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

Details

Stereochemistry ABSOLUTE
Molecular Formula C19H25NOS.ClH
Molecular Weight 351.934
Optical Activity ( - )
Defined Stereocenters 1 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of ROTIGOTINE HYDROCHLORIDE

SMILES

Cl.CCCN(CCC1=CC=CS1)[C@H]2CCC3=C(C2)C=CC=C3O

InChI

InChIKey=CEXBONHIOKGWNU-NTISSMGPSA-N
InChI=1S/C19H25NOS.ClH/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;1H/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

2007
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

2007
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
Affinity for dopamine D2, D3, and D4 receptors of 2-aminotetralins. Relevance of D2 agonist binding for determination of receptor subtype selectivity.
1996 Oct 11
Rotigotine transdermal patch in the treatment of Parkinson's disease and restless legs syndrome.
2007 Jun
[Restless-legs syndrome].
2008 Aug-Sep
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 HYDROCHLORIDE
MI  
Common Name English
ROTIGOTINE HYDROCHLORIDE [MI]
Common Name English
1-NAPHTHALENOL, 5,6,7,8-TETRAHYDRO-6-(PROPYL(2-(2-THIENYL)ETHYL)AMINO)-, HYDROCHLORIDE (1:1), (6S)-
Systematic Name English
(-)-5,6,7,8-TETRAHYDRO-6-(PROPYL(2-(2-THIENYL)ETHYL)AMINO)-1-NAPHTHOL HYDROCHLORIDE
Systematic Name English
ROTIGOTINE HYDROCHLORIDE [USP-RS]
Common Name English
ROTIGOTINE HYDROCHLORIDE, (-)-
Common Name English
Code System Code Type Description
DRUG BANK
DBSALT000155
Created by admin on Fri Dec 15 15:55:31 GMT 2023 , Edited by admin on Fri Dec 15 15:55:31 GMT 2023
PRIMARY
RS_ITEM_NUM
1606079
Created by admin on Fri Dec 15 15:55:31 GMT 2023 , Edited by admin on Fri Dec 15 15:55:31 GMT 2023
PRIMARY
PUBCHEM
59226
Created by admin on Fri Dec 15 15:55:31 GMT 2023 , Edited by admin on Fri Dec 15 15:55:31 GMT 2023
PRIMARY
CAS
125572-93-2
Created by admin on Fri Dec 15 15:55:31 GMT 2023 , Edited by admin on Fri Dec 15 15:55:31 GMT 2023
PRIMARY
EPA CompTox
DTXSID80154792
Created by admin on Fri Dec 15 15:55:31 GMT 2023 , Edited by admin on Fri Dec 15 15:55:31 GMT 2023
PRIMARY
FDA UNII
6Q1W9573L2
Created by admin on Fri Dec 15 15:55:31 GMT 2023 , Edited by admin on Fri Dec 15 15:55:31 GMT 2023
PRIMARY
MERCK INDEX
m9674
Created by admin on Fri Dec 15 15:55:31 GMT 2023 , Edited by admin on Fri Dec 15 15:55:31 GMT 2023
PRIMARY Merck Index