Details of the Drug Metabolized by Drug-Metabolizing Enzyme (DME)

General Information of Drug (ID: DR3548)
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 Restless legs syndrome [ICD11: 7A80] Phase 4 [1]
Parkinsonism [ICD11: ICD11: 8A00] Phase 3 [2]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 315.5 Topological Polar Surface Area 51.7
Heavy Atom Count 22 Rotatable Bond Count 6
Hydrogen Bond Donor Count 1 Hydrogen Bond Acceptor Count 3
Cross-matching ID
PubChem CID
59227
ChEBI ID
CHEBI:135351
CAS Number
99755-59-6
TTD Drug ID
D81KMY
Formula
C19H25NOS
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
The Metabolic Roadmap of This Drug
The Full List of Drug Metabolites (DM) of This Drug
DM Name DM ID PubChem ID Reaction DM Level REF
N-despropyl-rotigotine DM015902
15107528
Unclear - Unclear 1 [5] , [3]
N-desthienylethyl-rotigotine DM015666
10375676
Unclear - Unclear 1 [5]
Neupro Metabolite M4 DM017737 N. A. Unclear - Unclear 1 [5]
Neupro Metabolite M5 DM016424
91995539
Unclear - Unclear 1 [5] , [4]
Neupro Metabolite M1 DM017734 N. A. Unclear - Unclear 2 [5]
Neupro Metabolite M2 DM016695
139600627
Unclear - Unclear 2 [5] , [3]
Neupro Metabolite M3 DM017735 N. A. Unclear - Unclear 2 [5]
Neupro Metabolite M6 DM017736 N. A. Unclear - Unclear 2 [5]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR009255 Neupro N-despropyl-rotigotine Unclear - Unclear CYP1A2 ... [5], [3]
MR009258 Neupro N-desthienylethyl-rotigotine Unclear - Unclear Unclear [5]
MR009261 Neupro Neupro Metabolite M4 Unclear - Unclear Unclear [5]
MR009262 Neupro Neupro Metabolite M5 Unclear - Unclear SULT1A1 ... [5], [4]
MR009256 N-despropyl-rotigotine Neupro Metabolite M1 Unclear - Unclear Unclear [5]
MR009257 N-despropyl-rotigotine Neupro Metabolite M2 Unclear - Unclear CYP1A2 ... [5], [3]
MR009259 N-desthienylethyl-rotigotine Neupro Metabolite M3 Unclear - Unclear Unclear [5]
MR009260 N-desthienylethyl-rotigotine Neupro Metabolite M6 Unclear - Unclear Unclear [5]
⏷ Show the Full List of 8 MR(s)
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Cytochrome P450 1A2 (CYP1A2) DME0003 Homo sapiens
CP1A2_HUMAN
1.14.14.1
[3]
Cytochrome P450 2C9 (CYP2C9) DME0019 Homo sapiens
CP2C9_HUMAN
1.14.14.1
[3]
Cytochrome P450 2D6 (CYP2D6) DME0009 Homo sapiens
CP2D6_HUMAN
1.14.14.1
[3]
Cytochrome P450 3A4 (CYP3A4) DME0001 Homo sapiens
CP3A4_HUMAN
1.14.14.55
[3]
Mephenytoin 4-hydroxylase (CYP2C19) DME0021 Homo sapiens
CP2CJ_HUMAN
1.14.14.1
[3]
Sulfotransferase 1A1 (SULT1A1) DME0008 Homo sapiens
ST1A1_HUMAN
2.8.2.1
[4]
Sulfotransferase 1A2 (SULT1A2) DME0062 Homo sapiens
ST1A2_HUMAN
2.8.2.1
[4]
Sulfotransferase 1A3 (SULT1A3) DME0063 Homo sapiens
ST1A3_HUMAN
2.8.2.1
[4]
Sulfotransferase 1B1 (SULT1B1) DME0380 Homo sapiens
ST1B1_HUMAN
2.8.2.1
[4]
Sulfotransferase 1C4 (SULT1C4) DME0383 Homo sapiens
ST1C4_HUMAN
2.8.2.1
[4]
Sulfotransferase 1E1 (SULT1E1) DME0061 Homo sapiens
ST1E1_HUMAN
2.8.2.4
[4]
⏷ Show the Full List of 11  DME(s)
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 No influence of the CYP2C19-selective inhibitor omeprazole on the pharmacokinetics of the dopamine receptor agonist rotigotine
4 Identification of the human SULT enzymes involved in the metabolism of rotigotine. J Clin Pharmacol. 2016 Jun;56(6):754-60.
5 Absorption, disposition, metabolic fate, and elimination of the dopamine agonist rotigotine in man: administration by intravenous infusion or transdermal delivery

If you find any error in data or bug in web service, please kindly report it to Dr. Yin and Dr. Li.