Clinical data | |
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Trade names | Nucynta, Palexia, Yantil, Tapenta, Tapal, Aspadol, others |
Other names | BN-200 CG-5503 R-331333 |
AHFS/Drugs.com | Monograph |
MedlinePlus | a610006 |
Pregnancy category |
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Dependence liability | Very High[1] |
Routes of administration | By mouth |
Drug class | Opioid |
ATC code | |
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Pharmacokinetic data | |
Bioavailability | 32% (oral)[4] |
Protein binding | 20%[5] |
Metabolism | Hepatic (mostly via glucuronidation but also by CYP2C9, CYP2C19, CYP2D6)[4] |
Onset of action | ~30 minutes |
Elimination half-life | 4 hours |
Duration of action | 4-6 hours[4] |
Excretion | Urine and faeces (1%)[4] |
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CompTox Dashboard (EPA) | |
ECHA InfoCard | 100.131.247 |
Chemical and physical data | |
Formula | C14H23NO |
Molar mass | 221.344 g·mol−1 |
3D model (JSmol) | |
Boiling point | (decomposes) |
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Tapentadol, sold under the brand name Nucynta among others, is an opioid analgesic of the benzenoid class with a dual mode of action as an agonist of the μ-opioid receptor and as a norepinephrine reuptake inhibitor (NRI).[4] Analgesia occurs within 32 minutes of oral administration, and lasts for 4–6 hours.[6]
It is similar to tramadol in its dual mechanism of action; namely, its ability to activate the μ-opioid receptor and inhibit the reuptake of norepinephrine.[6] Unlike tramadol, it has only weak effects on the reuptake of serotonin and is a significantly more potent opioid with no known active metabolites.[6][7] Tapentadol is not a pro-drug and therefore does not rely on metabolism to produce its therapeutic effects; this makes it a useful moderate-potency analgesic option for patients who do not respond adequately to more commonly used opioids due to genetic disposition (poor metabolizers of CYP3A4 and CYP2D6), as well as providing a more consistent dosage-response range among the patient population.
The potency of tapentadol is somewhere between that of tramadol and morphine,[8] with an analgesic efficacy comparable to that of oxycodone despite a lower incidence of side effects.[4] It is generally regarded as a moderately strong opioid. The CDC Opioid Guidelines Calculator estimates a conversation rate of 50mg of tapentadol equaling 10 mg of oral oxycodone in terms of opioid receptor activation.[9]
Tapentadol was approved by the US FDA in November 2008,[10] by the TGA of Australia in December 2010[11] and by the MHRA of the UK in February 2011.[12] In India, Central Drug Standard Control Organisation (CDSCO) approved tapentadol immediate-release (IR) preparations (50, 75 and 100 mg) for moderate to severe acute pain and extended-release (ER) preparations (50,100,150 and 200 mg) for severe acute pain in April 2011 and December 2013 respectively.[13]
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