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

General Information of Drug (ID: DR1531)
Drug Name
Tapentadol
Synonyms
Tapentadol; Tapentadol (USAN/INN); Tapentadol [USAN:INN]; (R,R)-Tapentadol; 175591-23-8; 3-((1R,2R)-3-(Dimethylamino)-1-ethyl-2-methylpropyl)phenol; Nucynta; Palexia; 3-((2R,3R)-1-(dimethylamino)-2-methylpentan-3-yl)phenol; 3-(1-DIMETHYLAMINO-2-METHYL-PENTAN-3-YL)PHENOL; 3-[(2R,3R)-1-(dimethylamino)-2-methylpentan-3-yl]phenol; BN 200; BN-200; CG 5503; CG-5503; CG5503; H8A007M585; Phenol, 3-((1R,2R)-3-(dimethylamino)-1-ethyl-2-methylpropyl)-; UNII-H8A007M585; phenol, 3-[(1r,2r)-3-(dimethylamino)-1-ethyl-2-methylpropyl]-
Indication Neuropathic pain [ICD11: 8E43] Approved [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 221.34 Topological Polar Surface Area 23.5
Heavy Atom Count 16 Rotatable Bond Count 5
Hydrogen Bond Donor Count 1 Hydrogen Bond Acceptor Count 2
Cross-matching ID
PubChem CID
9838022
PubChem SID
14892326 ; 24136893 ; 44936111 ; 47207665 ; 50598570 ; 57373488 ; 87692438 ; 124772162 ; 126644483 ; 126666948 ; 128445985 ; 135207317 ; 135693229 ; 135693230 ; 136980026 ; 137147726 ; 142418252 ; 144115428 ; 152090609 ; 160693267 ; 160865464 ; 162012004 ; 164041986 ; 172919383 ; 174527899 ; 175267498 ; 175427057 ; 179150074 ; 187051780 ; 210276624 ; 223519387 ; 223661873 ; 224282350 ; 226489097 ; 252481185
ChEBI ID
CHEBI:135935
CAS Number
175591-23-8
TTD Drug ID
D0K4MH
Formula
C14H23NO
Canonical SMILES
CCC(C1=CC(=CC=C1)O)C(C)CN(C)C
InChI
1S/C14H23NO/c1-5-14(11(2)10-15(3)4)12-7-6-8-13(16)9-12/h6-9,11,14,16H,5,10H2,1-4H3/t11-,14+/m0/s1
InChIKey
KWTWDQCKEHXFFR-SMDDNHRTSA-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
hydroxy tapentado DM000449 N. A. Oxidation - Hydroxylation 1 [3]
N-desmethyl tapentadol DM000446
71159880
Unclear 1 [3] , [6]
Tapentadol O-sulfate DM000450
71752327
Conjugation - Conjugation 1 [5] , [3] , [2]
Tapentadol-O-glucuronide DM000451
71752323
Conjugation - Conjugation 1 [3] , [7]
N-Demethyltapentadol-O-glucuronide DM000447 N. A. Conjugation - Conjugation 2 [6] , [2]
N-desmethyltapentadol-O-sulfate DM000448 N. A. Oxidation - Deamination 2 [2] , [2]
Unclear DM009999 N. A. Conjugation - Conjugation 2 [6]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR002334 Tapentadol N-desmethyl tapentadol Unclear CYP2C9 ... [3], [6]
MR002335 Tapentadol hydroxy tapentado Oxidation - Hydroxylation CYP2D6 [3]
MR002336 Tapentadol Tapentadol O-sulfate Conjugation - Conjugation UGT1A9 ... [5], [3], [2]
MR002337 Tapentadol Tapentadol-O-glucuronide Conjugation - Conjugation SULT1A3 ... [3], [7]
MR002333 hydroxy tapentado . Conjugation - Conjugation Unclear [6]
MR002331 N-desmethyl tapentadol N-Demethyltapentadol-O-glucuronide Conjugation - Conjugation Unclear [6], [2]
MR002332 N-desmethyl tapentadol N-desmethyltapentadol-O-sulfate Oxidation - Deamination ADA [2], [2]
⏷ Show the Full List of 7 MR(s)
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Adenosine aminohydrolase (ADA) DME0060 Homo sapiens
ADA_HUMAN
3.5.4.4
[2]
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]
Mephenytoin 4-hydroxylase (CYP2C19) DME0021 Homo sapiens
CP2CJ_HUMAN
1.14.14.1
[4]
Sulfotransferase 1A1 (SULT1A1) DME0008 Homo sapiens
ST1A1_HUMAN
2.8.2.1
[5]
Sulfotransferase 1A3 (SULT1A3) DME0063 Homo sapiens
ST1A3_HUMAN
2.8.2.1
[5]
Sulfotransferase 1C4 (SULT1C4) DME0383 Homo sapiens
ST1C4_HUMAN
2.8.2.1
[5]
UDP-glucuronosyltransferase 1A9 (UGT1A9) DME0042 Homo sapiens
UD19_HUMAN
2.4.1.17
[3]
UDP-glucuronosyltransferase 2B7 (UGT2B7) DME0040 Homo sapiens
UD2B7_HUMAN
2.4.1.17
[3]
⏷ Show the Full List of 9  DME(s)
References
1 Tapentadol was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 A case report on fatal intoxication by tapentadol: Study of distribution and metabolism Forensic Sci Int. 2021 Jul;324:110825. doi: 10.1016/j.forsciint.2021.110825.
3 Investigations into the drug-drug interaction potential of tapentadol in human liver microsomes and fresh human hepatocytes. Drug Metab Lett. 2008 Jan;2(1):67-75.
4 Investigations into the drug-drug interaction potential of tapentadol in human liver microsomes and fresh human hepatocytes Drug Metab Lett. 2008 Jan;2(1):67-75. doi: 10.2174/187231208783478434.
5 On the Molecular Basis Underlying the Metabolism of Tapentadol Through Sulfation Eur J Drug Metab Pharmacokinet. 2017 Oct;42(5):793-800. doi: 10.1007/s13318-016-0392-8.
6 LABEL:UCYNTA- tapentadol hydrochloride tablet, film coated
7 In vitro and in vivo characterization of tapentadol metabolites Methods Find Exp Clin Pharmacol. 2010 Jan-Feb;32(1):31-8. doi: 10.1358/mf.2010.32.1.1434165.

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