Tapentadol

Tapentadol
Clinical data
Trade namesNucynta, Palexia, Yantil, Tapenta, Tapal, Aspadol, others
Other namesBN-200
CG-5503
R-331333
AHFS/Drugs.comMonograph
MedlinePlusa610006
Pregnancy
category
  • AU: C
Dependence
liability		Very High[1]
Routes of
administration		By mouth
ATC code
Legal status
Legal status
Pharmacokinetic data
Bioavailability32% (oral)[4]
Protein binding20%[5]
MetabolismHepatic (mostly via glucuronidation but also by CYP2C9, CYP2C19, CYP2D6)[4]
Elimination half-life4 hours< (duration 4-6 hours)[4]
ExcretionUrine and faeces (1%)[4]
Identifiers
  • 3-[(1R,2R)-3-(Dimethylamino)-1-ethyl-2-methylpropyl]phenol
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.131.247 Edit this at Wikidata
Chemical and physical data
FormulaC14H23NO
Molar mass221.344 g·mol−1
3D model (JSmol)
Boiling point(decomposes)
  • Oc1cc(ccc1)[C@@H]([C@@H](C)CN(C)C)CC
  • InChI=1S/C14H23NO/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/t11-,14+/m0/s1 checkY
  • Key:KWTWDQCKEHXFFR-SMDDNHRTSA-N checkY
 ☒NcheckY (what is this?)  (verify)

Tapentadol, brand names Nucynta among others, is a centrally acting 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]

  1. ^ "Tapentadol (Monograph)". American Society of Health-System Pharmacists (AHFS) – via Drugs.com.
  2. ^ Anvisa (2023-03-31). "RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 784 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese). Diário Oficial da União (published 2023-04-04). Archived from the original on 2023-08-03. Retrieved 2023-08-16.
  3. ^ "Active substance(s): tapentadol" (PDF). List of nationally authorised medicinal products. European Medicines Agency. 21 July 2022. Archived (PDF) from the original on 2022-09-06. Retrieved 2022-09-06.
  4. ^ a b c d e f Cite error: The named reference Fidman2010rev was invoked but never defined (see the help page).
  5. ^ Brayfield A, ed. (14 November 2011). "Tapentadol". Martindale: The Complete Drug Reference. Pharmaceutical Press. Archived from the original on 29 August 2021. Retrieved 2 April 2014.
  6. ^ a b c Singh DR, Nag K, Shetti AN, Krishnaveni N (July 2013). "Tapentadol hydrochloride: A novel analgesic". Saudi Journal of Anaesthesia. 7 (3): 322–326. doi:10.4103/1658-354X.115319. PMC 3757808. PMID 24015138.
  7. ^ Raffa RB, Buschmann H, Christoph T, Eichenbaum G, Englberger W, Flores CM, et al. (July 2012). "Mechanistic and functional differentiation of tapentadol and tramadol". Expert Opinion on Pharmacotherapy. 13 (10): 1437–1449. doi:10.1517/14656566.2012.696097. PMID 22698264. S2CID 24226747.
  8. ^ Tschentke TM, De Vry J, Terlinden R, Hennies HH, Lange C, Strassburger W, et al. (2006). "Tapentadol Hydrochloride". Drugs of the Future. 31 (12): 1053. doi:10.1358/dof.2006.031.12.1047744.
  9. ^ "CDC Opioid Calculator". 13 October 2022.
  10. ^ "Nucynta History". drugs.com. Archived from the original on April 12, 2015. Retrieved April 5, 2015.
  11. ^ "PALEXIA® SR PRODUCT INFORMATION" (PDF). TGA eBusiness Services. CSL Limited. 26 June 2013. Archived from the original on 6 April 2017. Retrieved 2 April 2014.
  12. ^ "Palexia film coated tablets". electronic Medicines Compendium. Grunenthal Ltd. 13 November 2013. Archived from the original on 7 April 2014. Retrieved 2 April 2014.
  13. ^ Mukherjee D, Shukla L, Saha P, Mahadevan J, Kandasamy A, Chand P, et al. (March 2020). "Tapentadol abuse and dependence in India". Asian Journal of Psychiatry. 49: 101978. doi:10.1016/j.ajp.2020.101978. PMID 32120298. S2CID 211834859. Archived from the original on 2021-12-20. Retrieved 2021-10-10.