Fexofenadine

Fexofenadine
Clinical data
Trade namesAllegra, others
AHFS/Drugs.comMonograph
MedlinePlusa697035
License data
Pregnancy
category
Routes of
administration		By mouth
Drug classAntihistamine; H1 receptor antagonist
ATC code
Legal status
Legal status
Pharmacokinetic data
Bioavailability30–41%[8]
Protein binding60–70%[9]
MetabolismHepatic (≤5% of dose)[9]
Elimination half-life14.4 hours
ExcretionFeces (~80%) and urine (~10%) as unchanged drug[9]
Identifiers
IUPAC name
  • (±)-4-[1-Hydroxy-4-[4-(hydroxydiphenylmethyl)-1-piperidinyl]-butyl]-α, α-dimethyl benzeneacetic acid
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.228.648
Chemical and physical data
FormulaC32H39NO4
Molar mass501.667 g·mol−1
3D model (JSmol)
ChiralityRacemic mixture
SMILES
  • O=C(O)C(c1ccc(cc1)C(O)CCCN2CCC(CC2)C(O)(c3ccccc3)c4ccccc4)(C)C
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) N
  • Key:RWTNPBWLLIMQHL-UHFFFAOYSA-N Y
 NY (what is this?)  (verify)

Fexofenadine, sold under the brand name Allegra among others,[10] is an antihistamine medication used in the treatment of allergy symptoms such as allergic rhinitis and urticaria.[11]

Therapeutically, fexofenadine is a selective peripheral H1 blocker. It is classified as a second-generation antihistamine because it is less able to pass the blood–brain barrier and cause sedation, compared to first-generation antihistamines.[12][13]

It was patented in 1979 and came into medical use in 1996.[14] It is on the World Health Organization's List of Essential Medicines.[15] Fexofenadine has been manufactured in generic form since 2011.[16] In 2022, it was the 257th most commonly prescribed medication in the United States, with more than 1 million prescriptions.[17][18]

  1. ^ "Fexofenadine Use During Pregnancy". Drugs.com. 1 April 2019. Retrieved 26 July 2020.
  2. ^ "Telfast 30mg Film-coated Tablets - Summary of Product Characteristics (SmPC)". (emc). 25 October 2019. Retrieved 20 June 2021.
  3. ^ "Almerg 180 mg Film-Coated Tablets - Summary of Product Characteristics (SmPC)". (emc). Retrieved 20 June 2021.
  4. ^ "Fexofenadine Hydrochloride 120 mg Film-Coated Tablets - Summary of Product Characteristics (SmPC)". (emc). 22 March 2021. Archived from the original on 24 June 2021. Retrieved 20 June 2021.
  5. ^ "Allegra (fexofenadine hydrochloride) tablet, orally disintegrating for oral use Allegra (fexofenadine hydrochloride) tablet, film coated for oral use Allegra (fexofenadine hydrochloride) suspension for oral useInitial U.S. Approval: 1996". DailyMed. 15 December 2008. Retrieved 13 February 2022.
  6. ^ "Allegra Allergy- fexofenadine hydrochloride tablet, coated". DailyMed. Retrieved 12 February 2022.
  7. ^ "ALLEGRA (fexofenadine hydrochloride) Product Monograph" (PDF). Sanofi Consumer Health Inc. 7 November 2019. Archived from the original (PDF) on 22 January 2021. Retrieved 2 November 2020.
  8. ^ Lappin G, Shishikura Y, Jochemsen R, Weaver RJ, Gesson C, Houston B, et al. (May 2010). "Pharmacokinetics of fexofenadine: evaluation of a microdose and assessment of absolute oral bioavailability". European Journal of Pharmaceutical Sciences. 40 (2): 125–131. doi:10.1016/j.ejps.2010.03.009. PMID 20307657.
  9. ^ a b c Smith SM, Gums JG (July 2009). "Fexofenadine: biochemical, pharmacokinetic and pharmacodynamic properties and its unique role in allergic disorders". Expert Opinion on Drug Metabolism & Toxicology. 5 (7): 813–822. doi:10.1517/17425250903044967. PMID 19545214. S2CID 19048690.
  10. ^ Cite error: The named reference Brands was invoked but never defined (see the help page).
  11. ^ Bachert C (May 2009). "A review of the efficacy of desloratadine, fexofenadine, and levocetirizine in the treatment of nasal congestion in patients with allergic rhinitis". Clinical Therapeutics. 31 (5): 921–944. doi:10.1016/j.clinthera.2009.05.017. PMID 19539095.
  12. ^ Compalati E, Baena-Cagnani R, Penagos M, Badellino H, Braido F, Gómez RM, et al. (2011). "Systematic review on the efficacy of fexofenadine in seasonal allergic rhinitis: a meta-analysis of randomized, double-blind, placebo-controlled clinical trials". International Archives of Allergy and Immunology. 156 (1): 1–15. doi:10.1159/000321896. PMID 21969990.
  13. ^ 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): 501–504. doi:10.1046/j.1365-2125.2003.01902.x. PMC 1884387. PMID 14651723.
  14. ^ Fischer J, Ganellin CR (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 548. ISBN 9783527607495.
  15. ^ World Health Organization (2021). World Health Organization model list of essential medicines: 22nd list (2021). Geneva: World Health Organization. hdl:10665/345533. WHO/MHP/HPS/EML/2021.02.
  16. ^ "Dr. Reddy's announces the launch of Over-the-Counter Fexofenadine HCl and Pseudoephedrine HCl extended-release tablets". Dr. Reddy's Laboratories Ltd. 30 August 2011. Archived from the original on 12 October 2016. Retrieved 27 May 2016.
  17. ^ "The Top 300 of 2022". ClinCalc. Archived from the original on 30 August 2024. Retrieved 30 August 2024.
  18. ^ "Fexofenadine Drug Usage Statistics, United States, 2013 - 2022". ClinCalc. Retrieved 30 August 2024.
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