Tapentadol
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Tapentadol
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| Systematic (IUPAC) name | |
| 3-[(1R,2R)-3-(dimethylamino)-1-ethyl-2- methylpropyl]phenol hydrochloride |
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| Identifiers | |
| CAS number | |
| ATC code | ? |
| PubChem | |
| Chemical data | |
| Formula | C14H24NO |
| Mol. mass | 257.799 g/mol |
| SMILES | & |
| 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 |
Under Regulatory Review 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]
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 regulatory review as of 2008. If approved, it would be the first new drug in its class in more than 25 years.[4]
On January 23, 2008, a New Drug Application (NDA) for tapentadol was submitted to the United States Food and Drug Administration.
[edit] 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]
[edit] 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.
[edit] External links
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