Drug Details

General Information of the Drug (ID: DR1957)
Name
Tapentadol
Synonyms
Nucynta; Palexia; UNII-H8A007M585; 3-((1R,2R)-3-(Dimethylamino)-1-ethyl-2-methylpropyl)phenol; 3-((2R,3R)-1-(dimethylamino)-2-methylpentan-3-yl)phenol; phenol, 3-[(1r,2r)-3-(dimethylamino)-1-ethyl-2-methylpropyl]-; BN-200; H8A007M585; CG-5503; (R,R)-Tapentadol; Tapentadol [USAN:INN]; 3-[(2R,3R)-1-(dimethylamino)-2-methylpentan-3-yl]phenol; Phenol, 3-((1R,2R)-3-(dimethylamino)-1-ethyl-2-methylpropyl)-; CG5503; BN 200; CG 5503; Tapentadol (USAN/INN); 3-(1-DIMETHYLAMINO-2-METHYL-PENTAN-3-YL)PHENOL; 175591-23-8
    Click to Show/Hide
Molecular Type
Small molecule
Disease Acute pain [ICD-11: MG31] Approved [1]
Structure
Click to Download Mol
2D MOL

3D MOL

    Click to Show/Hide the Molecular Information and External Link(s) of This Natural Product
Formula
C14H23NO
PubChem CID
9838022
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
CAS Number
CAS 175591-23-8
TTD Drug ID
D0K4MH
DrugBank ID
DB06204
Combinatorial Therapeutic Effect(s) Validated Clinically or Experimentally
    α. A List of Natural Product(s) Able to Enhance the Efficacy of This Drug
          Epigallocatechin gallate      Hamamelis virginiana     Click to Show/Hide the Molecular Data of This NP
                 Augmenting Drug Sensitivity     Click to Show/Hide
                    Representative Experiment Reporting the Effect of This Combination [2]
                    Detail(s)  Combination Info  click to show the detail info of this combination
                    In-vitro Model MDA-MB-231 CVCL_0062 Breast adenocarcinoma Homo sapiens
                    Experimental
                    Result(s)		 EGCG and TAP reduced the proliferation of MDA-MB-231 cells by impairing cell-cycle progression.
          Pregabalin      Homo sapiens     Click to Show/Hide the Molecular Data of This NP
                 Achieving Therapeutic Synergy     Click to Show/Hide
                    Representative Experiment Reporting the Effect of This Combination [3]
                    Detail(s)  Combination Info  click to show the detail info of this combination
                    In-vivo Model For a xenograft model: Male Sprague Dawley rats (120-140 g) were anaesthetized with isoflurane, and arthritis was induced in the left knee by an intrarticular injection of 2 mg MIA in 25 ul of 0.9% saline.
                    Experimental
                    Result(s)		 The combination therapy of tapentadol and pregabalin restored descending noradrenergic inhibitory tone and also inhibited nociceptive transmission at the level of the spinal cord can provide superior analgesia.
Target and Pathway
Target(s) Norepinephrine transporter (NET)  Molecule Info  [1]
Opioid receptor mu (MOR)  Molecule Info  [1]
KEGG Pathway Neuroactive ligand-receptor interaction Click to Show/Hide
2 Estrogen signaling pathway
3 Morphine addiction
NetPath Pathway TCR Signaling Pathway Click to Show/Hide
Panther Pathway Heterotrimeric G-protein signaling pathway-Gi alpha and Gs alpha mediated pathway Click to Show/Hide
2 Heterotrimeric G-protein signaling pathway-Gq alpha and Go alpha mediated pathway
3 Enkephalin release
4 Adrenaline and noradrenaline biosynthesis
Pathway Interaction Database IL4-mediated signaling events Click to Show/Hide
Reactome Peptide ligand-binding receptors Click to Show/Hide
2 G alpha (i) signalling events
3 Na+/Cl- dependent neurotransmitter transporters
WikiPathways TCR Signaling Pathway Click to Show/Hide
2 GPCRs, Class A Rhodopsin-like
3 Peptide GPCRs
4 Opioid Signalling
5 GPCR ligand binding
6 GPCR downstream signaling
7 Monoamine Transport
8 NRF2 pathway
9 Transport of glucose and other sugars, bile salts and organic acids, metal ions and amine compounds
References
Reference 1 2008 FDA drug approvals. Nat Rev Drug Discov. 2009 Feb;8(2):93-6.
Reference 2 Shining a Light on the Effects of the Combination of (-)-Epigallocatechin-3-gallate and Tapentadol on the Growth of Human Triple-negative Breast Cancer Cells. In Vivo. Sep-Oct 2019;33(5):1463-1468.
Reference 3 A combination pharmacotherapy of tapentadol and pregabalin to tackle centrally driven osteoarthritis pain. Eur J Pain. 2019 Jul;23(6):1185-1195.
 Download Picture         KEGG Link