Oksimetazolin

Oksimetazolin
(IUPAC) ime
	3-(4,5-dihidro-1H-imidazol-2-ilmetil)- 2,4-dimetil-6-tert-setil-fenol
Klinički podaci
Robne marke	Afrin, Ocuclear, Drixine
AHFS/Drugs.com	Monografija
Identifikatori
CAS broj	1491-59-4
ATC kod	R01AA05 R01AB07, S01GA04
PubChem	4636
DrugBank	DB00935
ChemSpider	4475
UNII	8VLN5B44ZY
KEGG	D08322
ChEMBL	CHEMBL762
Hemijski podaci
Formula	C16H24N2O
Mol. masa	260,375 g·mol−1
SMILES	eMolekuli & PubHem
InChI
	InChI=1S/C16H24N2O/c1-10-8-13(16(3,4)5)15(19)11(2)12(10)9-14-17-6-7-18-14/h8,19H,6-7,9H2,1-5H3,(H,17,18) ; Key: WYWIFABBXFUGLM-UHFFFAOYSA-N
Fizički podaci
Tačka topljenja	301.5 °C (575 °F)
Farmakokinetički podaci
Poluvreme eliminacije	5-6 sata
Farmakoinformacioni podaci
Trudnoća	?
Pravni status	GSL (UK) OTC (SAD)

Oksimetazolin je topikalni dekongestiv. On je adrenomimetik koji selektivno agonizuje α1 i parcijalno α2 adrenergičke receptore.^[6] On se koristi u obliku oksimetazolin hidrohlorida u proizvodima kao što su Afrin, Dristan, Nasivin, Logicin, Vicks Sineks, Visin L.R., Sudafed OM, i Zicam. Ovaj lek je razvijen iz ksilometazolina 1961.^[7] Oksimetazolin je dostupan kao nazalni sprej.

Klinička upotreba

Oksimetazolin je dostupan na slobodno kao topikalni dekongestiv u obliku oksimetazolin hidrohlorida u nazalnim sprejevima.^[8]

Oksimetazolin takođe ima vazokonstrikciona svojstava, te se koristi i za tretiranje krvarenja nosa^[9]^[10] i crvenila očiju usled manje iritacije. U prodaji je pod imenom Visine L.R. u obliku kapi za oči.^[11]

Hemija

Oksimetazolin se sintetiše hlorometilacijom 6-tert-butil-2,4-dimetilfenola i daljom transformacijom rezultirajućeg hlorometil derivata u nitril.^[12]^[13] Reakcija tog intermedijara sa etilen diaminom daje oksimetazolin.

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
↑ Westfall Thomas C, Westfall David P, "Chapter 6. Neurotransmission: The Autonomic and Somatic Motor Nervous Systems" (Chapter). Brunton LL, Lazo JS, Parker KL: Goodman & Gilman's The Pharmacological Basis of Therapeutics, 11e: http://www.accessmedicine.com/content.aspx?aID=954433.
↑ German Patent 1,117,588
↑ Oxymetazoline
↑ Katz, R.I. i dr.. (1990). „A comparison of cocaine, lidocaine with epinephrine, and oxymetazoline for prevention of epistaxis on nasotracheal intubation”. J Clin Anesth 2 (1): 16–20. DOI:10.1016/0952-8180(90)90043-3. PMID 2310576.
↑ Krempl, G.A. and A.D. Noorily (1995). „Use of oxymetazoline in the management of epistaxis”. Ann Otol Rhinol Laryngol 104 (9 Pt 1): 704–6. PMID 7661519.
↑ „Visine”. Arhivirano iz originala na datum 2010-12-02. Pristupljeno 2014-04-05.
↑ W. Fruhstorher, H. Muller-Calgan, U.S. Patent 3.147.275 (1964)
↑ W. Fruhstorher, H. Muller-Calgan, DE 1117588 (1961).

Spoljašnje veze

	Portal Medicina
	Portal Hemija

[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

[adrenomimetic-6] Westfall Thomas C, Westfall David P, "Chapter 6. Neurotransmission: The Autonomic and Somatic Motor Nervous Systems" (Chapter). Brunton LL, Lazo JS, Parker KL: Goodman & Gilman's The Pharmacological Basis of Therapeutics, 11e: http://www.accessmedicine.com/content.aspx?aID=954433.

[7] German Patent 1,117,588

[8] Oxymetazoline

[9] Katz, R.I. i dr.. (1990). „A comparison of cocaine, lidocaine with epinephrine, and oxymetazoline for prevention of epistaxis on nasotracheal intubation”. J Clin Anesth 2 (1): 16–20. DOI:10.1016/0952-8180(90)90043-3. PMID 2310576.

[10] Krempl, G.A. and A.D. Noorily (1995). „Use of oxymetazoline in the management of epistaxis”. Ann Otol Rhinol Laryngol 104 (9 Pt 1): 704–6. PMID 7661519.

[11] „Visine”. Arhivirano iz originala na datum 2010-12-02. Pristupljeno 2014-04-05.

[12] W. Fruhstorher, H. Muller-Calgan, U.S. Patent 3.147.275 (1964)

[13] W. Fruhstorher, H. Muller-Calgan, DE 1117588 (1961).

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