Tapentadol

Tapentadol
ATC Code N02AX06
Formula C14H23NO
Molar Mass (g·mol−1) 221,344
Physical State solid
PKS Value 9,34 -10,45
CAS Number 175591-23-8
PUB Number 9838022
Drugbank ID DB06204

Basics

Tapentadol is a centrally acting opioid analgesic with a dual mechanism of action. It is not only an agonist of the μ-opioid receptor but also acts as a norepinephrine reuptake inhibitor (NRI). It can be given as an immediate-release (IR) formulation to treat acute moderate to severe pain, or as an extended-release (ER) formulation to treat chronic pain or neuropathic pain.

Tapentadol emerged in the late 1980s as a result of a Grünenthal research program. Various derivatives of the substance tramadol were investigated and optimized. After a collaboration with Johnson & Johnson, which took over the distribution, the substance was approved in 2008 (USA) and 2010 (Europe).

Pharmacology

Pharmacodynamics

Tapentadol is a centrally acting synthetic analgesic and NRI (norepinephrine reuptake inhibitor). Its action is approximately one-eighteenth that of morphine and similar to that of tramadol. It binds mainly to the μ-opioid receptor. It also increases the concentration of norepinephrine in the brain through a process called reuptake inhibition. This is the reason why tapentadol, in addition to the analgesic effect, also exerts a pronounced anxiolytic and euphoric effect. The analgesic effect usually occurs after about 30 minutes and usually lasts between 4 and 6 hours.

Pharmacokinetics

Tapentadol is not a prodrug and therefore does not rely on metabolism to exert its therapeutic effect. This makes it an agent of choice for patients who do not respond adequately to more commonly used opioids due to genetic predisposition (slow metabolizers of CYP3A4 and CYP2D6).

Oral bioavailability is approximately 32%. The peak effect is reached after approximately 1.5 hours. Plasma protein binding is about 20% and elimination half-life is about 4 hours.

Drug Interactions

Combination with SSRIs/SNRIs, SRAs, and serotonin receptor agonists may result in potentially fatal serotonin syndrome. Combination with MAOIs can also lead to what is called an "adrenergic storm," a dangerously rapid increase in certain neurotransmitters in the brain.

Taking tapentadol together with sedatives such as benzodiazepines, barbiturates, phenothiazines, and other opiates can lead to increased impairment, sedation, respiratory depression, and in severe cases, death.

The combination of tapentadol and alcohol may result in increased plasma concentrations of tapentadol and cause respiratory depression. Patients should therefore never consume alcohol while taking tapentadol.

Co-administration with anticholinergics should be avoided, if possible, as this may lead to urinary retention and subsequent renal damage.

Toxicity

Side effects

  • Dizziness
  • Nausea
  • Vomiting
  • Drowsiness
  • Headache
  • Itching
  • Dry mouth

Contraindications

Tapentadol is contraindicated in people with epilepsy or who are otherwise prone to seizures. It increases intracranial pressure and therefore should not be used in people with head injuries, brain tumors, or other conditions that increase intracranial pressure. It increases the risk of respiratory depression and therefore should not be used in people with asthma.

Toxicological Data:

LD50, rabbit, oral: 3200 mg/kg.

LD50, rat, oral: 300 mg/kg

LD50, mouse, oral: 980 mg/kg

Sources

Markus Falkenstätter

Markus Falkenstätter
Author

Markus Falkenstätter ist Autor zu pharmazeutischen Themen in der Medizin-Redaktion von Medikamio. Er befindet sich im letzten Semester seines Pharmaziestudiums an der Universität Wien und liebt das wissenschaftliche Arbeiten im Bereich der Naturwissenschaften.

Mag. pharm Stefanie Lehenauer

Mag. pharm Stefanie Lehenauer
Lector

Stefanie Lehenauer ist seit 2020 freie Autorin bei Medikamio und studierte Pharmazie an der Universität Wien. Sie arbeitet als Apothekerin in Wien und ihre Leidenschaft sind pflanzliche Arzneimittel und deren Wirkung.

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