Details of the Drug

General Information of Drug (ID: DMXLSH3)

Drug Name
Tapentadol hydrochloride
Synonyms
Tapentadol; 175591-23-8; 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
Indication
Disease Entry ICD 11 Status REF
Acute pain MG31 Approved [1]
Affected Organisms
Humans and other mammals
ATC Code
N02AX06: Tapentadol hydrochloride
N02AX: Other opioids
N02A: OPIOIDS
N02: ANALGESICS
N: NERVOUS SYSTEM
Drug Type
Small molecular drug
Structure
3D MOL is unavailable 2D MOL
#Ro5 Violations (Lipinski):
0		 Molecular Weight 257.8
Logarithm of the Partition Coefficient Not Available
Rotatable Bond Count 5
Hydrogen Bond Donor Count 2
Hydrogen Bond Acceptor Count 2
ADMET Property
Bioavailability
The bioavailability of drug is 32% []
Clearance
The total clearance of drug is 1530 +/- 177 mL/min []
Half-life
The concentration or amount of drug in body reduced by one-half in 4 hours [2]
Metabolism
The drug is metabolized via the conjugation with glucuronic acid to produce glucuronides []
Vd
The volume of distribution (Vd) of drug is 540 +/- 98 L []
Chemical Identifiers
Formula
C14H24ClNO
IUPAC Name
3-[(2R,3R)-1-(dimethylamino)-2-methylpentan-3-yl]phenol;hydrochloride
Canonical SMILES
CC[C@@H](C1=CC(=CC=C1)O)[C@@H](C)CN(C)C.Cl
InChI
InChI=1S/C14H23NO.ClH/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;1H/t11-,14+;/m0./s1
InChIKey
ZELFLGGRLLOERW-YECZQDJWSA-N
Cross-matching ID
PubChem CID
9838021
CAS Number
175591-09-0
UNII
H8A007M585
DrugBank ID
DB06204
TTD ID
D0K4MH
VARIDT ID
DR01146
INTEDE ID
DR1531
Combinatorial Drugs (CBD) Click to Jump to the Detailed CBD Information of This Drug

Molecular Interaction Atlas of This Drug


Drug Therapeutic Target (DTT)
DTT Name DTT ID UniProt ID MOA REF
Norepinephrine transporter (NET) TTAWNKZ SC6A2_HUMAN Modulator [1]
Opioid receptor mu (MOP) TTKWM86 OPRM_HUMAN Modulator [1]

Drug-Metabolizing Enzyme (DME)
DME Name DME ID UniProt ID MOA REF
Cytochrome P450 2D6 (CYP2D6) DECB0K3 CP2D6_HUMAN Substrate [3]
Cytochrome P450 2C9 (CYP2C9)
Main DME 		DE5IED8 CP2C9_HUMAN Substrate [3]
UDP-glucuronosyltransferase 2B7 (UGT2B7) DEB3CV1 UD2B7_HUMAN Substrate [3]
UDP-glucuronosyltransferase 1A9 (UGT1A9) DE85D2P UD19_HUMAN Substrate [3]
Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction Atlas of This Drug

Molecular Expression Atlas of This Drug

The Studied Disease Acute pain
ICD Disease Classification MG31
Molecule Name Molecule Type Gene Name p-value Fold-Change Z-score
Opioid receptor mu (MOP) DTT OPRM1 5.94E-01 -0.02 -0.17
Norepinephrine transporter (NET) DTT SLC6A2 7.05E-01 7.02E-03 0.07
Cytochrome P450 2D6 (CYP2D6) DME CYP2D6 5.64E-01 2.36E-02 1.75E-01
Cytochrome P450 2C9 (CYP2C9) DME CYP2C9 7.83E-01 2.32E-03 1.53E-02
Molecular Expression Atlas (MEA) Jump to Detail Molecular Expression Atlas of This Drug

References

1 2008 FDA drug approvals. Nat Rev Drug Discov. 2009 Feb;8(2):93-6.
2 Trend Analysis of a Database of Intravenous Pharmacokinetic Parameters in Humans for 1352 Drug Compounds
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.