
Nightmare 66.71 43.38 19 774 2768 1743220
Decreased interest 66.45 43.38 13 780 367 1745621
Sexual dysfunction 64.94 43.38 17 776 1806 1744182
Insomnia 63.97 43.38 29 764 16247 1729741
Disturbance in attention 62.99 43.38 20 773 4214 1741774
Drooling 62.44 43.38 14 779 773 1745215
Dizziness 61.48 43.38 36 757 34325 1711663
Somnolence 60.06 43.38 28 765 16711 1729277
Confusional state 59.50 43.38 30 763 21248 1724740
Dropped head syndrome 54.40 43.38 8 785 35 1745953
Initial insomnia 51.91 43.38 11 782 465 1745523
Application site rash 51.85 43.38 10 783 261 1745727
On and off phenomenon 51.70 43.38 10 783 265 1745723
Speech disorder 49.60 43.38 17 776 4531 1741457
Balance disorder 49.22 43.38 18 775 5794 1740194
Application site irritation 47.96 43.38 9 784 202 1745786
Musculoskeletal stiffness 45.35 43.38 17 776 5859 1740129
Agitation 44.35 43.38 20 773 11006 1734982

Pharmacologic Action:

SourceCodeDescription
ATC N04BC09 NERVOUS SYSTEM
ANTI-PARKINSON DRUGS
DOPAMINERGIC AGENTS
Dopamine agonists
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
Dyskinesia contraindication 9748009
Orthostatic hypotension contraindication 28651003
Hypertensive disorder contraindication 38341003 DOID:10763
Body fluid retention contraindication 43498006
Chronic heart failure contraindication 48447003
Acute nephropathy contraindication 58574008
Magnetic resonance imaging contraindication 113091000
Syncope contraindication 271594007
Drowsy contraindication 271782001
Peripheral edema contraindication 271809000
Breastfeeding (mother) contraindication 413712001

Acid dissociation constants calculated using MoKa v3.0.0

Dissociation levelDissociation constantType (acidic/basic)
pKa1 10.6 acidic
pKa2 8.87 Basic

Orange Book patent data (new drug applications)

Formulation strengthTrade nameApplicantApplication numberApproval dateTypeDose formRoutePatent numberPatent expiration datePatent use
1MG/24HR NEUPRO UCB INC N021829 April 2, 2012 RX FILM, EXTENDED RELEASE TRANSDERMAL 8617591 July 22, 2023 A METHOD FOR THE TREATMENT OF A PATIENT SUFFERING FROM A DISEASE TREATABLE WITH ROTIGOTINE, COMPRISING APPLYING THE CLAIMED TRANSDERMAL DELIVERY SYSTEM (TDS) TO THE SKIN OF THE PATIENT
2MG/24HR NEUPRO UCB INC N021829 May 9, 2007 RX FILM, EXTENDED RELEASE TRANSDERMAL 8617591 July 22, 2023 A METHOD FOR THE TREATMENT OF A PATIENT SUFFERING FROM A DISEASE TREATABLE WITH ROTIGOTINE, COMPRISING APPLYING THE CLAIMED TRANSDERMAL DELIVERY SYSTEM (TDS) TO THE SKIN OF THE PATIENT
3MG/24HR NEUPRO UCB INC N021829 April 2, 2012 RX FILM, EXTENDED RELEASE TRANSDERMAL 8617591 July 22, 2023 A METHOD FOR THE TREATMENT OF A PATIENT SUFFERING FROM A DISEASE TREATABLE WITH ROTIGOTINE, COMPRISING APPLYING THE CLAIMED TRANSDERMAL DELIVERY SYSTEM (TDS) TO THE SKIN OF THE PATIENT
4MG/24HR NEUPRO UCB INC N021829 May 9, 2007 RX FILM, EXTENDED RELEASE TRANSDERMAL 8617591 July 22, 2023 A METHOD FOR THE TREATMENT OF A PATIENT SUFFERING FROM A DISEASE TREATABLE WITH ROTIGOTINE, COMPRISING APPLYING THE CLAIMED TRANSDERMAL DELIVERY SYSTEM (TDS) TO THE SKIN OF THE PATIENT
6MG/24HR NEUPRO UCB INC N021829 May 9, 2007 RX FILM, EXTENDED RELEASE TRANSDERMAL 8617591 July 22, 2023 A METHOD FOR THE TREATMENT OF A PATIENT SUFFERING FROM A DISEASE TREATABLE WITH ROTIGOTINE, COMPRISING APPLYING THE CLAIMED TRANSDERMAL DELIVERY SYSTEM (TDS) TO THE SKIN OF THE PATIENT
8MG/24HR NEUPRO UCB INC N021829 April 2, 2012 RX FILM, EXTENDED RELEASE TRANSDERMAL 8617591 July 22, 2023 A METHOD FOR THE TREATMENT OF A PATIENT SUFFERING FROM A DISEASE TREATABLE WITH ROTIGOTINE, COMPRISING APPLYING THE CLAIMED TRANSDERMAL DELIVERY SYSTEM (TDS) TO THE SKIN OF THE PATIENT
1MG/24HR NEUPRO UCB INC N021829 April 2, 2012 RX FILM, EXTENDED RELEASE TRANSDERMAL 8246979 Sept. 1, 2027 TREATMENT OF RESTLESS LEGS SYNDROME BY APPLICATION OF CLAIMED TRANSDERMAL DELIVERY SYSTEM
1MG/24HR NEUPRO UCB INC N021829 April 2, 2012 RX FILM, EXTENDED RELEASE TRANSDERMAL 8246979 Sept. 1, 2027 TREATMENT OF SIGNS AND SYMPTOMS OF PARKINSON'S DISEASE BY APPLICATION OF CLAIMED TRANSDERMAL SYSTEM
2MG/24HR NEUPRO UCB INC N021829 May 9, 2007 RX FILM, EXTENDED RELEASE TRANSDERMAL 8246979 Sept. 1, 2027 TREATMENT OF RESTLESS LEGS SYNDROME BY APPLICATION OF CLAIMED TRANSDERMAL DELIVERY SYSTEM
2MG/24HR NEUPRO UCB INC N021829 May 9, 2007 RX FILM, EXTENDED RELEASE TRANSDERMAL 8246979 Sept. 1, 2027 TREATMENT OF SIGNS AND SYMPTOMS OF PARKINSON'S DISEASE BY APPLICATION OF CLAIMED TRANSDERMAL SYSTEM
3MG/24HR NEUPRO UCB INC N021829 April 2, 2012 RX FILM, EXTENDED RELEASE TRANSDERMAL 8246979 Sept. 1, 2027 TREATMENT OF RESTLESS LEGS SYNDROME BY APPLICATION OF CLAIMED TRANSDERMAL DELIVERY SYSTEM
3MG/24HR NEUPRO UCB INC N021829 April 2, 2012 RX FILM, EXTENDED RELEASE TRANSDERMAL 8246979 Sept. 1, 2027 TREATMENT OF SIGNS AND SYMPTOMS OF PARKINSON'S DISEASE BY APPLICATION OF CLAIMED TRANSDERMAL SYSTEM
4MG/24HR NEUPRO UCB INC N021829 May 9, 2007 RX FILM, EXTENDED RELEASE TRANSDERMAL 8246979 Sept. 1, 2027 TREATMENT OF RESTLESS LEGS SYNDROME BY APPLICATION OF CLAIMED TRANSDERMAL DELIVERY SYSTEM
4MG/24HR NEUPRO UCB INC N021829 May 9, 2007 RX FILM, EXTENDED RELEASE TRANSDERMAL 8246979 Sept. 1, 2027 TREATMENT OF SIGNS AND SYMPTOMS OF PARKINSON'S DISEASE BY APPLICATION OF CLAIMED TRANSDERMAL SYSTEM
6MG/24HR NEUPRO UCB INC N021829 May 9, 2007 RX FILM, EXTENDED RELEASE TRANSDERMAL 8246979 Sept. 1, 2027 TREATMENT OF RESTLESS LEGS SYNDROME BY APPLICATION OF CLAIMED TRANSDERMAL DELIVERY SYSTEM
6MG/24HR NEUPRO UCB INC N021829 May 9, 2007 RX FILM, EXTENDED RELEASE TRANSDERMAL 8246979 Sept. 1, 2027 TREATMENT OF SIGNS AND SYMPTOMS OF PARKINSON'S DISEASE BY APPLICATION OF CLAIMED TRANSDERMAL SYSTEM
8MG/24HR NEUPRO UCB INC N021829 April 2, 2012 RX FILM, EXTENDED RELEASE TRANSDERMAL 8246979 Sept. 1, 2027 TREATMENT OF RESTLESS LEGS SYNDROME BY APPLICATION OF CLAIMED TRANSDERMAL DELIVERY SYSTEM
8MG/24HR NEUPRO UCB INC N021829 April 2, 2012 RX FILM, EXTENDED RELEASE TRANSDERMAL 8246979 Sept. 1, 2027 TREATMENT OF SIGNS AND SYMPTOMS OF PARKINSON'S DISEASE BY APPLICATION OF CLAIMED TRANSDERMAL SYSTEM

Orange Book exclusivity data (new drug applications)

None

Bioactivity Summary:

TargetClassPharosUniProtActionTypeActivity value
(-log[M])
Mechanism
action
Bioact sourceMoA source
D(2) dopamine receptor GPCR AGONIST Ki 10.22 IUPHAR IUPHAR
D(1A) dopamine receptor GPCR AGONIST Ki 5.60 IUPHAR
D(3) dopamine receptor GPCR AGONIST Ki 8.40 IUPHAR
D(4) dopamine receptor GPCR AGONIST Ki 7.26 CHEMBL
D(1B) dopamine receptor GPCR AGONIST Ki 6 IUPHAR
D(1A) dopamine receptor GPCR Ki 6.30 CHEMBL
D(2) dopamine receptor GPCR Ki 7.82 CHEMBL

External reference:

IDSource
4025266 VUID
N0000171794 NUI
C1700683 UMLSCUI
D05768 KEGG_DRUG
421915002 SNOMEDCT_US
421924006 SNOMEDCT_US
4025266 VANDF
21751 MMSL
d05848 MMSL
616739 RXNORM
011270 NDDF
87T4T8BO2E UNII
7897 INN_ID
CHEMBL1303 ChEMBL_ID
DB05271 DRUGBANK_ID
CHEBI:135351 CHEBI
59227 PUBCHEM_CID
941 IUPHAR_LIGAND_ID
C047508 MESH_SUPPLEMENTAL_RECORD_UI

Pharmaceutical products:

ProductCategoryIngredientsNDCFormQuantityRouteMarketingLabel
Neupro HUMAN PRESCRIPTION DRUG LABEL 1 50474-801 PATCH, EXTENDED RELEASE 1 mg TRANSDERMAL NDA 20 sections
Neupro HUMAN PRESCRIPTION DRUG LABEL 1 50474-802 PATCH, EXTENDED RELEASE 2 mg TRANSDERMAL NDA 20 sections
Neupro HUMAN PRESCRIPTION DRUG LABEL 1 50474-803 PATCH, EXTENDED RELEASE 3 mg TRANSDERMAL NDA 20 sections
Neupro HUMAN PRESCRIPTION DRUG LABEL 1 50474-804 PATCH, EXTENDED RELEASE 4 mg TRANSDERMAL NDA 20 sections
Neupro HUMAN PRESCRIPTION DRUG LABEL 1 50474-805 PATCH, EXTENDED RELEASE 6 mg TRANSDERMAL NDA 20 sections
Neupro HUMAN PRESCRIPTION DRUG LABEL 1 50474-806 PATCH, EXTENDED RELEASE 8 mg TRANSDERMAL NDA 20 sections
Neupro HUMAN PRESCRIPTION DRUG LABEL 2 50474-808 KIT 4 mg None NDA 20 sections
Neupro HUMAN PRESCRIPTION DRUG LABEL 2 50474-808 KIT 2 mg None NDA 20 sections