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Tapentadol



Tapentadol
Systematic (IUPAC) name
3-[(1R,2R)-3-(dimethylamino)-1-ethyl-2- methylpropyl]phenol hydrochloride
Identifiers
CAS number	175591-23-8
ATC code	?
PubChem	9838021
Chemical data
Formula	C₁₄H₂₄NO
Mol. mass	257.799 g/mol
SMILES	search in eMolecules, PubChem
Synonyms	Tapentadol hydrochloride BN-200 CG-5503 R-331333
Pharmacokinetic data
Bioavailability	31.9 ± 6.8% (oral)^[1]
Metabolism	Hepatic glucuronidation and sulfate conjugation
Half life	?
Excretion	Renal (>95%) and fecal
Therapeutic considerations
Pregnancy cat.	?
Legal status	Phase III Clinical Trials in US
Routes	?

Tapentadol (INN) is a centrally-acting analgesic with a unique dual mode of action as an agonist at the μ-opioid receptor and as a norepinephrine reuptake inhibitor.^[2] It is considered to have a potency between morphine and tramadol.^[3]

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Its dual mode of action provides analgesia at similar levels of more potent narcotic analgesics such as hydrocodone, oxycodone, and morphine with a more tolerable side effect profile.

Tapentadol was developed by Grünenthal in conjunction with Johnson & Johnson Pharmaceutical Research and Development. It is currently undergoing phase III clinical trials. If approved, it would be the first new drug in its class in more than 25 years.^[4]

Adverse effects

Nausea, dizziness, constipation, and CNS sedation are common side effects of opioid pain medications. In phase II trials, tapentadol has been shown to provide equianalgesic effect with a lower incidence of side effects compared to oxycodone and morphine. One trial, sponsored by Grünenthal, comparing tapentadol to morphine and ibuprofen for relief of postoperative pain found tapentadol to cause less nausea and dizziness than morphine, with no significant difference in the incidence of vomiting or drowsiness.^[5]

References

^ Terlinden R, Ossig J, Fliegert F, Gohler K (2006). "Pharmacokinetics, excretion and metabolism of tapentadol HCl, a novel centrally acting analgesic in healthy subjects". Program and abstracts of the 25th Annual Scientific Meeting of the American Pain Society; May 3-6, 2006; San Antonio, Texas. Poster 689.
^ Tzschentke TM, Christoph T, Kögel B, Schiene K, Hennies HH, Englberger W, Haurand M, Jahnel U, Cremers TI, Friderichs E, De Vry J. (1R,2R)-3-(3-Dimethylamino-1-ethyl-2-methyl-propyl)-phenol Hydrochloride (Tapentadol HCl): a Novel μ-Opioid Receptor Agonist/Norepinephrine Reuptake Inhibitor with Broad-Spectrum Analgesic Properties. Journal of Pharmacology and Experimental Therapeutics. 2007 Oct;323(1):265-76.
^ Tschentke, T.M. et al. "Tapentadol Hydrochloride." Drugs of the Future. 2006, Vol. 31, Issue 12, p. 1053. DOI: 10.1358/dof.2006.031.12.1047744
^ Krüger-Hellwig, Anke. "Grünenthal GmbH Presents Tapentadol, a Novel Centrally Acting Analgesic, at the 25th Annual Scientific Meeting of The American Pain Society." PR Newswire. June 6, 2006. Retrieved on September 20, 2007.
^ "Two New Analgesics May Help Patients After Bunionectomy", Journal of Anaesthesiology Clinical Pharmacology, September 26 2006. Retrieved on 2007-09-20.

Categories: Mu-opioid agonists | Norepinephrine reuptake inhibitors

This article is licensed under the GNU Free Documentation License. It uses material from the Wikipedia article "Tapentadol". A list of authors is available in Wikipedia.