Tapentadol

Tapentadol

Clinical data
Synonyms	Tapentadol hydrochloride BN-200 CG-5503 R-331333
Legal status
Legal status	Phase III Clinical Trials in US
Pharmacokinetic data
Bioavailability	31.9 ± 6.8% (oral)
Metabolism	Hepatic glucuronidation and sulfate conjugation
Excretion	Renal (>95%) and fecal
Identifiers
IUPAC name 3-[(1R,2R)-3-(dimethylamino)-1-ethyl-2- methylpropyl]phenol hydrochloride
CAS Number	175591-23-8
PubChem CID	9838021
E number	{{#property:P628}}
ECHA InfoCard	{{#property:P2566}}
Chemical and physical data
Formula	C14H24NO
Molar mass	257.799 g/mol
3D model (JSmol)	Interactive image
Boiling point	(decomposes)
SMILES CCC(C1=CC(=CC=C1)O)C(C)CN(C)C.Cl

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Overview

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. It is considered to have a potency between morphine and tramadol.

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.

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.