Details of the Drug

General Information of Drug (ID: DMHEAB1)

Drug Name

Neupro

Synonyms

Rotigotine; 99755-59-6; Leganto; SPM 962; (S)-6-(propyl(2-(thiophen-2-yl)ethyl)amino)-5,6,7,8-tetrahydronaphthalen-1-ol; (6S)-rotigotine; UNII-87T4T8BO2E; (6S)-6-[propyl(2-thiophen-2-ylethyl)amino]-5,6,7,8-tetrahydronaphthalen-1-ol; SPM-962; N 0923; CHEMBL1303; 87T4T8BO2E; 99755-59-6 (free base); (6S)-6-(Propyl(2-(2-thienyl)ethyl)amino)-5,6,7,8-tetrahydro-1-naphthalenol; NCGC00168748-01; Rotigotine CDS Patch; (6s)-5,6,7,8-tetrahydro-6-[propyl[2-(2-thienyl)ethyl]amino]-1-naphthalenol; DSSTox_CID_26772; DSSTox_RID_81893; DSSTox_GSID_46772; C19H25NOS; Rotigotine CDS; (S)-5,6,7,8-Tetrahydro-6-(propyl(2-(2-thienyl)ethyl)amino)-1-naphthol; (S)-6-[Propyl-(2-thiophen-2-yl-ethyl)-amino]-5,6,7,8-tetrahydro-naphthalen-1-ol; CAS-99755-59-6; Neupro (TN); N-0923; Rotigotine [USAN:INN:BAN]; (S)-5,6,7,8-tetrahydro-6-[propyl[2-(2-thienyl)ethyl]amino]-1-naphthol; (S)-6-[Propyl[2-(thiophen-2-yl)ethyl]amino]-5,6,7,8-tetrahydronaphthalen-1-ol; SPM-936; SPM-937; PubChem16423; (-)-(S)-5,6,7,8-Tetrahydro-6-(propyl(2-(2-thienyl)ethyl)amino)-1-naphthol; GTPL941; cc-129; Rotigotine (JAN/USAN/INN); (-)-N-0437; SCHEMBL1088585; ZINC4028; DTXSID5046772; HSDB 8254; (2S)-2-[propyl-[2-(2-thienyl)ethyl]amino]tetralin-5-ol; CHEBI:135351; HMS3885D17; EX-A1164; Tox21_112627; 2696AH; BDBM50123626; MFCD00870193; s4274; AKOS016340728; Tox21_112627_1; AC-3547; CCG-267650; CS-0376; DB05271; SB19528; SS-4572; 1-naphthalenol, 5,6,7,8-tetrahydro-6-(propyl (2-(2-thienyl)ethyl)amino-(6S)-; NCGC00168748-02; HY-75502; AB0088886; SW220014-1; D05768; W-5179; 572R932; A846076; Q411985; J-502471; UNII-5QTR54Z0E1 component KFQYTPMOWPVWEJ-INIZCTEOSA-N; (6S)-6-(propyl-(2-thiophen-2-ylethyl)amino)-5,6,7,8-tetrahydronaphthalen-1-ol; 1-Naphthalenol, 5,6,7,8-tetrahydro-6-(propyl(2-(2-thienyl)ethyl)amino)-, (6S)-

Indication

Disease Entry	ICD 11	Status	REF
Restless legs syndrome	7A80	Phase 4	[1]
Parkinson disease	8A00.0	Phase 3	[2]
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Drug Type

Small molecular drug

Structure

3D MOL

2D MOL

#Ro5 Violations (Lipinski): 0

Molecular Weight (mw)

315.5

Logarithm of the Partition Coefficient (xlogp)

4.9

Rotatable Bond Count (rotbonds)

6

Hydrogen Bond Donor Count (hbonddonor)

1

Hydrogen Bond Acceptor Count (hbondacc)

3

ADMET Property

BDDCS Class: Biopharmaceutics Drug Disposition Classification System (BDDCS) Class 1: high solubility and high permeability [3]
Clearance: The drug present in the plasma can be removed from the body at the rate of 37 mL/min/kg [4]
Elimination: 0% of drug is excreted from urine in the unchanged form [3]
Half-life: The concentration or amount of drug in body reduced by one-half in 4 hours [4]
MRTD: The Maximum Recommended Therapeutic Dose (MRTD) of drug that ensured maximising efficacy and moderate side effect is 0.36226 micromolar/kg/day [5]
Unbound Fraction: The unbound fraction of drug in plasma is 0.08% [4]
Vd: Fluid volume that would be required to contain the amount of drug present in the body at the same concentration as in the plasma 5.7 L/kg [4]
Water Solubility: The ability of drug to dissolve in water is measured as 5.6 mg/mL [3]

Chemical Identifiers

Formula: C19H25NOS
IUPAC Name: (6S)-6-[propyl(2-thiophen-2-ylethyl)amino]-5,6,7,8-tetrahydronaphthalen-1-ol
Canonical SMILES: CCCN(CCC1=CC=CS1)[C@H]2CCC3=C(C2)C=CC=C3O
InChI: 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
InChIKey: KFQYTPMOWPVWEJ-INIZCTEOSA-N

Cross-matching ID

PubChem CID: 59227
ChEBI ID: CHEBI:135351
CAS Number: 99755-59-6
DrugBank ID: DB05271
TTD ID: D81KMY
ACDINA ID: D01405

Repurposed Drugs (RPD)

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Molecular Interaction Atlas of This Drug

Drug Therapeutic Target (DTT)

DTT Name	DTT ID	UniProt ID	MOA	REF
Dopamine receptor (DR)	TTWFZ1N	NOUNIPROTAC	Agonist	[6]

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Molecular Interaction Atlas (MIA)

MIA Detail

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Drug-Drug Interaction (DDI) Information of This Drug

Coadministration of a Drug Treating the Disease Different from Neupro (Comorbidity)

DDI Drug Name	DDI Drug ID	Severity	Mechanism	Comorbidity	REF
OPC-34712	DMHG57U	Moderate	Additive hypotensive effects by the combination of Neupro and OPC-34712.	Depression [6A70-6A7Z]	[7]
Esketamine	DMVU687	Moderate	Additive CNS depression effects by the combination of Neupro and Esketamine.	Depression [6A70-6A7Z]	[8]
ITI-007	DMUQ1DO	Moderate	Antagonize the effect of Neupro when combined with ITI-007.	Insomnia [7A00-7A0Z]	[7]
Allopregnanolone	DMNLHAC	Moderate	Additive CNS depression effects by the combination of Neupro and Allopregnanolone.	Mental/behavioural/neurodevelopmental disorder [6E20-6E8Z]	[9]
Lasmiditan	DMXLVDT	Moderate	Additive CNS depression effects by the combination of Neupro and Lasmiditan.	Migraine [8A80]	[10]
Amisulpride	DMSJVAM	Major	Additive CNS depression effects by the combination of Neupro and Amisulpride.	Schizophrenia [6A20]	[8]
Asenapine	DMSQZE2	Moderate	Antagonize the effect of Neupro when combined with Asenapine.	Schizophrenia [6A20]	[7]
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⏷ Show the Full List of 7 DDI Information of This Drug

Drug Inactive Ingredient(s) (DIG) and Formulation(s) of This Drug

DIG

DIG Name	DIG ID	PubChem CID	Functional Classification
Ascorbyl palmitate	E00581	54680660	Antioxidant
DL-alpha-tocopherol	E00052	2116	Antioxidant
Povidone	E00667	Not Available	Binding agent; Coating agent; Disintegrant; Film/membrane-forming agent; Solubilizing agent; Suspending agent
Sodium metabisulfite	E00444	656671	Antimicrobial preservative; Antioxidant
Silicone adhesive	E00683	17317	Binding agent
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Pharmaceutical Formulation

Formulation Name	Drug Dosage	Dosage Form	Route
Rotigotine 1mg extended release film	1mg	Extended Release Film	Transdermal
Rotigotine 2mg extended release film	2mg	Extended Release Film	Transdermal
Rotigotine 3mg extended release film	3mg	Extended Release Film	Transdermal
Rotigotine 4mg extended release film	4mg	Extended Release Film	Transdermal
Rotigotine 6mg extended release film	6mg	Extended Release Film	Transdermal
Rotigotine 8mg extended release film	8mg	Extended Release Film	Transdermal

Jump to Detail Pharmaceutical Formulation Page of This Drug

References

1	ClinicalTrials.gov (NCT01976871) Switching From Oral Dopamine Agonists to Rotigotine (SWITCH). U.S. National Institutes of Health.
2	ClinicalTrials.gov (NCT01723904) A Phase 3b, Open-Label, Safety and Efficacy Study of Rotigotine as Add-On Therapy With Low Doses of Pramipexole or Ropinirole in Patients With Advanced Parkinson's Disease. U.S. National Institutes of Health.
3	BDDCS applied to over 900 drugs
4	Trend Analysis of a Database of Intravenous Pharmacokinetic Parameters in Humans for 1352 Drug Compounds
5	Estimating the safe starting dose in phase I clinical trials and no observed effect level based on QSAR modeling of the human maximum recommended daily dose
6	Rotigotine Transdermal Patch: A Review in Parkinson's Disease. CNS Drugs. 2019 Jul;33(7):707-718.
7	Mims RB, Scott CL, Modebe O, Bethune JE "Inhibition of L-dopa-induced growth hormone stimulation by pyridoxine and chlorpromazine." J Clin Endocrinol Metab 40 (1975): 256-9. [PMID: 1117978]
8	Cerner Multum, Inc. "Australian Product Information.".
9	Product Information. Zulresso (brexanolone). Sage Therapeutics, Inc., Cambridge, MA.
10	Product Information. Reyvow (lasmiditan). Lilly, Eli and Company, Indianapolis, IN.