O-Desmetiltramadol
| |||
| (IUPAC) ime | |||
|---|---|---|---|
| 3-[2-(1-Amino-1-metiletil)-1-hidroksicikloheksil]fenol | |||
| Klinički podaci | |||
| Identifikatori | |||
| CAS broj | 73986-53-5 | ||
| ATC kod | nije dodeljen | ||
| PubChem[1][2] | 130829 | ||
| ChemSpider[3] | 115703 | ||
| ChEMBL[4] | CHEMBL1400 
| ||
| Hemijski podaci | |||
| Formula | C15H23NO2 | ||
| Mol. masa | 249,349 g/mol | ||
| SMILES | eMolekuli & PubHem | ||
| |||
| Farmakokinetički podaci | |||
| Poluvreme eliminacije | ~ 9 h | ||
| Farmakoinformacioni podaci | |||
| Trudnoća | ? | ||
| Pravni status | ? (SAD) | ||
| Način primene | konvertovani metabolit | ||
O-Desmetiltramadol (O-DT) je opioidni analgetik i glavni aktivni metabolit tramadola.[5]
(+)-O-Desmetiltramadol je najvažniji metabolit tramadola, koji se proizvodi u jetri nakon konzumacije tramadola. Ovaj metabolit je znatno potentniji agonist μ opioidnog receptora nego početno jedinjenje.[6]
Tramadol se demetiliše jetrenim enzimom CYP2D6[7] na isti način kao i kodein, tako da su poput odgovora na kodein, osobe koje imaju manje aktivnu formu CYP2D6 manje responsivne.
Dva enantiomera O-desmetiltramadola pokazuju veoma različite farmakološke profile.[8] Oba, (+) i (-)-O-desmetiltramadol, su neaktivna kao inhibitori preuzimanja serotonina,[9] ali (-)-O-desmetiltramadol zadržava aktivnost kao inhibitor noradrenalinskog preuzimanja[10].
- ↑ Li Q, Cheng T, Wang Y, Bryant SH (2010). „PubChem as a public resource for drug discovery.”. Drug Discov Today 15 (23-24): 1052-7. DOI:10.1016/j.drudis.2010.10.003. PMID 20970519.
- ↑ Evan E. Bolton, Yanli Wang, Paul A. Thiessen, Stephen H. Bryant (2008). „Chapter 12 PubChem: Integrated Platform of Small Molecules and Biological Activities”. Annual Reports in Computational Chemistry 4: 217-241. DOI:10.1016/S1574-1400(08)00012-1.
- ↑ Hettne KM, Williams AJ, van Mulligen EM, Kleinjans J, Tkachenko V, Kors JA. (2010). „Automatic vs. manual curation of a multi-source chemical dictionary: the impact on text mining”. J Cheminform 2 (1): 3. DOI:10.1186/1758-2946-2-3. PMID 20331846.
- ↑ Gaulton A, Bellis LJ, Bento AP, Chambers J, Davies M, Hersey A, Light Y, McGlinchey S, Michalovich D, Al-Lazikani B, Overington JP. (2012). „ChEMBL: a large-scale bioactivity database for drug discovery”. Nucleic Acids Res 40 (Database issue): D1100-7. DOI:10.1093/nar/gkr777. PMID 21948594.
- ↑ Sevcik, J; Nieber, K; Driessen, B; Illes, P (1993). „Effects of the central analgesic tramadol and its main metabolite, O-desmethyltramadol, on rat locus coeruleus neurones”. British Journal of Pharmacology 110 (1): 169–76. PMC 2175982. PMID 8220877.
- ↑ Dayer, P; Desmeules, J; Collart, L (1997). „Pharmacology of tramadol”. Drugs 53 Suppl 2: 18–24. DOI:10.2165/00003495-199700532-00006. PMID 9190321.
- ↑ Borlak, J; Hermann, R; Erb, K; Thum, T (2003). „A rapid and simple CYP2D6 genotyping assay--case study with the analgetic tramadol”. Metabolism: clinical and experimental 52 (11): 1439–43. DOI:10.1016/S0026-0495(03)00256-7. PMID 14624403.
- ↑ Garrido, MJ; Valle, M; Campanero, MA; Calvo, R; Trocóniz, IF (2000). „Modeling of the in vivo antinociceptive interaction between an opioid agonist, (+)-O-desmethyltramadol, and a monoamine reuptake inhibitor, (-)-O-desmethyltramadol, in rats”. The Journal of Pharmacology and Experimental Therapeutics 295 (1): 352–9. PMID 10992001.
- ↑ Bamigbade, T. A.; Davidson, C.; Langford, R. M.; Stamford, J. A. (1997). „Actions of tramadol, its enantiomers and principal metabolite, O-desmethyltramadol, on serotonin (5-HT) efflux and uptake in the rat dorsal raphe nucleus”. British journal of anaesthesia 79 (3): 352–356. DOI:10.1093/bja/79.3.352. PMID 9389855.
- ↑ Driessen, B; Reimann, W; Giertz, H (1993). „Effects of the central analgesic tramadol on the uptake and release of noradrenaline and dopamine in vitro”. British Journal of Pharmacology 108 (3): 806–11. PMC 1908052. PMID 8467366.
