Terfenadine

• CAT Number: I003801
• CAS Number: 50679-08-8
• Molecular Formula: C32H41NO2
• Molecular Weight: 471.7
• Purity: ≥95%
• Synonyms: MDL 9918;NSC 665802;(±)-Terfenadine;DL-Terfenadine
• Target: HERG
• Solubility: 100 mM in DMSO
• Storage: -20°C
• IC50: 204 nM
• InChIKey: GUGOEEXESWIERI-UHFFFAOYSA-N

Terfenadine (Cat.No:I003801) was an antihistamine used to treat allergies and hay fever. Due to its potential to cause cardiac arrhythmias, it was withdrawn from the market in many countries and replaced with fexofenadine. Terfenadine’s metabolite, fexofenadine, is now widely used as a safer alternative for allergy relief.

Reference

1:Terfenadine t-butyl hydroxylation catalyzed by human and marmoset cytochrome P450 3A and 4F enzymes in livers and small intestines. Uehara S, Yuki Y, Uno Y, Inoue T, Sasaki E, Yamazaki H.Xenobiotica. 2017 May 15:1-6. doi: 10.1080/00498254.2017.1321811. [Epub ahead of print] PMID: 28436281 2:Virtual Clinical Trial Toward Polytherapy Safety Assessment: Combination of Physiologically Based Pharmacokinetic/Pharmacodynamic-Based Modeling and Simulation Approach With Drug-Drug Interactions Involving Terfenadine as an Example. Wiśniowska B, Polak S.J Pharm Sci. 2016 Nov;105(11):3415-3424. doi: 10.1016/j.xphs.2016.08.002. Epub 2016 Sep 15. PMID: 27640752 3:Stimulating Effect of Terfenadine on Erythrocyte Cell Membrane Scrambling. Signoretto E, Castagna M, Al Mamun Bhuyan A, Lang F.Cell Physiol Biochem. 2016;38(4):1425-34. doi: 10.1159/000443085. Epub 2016 Apr 4. PMID: 27035465 Free Article4:Marmoset cytochrome P450 2J2 mainly expressed in small intestines and livers effectively metabolizes human P450 2J2 probe substrates, astemizole and terfenadine. Uehara S, Uno Y, Inoue T, Okamoto E, Sasaki E, Yamazaki H.Xenobiotica. 2016 Nov;46(11):977-85. doi: 10.3109/00498254.2016.1146366. Epub 2016 Feb 22. PMID: 26899760 5:Liquid microjunction surface sampling of acetaminophen, terfenadine and their metabolites in thin tissue sections. Kertesz V, Paranthaman N, Moench P, Catoire A, Flarakos J, Van Berkel GJ.Bioanalysis. 2014;6(19):2599-606. doi: 10.4155/bio.14.130. PMID: 25411703 6:Distribution of terfenadine and its metabolites in locusts studied by desorption electrospray ionization mass spectrometry imaging. Olsen LR, Hansen SH, Janfelt C.Anal Bioanal Chem. 2015 Mar;407(8):2149-58. doi: 10.1007/s00216-014-8292-8. Epub 2014 Nov 18. PMID: 25404166 7:Effect of terfenadine and pentamidine on the HERG channel and its intracellular trafficking: combined analysis with automated voltage clamp and confocal microscopy. Tanaka H, Takahashi Y, Hamaguchi S, Iida-Tanaka N, Oka T, Nishio M, Ohtsuki A, Namekata I.Biol Pharm Bull. 2014;37(11):1826-30. PMID: 25366487 Free Article8:Comparative study of the protective effects of terfenadine and amiodarone on barium chloride/aconitine-induced ventricular arrhythmias in rats: a potential role of terfenadine. Liu B, Li S, Su Y, Xiong M, Xu Y.Mol Med Rep. 2014 Dec;10(6):3217-26. doi: 10.3892/mmr.2014.2640. Epub 2014 Oct 14. PMID: 25322793 9:Repurposing the antihistamine terfenadine for antimicrobial activity against Staphylococcus aureus. Perlmutter JI, Forbes LT, Krysan DJ, Ebsworth-Mojica K, Colquhoun JM, Wang JL, Dunman PM, Flaherty DP.J Med Chem. 2014 Oct 23;57(20):8540-62. doi: 10.1021/jm5010682. Epub 2014 Oct 6. PMID: 25238555 Free PMC Article10:Response to comment: /A note on CYP2J2-mediated terfenadine hydroxylation in human liver microsomes/. Lee B, Wu Z, Liu KH.Food Chem Toxicol. 2014 Sep;71:286-7. doi: 10.1016/j.fct.2014.07.002. Epub 2014 Jul 3. No abstract available. PMID: 24998194