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20-September-2008 09:55:57 - Fexofenadine Fexofenadine Systematic IUPAC name 2-4-1-hydroxy-4-4-hydroxy-diphenyl- methyl-1-piperidylbutylphenyl-2- methyl-propanoic acid Identifiers CAS number 153439-40-8 ATC code R06A626 PubChem 3348 DrugBank APRD00349 Chemical data Formula C32H39NO4 Mol. mass 501.656 SMILES eMolecules PubChem Pharmacokinetic data Bioavailability Not yet established Protein binding 60-70% Metabolism Hepatic 5% of dose Half life 14.4 hours Excretion Biliary , fecal and renal Therapeutic considerations Pregnancy cat. C US B2 Australia Legal status Prescription Only US, UK OTC Canada, Australia Routes Oral Fexofenadine hydrochloride brand names include Allegra and Telfast is an antihistamine drug used in the treatment of hayfever and similar allergy symptoms. It was developed as a successor of and alternative to terfenadine brand names include Triludan and Seldane, an antihistamine with potentially serious contraindications. Fexofenadine, like other second and third-generation antihistamines, does not readily cross the blood-brain barrier, and so causes less drowsiness than first-generation histamine-receptor antagonists. It works by being an antagonist to the H1 receptor.1 Contents 1 Common side effects 2 Drug Interactions 3 Usage 4 Overdose 5 History 6 Synthesis 7 Notes 8 References 9 External links Common side effects Nausea Vomiting Weakness Drowsiness, sleepiness Fatigue Diarrhea Unusual bowel movements Drug Interactions In controlled clinical studies there were no interactions with other drugs that significantly affected the safety or effectiveness of fexofenadine.citation needed Usage For seasonal allergies the recommended dose for adults and children 12 years or older is 60 mg twice daily or 180 mg once daily. Children 6-11 years of age should be given 30 mg twice daily. For chronic urticaria, adults and children 12 years or older should use 60 mg twice daily, and children 6-11 years of age should use 30 mg twice daily. Take Fexofenadine with water not fruit juice.2 Fexofenadine can be taken with or without food. Overdose Reports of fexofenadine overdose are infrequent, and because of this, the effects are not well established. No deaths occurred in testing on mice, at 5000 mg/kg, which is 110 times the maximum recommended dose for an adult human. Further research shows no deaths in rats at the same concentration, which equates four hundred times the recommended dose in an adult human. Research on humans ranges from a single 800 mg dose, to a twice-daily 690 mg dose for a month, with no clinically significant adverse effects, when compared to a placebo. History The older antihistaminic agent terfenadine was found to metabolize into the related carboxylic acid, fexofenadine. Fexofenadine was found to retain all of the biological activity of its parent while giving fewer adverse reactions in patients, so terfenadine was replaced in the market by its metabolite.3 Fexofenadine was originally synthesized in 1993 by Massachusetts-based biotechnology company Sepracor, which then sold the development rights to Hoechst Marion Roussel now part of Sanofi-Aventis, and was later approved by the Food and Drug Administration FDA in 1996. AMRI holds the patents to the intermediates and production of fexofenadine HCl along with Roussel. Since that time, it has achieved blockbuster drug status with global sales of $1.87B USD in 2004 with $1.49B USD coming from the United States. AMRI received royalty payments from Aventis that enabled the growth of AMRI. Synthesis Fexofenadine may be synthesized as shown from piperidine-4-carboxylate ester and 4-bromophenylacetonitrile.3 Chemical synthesis of fexofenadine To produce the piperidine piece, two phenyl groups are first introduced using a Grignard reaction on the ester, giving a tertiary alcohol. The amine group is then alkylated with a protected aldehyde, then the aldehyde is recovered by deprotection with acid. The remaining piece of the molecule is produced by a double alkylation by iodomethane of the carbanion derived from the nitrile. The nitrile group is then hydrolyzed to a carboxylic acid. The aryl bromide is then lithiated to produce the organolithium compound, which can be coupled with the aldehyde piece to give after workup fexofenadine. Notes ^ IngentaConnect - Fexofenadine, an H1-receptor antagonist, partially ... ^ MedlinePlus Drug Information: Fexofenadine and BBC - Fruit juice 'could affect drugs' ^ a b Daniel Lednicer 1999. The Organic Chemistry of Drug Synthesis 6. New York: Wiley Interscience, 38-40. ISBN 0-471-24510-0. References Synthesis: J. Org. Chem. 1994, 59, 2620. Biological effects: Mol. Pharmacol. 1993, 44, 1240. External links Fexofenadine UK patient information leaflet Allegra Fexofenadine Hydrochloride label and research information Sanofi-aventis Home page Fexofenadine MedicineNet Written by Pharmacists; Reviewed by Doctors v d e Histamine antagonists H1 or non-selective Alkylamines Bepotastine Bamipine Brompheniramine Chlorpheniramine Dexbrompheniramine Dexchlorpheniramine Dimethindene Metron S Pheniramine Pyrrobutamine Talastine Thenaldine Tolpropamine Triprolidine Ethanolamines Aminoalkyl ethers Bietanautine Bromazine/Bromodiphenhydramine Carbinoxamine Chlorphenoxamine Clemastine Diphenylpyraline Diphenhydramine Doxylamine Embramine p-Methyldiphenhydramine Moxastine Orphenadrine Phenyltoloxamine Setastine Ethylenediamines Chloropyramine Chlorothen Histapyrrodine Methafurylene Mepyramine Methapyrilene Pyrilamine Talastine Thenyldiamine Thonzylamine Tripelennamine Pyribenzamine Phenothiazine Tricyclics Ahistan Etymemazine Hydroxyethylpromethazine Isopromethazine Isothipendyl Mequitazine Methdilazine Oxomemazine Promethazine Thiazinamium Other Tricyclics Azatadine Clobenzepam Cyproheptadine Deptropine Isothipendyl Loratidine Piperazine Buclizine Chlorcyclizine Cinnarizine Clocinizine Hydroxyzine Niaprazine Oxatomide Benzhydryl compounds Cyclizine, Meclizine Others including selective, 2nd gen, 3rd gen Antazoline Astemizole Azatadine Azelastine Bepottastine Bamipine Cetoxine Clemizole Clobenztropine Deptropine Desloratadine Dimebon Ebastine Emedastine Epinastine Ketotifen Levocabastine Loratadine Mebhydrolin Mizolastine Phenindamine Pimethixene Pyrrobutamine Rupatadine Thenalidine Tritoqualine Alkylamine Acrivastine Tricyclic Olopatadine Piperazine Levocetirizine, Cetirizine Benzhydryl compounds Fexofenadine, Terfenadine H2 Cimetidine Famotidine Ranitidine Roxatidine Lafutidine Niperotidine Nizatidine H3 A-349,821 ABT-239 Burimamide Ciproxifan Clobenpropit Conessine Impentamine Iodophenpropit Thioperamide VUF-5681 H4 JNJ 7777120 Thioperamide VUF-6002 Retrieved from http://en..org/wiki/Fexofenadine Categories: Antihistamines | Sanofi-AventisHidden categories: All articles with statements | Articles with statements since April 2008 Views Article Discussion this page History Personal tools Log in / create account Navigation Main page Contents Featured content Current events Random article Search Go Search Interaction Community portal Recent changes Contact Donate to Help Toolbox What links here Related changes Upload file Special pages Printable version Permanent link Cite this page Languages Deutsch Français 日本語 ไทย This page was last modified on 20 August 2008, at 17:36
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