(6S)-5,6,7,8-Tetrahydro-6-[propyl[2-(2-thienyl)ethyl]amino]-1-naphthalenyl docosanoate

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C41H67NO2S
Molecular Weight	638.041
Optical Activity	UNSPECIFIED
Defined Stereocenters	1 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure of (6S)-5,6,7,8-Tetrahydro-6-[propyl[2-(2-thienyl)ethyl]amino]-1-naphthalenyl docosanoate

Structure Search

SMILES

CCCCCCCCCCCCCCCCCCCCCC(=O)OC1=C2CC[C@@H](CC2=CC=C1)N(CCC)CCC3=CC=CS3

InChI

InChIKey=RBXGHMXFCARHAZ-QNGWXLTQSA-N

InChI=1S/C41H67NO2S/c1-3-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-22-28-41(43)44-40-27-23-25-36-35-37(29-30-39(36)40)42(32-4-2)33-31-38-26-24-34-45-38/h23-27,34,37H,3-22,28-33,35H2,1-2H3/t37-/m0/s1

HIDE SMILES / InChI

Molecular Formula	C41H67NO2S
Molecular Weight	638.041
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	1 / 1
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2015/021829s007lbl.pdf
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.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Potency
Dopamine D2 receptor 311 Target ID: CHEMBL217 Sources: https://www.ncbi.nlm.nih.gov/pubmed/18704368	Agonist 2752	13.5 nM [Ki]
Dopamine D1 receptor 106 Target ID: CHEMBL2056 Sources: https://www.ncbi.nlm.nih.gov/pubmed/18704368 http://www.ema.europa.eu/docs/en_GB/document_library/EPAR_-_Scientific_Discussion/human/000626/WC500026394.pdf	Agonist 2752	83.0 nM [Ki]
Dopamine D5 receptor 15 Target ID: CHEMBL1850 Sources: https://www.ncbi.nlm.nih.gov/pubmed/18704368	Agonist 2752	5.4 nM [Ki]
Dopamine D4 receptor 76 Target ID: CHEMBL219 Sources: https://www.ncbi.nlm.nih.gov/pubmed/18704368	Agonist 2752	15.0 nM [Ki]
Serotonin 1a (5-HT1a) receptor 177 Target ID: CHEMBL214 Sources: https://www.ncbi.nlm.nih.gov/pubmed/18704368	Agonist 2752	30.0 nM [Ki]
Alpha-2b adrenergic receptor 35 Target ID: CHEMBL1942 Sources: https://www.ncbi.nlm.nih.gov/pubmed/18704368	Antagonist 2849	27.0 nM [Ki]
Dopamine D3 receptor 97 Target ID: CHEMBL234 Sources: http://www.ema.europa.eu/docs/en_GB/document_library/EPAR_-_Scientific_Discussion/human/000626/WC500026394.pdf	Agonist 2752	0.7 nM [Ki]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Parkinson's disease 232 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2015/021829s007lbl.pdf	Primary		Approved 8583	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
Restless legs syndrome 17 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2015/021829s007lbl.pdf	Primary		Approved 8583	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

C_max

Value	Dose	Co-administered	Analyte	Population
0.34 ng/mL REVIEW https://pubmed.ncbi.nlm.nih.gov/25795100/	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 REVIEW https://pubmed.ncbi.nlm.nih.gov/25795100/	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

T_1/2

Value	Dose	Co-administered	Analyte	Population
6.5 h REVIEW https://pubmed.ncbi.nlm.nih.gov/25795100/	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

F_unbound

Value	Dose	Co-administered	Analyte	Population
10% DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2020/021829s019lbl.pdf	unknown		ROTIGOTINE plasma	Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
inhibitor 2252 inducer 1087 substrate 1946	inhibitor 2438 inducer 440	inhibitor 2507	inhibitor 2217

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
CYP1A2 2153 CYP2C19 2057 P-gp 1741	UGT1A9 423 UGT2B15 236 CYP2C19 1119 SULT1A3 31 UGT1A1 479 UGT1A3 470 UGT1A4 399 UGT1A6 343 UGT1A7 249 UGT2B4 278 UGT2B7 456 UGT2B17 237 UGT1A8 323 UGT1A10 331 CYP1A2 1197	CYP1A2 832 CYP2C19 329

Drug as perpetrator

Target	Modality	Activity	Clinical evidence
CYP1A2 2333	inducer 1966 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2007/021829s000_ClinPharmR_P1.pdf Page: 51.0	no
CYP1A2 2333	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2007/021829s000_ClinPharmR_P1.pdf Page: 51.0	no
CYP2C19 2141	inducer 1966 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2007/021829s000_ClinPharmR_P1.pdf Page: 51.0	no
CYP2C19 2141	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2007/021829s000_ClinPharmR_P1.pdf Page: 51.0	no
CYP2C9 2497	inducer 1966 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2007/021829s000_ClinPharmR_P1.pdf Page: 51.0	no
CYP2C9 2497	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2007/021829s000_ClinPharmR_P1.pdf Page: 51.0	no
CYP2D6 2546	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2007/021829s000_ClinPharmR_P1.pdf Page: 51.0	no
CYP3A4 2633	inducer 1966 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2007/021829s000_ClinPharmR_P1.pdf Page: 51.0	no
CYP3A4 2633	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2007/021829s000_ClinPharmR_P1.pdf Page: 51.0	no
P-gp 1932	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2007/021829s000_ClinPharmR_P1.pdf Page: 50.0	no	no (co-administration study) Comment: rotigone did not influence the transport of digoxin Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2007/021829s000_ClinPharmR_P1.pdf Page: 50.0

Drug as victim

Target	Modality	Activity
UGT1A10 331	substrate 4014 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2007/021829s000_ClinPharmR_P1.pdf Page: 27.0	minor [Km >1000 uM]
UGT1A8 323	substrate 4014 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2007/021829s000_ClinPharmR_P1.pdf Page: 27.0	minor [Km >1000 uM]
UGT1A1 479	substrate 4014 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2007/021829s000_ClinPharmR_P1.pdf Page: 27.0	no
UGT1A3 470	substrate 4014 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2007/021829s000_ClinPharmR_P1.pdf Page: 27.0	no
UGT1A4 399	substrate 4014 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2007/021829s000_ClinPharmR_P1.pdf Page: 27.0	no
UGT1A6 343	substrate 4014 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2007/021829s000_ClinPharmR_P1.pdf Page: 27.0	no
UGT1A7 249	substrate 4014 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2007/021829s000_ClinPharmR_P1.pdf Page: 27.0	no
UGT2B17 237	substrate 4014 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2007/021829s000_ClinPharmR_P1.pdf Page: 27.0	no
UGT2B4 278	substrate 4014 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2007/021829s000_ClinPharmR_P1.pdf Page: 27.0	no
UGT2B7 456	substrate 4014 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2007/021829s000_ClinPharmR_P1.pdf Page: 27.0	no
CYP1A2 1197	substrate 4014 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2007/021829s000_ClinPharmR_P1.pdf Page: 42.0	yes
CYP2C19 1119	substrate 4014 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2007/021829s000_ClinPharmR_P1.pdf Page: 42.0	yes
CYP3A4 1946	substrate 4014 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2007/021829s000_ClinPharmR_P1.pdf Page: 42.0	yes
SULT1A3 31	substrate 4014 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2007/021829s000_ClinPharmR_P1.pdf Page: 25.0	yes
UGT1A9 423	substrate 4014 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2007/021829s000_ClinPharmR_P1.pdf Page: 27.0	yes
UGT2B15 236	substrate 4014 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2007/021829s000_ClinPharmR_P1.pdf Page: 27.0	yes

Tox targets

Target	Modality	Activity	Metabolite	Clinical evidence
hERG 2263	inhibitor 2237 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2007/021829s000_PharmR_P1.pdf Page: 42.0

Sourcing

Vendor/Aggregator	ID	URL
AA Blocks	AA0039VR	https://www.aablocks.com/goods/Goods/detail?id=AA0039VR
Aaron Chemicals	AR003ANJ	http://www.aaronchem.com/99755-59-6
abcr GmbH	AB462946	http://www.abcr.com/shop/en/AB462946
AbMole Bioscience	M3675	http://www.abmole.com/products/rotigotine.html
Achemtek	0102-020374	http://www.achemtek.com/99755-59-6
Adooq BioScience	A11553	https://www.adooq.com/rotigotine.html
AK Scientific, Inc. (AKSCI)	2696AH	http://www.aksci.com/item_detail.php?cat=2696AH
Alichem	169006390	http://www.alichem.com/en/products/99755-59-6.html
ApexBio Technology	A3776	http://www.apexbt.com/rotigotine.html
Ark Pharma Scientific Limited	H-015999	http://www.arkpharmtech.com/product/21054.html
Aurora Fine Chemicals LLC	A24.076.584	http://online.aurorafinechemicals.com/info?ID=A24.076.584
Aurum Pharmatech LLC	W-5179	http://www.Aurumpharmatech.com/Product/ProductDetails/W_5179
AvaChem Scientific	2566B	http://www.avachem.com/productSearch.asp?2566B
Axon MedChem	1040	https://www.axonmedchem.com/product/1040
BioSynth	J-502471	https://www.biosynth.com/en/products/all-products/products/J-502471.html
Boerchem	BC677693	http://www.boerchem.com/?product_39574.html
Capot Chemical	16423	http://www.capotchem.com/en/16423.htm
Capot Chemical	PubChem16423	http://www.capotchem.com/en/16423.htm
Chem Scene	CS-0376	http://www.chemscene.com/99755-59-6.html
ChemMol	30109750	http://www.chemmol.com/chemmol/30109750.html
ChemMol	44006753	http://www.chemmol.com/chemmol/44006753.html
ChemMol	44009998	http://www.chemmol.com/chemmol/44009998.html
ChemMol	49406931	http://www.chemmol.com/chemmol/49406931.html
Chemspace	CSSB00015192657	https://chem-space.com/CSSB00015192657
DC Chemicals	DC22619	http://www.dcchemicals.com/product_show-DC22619.html
eNovation Chemicals	Y0991885	https://www.enovationchem.com/ProductDetails.asp?ProductID=Y0991885
Excenen	EX-A1164	http://www.excenen.com/searchresultlist.php?id=99755-59-6
Lab Network	LN01343330	https://labnetwork.com/frontend-app/p/#!/moleculedetails/LN01343330
LGC Standards	LGCFOR1403.00	https://www.lgcstandards.com/US/en/p/LGCFOR1403.00
LGC Standards	MM1403.00	https://www.lgcstandards.com/US/en/p/MM1403.00
Matrix Scientific	133323	https://www.matrixscientific.com/133323.html
MedChem Express	HY-75502	https://www.medchemexpress.com/rotigotine.html
MuseChem	A000135	https://www.musechem.com/product/A000135.html
OChem	23571	http://www.ocheminc.com/index.php?act=psearch&pid=572R932
Renno Tech	RL06136	http://www.rennotech.com/product_show.asp?id=6384
Smolecule	S541846	http://www.smolecule.com/products/s541846
Synblock Inc	SB19528	http://www.synblock.com/product/99755-59-6.html
THE BioTek	bt-282084	https://www.thebiotek.com/product/inhibitors/bt-282084
THE BioTek	bt-459851	https://www.thebiotek.com/product/others/bt-459851
Yuhao Chemical	XJ6723	http://www.chemyuhao.com/99755-59-6.html

PubMed

Title	Date	PubMed
Three-month subchronic intramuscular toxicity study of rotigotine-loaded microspheres in Cynomolgus monkeys.	2013-02	23165154
[Restless-legs syndrome].	2008-02-08	18656214
Rotigotine transdermal patch in the treatment of Parkinson's disease and restless legs syndrome.	2007-06	17563266
Further characterization of structural requirements for ligands at the dopamine D(2) and D(3) receptor: exploring the thiophene moiety.	2002-07-04	12086487
Affinity for dopamine D2, D3, and D4 receptors of 2-aminotetralins. Relevance of D2 agonist binding for determination of receptor subtype selectivity.	1996-10-11	8863800
Cloning of the gene for a human dopamine D5 receptor with higher affinity for dopamine than D1.	1991-04-18	1826762

Patents

Sample Use Guides

In Vivo Use Guide

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.

Substance Class	Chemical Created by `admin` on `Wed Apr 02 13:36:52 GMT 2025` Edited by `admin` on `Wed Apr 02 13:36:52 GMT 2025`
Record UNII	E9ML9M3ZYP
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

(6S)-5,6,7,8-Tetrahydro-6-[propyl[2-(2-thienyl)ethyl]amino]-1-naphthalenyl docosanoate

Systematic Name

English

Docosanoic acid, (6S)-5,6,7,8-tetrahydro-6-[propyl[2-(2-thienyl)ethyl]amino]-1-naphthalenyl ester

Preferred Name

English

Code System Code Type Description

FDA UNII

E9ML9M3ZYP

Created by admin on Wed Apr 02 13:36:52 GMT 2025 , Edited by admin on Wed Apr 02 13:36:52 GMT 2025

PRIMARY

CAS

2172880-48-5

Created by admin on Wed Apr 02 13:36:52 GMT 2025 , Edited by admin on Wed Apr 02 13:36:52 GMT 2025

PRIMARY

PUBCHEM

171390015

Created by admin on Wed Apr 02 13:36:52 GMT 2025 , Edited by admin on Wed Apr 02 13:36:52 GMT 2025

PRIMARY

Related Record Type Details


					87T4T8BO2E

ROTIGOTINE

METABOLITE ACTIVE -> PRODRUG

Amount:

Related Record Type Details


					87T4T8BO2E

ROTIGOTINE

ACTIVE MOIETY

Amount:

Details

SMILES

InChI

CNS Activity

Originator

Approval Year

Targets

Conditions

Approved Use

Launch Date

Approved Use

Launch Date

Cmax

AUC

T1/2

Funbound

Overview

OverviewOther

Drug as perpetrator​

Drug as victim

Tox targets

Sourcing

PubMed

Patents

Sample Use Guides

C_max

T_1/2

F_unbound

Drug as perpetrator