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

General Information of Drug (ID: DR1446)
Drug Name
Rotigotine
Synonyms
Rotigotine; Rotigotine CDS; Rotigotine CDS Patch; SPM 962; SPM-962; (-)-(S)-5,6,7,8-Tetrahydro-6-(propyl(2-(2-thienyl)ethyl)amino)-1-naphthol; Leganto; N 0923; Neupro; (6S)-6-(Propyl(2-(2-thienyl)ethyl)amino)-5,6,7,8-tetrahydro-1-naphthalenol; (6S)-6-[propyl(2-thiophen-2-ylethyl)amino]-5,6,7,8-tetrahydronaphthalen-1-ol; (S)-6-(propyl(2-(thiophen-2-yl)ethyl)amino)-5,6,7,8-tetrahydronaphthalen-1-ol; 87T4T8BO2E; 99755-59-6; C19H25NOS; CHEMBL1303; DSSTox_CID_26772; DSSTox_RID_81893; NCGC00168748-01; UNII-87T4T8BO2E
Indication Parkinsonism [ICD11: 8A00] Approved [1]
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
Formula
C19H25NOS
Canonical SMILES
CCCN(CCC1=CC=CS1)C2CCC3=C(C2)C=CC=C3O
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 [4]
N-desthienylethyl-rotigotine DM015666
10375676
Unclear - Unclear 1 [4]
Rotigotine glucuronide DM016336
71752119
Conjugation - Glucuronidation 1 [4]
Rotigotine Sulfate DM016338
71752122
Oxidation - Sulfonation 1 [4]
N-Despropyl rotigotine glucuronide DM016796
155928961
Conjugation - Glucuronidation 2 [4]
N-Despropyl rotigotine sulfate DM016409
91800200
Oxidation - Sulfonation 2 [4]
N-desthienylethyl-rotigotine Glucuronide DM017927 N. A. Conjugation - Glucuronidation 2 [4]
N-desthienylethyl-rotigotine Sulfate DM017926 N. A. Oxidation - Sulfonation 2 [4]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR009594 Rotigotine N-despropyl-rotigotine Unclear - Unclear Unclear [4]
MR009597 Rotigotine N-desthienylethyl-rotigotine Unclear - Unclear Unclear [4]
MR009600 Rotigotine Rotigotine Sulfate Oxidation - Sulfonation Unclear [4]
MR009601 Rotigotine Rotigotine glucuronide Conjugation - Glucuronidation Unclear [4]
MR009595 N-despropyl-rotigotine N-Despropyl rotigotine sulfate Oxidation - Sulfonation Unclear [4]
MR009596 N-despropyl-rotigotine N-Despropyl rotigotine glucuronide Conjugation - Glucuronidation Unclear [4]
MR009598 N-desthienylethyl-rotigotine N-desthienylethyl-rotigotine Sulfate Oxidation - Sulfonation Unclear [4]
MR009599 N-desthienylethyl-rotigotine N-desthienylethyl-rotigotine Glucuronide Conjugation - Glucuronidation Unclear [4]
⏷ 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 3A4 (CYP3A4) DME0001 Homo sapiens
CP3A4_HUMAN
1.14.14.55
[2]
Sulfotransferase 1A1 (SULT1A1) DME0008 Homo sapiens
ST1A1_HUMAN
2.8.2.1
[3]
Sulfotransferase 1A2 (SULT1A2) DME0062 Homo sapiens
ST1A2_HUMAN
2.8.2.1
[3]
Sulfotransferase 1A3 (SULT1A3) DME0063 Homo sapiens
ST1A3_HUMAN
2.8.2.1
[3]
Sulfotransferase 1B1 (SULT1B1) DME0380 Homo sapiens
ST1B1_HUMAN
2.8.2.1
[3]
Sulfotransferase 1C4 (SULT1C4) DME0383 Homo sapiens
ST1C4_HUMAN
2.8.2.1
[3]
Sulfotransferase 1E1 (SULT1E1) DME0061 Homo sapiens
ST1E1_HUMAN
2.8.2.4
[3]
⏷ Show the Full List of 7  DME(s)
References
1 Rotigotine was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 Receptor-binding and pharmacokinetic properties of dopaminergic agonists. Curr Top Med Chem. 2008;8(12):1049-67.
3 Identification of the human SULT enzymes involved in the metabolism of rotigotine. J Clin Pharmacol. 2016 Jun;56(6):754-60.
4 Absorption, disposition, metabolic fate, and elimination of the dopamine agonist rotigotine in man: administration by intravenous infusion or transdermal delivery

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