Feksofenadin

Fexofenadine
(IUPAC) ime
	(RS)- 2-[4-[1-hidroksi- 4-[4-(hidroksi- difenil- metil) - 1-piperidil]butil]fenil]- 2-metil- propanska kiselina
Klinički podaci
Robne marke	Allegra
AHFS/Drugs.com	Monografija
MedlinePlus	a697035
Identifikatori
CAS broj	83799-24-0
ATC kod	R06AX26
PubChem	3348
DrugBank	DB00950
ChemSpider	3231
UNII	E6582LOH6V
KEGG	D07958
ChEBI	CHEBI:5050
ChEMBL	CHEMBL914
Hemijski podaci
Formula	C32H39NO4
Mol. masa	501,656
SMILES	eMolekuli & PubHem
InChI
	InChI=1S/C32H39NO4/c1-31(2,30(35)36)25-17-15-24(16-18-25) 29(34)14-9-21-33-22-19-28(20-23-33)32(37, 26-10-5-3-6-11-26)27-12-7-4-8-13-27/h3-8, 10-13,15-18,28-29,34,37H,9,14,19-23H2,1-2H3,(H,35,36) ; Key: RWTNPBWLLIMQHL-UHFFFAOYSA-N
Farmakokinetički podaci
Bioraspoloživost	30-41%
Vezivanje za proteine plazme	60-70%
Metabolizam	Hepatički (5% doze)
Poluvreme eliminacije	14k4 sata
Izlučivanje	Fekalije (~80%) i urin (~11%) kao nepromenjen lek
Farmakoinformacioni podaci
Licenca	US FDA:link
Trudnoća	B2(AU) C(US)
Pravni status	Unscheduled (AU) OTC (CA) POM (UK) OTC (SAD)
Način primene	Oralno

Feksofenadin (Alegra, Telfast, Fastofen, Tilfur, Vifas, Telfekso, Alerfekso) je antihistaminski lek koji se koristi za treatman alergijskog rinitisa, simptoma alergije, i urtikarije.^[7]

On je razvijen kao zamena i alternativa za terfenadin (prodajna imena: Triludan i Seldane), koji uzrokuje produženje QT intervala, što potencijalno može da dovede od srčane aritmije. Feksofenadin, kao i drugi antihistamini druge i treće generacije, ne prolaze lako kroz krvno moždanu barijeru, i stoga u manjoj meri uzrokuju pospanost od antagonista histaminskog receptor prve generacije. Feksofenadin je antagonist H₁ receptora.^[8]

Feksofenadin se opisuje kao bilo antihistamin druge^[9] ili treće generacije.^[10]

Sinteza

Feksofenadin se može sintetisati počevši od etil piperidin-4-karboksilata i 4-bromofenilacetonitrila.^[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
↑ Lappin G, Shishikura Y, Jochemsen R, Weaver RJ, Gesson C, Houston B, Oosterhuis B, Bjerrum OJ, Rowland M, Garner C (May 2010). „Pharmacokinetics of fexofenadine: evaluation of a microdose and assessment of absolute oral bioavailability”. Eur J Pharm Sci 40 (2): 125–31. DOI:10.1016/j.ejps.2010.03.009. PMID 20307657.
↑ Greaves MW, Tan KT (2007). „Chronic Urticaria: Recent Advances”. Clin Rev Allergy Immunol 33 (1–2): 134–143. DOI:10.1007/s12016-007-0038-3. PMID 18094952.
↑ Katagiri, K.; Arakawa, S.; Hatano, Y.; Fujiwara, S. (2006). „Fexofenadine, an H1-receptor antagonist, partially but rapidly inhibits the itch of contact dermatitis induced by diphenylcyclopropenone in patients with alopecia areata”. The Journal of Dermatology 33 (2): 75. DOI:10.1111/j.1346-8138.2006.00017.x. PMID 16556272.
↑ Dicpinigaitis PV, Gayle YE (November 2003). „Effect of the second-generation antihistamine, fexofenadine, on cough reflex sensitivity and pulmonary function”. British Journal of Clinical Pharmacology 56 (5): 501–4. DOI:10.1046/j.1365-2125.2003.01902.x. PMC 1884387. PMID 14651723.
↑ Vena GA, Cassano N, Filieri M, Filotico R, D'Argento V, Coviello C (2002). „Fexofenadine in chronic idiopathic urticaria: a clinical and immunohistochemical evaluation”. Int J Immunopathol Pharmacol 15 (3): 217–24. PMID 12575922.
↑ Daniel Lednicer (1999). The Organic Chemistry of Drug Synthesis. 6. New York: Wiley Interscience. ISBN 0-471-24510-0.
↑ Kawai, SH; Hambalek, RJ; Just, G (May 1994). „A facile synthesis of an oxidation product of terfenadine”. J. Org. Chem. 59 (9): 2620–22. DOI:10.1021/jo00088a056.

Literatura

Rampe, D; Wible, B; Brown, AM; Dage, RC (December 1993). „Effects of terfenadine and its metabolites on a delayed rectifier K+ channel cloned from human heart”. Molecular Pharmacology 44 (6): 1240–5. PMID 8264561.

Vanjske veze

Fexofenadine Arhivirano 2012-02-12 na Wayback Machine-u (UK patient information leaflet)
Allegra (Fexofenadine Hydrochloride) label and research information Arhivirano 2012-10-16 na Wayback Machine-u

[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

[6] Lappin G, Shishikura Y, Jochemsen R, Weaver RJ, Gesson C, Houston B, Oosterhuis B, Bjerrum OJ, Rowland M, Garner C (May 2010). „Pharmacokinetics of fexofenadine: evaluation of a microdose and assessment of absolute oral bioavailability”. Eur J Pharm Sci 40 (2): 125–31. DOI:10.1016/j.ejps.2010.03.009. PMID 20307657.

[pmid18094952-7] Greaves MW, Tan KT (2007). „Chronic Urticaria: Recent Advances”. Clin Rev Allergy Immunol 33 (1–2): 134–143. DOI:10.1007/s12016-007-0038-3. PMID 18094952.

[8] Katagiri, K.; Arakawa, S.; Hatano, Y.; Fujiwara, S. (2006). „Fexofenadine, an H1-receptor antagonist, partially but rapidly inhibits the itch of contact dermatitis induced by diphenylcyclopropenone in patients with alopecia areata”. The Journal of Dermatology 33 (2): 75. DOI:10.1111/j.1346-8138.2006.00017.x. PMID 16556272.

[pmid14651723-9] Dicpinigaitis PV, Gayle YE (November 2003). „Effect of the second-generation antihistamine, fexofenadine, on cough reflex sensitivity and pulmonary function”. British Journal of Clinical Pharmacology 56 (5): 501–4. DOI:10.1046/j.1365-2125.2003.01902.x. PMC 1884387. PMID 14651723.

[pmid12575922-10] Vena GA, Cassano N, Filieri M, Filotico R, D'Argento V, Coviello C (2002). „Fexofenadine in chronic idiopathic urticaria: a clinical and immunohistochemical evaluation”. Int J Immunopathol Pharmacol 15 (3): 217–24. PMID 12575922.

[Lednicer1999-11] Daniel Lednicer (1999). The Organic Chemistry of Drug Synthesis. 6. New York: Wiley Interscience. ISBN 0-471-24510-0.

[12] Kawai, SH; Hambalek, RJ; Just, G (May 1994). „A facile synthesis of an oxidation product of terfenadine”. J. Org. Chem. 59 (9): 2620–22. DOI:10.1021/jo00088a056.

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