U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ABSOLUTE
Molecular Formula C19H25NOS
Molecular Weight 315.4747
Optical Activity UNSPECIFIED
Defined Stereocenters 1 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of ROTIGOTINE

SMILES

CCCN(CCc1cccs1)[C@@]2([H])CCc3c(cccc3O)C2

InChI

InChIKey=KFQYTPMOWPVWEJ-INIZCTEOSA-N
InChI=1S/C19H25NOS/c1-2-11-20(12-10-17-6-4-13-22-17)16-8-9-18-15(14-16)5-3-7-19(18)21/h3-7,13,16,21H,2,8-12,14H2,1H3/t16-/m0/s1

HIDE SMILES / InChI

Description
Curator's Comment:: description was created based on several sources, including: https://www.drugs.com/mtm/rotigotine-transdermal.html http://www.rxlist.com/neupro-drug.htm http://www.wikidoc.org/index.php/Rotigotine

Rotigotine is an agonist at all 5 dopamine receptor subtypes (D1-D5) but binds to the D3 receptor with the highest affinity. It is also an antagonist at α-2-adrenergic receptors and an agonist at the 5HT1A receptors. Rotigotine also inhibits dopamine uptake and prolactin secretion. It is FDA approved for the treatment of Parkinson's disease, restless legs syndrome. Dopamine antagonists, such as antipsychotics or metoclopramide, may diminish the effectiveness of Rotigotine. Common adverse reactions include nausea, vomiting, somnolence, application site reactions, dizziness, anorexia, hyperhidrosis, insomnia and dyskinesia.

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
NEUPRO

Approved Use

NEUPRO is a dopamine agonist indicated for the treatment of: Parkinson's disease (1.1) Moderate-to-severe primary Restless Legs Syndrome (1.2) 1.1 Parkinson's Disease (PD) NEUPRO is indicated for the treatment of Parkinson's disease. 1.2 Restless Legs Syndrome (RLS) NEUPRO is indicated for the treatment of moderate-to-severe primary Restless Legs Syndrome.

Launch Date

1.17866876E12
Primary
NEUPRO

Approved Use

NEUPRO is a dopamine agonist indicated for the treatment of: Parkinson's disease (1.1) Moderate-to-severe primary Restless Legs Syndrome (1.2) 1.1 Parkinson's Disease (PD) NEUPRO is indicated for the treatment of Parkinson's disease. 1.2 Restless Legs Syndrome (RLS) NEUPRO is indicated for the treatment of moderate-to-severe primary Restless Legs Syndrome.

Launch Date

1.17866876E12
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
0.34 ng/mL
3 mg 2 times / day steady-state, transdermal
dose: 3 mg
route of administration: Transdermal
experiment type: STEADY-STATE
co-administered:
ROTIGOTINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
4.63 ng × h/mL
3 mg 2 times / day steady-state, transdermal
dose: 3 mg
route of administration: Transdermal
experiment type: STEADY-STATE
co-administered:
ROTIGOTINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
6.5 h
3 mg 2 times / day steady-state, transdermal
dose: 3 mg
route of administration: Transdermal
experiment type: STEADY-STATE
co-administered:
ROTIGOTINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
Funbound

Funbound

ValueDoseCo-administeredAnalytePopulation
10%
unknown
ROTIGOTINE plasma
Homo sapiens
population: UNKNOWN
age: UNKNOWN
sex: UNKNOWN
food status: UNKNOWN
Doses

Doses

DosePopulationAdverse events​
54 mg 1 times / day multiple, topical
Highest studied dose
unhealthy, 29 - 88
n = 130
Health Status: unhealthy
Condition: Advanced-stage Parkinson’s disease
Age Group: 29 - 88
Sex: M+F
Population Size: 130
Sources: Page: p.10
24 mg 1 times / day multiple, topical
Studied dose
Dose: 24 mg, 1 times / day
Route: topical
Route: multiple
Dose: 24 mg, 1 times / day
Sources: Page: p.196
unhealthy, 68.8
n = 26
Health Status: unhealthy
Condition: Advanced-stage Parkinson’s disease
Age Group: 68.8
Sex: M+F
Population Size: 26
Sources: Page: p.196
Disc. AE: Abnormal ECG, Hypertension...
AEs leading to
discontinuation/dose reduction:
Abnormal ECG (mild, 3.85%)
Hypertension (mild, 3.85%)
Sensory hallucinations (moderate, 3.85%)
Application site reaction (moderate, 7.7%)
Sources: Page: p.196
8 mg 1 times / day multiple, topical
Recommended
Dose: 8 mg, 1 times / day
Route: topical
Route: multiple
Dose: 8 mg, 1 times / day
Sources: Page: p.1
unhealthy
Health Status: unhealthy
Condition: Advanced-stage Parkinson’s disease
Sources: Page: p.1
Disc. AE: Allergic reaction, Somnolence...
AEs leading to
discontinuation/dose reduction:
Allergic reaction
Somnolence
Hallucinations
Psychotic behavior
Dyskinesia
Hypotension symptomatic
Syncope
Blood pressure increased
Tachycardia
Impulse-control disorder
Compulsive personality disorder
Daytime sleepiness
Sources: Page: p.1
8 mg 1 times / day multiple, topical
Recommended
Dose: 8 mg, 1 times / day
Route: topical
Route: multiple
Dose: 8 mg, 1 times / day
Sources: Page: p.1, p.5
unhealthy
Health Status: unhealthy
Condition: Advanced-stage Parkinson’s disease
Sources: Page: p.1, p.5
Disc. AE: Application site reaction...
AEs leading to
discontinuation/dose reduction:
Application site reaction (2%)
Sources: Page: p.1, p.5
AEs

AEs

AESignificanceDosePopulation
Abnormal ECG mild, 3.85%
Disc. AE
24 mg 1 times / day multiple, topical
Studied dose
Dose: 24 mg, 1 times / day
Route: topical
Route: multiple
Dose: 24 mg, 1 times / day
Sources: Page: p.196
unhealthy, 68.8
n = 26
Health Status: unhealthy
Condition: Advanced-stage Parkinson’s disease
Age Group: 68.8
Sex: M+F
Population Size: 26
Sources: Page: p.196
Hypertension mild, 3.85%
Disc. AE
24 mg 1 times / day multiple, topical
Studied dose
Dose: 24 mg, 1 times / day
Route: topical
Route: multiple
Dose: 24 mg, 1 times / day
Sources: Page: p.196
unhealthy, 68.8
n = 26
Health Status: unhealthy
Condition: Advanced-stage Parkinson’s disease
Age Group: 68.8
Sex: M+F
Population Size: 26
Sources: Page: p.196
Sensory hallucinations moderate, 3.85%
Disc. AE
24 mg 1 times / day multiple, topical
Studied dose
Dose: 24 mg, 1 times / day
Route: topical
Route: multiple
Dose: 24 mg, 1 times / day
Sources: Page: p.196
unhealthy, 68.8
n = 26
Health Status: unhealthy
Condition: Advanced-stage Parkinson’s disease
Age Group: 68.8
Sex: M+F
Population Size: 26
Sources: Page: p.196
Application site reaction moderate, 7.7%
Disc. AE
24 mg 1 times / day multiple, topical
Studied dose
Dose: 24 mg, 1 times / day
Route: topical
Route: multiple
Dose: 24 mg, 1 times / day
Sources: Page: p.196
unhealthy, 68.8
n = 26
Health Status: unhealthy
Condition: Advanced-stage Parkinson’s disease
Age Group: 68.8
Sex: M+F
Population Size: 26
Sources: Page: p.196
Allergic reaction Disc. AE
8 mg 1 times / day multiple, topical
Recommended
Dose: 8 mg, 1 times / day
Route: topical
Route: multiple
Dose: 8 mg, 1 times / day
Sources: Page: p.1
unhealthy
Health Status: unhealthy
Condition: Advanced-stage Parkinson’s disease
Sources: Page: p.1
Blood pressure increased Disc. AE
8 mg 1 times / day multiple, topical
Recommended
Dose: 8 mg, 1 times / day
Route: topical
Route: multiple
Dose: 8 mg, 1 times / day
Sources: Page: p.1
unhealthy
Health Status: unhealthy
Condition: Advanced-stage Parkinson’s disease
Sources: Page: p.1
Compulsive personality disorder Disc. AE
8 mg 1 times / day multiple, topical
Recommended
Dose: 8 mg, 1 times / day
Route: topical
Route: multiple
Dose: 8 mg, 1 times / day
Sources: Page: p.1
unhealthy
Health Status: unhealthy
Condition: Advanced-stage Parkinson’s disease
Sources: Page: p.1
Daytime sleepiness Disc. AE
8 mg 1 times / day multiple, topical
Recommended
Dose: 8 mg, 1 times / day
Route: topical
Route: multiple
Dose: 8 mg, 1 times / day
Sources: Page: p.1
unhealthy
Health Status: unhealthy
Condition: Advanced-stage Parkinson’s disease
Sources: Page: p.1
Dyskinesia Disc. AE
8 mg 1 times / day multiple, topical
Recommended
Dose: 8 mg, 1 times / day
Route: topical
Route: multiple
Dose: 8 mg, 1 times / day
Sources: Page: p.1
unhealthy
Health Status: unhealthy
Condition: Advanced-stage Parkinson’s disease
Sources: Page: p.1
Hallucinations Disc. AE
8 mg 1 times / day multiple, topical
Recommended
Dose: 8 mg, 1 times / day
Route: topical
Route: multiple
Dose: 8 mg, 1 times / day
Sources: Page: p.1
unhealthy
Health Status: unhealthy
Condition: Advanced-stage Parkinson’s disease
Sources: Page: p.1
Hypotension symptomatic Disc. AE
8 mg 1 times / day multiple, topical
Recommended
Dose: 8 mg, 1 times / day
Route: topical
Route: multiple
Dose: 8 mg, 1 times / day
Sources: Page: p.1
unhealthy
Health Status: unhealthy
Condition: Advanced-stage Parkinson’s disease
Sources: Page: p.1
Impulse-control disorder Disc. AE
8 mg 1 times / day multiple, topical
Recommended
Dose: 8 mg, 1 times / day
Route: topical
Route: multiple
Dose: 8 mg, 1 times / day
Sources: Page: p.1
unhealthy
Health Status: unhealthy
Condition: Advanced-stage Parkinson’s disease
Sources: Page: p.1
Psychotic behavior Disc. AE
8 mg 1 times / day multiple, topical
Recommended
Dose: 8 mg, 1 times / day
Route: topical
Route: multiple
Dose: 8 mg, 1 times / day
Sources: Page: p.1
unhealthy
Health Status: unhealthy
Condition: Advanced-stage Parkinson’s disease
Sources: Page: p.1
Somnolence Disc. AE
8 mg 1 times / day multiple, topical
Recommended
Dose: 8 mg, 1 times / day
Route: topical
Route: multiple
Dose: 8 mg, 1 times / day
Sources: Page: p.1
unhealthy
Health Status: unhealthy
Condition: Advanced-stage Parkinson’s disease
Sources: Page: p.1
Syncope Disc. AE
8 mg 1 times / day multiple, topical
Recommended
Dose: 8 mg, 1 times / day
Route: topical
Route: multiple
Dose: 8 mg, 1 times / day
Sources: Page: p.1
unhealthy
Health Status: unhealthy
Condition: Advanced-stage Parkinson’s disease
Sources: Page: p.1
Tachycardia Disc. AE
8 mg 1 times / day multiple, topical
Recommended
Dose: 8 mg, 1 times / day
Route: topical
Route: multiple
Dose: 8 mg, 1 times / day
Sources: Page: p.1
unhealthy
Health Status: unhealthy
Condition: Advanced-stage Parkinson’s disease
Sources: Page: p.1
Application site reaction 2%
Disc. AE
8 mg 1 times / day multiple, topical
Recommended
Dose: 8 mg, 1 times / day
Route: topical
Route: multiple
Dose: 8 mg, 1 times / day
Sources: Page: p.1, p.5
unhealthy
Health Status: unhealthy
Condition: Advanced-stage Parkinson’s disease
Sources: Page: p.1, p.5
OverviewDrug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
no
no
no
no
no
no
no
no
no
no
no (co-administration study)
Comment: rotigone did not influence the transport of digoxin
Page: 50.0
Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
minor [Km >1000 uM]
minor [Km >1000 uM]
no
no
no
no
no
no
no
no
yes
yes
yes
yes
yes
yes
Tox targets

Tox targets

TargetModalityActivityMetaboliteClinical evidence
Sourcing

Sourcing

Vendor/AggregatorIDURL
PubMed

PubMed

TitleDatePubMed
Cloning of the gene for a human dopamine D5 receptor with higher affinity for dopamine than D1.
1991 Apr 18
Patents

Sample Use Guides

Parkinson’s disease: Initially, 2 mg/24 hours for early-stage disease or 4 mg/24 hours for advanced-stage disease. The dose may be increased as needed by 2 mg/24 hours at weekly intervals, up to 6 mg/24 hours for earlystage disease and up to 8 mg/24 hours for advanced-stage disease. Restless Legs Syndrome: Initially, 1 mg/24 hours, increased as needed by 1 mg/24 hours at weekly intervals, up to 3 mg/24 hours.
Route of Administration: Transdermal
In Vitro Use Guide
The binding of [3H]N-0437 (specific activity 80.6 Ci/mmol) to calf caudate membranes is described. It was found that [3H]N-0437 binds with a high affinity (KD = 0.17 nM) and a low proportion of non-specific binding.
Name Type Language
ROTIGOTINE
EMA EPAR   INN   JAN   MART.   MI   ORANGE BOOK   USAN   VANDF   WHO-DD  
USAN   INN  
Official Name English
ROTIGOTINE [USP MONOGRAPH]
Common Name English
ROTIGOTINE [EP MONOGRAPH]
Common Name English
NEUPRO
Brand Name English
ROTIGOTINE [WHO-DD]
Common Name English
ROTIGOTINE [MI]
Common Name English
ROTIGOTINE [INN]
Common Name English
ROTIGOTINE [VANDF]
Common Name English
ROTIGOTINE [EMA EPAR]
Common Name English
SPM 962
Code English
(6S)-6-(PROPYL(2-(2-THIENYL)ETHYL)AMINO)-5,6,7,8-TETRAHYDRO-1-NAPHTHALENOL
Systematic Name English
SPM-962
Code English
ROTIGOTINE [ORANGE BOOK]
Common Name English
(-)-(S)-5,6,7,8-TETRAHYDRO-6-(PROPYL(2-(2-THIENYL)ETHYL)AMINO)-1-NAPHTHOL
Systematic Name English
ROTIGOTINE [JAN]
Common Name English
ROTIGOTINE [USAN]
Common Name English
1-NAPHTHALENOL, 5,6,7,8-TETRAHYDRO-6-(PROPYL(2-(2-THIENYL)ETHYL)AMINO-(6S)-
Common Name English
ROTIGOTINE [MART.]
Common Name English
LEGANTO
Brand Name English
ROTIGOTINE [USP-RS]
Common Name English
Classification Tree Code System Code
EMA ASSESSMENT REPORTS NEUPRO (AUTHORIZED: PARKINSON DISEASE)
Created by admin on Fri Jun 25 21:08:44 UTC 2021 , Edited by admin on Fri Jun 25 21:08:44 UTC 2021
WHO-ATC N04BC09
Created by admin on Fri Jun 25 21:08:44 UTC 2021 , Edited by admin on Fri Jun 25 21:08:44 UTC 2021
EMA ASSESSMENT REPORTS NEUPRO (AUTHORIZED: RESTLESS LEGS SYNDROME)
Created by admin on Fri Jun 25 21:08:44 UTC 2021 , Edited by admin on Fri Jun 25 21:08:44 UTC 2021
EMA ASSESSMENT REPORTS LEGANTO (AUTHORIZED: RESTLESS LEGS SYNDROME)
Created by admin on Fri Jun 25 21:08:44 UTC 2021 , Edited by admin on Fri Jun 25 21:08:44 UTC 2021
WHO-VATC QN04BC09
Created by admin on Fri Jun 25 21:08:44 UTC 2021 , Edited by admin on Fri Jun 25 21:08:44 UTC 2021
NCI_THESAURUS C66884
Created by admin on Fri Jun 25 21:08:44 UTC 2021 , Edited by admin on Fri Jun 25 21:08:44 UTC 2021
EMA ASSESSMENT REPORTS LEGANTO (AUTHORIZED: PARKINSON DISEASE)
Created by admin on Fri Jun 25 21:08:44 UTC 2021 , Edited by admin on Fri Jun 25 21:08:44 UTC 2021
Code System Code Type Description
IUPHAR
941
Created by admin on Fri Jun 25 21:08:44 UTC 2021 , Edited by admin on Fri Jun 25 21:08:44 UTC 2021
PRIMARY
INN
7897
Created by admin on Fri Jun 25 21:08:44 UTC 2021 , Edited by admin on Fri Jun 25 21:08:44 UTC 2021
PRIMARY
PUBCHEM
59227
Created by admin on Fri Jun 25 21:08:44 UTC 2021 , Edited by admin on Fri Jun 25 21:08:44 UTC 2021
PRIMARY
DRUG BANK
DB05271
Created by admin on Fri Jun 25 21:08:44 UTC 2021 , Edited by admin on Fri Jun 25 21:08:44 UTC 2021
PRIMARY
FDA UNII
87T4T8BO2E
Created by admin on Fri Jun 25 21:08:44 UTC 2021 , Edited by admin on Fri Jun 25 21:08:44 UTC 2021
PRIMARY
RXCUI
616739
Created by admin on Fri Jun 25 21:08:44 UTC 2021 , Edited by admin on Fri Jun 25 21:08:44 UTC 2021
PRIMARY RxNorm
WIKIPEDIA
ROTIGOTINE
Created by admin on Fri Jun 25 21:08:44 UTC 2021 , Edited by admin on Fri Jun 25 21:08:44 UTC 2021
PRIMARY
EVMPD
SUB21254
Created by admin on Fri Jun 25 21:08:44 UTC 2021 , Edited by admin on Fri Jun 25 21:08:44 UTC 2021
PRIMARY
HSDB
8254
Created by admin on Fri Jun 25 21:08:44 UTC 2021 , Edited by admin on Fri Jun 25 21:08:44 UTC 2021
PRIMARY
LACTMED
Rotigotine
Created by admin on Fri Jun 25 21:08:44 UTC 2021 , Edited by admin on Fri Jun 25 21:08:44 UTC 2021
PRIMARY
NCI_THESAURUS
C77566
Created by admin on Fri Jun 25 21:08:44 UTC 2021 , Edited by admin on Fri Jun 25 21:08:44 UTC 2021
PRIMARY
CAS
99755-59-6
Created by admin on Fri Jun 25 21:08:44 UTC 2021 , Edited by admin on Fri Jun 25 21:08:44 UTC 2021
PRIMARY
ChEMBL
CHEMBL1303
Created by admin on Fri Jun 25 21:08:44 UTC 2021 , Edited by admin on Fri Jun 25 21:08:44 UTC 2021
PRIMARY
MERCK INDEX
M9674
Created by admin on Fri Jun 25 21:08:44 UTC 2021 , Edited by admin on Fri Jun 25 21:08:44 UTC 2021
PRIMARY Merck Index
DRUG CENTRAL
2407
Created by admin on Fri Jun 25 21:08:44 UTC 2021 , Edited by admin on Fri Jun 25 21:08:44 UTC 2021
PRIMARY
EPA CompTox
99755-59-6
Created by admin on Fri Jun 25 21:08:44 UTC 2021 , Edited by admin on Fri Jun 25 21:08:44 UTC 2021
PRIMARY
USP_CATALOG
1606060
Created by admin on Fri Jun 25 21:08:44 UTC 2021 , Edited by admin on Fri Jun 25 21:08:44 UTC 2021
PRIMARY USP-RS