Oksikodon

Oksikodon
(IUPAC) ime
	(5R,9R,13S,14S)-4,5α-epoxy-14-hydroxy-3-methoxy-17-methylmorphinan-6-one
Klinički podaci
Identifikatori
CAS broj	76-42-6
ATC kod	N02AA05 ; N02AA55 (u kombinaciji)
PubChem	5284603
DrugBank	DB00497
ChemSpider	4447649
UNII	CD35PMG570
KEGG	D05312
ChEMBL	CHEMBL656
Hemijski podaci
Formula	C18H21NO4
Mol. masa	315.364 g/mol
SMILES	eMolekuli & PubHem
InChI
	InChI=1S/C18H21NO4/c1-19-8-7-17-14-10-3-4-12(22-2)15(14)23-16(17)11(20)5-6-18(17,21)13(19)9-10/h3-4,13,16,21H,5-9H2,1-2H3/t13-,16+,17+,18-/m1/s1 ; Key: BRUQQQPBMZOVGD-XFKAJCMBSA-N
Sinonimi	dihydrohydroxycodeinone, 14-hydroxydihydrocodeinone, 6-deoxy-7,8-dihydro-14-hydroxy-3-O-methyl-6-oxomorphine
Farmakokinetički podaci
Bioraspoloživost	Up to 87%
Vezivanje za proteine plazme	45%
Metabolizam	Hepatički: primarno CYP3A, sekondarno CYP2D6
Poluvreme eliminacije	3–4.5 h
Izlučivanje	Urin (19% nepromenjen)
Farmakoinformacioni podaci
Trudnoća	?
Pravni status	Droga (S8) (AU) Schedule I (CA) ? (UK) Schedule II (SAD)
Opojna droga	umereno–visoka
Način primene	oralno, IM, IV, intranazalno, supkutano, transdermalno, rektalno, epiduralno

Oksikodon je opioidni analgetik koji se sintetiše iz opijumskog derivata tebaina. On je razvijen u Nemačkoj 1916, kao jedan od nekoliko semi-sintetičkih opioida u pokušaju da se poboljšaju postojeći opioidi: morfin, diacetilmorfin, i kodein.^[8]

Oksikodon je oralni lek koji se generalno propisuje za olakšavanje umerenog do jakog bola. Niske doze se takođe propisuju za privremeno olakšavanje dijareje. On je na tržištu u oblik proizvoda sa jednim ili više ingredijenata. Neki uobičajeni primeri proizvoda sa više sastojaka su oksikodon sa acetaminofen/paracetamolom, ili NSAID kao što je ibuprofen. Formulacije su dostupne kao generici, a i pod raznim brand imenima.

Hemija i nomenklatura

Hemijsko ime oksikodona je izvedeno iz kodeina. Njihove hemijske strukture su veoma slične. Razlikuju se samo u tome da je

Oksikodon ima hidroksilnu grupu na ugljeniku-14 (kodein ima samo vodonik na tom mestu), otuda oksikodon;
Oksikodon ima 7,8-dihidro osobinu, dok kodein ima dvostruku vezu između ta dva ugljenika; i
Oksikodon ima karbonilnu grupu (kao u ketonima) umesto hidroksilne grupe kodeina, otuda sufiks „-on“.

On je isto tako sličan da hidrokodonu. Razlikuju se samo po tome da oksikodon ima hidroksilnu grupu na ugljeniku-14.^[9]

Oksikodon je poznat pod imenima "dihidrohidroksikodeinon",^[10]^[11]^[12] Eucodal,^[11]^[12] Eukodal,^[8]^[13] "14-hidroksidihidrokodeinon",^[6]^[11] i "Nukodan".^[11]^[12]

Reference

↑ 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. edit
↑ 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. edit
↑ Joanne Wixon, Douglas Kell (2000). „Website Review: The Kyoto Encyclopedia of Genes and Genomes — KEGG”. Yeast 17 (1): 48–55. DOI:10.1002/(SICI)1097-0061(200004)17:1<48::AID-YEA2>3.0.CO;2-H.
↑ 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. edit
↑ ^6,0 ^6,1 Maryadele J. O'Neil (2006). The Merck index (14 izd.). Whitehouse Station, NJ: Merck & Co.. ISBN 978-0-911910-00-1.
↑ Lalovic B, Kharasch E, Hoffer C, Risler L, Liu-Chen LY, Shen DD (2006). „Pharmacokinetics and pharmacodynamics of oral oxycodone in healthy human subjects: role of circulating active metabolites” (PDF). Clin Pharmacol Ther 79 (5): 461–479. DOI:10.1016/j.clpt.2006.01.009. PMID 16678548. Arhivirano iz originala na datum 2010-06-07. Pristupljeno 2009-03-28.
↑ ^8,0 ^8,1 ^8,2 Kalso E (2005). „Oxycodone”. Journal of Pain and Symptom Management 29 (5S): S47–S56. DOI:10.1016/j.jpainsymman.2005.01.010. PMID 15907646.
↑ „AHFS Drug Information. Oxycodone (28:08.08) – 382132”. American Society of Health-System Pharmacists. March 2008. Arhivirano iz originala na datum 2008-10-04. Pristupljeno 2009-03-27.
↑ Maryadele J. O'Neil, editor ... (2006). The Merck index (14 izd.). Whitehouse Station, NJ: Merck & Co.. ISBN 978-0-911910-00-1.
↑ ^11,0 ^11,1 ^11,2 ^11,3 Eddy NB (1973). The National Research Council involvement in the opiate problem, 1928–1971. Washington: National Academy of Sciences.
↑ ^12,0 ^12,1 ^12,2 May EL, Jacobson AE (1989). „The Committee on Problems of Drug Dependence: a legacy of the National Academy of Sciences. A historical account”. Drug Alcohol Depend 23 (3): 183–218. DOI:10.1016/0376-8716(89)90083-5. PMID 2666074.
↑ Sunshine A, Olson NZ, Colon A, Rivera J, Kaiko RF, Fitzmartin RD, Reder RF, Goldenheim PD (1996-07-01). „Analgesic efficacy of controlled-release oxycodone in postoperative pain”. J Clin Pharmacol 36 (7): 595–603. PMID 8844441. Pristupljeno 2009-03-25.

Literatura

Meier, Barry (2003). Pain killer: a "wonder" drug's trail of addiction and death. Emmaus, PA: Rodale. ISBN 1579546382.
Pinsky, Drew (2004). When painkillers become dangerous: what everyone needs to know about OxyContin and other prescription drugs. Center City, MN: Hazelden. ISBN 159285107X.
Lockwood, Brad (2006). Oxycontin: from pain relief to addiction. New York: Rosen Pub. Group, Inc. ISBN 9781404209138.
Maryadele J. O'Neil (2006). The Merck index (14 izd.). Whitehouse Station, NJ: Merck & Co.. ISBN 978-0-911910-00-1.
Maryadele J. O'Neil, editor ... (2006). The Merck index (14 izd.). Whitehouse Station, NJ: Merck & Co.. ISBN 978-0-911910-00-1.
Eddy NB (1973). The National Research Council involvement in the opiate problem, 1928–1971. Washington: National Academy of Sciences.

Spoljašnje veze

	Portal Medicina
	Portal Hemija

Farmakološki profil
Ubitačna kombinacija Arhivirano 2011-06-07 na Wayback Machine-u
Informacije o leku

[1] 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. edit

[2] 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.

[3] 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. edit

[4] Joanne Wixon, Douglas Kell (2000). „Website Review: The Kyoto Encyclopedia of Genes and Genomes — KEGG”. Yeast 17 (1): 48–55. DOI:10.1002/(SICI)1097-0061(200004)17:1<48::AID-YEA2>3.0.CO;2-H.

[5] 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. edit

[MerckIndex-6] 6,0 ^6,1 Maryadele J. O'Neil (2006). The Merck index (14 izd.). Whitehouse Station, NJ: Merck & Co.. ISBN 978-0-911910-00-1.

[Lalovic2006-7] Lalovic B, Kharasch E, Hoffer C, Risler L, Liu-Chen LY, Shen DD (2006). „Pharmacokinetics and pharmacodynamics of oral oxycodone in healthy human subjects: role of circulating active metabolites” (PDF). Clin Pharmacol Ther 79 (5): 461–479. DOI:10.1016/j.clpt.2006.01.009. PMID 16678548. Arhivirano iz originala na datum 2010-06-07. Pristupljeno 2009-03-28.

[Kalso-8] 8,0 ^8,1 ^8,2 Kalso E (2005). „Oxycodone”. Journal of Pain and Symptom Management 29 (5S): S47–S56. DOI:10.1016/j.jpainsymman.2005.01.010. PMID 15907646.

[AHFS-9] „AHFS Drug Information. Oxycodone (28:08.08) – 382132”. American Society of Health-System Pharmacists. March 2008. Arhivirano iz originala na datum 2008-10-04. Pristupljeno 2009-03-27.

[autogenerated1-10] Maryadele J. O'Neil, editor ... (2006). The Merck index (14 izd.). Whitehouse Station, NJ: Merck & Co.. ISBN 978-0-911910-00-1.

[Eddy1973-11] 11,0 ^11,1 ^11,2 ^11,3 Eddy NB (1973). The National Research Council involvement in the opiate problem, 1928–1971. Washington: National Academy of Sciences.

[MayJacobson-12] 12,0 ^12,1 ^12,2 May EL, Jacobson AE (1989). „The Committee on Problems of Drug Dependence: a legacy of the National Academy of Sciences. A historical account”. Drug Alcohol Depend 23 (3): 183–218. DOI:10.1016/0376-8716(89)90083-5. PMID 2666074.

[Sunshine-13] Sunshine A, Olson NZ, Colon A, Rivera J, Kaiko RF, Fitzmartin RD, Reder RF, Goldenheim PD (1996-07-01). „Analgesic efficacy of controlled-release oxycodone in postoperative pain”. J Clin Pharmacol 36 (7): 595–603. PMID 8844441. Pristupljeno 2009-03-25.

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