TAPENTADOL HYDROCHLORIDE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C14H23NO.ClH
Molecular Weight	257.799
Optical Activity	( - )
Defined Stereocenters	2 / 2
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

Cl.CC[C@H]([C@@H](C)CN(C)C)C1=CC=CC(O)=C1

InChI

InChIKey=ZELFLGGRLLOERW-YECZQDJWSA-N

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

HIDE SMILES / InChI

Molecular Formula	ClH
Molecular Weight	36.461
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Molecular Formula	C14H23NO
Molecular Weight	221.3385
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	2 / 2
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/17656655
Curator's Comment: Description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/21476608 | https://www.nucynta.com/hcp/er/mechanism-of-action#isi-0

Tapentadol is the first US FDA-approved centrally acting analgesic having both μ-opioid receptor agonist and noradrenaline (norepinephrine) reuptake inhibition activity with minimal serotonin reuptake inhibition. Tapentadol is indicated for the management of pain severe enough to require daily, around-the-clock, long-term opioid treatment and for which alternative treatment options are inadequate, neuropathic pain associated with diabetic peripheral neuropathy (DPN) severe enough to require daily, around-the-clock, long-term opioid treatment and for which alternative treatment options are inadequate.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Potency
Mu opioid receptor 231 Target ID: CHEMBL233 Sources: https://www.ncbi.nlm.nih.gov/pubmed/17656655	Agonist 2752	0.16 µM [Ki]
Norepinephrine transporter 197 Target ID: CHEMBL222 Sources: https://www.ncbi.nlm.nih.gov/pubmed/17656655	Inhibitor 8504	8.8 µM [Ki]
Serotonin transporter 183 Target ID: CHEMBL228 Sources: https://www.ncbi.nlm.nih.gov/pubmed/17656655	Inhibitor 8504	5.28 µM [Ki]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Pain 619 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2010/022304s003lbl.pdf	Primary		Approved 8583	NUCYNTA Approved Use NUCYNTA ER (tapentadol) is indicated for the management of: pain severe enough to require daily, around-the-clock, long-term opioid treatment and for which alternative treatment options are inadequate neuropathic pain associated with diabetic peripheral neuropathy (DPN) severe enough to require daily, around-the-clock, long-term opioid treatment and for which alternative treatment options are inadequate. Launch Date 2008

C_max

Value	Dose	Co-administered	Analyte	Population
221.34 ng/mL REVIEW https://pubmed.ncbi.nlm.nih.gov/23357834/	86 mg single, oral dose: 86 mg route of administration: Oral experiment type: SINGLE co-administered:		TAPENTADOL plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED

AUC

Value	Dose	Co-administered	Analyte	Population
221.34 ng × h/mL REVIEW https://pubmed.ncbi.nlm.nih.gov/23357834/	86 mg single, oral dose: 86 mg route of administration: Oral experiment type: SINGLE co-administered:		TAPENTADOL plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED

T_1/2

Value	Dose	Co-administered	Analyte	Population
1.16 h REVIEW https://pubmed.ncbi.nlm.nih.gov/23357834/	86 mg single, oral dose: 86 mg route of administration: Oral experiment type: SINGLE co-administered:		TAPENTADOL plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
4 h DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/022304s022lbl.pdf	100 mg single, oral dose: 100 mg route of administration: Oral experiment type: SINGLE co-administered:		TAPENTADOL plasma	Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN

F_unbound

Value	Dose	Co-administered	Analyte	Population
80% DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/022304s022lbl.pdf	100 mg single, oral dose: 100 mg route of administration: Oral experiment type: SINGLE co-administered:		TAPENTADOL plasma	Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
inhibitor 2252 inducer 1087	substrate 1193 inhibitor 2438 inducer 440	substrate 1388 inhibitor 2507	inhibitor 2217

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
CYP1A2 2153 CYP2A6 879 CYP2C19 2057 CYP2E1 1060	CYP2C19 1119	CYP1A2 832

Drug as perpetrator

Target	Modality	Activity
CYP1A2 2333	inducer 1966 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2011/200533Orig1s000ClinPharmR.pdf#page=82 Page: 82.0	no
CYP1A2 2333	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2011/200533Orig1s000ClinPharmR.pdf#page=82 Page: 82.0	no
CYP2A6 911	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2011/200533Orig1s000ClinPharmR.pdf#page=82 Page: 82.0	no
CYP2C19 2141	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2011/200533Orig1s000ClinPharmR.pdf#page=82 Page: 82.0	no
CYP2C9 2497	inducer 1966 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2011/200533Orig1s000ClinPharmR.pdf#page=82 Page: 82.0	no
CYP2C9 2497	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2011/200533Orig1s000ClinPharmR.pdf#page=82 Page: 82.0	no
CYP2D6 2546	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2011/200533Orig1s000ClinPharmR.pdf#page=82 Page: 82.0	no
CYP2E1 1146	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2011/200533Orig1s000ClinPharmR.pdf#page=82 Page: 82.0	no
CYP3A4 2633	inducer 1966 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2011/200533Orig1s000ClinPharmR.pdf#page=82 Page: 82.0	no
CYP3A4 2633	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2011/200533Orig1s000ClinPharmR.pdf#page=82 Page: 82.0	no

Drug as victim

Target	Modality	Activity
CYP2C19 1119	substrate 4014 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2011/200533Orig1s000ClinPharmR.pdf#page=5 Page: 5.0	yes
CYP2C9 1193	substrate 4014 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2011/200533Orig1s000ClinPharmR.pdf#page=5 Page: 5.0	yes
CYP2D6 1388	substrate 4014 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2011/200533Orig1s000ClinPharmR.pdf#page=5 Page: 5.0	yes

Tox targets

Target	Modality	Activity	Metabolite	Clinical evidence
hERG 2263	inhibitor 2237 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2011/200533Orig1s000PharmR.pdf#page=22 Page: 22.0

Sourcing

Vendor/Aggregator	ID	URL
Acadechem	ACDS-061982	http://www.acadechemical.com/product/136681
Achemtek	0102-020035	http://www.achemtek.com/175591-23-8
Acorn PharmaTech	ACN-050883	http://www.acornpharmatech.com/
AK Scientific, Inc. (AKSCI)	4084AH	http://www.aksci.com/item_detail.php?cat=4084AH
Aurora Fine Chemicals LLC	K16.552.242	http://online.aurorafinechemicals.com/info?ID=K16.552.242
Aurum Pharmatech LLC	B-1798	http://www.Aurumpharmatech.com/Product/ProductDetails/B_1798
Chem Scene	CS-M0020	http://www.chemscene.com/175591-23-8.html
ChemMol	44014575	http://www.chemmol.com/chemmol/44014575.html
ChemMol	49400147	http://www.chemmol.com/chemmol/49400147.html
ChemMol	97300664	http://www.chemmol.com/chemmol/97300664.html
ChemMol	97300665	http://www.chemmol.com/chemmol/97300665.html
Clearsynth	CS-O-02454	https://www.clearsynth.com/en/CSO02454.html
Finetech	FT-0699883	http://www.finetechnology-ind.com/online_service.shtml
iChemical	EBD44459	http://www.ichemical.com/chemicals/cas-175591-23-8
Renno Tech	RL02248	http://www.rennotech.com/product_show.asp?id=2497
Sinfoo Biotech	S046325	http://www.sinfoobiotech.com/product/1049723
Smolecule	S544552	http://www.smolecule.com/products/s544552
Specs	AR-270/43507984	http://www.specs.net/enter.php?specsid=AR-270/43507984
Synblock Inc	SB17333	http://www.synblock.com/product/175591-23-8.html
THE BioTek	bt-283455	https://www.thebiotek.com/product/inhibitors/bt-283455

PubMed

Title	Date	PubMed
Investigations into the drug-drug interaction potential of tapentadol in human liver microsomes and fresh human hepatocytes.	2008 Jan	19356073
Tapentadol a 'realistic alternative' to strong opioids for severe pain.	2008 Sep	18819294
Tapentadol hydrochloride: a centrally acting oral analgesic.	2009 Dec	20110020
The importance of the descending monoamine system for the pain experience and its treatment.	2009 Oct 29	20948695
Advances in perioperative pain management: use of medications with dual analgesic mechanisms, tramadol & tapentadol.	2010 Dec	21074743
In vitro and in vivo characterization of tapentadol metabolites.	2010 Jan-Feb	20383344
Dose conversion between tapentadol immediate and extended release for low back pain.	2010 Jan-Feb	20119464
Neuropathy, retinopathy, and glucose-lowering treatments.	2010 Jun	20508223
Recent advances in postoperative pain management.	2010 Mar	20351978
Evaluation of study discontinuations with tapentadol inmmediate release and oxycodone immediate release in patients with low back or osteoarthritis pain.	2010 May-Jun	20642246
Analgesic update: tapentadol hydrochloride.	2010 Oct	20960989
Tapentadol and its two mechanisms of action: is there a new pharmacological class of centrally-acting analgesics on the horizon?	2010 Sep	20659810
Differential contribution of opioid and noradrenergic mechanisms of tapentadol in rat models of nociceptive and neuropathic pain.	2010 Sep	20541444

Patents

Sample Use Guides

In Vivo Use Guide

As with many centrally-acting analgesic medications, the dosing regimen of NUCYNTA® should be individualized according to the severity of pain being treated, the previous experience with similar drugs and the ability to monitor the patient. Initiate NUCYNTA® with or without food at a dose of 50 mg, 75 mg, or 100 mg every 4 to 6 hours depending upon pain intensity. On the first day of dosing, the second dose may be administered as soon as one hour after the first dose, if adequate pain relief is not attained with the first dose. Subsequent dosing is 50 mg, 75 mg, or 100 mg every 4 to 6 hours and should be adjusted to maintain adequate analgesia with acceptable tolerability. Daily doses greater than 700 mg on the first day of therapy and 600 mg on subsequent days have not been studied and are, therefore, not recommended.

Route of Administration: Oral

In Vitro Use Guide

Upon exposure to tramadol and tapentadol concentrations up to 600μM, cell toxicity was assessed through evaluation of oxidative stress, mitochondrial and metabolic alterations, as well as cell viability and death mechanisms through necrosis or apoptosis, and related signalling. Tapentadol was observed to trigger much more prominent toxic effects than tramadol, ultimately leading to energy deficit and cell death.

Substance Class	Chemical Created by `admin` on `Mon Mar 31 18:11:58 GMT 2025` Edited by `admin` on `Mon Mar 31 18:11:58 GMT 2025`
Record UNII	71204KII53
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

TAPENTADOL HYDROCHLORIDE

Common Name

English

PHENOL, 3-((1R,2R)-3-(DIMETHYLAMINO)-1-ETHYL-2-METHYLPROPYL)-, HYDROCHLORIDE

Preferred Name

English

PHENOL, 3-((1R,2R)-3-(DIMETHYLAMINO)-1-ETHYL-2-METHYLPROPYL)-, HYDROCHLORIDE (1:1)

Systematic Name

English

TAPENTADOL HYDROCHLORIDE [VANDF]

Common Name

English

Tapentadol Hydrochloride [WHO-DD]

Common Name

English

PALEXIA

Brand Name

English

PHENOL, 3-(3-(DIMETHYLAMINO)-1-ETHYL-2-METHYLPROPYL)-, HYDROCHLORIDE, (R-(R*,R*))-

Common Name

English

BN-200 HYDROCHLORIDE

Code

English

TAPENTADOL HYDROCHLORIDE [ORANGE BOOK]

Common Name

English

TAPENTADOL HYDROCHLORIDE [MART.]

Common Name

English

TAPENTADOL HYDROCHLORIDE [JAN]

Common Name

English

NUCYNTA

Brand Name

English

TAPENTADOL HYDROCHLORIDE [MI]

Common Name

English

CG5503 HYDROCHLORIDE

Code

English

CG-5503 HYDROCHLORIDE

Code

English

TAPENTADOL HCL

Common Name

English

TAPENTADOL HYDROCHLORIDE [EP MONOGRAPH]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C67413