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
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
DescriptionCurator'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
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.
Originator
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL217 Sources: https://www.ncbi.nlm.nih.gov/pubmed/18704368 |
13.5 nM [Ki] | ||
83.0 nM [Ki] | |||
Target ID: CHEMBL1850 Sources: https://www.ncbi.nlm.nih.gov/pubmed/18704368 |
5.4 nM [Ki] | ||
Target ID: CHEMBL219 Sources: https://www.ncbi.nlm.nih.gov/pubmed/18704368 |
15.0 nM [Ki] | ||
Target ID: CHEMBL214 Sources: https://www.ncbi.nlm.nih.gov/pubmed/18704368 |
30.0 nM [Ki] | ||
Target ID: CHEMBL1942 Sources: https://www.ncbi.nlm.nih.gov/pubmed/18704368 |
27.0 nM [Ki] | ||
Target ID: CHEMBL234 |
0.7 nM [Ki] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | NEUPRO Approved UseNEUPRO 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 Date2007 |
|||
Primary | NEUPRO Approved UseNEUPRO 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 Date2007 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
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
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
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
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
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
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
10% |
unknown |
ROTIGOTINE plasma | Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN |
Doses
Dose | Population | Adverse events |
---|---|---|
54 mg 1 times / day multiple, topical Highest studied dose Dose: 54 mg, 1 times / day Route: topical Route: multiple Dose: 54 mg, 1 times / day Sources: Page: p.10 |
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%) Sources: Page: p.196Hypertension (mild, 3.85%) Sensory hallucinations (moderate, 3.85%) Application site reaction (moderate, 7.7%) |
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 Sources: Page: p.1Somnolence Hallucinations Psychotic behavior Dyskinesia Hypotension symptomatic Syncope Blood pressure increased Tachycardia Impulse-control disorder Compulsive personality disorder Daytime sleepiness |
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
AE | Significance | Dose | Population |
---|---|---|---|
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 |
Overview
CYP3A4 | CYP2C9 | CYP2D6 | hERG |
---|---|---|---|
OverviewOther
Drug as perpetrator
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
Page: 51.0 |
no | |||
Page: 51.0 |
no | |||
Page: 51.0 |
no | |||
Page: 51.0 |
no | |||
Page: 51.0 |
no | |||
Page: 51.0 |
no | |||
Page: 51.0 |
no | |||
Page: 51.0 |
no | |||
Page: 51.0 |
no | |||
Page: 50.0 |
no | no (co-administration study) Comment: rotigone did not influence the transport of digoxin Page: 50.0 |
Drug as victim
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
Page: 27.0 |
minor [Km >1000 uM] | |||
Page: 27.0 |
minor [Km >1000 uM] | |||
Page: 27.0 |
no | |||
Page: 27.0 |
no | |||
Page: 27.0 |
no | |||
Page: 27.0 |
no | |||
Page: 27.0 |
no | |||
Page: 27.0 |
no | |||
Page: 27.0 |
no | |||
Page: 27.0 |
no | |||
Page: 42.0 |
yes | |||
Page: 42.0 |
yes | |||
Page: 42.0 |
yes | |||
Page: 25.0 |
yes | |||
Page: 27.0 |
yes | |||
Page: 27.0 |
yes |
Tox targets
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
Page: 42.0 |
PubMed
Title | Date | PubMed |
---|---|---|
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 |
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
Sources: https://www.ncbi.nlm.nih.gov/pubmed/3569410
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.
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Code System | Code | Type | Description | ||
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DBSALT000155
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1606079
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59226
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125572-93-2
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DTXSID80154792
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6Q1W9573L2
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m9674
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PRIMARY | Merck Index |
SUBSTANCE RECORD