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

General Information of Drug (ID: DR1627)
Drug Name
Tramadol hydrochloride
Synonyms
Tadol; Trabar; Tradol-Puren; Tradonal; Tramadex; Tramadol HCl; Tramadol hydrochloride [USAN:JAN]; Tramagetic; Tramal; Tramazac; Tramed; Tramol; Tridol; Tridural; Ultram ER; Zumatran; Zydol; Zydol hydrochloride; cis-Tramadol hydrochloride; tramadol hydrochloride; Tilodol; Ultram; 2-((Dimethylamino)methyl)-1-(3-methoxyphenyl)cyclohexan-1-ol; 2-(dimethylaminomethyl)-1-(3-methoxyphenyl)cyclohexan-1-ol; 2-Dimethylaminomethyl-1-(m-methoxyphenyl)cyclohexanol; 2-[(Dimethylamino)methyl]-1-(3-methoxyphenyl)cyclohexanol; 2914-77-4; AC1L1KJ8; AC1Q7AST; CHEBI:75722; CHEMBL1237044; CTK4G2807; Cyclohexanol, 2-(dimethylaminomethyl)-1-(m-methoxyphenyl)-; DTXSID00860388; EINECS 220-831-4; GTPL8286; Maxitram; SCHEMBL57496; TVYLLZQTGLZFBW-UHFFFAOYSA-N; (+)-Tramadol Hydrochloride; 148229-78-1; 22204-88-2; 36282-47-0; Amadol; Bellatram; CG 315; CG-315E; CHEBI:75733; Contramal; Dolana; EINECS 252-950-2; HSDB 7047; Mabron; Melanate; Omnidol; Poltram; Radol; Ryzolt
Indication Neuropathic pain [ICD11: 8E43] Approved [1]
Structure
3D MOL is unavailable 2D MOL
Pharmaceutical Properties Molecular Weight 299.83 Topological Polar Surface Area 32.7
Heavy Atom Count 20 Rotatable Bond Count 4
Hydrogen Bond Donor Count 2 Hydrogen Bond Acceptor Count 3
Cross-matching ID
PubChem CID
63013
ChEBI ID
CHEBI:75733
CAS Number
36282-47-0
TTD Drug ID
D05GKD
Formula
C16H26ClNO2
Canonical SMILES
CN(C)CC1CCCCC1(C2=CC(=CC=C2)OC)O.Cl
InChI
1S/C16H25NO2.ClH/c1-17(2)12-14-7-4-5-10-16(14,18)13-8-6-9-15(11-13)19-3;/h6,8-9,11,14,18H,4-5,7,10,12H2,1-3H3;1H/t14-,16+;/m1./s1
InChIKey
PPKXEPBICJTCRU-XMZRARIVSA-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-Desmethyltramadol DM002358
198555
Oxidation - N-Demethylation 1 [4] , [5]
O-Desmethyltramadol DM002354
130829
Oxidation - O-Demethylation 1 [4] , [5]
N,N-didesmethyltramadol DM002359
10105488
Oxidation - O-Demethylation 2 [6]
N,O-didesmethyltramadol DM002355
9816106
Oxidation - O-Demethylation 2 [6]
N,O-didesmethyltramadol DM002355
9816106
Oxidation - N-Demethylation 2 [6]
O-Desmethyl-tramado glucuronide metabolite DM002357
74600257
Oxidation - N-Demethylation 2 [3]
N,N,O-tridesmethyl-tramadol DM002356
10220107
Oxidation - O-Demethylation 3 [6]
N,N,O-tridesmethyl-tramadol DM002356
10220107
Unclear 3 [6]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR003380 Tramadol hydrochloride O-Desmethyltramadol Oxidation - O-Demethylation CYP2D6 [4], [5]
MR003381 Tramadol hydrochloride N-Desmethyltramadol Oxidation - N-Demethylation CYP2B6 ... [4], [5]
MR003377 N-Desmethyltramadol N,O-didesmethyltramadol Oxidation - O-Demethylation CYP2D6 [6]
MR003378 N-Desmethyltramadol N,N-didesmethyltramadol Oxidation - O-Demethylation CYP2B6 ... [6]
MR003374 O-Desmethyltramadol N,O-didesmethyltramadol Oxidation - N-Demethylation CYP2D6 [6]
MR003375 O-Desmethyltramadol O-Desmethyl-tramado glucuronide metabolite Oxidation - N-Demethylation UGT1A8 ... [3]
MR003379 N,N-didesmethyltramadol N,N,O-tridesmethyl-tramadol Oxidation - O-Demethylation Unclear [6]
MR003376 N,O-didesmethyltramadol N,N,O-tridesmethyl-tramadol Unclear Unclear [6]
⏷ 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 2B6 (CYP2B6) DME0020 Homo sapiens
CP2B6_HUMAN
1.14.14.1
[2]
Cytochrome P450 2D6 (CYP2D6) DME0009 Homo sapiens
CP2D6_HUMAN
1.14.14.1
[2]
Cytochrome P450 3A4 (CYP3A4) DME0001 Homo sapiens
CP3A4_HUMAN
1.14.14.55
[2]
UDP-glucuronosyltransferase 1A8 (UGT1A8) DME0064 Homo sapiens
UD18_HUMAN
2.4.1.17
[3]
UDP-glucuronosyltransferase 2B7 (UGT2B7) DME0040 Homo sapiens
UD2B7_HUMAN
2.4.1.17
[3]
References
1 Tramadol Hydrochloride was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 Clinical pharmacology of tramadol. Clin Pharmacokinet. 2004;43(13):879-923.
3 DrugBank : Tramadol hydrochloride
4 Trends in Tramadol: Pharmacology, Metabolism, and Misuse Anesth Analg. 2017 Jan;124(1):44-51. doi: 10.1213/ANE.0000000000001683.
5 Simultaneous LC-MS/MS quantification of oxycodone, tramadol and fentanyl and their metabolites (noroxycodone, oxymorphone, O- desmethyltramadol, N- desmethyltramadol, and norfentanyl) in human plasma and whole blood collected via venepuncture and volumetric absorptive micro sampling. J Pharm Biomed Anal. 2021 Sep 5;203:114171. doi: 10.1016/j.jpba.2021.114171.
6 Pharmacogenomics knowledge for personalized medicine Clin Pharmacol Ther. 2012 Oct;92(4):414-7. doi: 10.1038/clpt.2012.96.

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