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]
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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

Hydrogen Bond Donor Count

Hydrogen Bond Acceptor Count

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
TTD ID: D0K4MH
VARIDT ID: DR01146
INTEDE ID: DR1531

Combinatorial Drugs (CBD)

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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]

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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]

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Molecular Interaction Atlas (MIA)

MIA Detail

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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)

MEA Detail

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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.