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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 of TAPENTADOL HYDROCHLORIDE

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 C14H23NO
Molecular Weight 221.3385
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 2 / 2
E/Z Centers 0
Optical Activity UNSPECIFIED

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

Description
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.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
0.16 µM [Ki]
8.8 µM [Ki]
5.28 µM [Ki]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
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

1.22713919E12
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
221.34 ng/mL
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

AUC

ValueDoseCo-administeredAnalytePopulation
221.34 ng × h/mL
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
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
1.16 h
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
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
Funbound

Funbound

ValueDoseCo-administeredAnalytePopulation
80%
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
Doses

Doses

DosePopulationAdverse events​
250 mg 2 times / day multiple, oral (max)
Recommended
Dose: 250 mg, 2 times / day
Route: oral
Route: multiple
Dose: 250 mg, 2 times / day
Sources: Page: p.424
unhealthy, 56.8
n = 894
Health Status: unhealthy
Condition: Chronic low back pain|Osteoarthritis pain
Age Group: 56.8
Sex: M+F
Population Size: 894
Sources: Page: p.424
Disc. AE: Nausea, Constipation...
AEs leading to
discontinuation/dose reduction:
Nausea (3.4%)
Constipation (1.6%)
Dizziness (3%)
Vomiting (2.6%)
Fatigue (1.8%)
Somnolence (3.4%)
Pruritus (0.6%)
Sources: Page: p.424
100 mg 6 times / day multiple, oral
Recommended
Dose: 100 mg, 6 times / day
Route: oral
Route: multiple
Dose: 100 mg, 6 times / day
Sources: Page: p.7
unhealthy
Health Status: unhealthy
Condition: Acute pain
Sources: Page: p.7
Disc. AE: Dizziness, Nausea...
AEs leading to
discontinuation/dose reduction:
Dizziness
Nausea
Vomiting
Somnolence
Headache
Sources: Page: p.7
700 mg 6 times / day multiple, oral (total)
Recommended
Dose: 700 mg, 6 times / day
Route: oral
Route: multiple
Dose: 700 mg, 6 times / day
Sources: Page: p.1
unhealthy
Health Status: unhealthy
Condition: Acute pain
Sources: Page: p.1
Disc. AE: Respiratory depression, CNS disorder (NOS)...
AEs leading to
discontinuation/dose reduction:
Respiratory depression
CNS disorder (NOS)
Intracranial pressure increased
Abuse NOS
Mental function decreased
Physical impairment
Seizures
Serotonin syndrome (grade 4)
Sources: Page: p.1
AEs

AEs

AESignificanceDosePopulation
Pruritus 0.6%
Disc. AE
250 mg 2 times / day multiple, oral (max)
Recommended
Dose: 250 mg, 2 times / day
Route: oral
Route: multiple
Dose: 250 mg, 2 times / day
Sources: Page: p.424
unhealthy, 56.8
n = 894
Health Status: unhealthy
Condition: Chronic low back pain|Osteoarthritis pain
Age Group: 56.8
Sex: M+F
Population Size: 894
Sources: Page: p.424
Constipation 1.6%
Disc. AE
250 mg 2 times / day multiple, oral (max)
Recommended
Dose: 250 mg, 2 times / day
Route: oral
Route: multiple
Dose: 250 mg, 2 times / day
Sources: Page: p.424
unhealthy, 56.8
n = 894
Health Status: unhealthy
Condition: Chronic low back pain|Osteoarthritis pain
Age Group: 56.8
Sex: M+F
Population Size: 894
Sources: Page: p.424
Fatigue 1.8%
Disc. AE
250 mg 2 times / day multiple, oral (max)
Recommended
Dose: 250 mg, 2 times / day
Route: oral
Route: multiple
Dose: 250 mg, 2 times / day
Sources: Page: p.424
unhealthy, 56.8
n = 894
Health Status: unhealthy
Condition: Chronic low back pain|Osteoarthritis pain
Age Group: 56.8
Sex: M+F
Population Size: 894
Sources: Page: p.424
Vomiting 2.6%
Disc. AE
250 mg 2 times / day multiple, oral (max)
Recommended
Dose: 250 mg, 2 times / day
Route: oral
Route: multiple
Dose: 250 mg, 2 times / day
Sources: Page: p.424
unhealthy, 56.8
n = 894
Health Status: unhealthy
Condition: Chronic low back pain|Osteoarthritis pain
Age Group: 56.8
Sex: M+F
Population Size: 894
Sources: Page: p.424
Dizziness 3%
Disc. AE
250 mg 2 times / day multiple, oral (max)
Recommended
Dose: 250 mg, 2 times / day
Route: oral
Route: multiple
Dose: 250 mg, 2 times / day
Sources: Page: p.424
unhealthy, 56.8
n = 894
Health Status: unhealthy
Condition: Chronic low back pain|Osteoarthritis pain
Age Group: 56.8
Sex: M+F
Population Size: 894
Sources: Page: p.424
Nausea 3.4%
Disc. AE
250 mg 2 times / day multiple, oral (max)
Recommended
Dose: 250 mg, 2 times / day
Route: oral
Route: multiple
Dose: 250 mg, 2 times / day
Sources: Page: p.424
unhealthy, 56.8
n = 894
Health Status: unhealthy
Condition: Chronic low back pain|Osteoarthritis pain
Age Group: 56.8
Sex: M+F
Population Size: 894
Sources: Page: p.424
Somnolence 3.4%
Disc. AE
250 mg 2 times / day multiple, oral (max)
Recommended
Dose: 250 mg, 2 times / day
Route: oral
Route: multiple
Dose: 250 mg, 2 times / day
Sources: Page: p.424
unhealthy, 56.8
n = 894
Health Status: unhealthy
Condition: Chronic low back pain|Osteoarthritis pain
Age Group: 56.8
Sex: M+F
Population Size: 894
Sources: Page: p.424
Dizziness Disc. AE
100 mg 6 times / day multiple, oral
Recommended
Dose: 100 mg, 6 times / day
Route: oral
Route: multiple
Dose: 100 mg, 6 times / day
Sources: Page: p.7
unhealthy
Health Status: unhealthy
Condition: Acute pain
Sources: Page: p.7
Headache Disc. AE
100 mg 6 times / day multiple, oral
Recommended
Dose: 100 mg, 6 times / day
Route: oral
Route: multiple
Dose: 100 mg, 6 times / day
Sources: Page: p.7
unhealthy
Health Status: unhealthy
Condition: Acute pain
Sources: Page: p.7
Nausea Disc. AE
100 mg 6 times / day multiple, oral
Recommended
Dose: 100 mg, 6 times / day
Route: oral
Route: multiple
Dose: 100 mg, 6 times / day
Sources: Page: p.7
unhealthy
Health Status: unhealthy
Condition: Acute pain
Sources: Page: p.7
Somnolence Disc. AE
100 mg 6 times / day multiple, oral
Recommended
Dose: 100 mg, 6 times / day
Route: oral
Route: multiple
Dose: 100 mg, 6 times / day
Sources: Page: p.7
unhealthy
Health Status: unhealthy
Condition: Acute pain
Sources: Page: p.7
Vomiting Disc. AE
100 mg 6 times / day multiple, oral
Recommended
Dose: 100 mg, 6 times / day
Route: oral
Route: multiple
Dose: 100 mg, 6 times / day
Sources: Page: p.7
unhealthy
Health Status: unhealthy
Condition: Acute pain
Sources: Page: p.7
Abuse NOS Disc. AE
700 mg 6 times / day multiple, oral (total)
Recommended
Dose: 700 mg, 6 times / day
Route: oral
Route: multiple
Dose: 700 mg, 6 times / day
Sources: Page: p.1
unhealthy
Health Status: unhealthy
Condition: Acute pain
Sources: Page: p.1
CNS disorder (NOS) Disc. AE
700 mg 6 times / day multiple, oral (total)
Recommended
Dose: 700 mg, 6 times / day
Route: oral
Route: multiple
Dose: 700 mg, 6 times / day
Sources: Page: p.1
unhealthy
Health Status: unhealthy
Condition: Acute pain
Sources: Page: p.1
Intracranial pressure increased Disc. AE
700 mg 6 times / day multiple, oral (total)
Recommended
Dose: 700 mg, 6 times / day
Route: oral
Route: multiple
Dose: 700 mg, 6 times / day
Sources: Page: p.1
unhealthy
Health Status: unhealthy
Condition: Acute pain
Sources: Page: p.1
Mental function decreased Disc. AE
700 mg 6 times / day multiple, oral (total)
Recommended
Dose: 700 mg, 6 times / day
Route: oral
Route: multiple
Dose: 700 mg, 6 times / day
Sources: Page: p.1
unhealthy
Health Status: unhealthy
Condition: Acute pain
Sources: Page: p.1
Physical impairment Disc. AE
700 mg 6 times / day multiple, oral (total)
Recommended
Dose: 700 mg, 6 times / day
Route: oral
Route: multiple
Dose: 700 mg, 6 times / day
Sources: Page: p.1
unhealthy
Health Status: unhealthy
Condition: Acute pain
Sources: Page: p.1
Respiratory depression Disc. AE
700 mg 6 times / day multiple, oral (total)
Recommended
Dose: 700 mg, 6 times / day
Route: oral
Route: multiple
Dose: 700 mg, 6 times / day
Sources: Page: p.1
unhealthy
Health Status: unhealthy
Condition: Acute pain
Sources: Page: p.1
Seizures Disc. AE
700 mg 6 times / day multiple, oral (total)
Recommended
Dose: 700 mg, 6 times / day
Route: oral
Route: multiple
Dose: 700 mg, 6 times / day
Sources: Page: p.1
unhealthy
Health Status: unhealthy
Condition: Acute pain
Sources: Page: p.1
Serotonin syndrome grade 4
Disc. AE
700 mg 6 times / day multiple, oral (total)
Recommended
Dose: 700 mg, 6 times / day
Route: oral
Route: multiple
Dose: 700 mg, 6 times / day
Sources: Page: p.1
unhealthy
Health Status: unhealthy
Condition: Acute pain
Sources: Page: p.1
Overview

OverviewOther

Other InhibitorOther SubstrateOther Inducer






Drug as perpetrator​Drug as victimTox targets

Tox targets

TargetModalityActivityMetaboliteClinical evidence
PubMed

PubMed

TitleDatePubMed
Absorption, metabolism, and excretion of 14C-labeled tapentadol HCl in healthy male subjects.
2007 Jul-Sep
(-)-(1R,2R)-3-(3-dimethylamino-1-ethyl-2-methyl-propyl)-phenol hydrochloride (tapentadol HCl): a novel mu-opioid receptor agonist/norepinephrine reuptake inhibitor with broad-spectrum analgesic properties.
2007 Oct
Single dose analgesic efficacy of tapentadol in postsurgical dental pain: the results of a randomized, double-blind, placebo-controlled study.
2008 Dec
The efficacy and tolerability of multiple-dose tapentadol immediate release for the relief of acute pain following orthopedic (bunionectomy) surgery .
2008 Nov
Tapentadol hydrochloride: a centrally acting oral analgesic.
2009 Dec
Efficacy and tolerability of tapentadol immediate release and oxycodone HCl immediate release in patients awaiting primary joint replacement surgery for end-stage joint disease: a 10-day, phase III, randomized, double-blind, active- and placebo-controlled study.
2009 Feb
A randomized, double-blind, placebo-controlled phase 3 study of the relative efficacy and tolerability of tapentadol IR and oxycodone IR for acute pain.
2009 Jun
Tolerability of tapentadol immediate release in patients with lower back pain or osteoarthritis of the hip or knee over 90 days: a randomized, double-blind study.
2009 May
Schedules of controlled substances: placement of tapentadol into schedule II. Final rule.
2009 May 21
Tapentadol immediate release for the relief of moderate-to-severe acute pain.
2009 Nov
The importance of the descending monoamine system for the pain experience and its treatment.
2009 Oct 29
Efficacy and safety of Tapentadol extended release compared with oxycodone controlled release for the management of moderate to severe chronic pain related to osteoarthritis of the knee: a randomized, double-blind, placebo- and active-controlled phase III study.
2010
Efficacy and safety of tapentadol extended release for the management of chronic low back pain: results of a prospective, randomized, double-blind, placebo- and active-controlled Phase III study.
2010 Aug
[Tapentadol. Opioid analgesic and norepinephrine reuptake inhibitors].
2010 Dec
Tapentadol, but not morphine, selectively inhibits disease-related thermal hyperalgesia in a mouse model of diabetic neuropathic pain.
2010 Feb 12
Tapentadol immediate release: a new treatment option for acute pain management.
2010 Feb 8
A thorough QT/QTc study of multiple doses of tapentadol immediate release in healthy subjects.
2010 Oct
Cost-effectiveness analysis of tapentadol immediate release for the treatment of acute pain.
2010 Sep
Tapentadol and its two mechanisms of action: is there a new pharmacological class of centrally-acting analgesics on the horizon?
2010 Sep
Tapentadol immediate release: a review of its use in the treatment of moderate to severe acute pain.
2010 Sep 10
Long-term safety and tolerability of tapentadol extended release for the management of chronic low back pain or osteoarthritis pain.
2010 Sep-Oct
Comparative pharmacokinetics and bioavailability of tapentadol following oral administration of immediate- and prolonged-release formulations.
2013 Apr
Patents

Sample Use Guides

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
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 Fri Dec 15 15:52:59 UTC 2023
Edited
by admin
on Fri Dec 15 15:52:59 UTC 2023
Record UNII
71204KII53
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
TAPENTADOL HYDROCHLORIDE
MART.   MI   ORANGE BOOK   VANDF   WHO-DD  
Common 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
PHENOL, 3-((1R,2R)-3-(DIMETHYLAMINO)-1-ETHYL-2-METHYLPROPYL)-, HYDROCHLORIDE
Systematic Name English
TAPENTADOL HYDROCHLORIDE [EP MONOGRAPH]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C67413
Created by admin on Fri Dec 15 15:52:59 UTC 2023 , Edited by admin on Fri Dec 15 15:52:59 UTC 2023
Code System Code Type Description
DAILYMED
71204KII53
Created by admin on Fri Dec 15 15:52:59 UTC 2023 , Edited by admin on Fri Dec 15 15:52:59 UTC 2023
PRIMARY
NCI_THESAURUS
C68922
Created by admin on Fri Dec 15 15:52:59 UTC 2023 , Edited by admin on Fri Dec 15 15:52:59 UTC 2023
PRIMARY
MERCK INDEX
m10459
Created by admin on Fri Dec 15 15:52:59 UTC 2023 , Edited by admin on Fri Dec 15 15:52:59 UTC 2023
PRIMARY Merck Index
FDA UNII
71204KII53
Created by admin on Fri Dec 15 15:52:59 UTC 2023 , Edited by admin on Fri Dec 15 15:52:59 UTC 2023
PRIMARY
PUBCHEM
9838021
Created by admin on Fri Dec 15 15:52:59 UTC 2023 , Edited by admin on Fri Dec 15 15:52:59 UTC 2023
PRIMARY
CAS
175591-09-0
Created by admin on Fri Dec 15 15:52:59 UTC 2023 , Edited by admin on Fri Dec 15 15:52:59 UTC 2023
PRIMARY
DRUG BANK
DBSALT000169
Created by admin on Fri Dec 15 15:52:59 UTC 2023 , Edited by admin on Fri Dec 15 15:52:59 UTC 2023
PRIMARY
EVMPD
SUB32145
Created by admin on Fri Dec 15 15:52:59 UTC 2023 , Edited by admin on Fri Dec 15 15:52:59 UTC 2023
PRIMARY
RXCUI
857492
Created by admin on Fri Dec 15 15:52:59 UTC 2023 , Edited by admin on Fri Dec 15 15:52:59 UTC 2023
PRIMARY RxNorm
EPA CompTox
DTXSID00938677
Created by admin on Fri Dec 15 15:52:59 UTC 2023 , Edited by admin on Fri Dec 15 15:52:59 UTC 2023
PRIMARY
ChEMBL
CHEMBL1201776
Created by admin on Fri Dec 15 15:52:59 UTC 2023 , Edited by admin on Fri Dec 15 15:52:59 UTC 2023
PRIMARY
SMS_ID
100000124471
Created by admin on Fri Dec 15 15:52:59 UTC 2023 , Edited by admin on Fri Dec 15 15:52:59 UTC 2023
PRIMARY
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ACTIVE MOIETY