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

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[1][2] 3348
DrugBank DB00950
ChemSpider[3] 3231
UNII E6582LOH6V YesY
KEGG[4] D07958 YesY
ChEBI CHEBI:5050 YesY
ChEMBL[5] CHEMBL914 YesY
Hemijski podaci
Formula C32H39NO4 
Mol. masa 501,656
SMILES eMolekuli & PubHem
Farmakokinetički podaci
Bioraspoloživost 30-41%[6]
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

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]

SintezaUredi

Feksofenadin se može sintetisati počevši od etil piperidin-4-karboksilata i 4-bromofenilacetonitrila.[11][12]

 

ReferenceUredi

  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. PMID 20970519. doi:10.1016/j.drudis.2010.10.003.  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. PMID 20331846. doi:10.1186/1758-2946-2-3.  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. PMID 21948594. doi:10.1093/nar/gkr777.  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. PMID 20307657. doi:10.1016/j.ejps.2010.03.009. 
  7. Greaves MW, Tan KT (2007). "Chronic Urticaria: Recent Advances". Clin Rev Allergy Immunol 33 (1–2): 134–143. PMID 18094952. doi:10.1007/s12016-007-0038-3. 
  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. PMID 16556272. doi:10.1111/j.1346-8138.2006.00017.x. 
  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. PMC 1884387. PMID 14651723. doi:10.1046/j.1365-2125.2003.01902.x. 
  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. 
  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. 

LiteraturaUredi

  • 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. 

Spoljašnje vezeUredi