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Fexofenadine

Catalog No. DB00950 Name DrugBank
CAS Number 83799-24-0 Website http://www.ualberta.ca/
M. F. C32H39NO4 Telephone (780) 492-3111
M. W. 501.65636 Fax (780) 492-1071
Purity Email david.wishart@ualberta.ca
Storage Chembase ID: 826

SYNONYMS

IUPAC name
2-(4-{1-hydroxy-4-[4-(hydroxydiphenylmethyl)piperidin-1-yl]butyl}phenyl)-2-methylpropanoic acid
IUPAC Traditional name
telfast
Brand Name
Allegra-D 24 Hour
Allegra
Allegra-D 12 Hour
Synonyms
Fexofenadine hydrochloride
Terfenadine-COOH
Terfenadine carboxylate
Terfenadine acid metabolite
Fexofendine
Carboxyterfenadine

DATABASE IDS

CAS Number 83799-24-0
PubChem CID 3348
PubChem SID 46504676

PROPERTIES

Hydrophobicity(logP) 5.6
Solubility Slightly soluble

DETAILS

Description (English)
Item Information
Drug Groups approved
Description Fexofenadine hydrochloride (Allegra) 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. Fexofenadine, like other second and third-generation antihistamines, does not readily pass through the blood-brain barrier, and so causes less drowsiness than first-generation histamine-receptor antagonists.
Indication For management of Seasonal allergic rhinitis
Pharmacology Fexofenadine is a second-generation, long lasting H1-receptor antagonist (antihistamine) which has a selective and peripheral H1-antagonist action. Histamine is a chemical that causes many of the signs that are part of allergic reactions, such as the swelling of tissues. Histamine is released from histamine-storing cells (mast cells) and attaches to other cells that have receptors for histamine. The attachment of the histamine to the receptors causes the cell to be "activated," releasing other chemicals which produce the effects that we associate with allergy. Fexofenadine blocks one type of receptor for histamine (the H1 receptor) and thus prevents activation of cells by histamine. Unlike most other antihistamines, Fexofenadine does not enter the brain from the blood and, therefore, does not cause drowsiness. Fexofenadine lacks the cardiotoxic potential of terfenadine, since it does not block the potassium channel involved in repolarization of cardiac cells.
Toxicity Side effects include dizziness, drowsiness, and dry mouth.
Affected Organisms
Humans and other mammals
Biotransformation Approximately 5% of the total dose is metabolized, by cytochrome P450 3A4 and by intestinal microflora.
Absorption 33%
Half Life 14.4 hours
Protein Binding 60%-70%
References
Smith SM, Gums JG: Fexofenadine: biochemical, pharmacokinetic and pharmacodynamic properties and its unique role in allergic disorders. Expert Opin Drug Metab Toxicol. 2009 Jul;5(7):813-22. [Pubmed]
Bachert C: A review of the efficacy of desloratadine, fexofenadine, and levocetirizine in the treatment of nasal congestion in patients with allergic rhinitis. Clin Ther. 2009 May;31(5):921-44. [Pubmed]
Markham A, Wagstaff AJ: Fexofenadine. Drugs. 1998 Feb;55(2):269-74; discussion 275-6. [Pubmed]
Golightly LK, Greos LS: Second-generation antihistamines: actions and efficacy in the management of allergic disorders. Drugs. 2005;65(3):341-84. [Pubmed]
Molimard M, Diquet B, Benedetti MS: Comparison of pharmacokinetics and metabolism of desloratadine, fexofenadine, levocetirizine and mizolastine in humans. Fundam Clin Pharmacol. 2004 Aug;18(4):399-411. [Pubmed]
External Links
Wikipedia
RxList
Drugs.com

REFERENCES

  • Smith SM, Gums JG: Fexofenadine: biochemical, pharmacokinetic and pharmacodynamic properties and its unique role in allergic disorders. Expert Opin Drug Metab Toxicol. 2009 Jul;5(7):813-22. Pubmed
  • Bachert C: A review of the efficacy of desloratadine, fexofenadine, and levocetirizine in the treatment of nasal congestion in patients with allergic rhinitis. Clin Ther. 2009 May;31(5):921-44. Pubmed
  • Golightly LK, Greos LS: Second-generation antihistamines: actions and efficacy in the management of allergic disorders. Drugs. 2005;65(3):341-84. Pubmed
  • Molimard M, Diquet B, Benedetti MS: Comparison of pharmacokinetics and metabolism of desloratadine, fexofenadine, levocetirizine and mizolastine in humans. Fundam Clin Pharmacol. 2004 Aug;18(4):399-411. Pubmed
  • Markham A, Wagstaff AJ: Fexofenadine. Drugs. 1998 Feb;55(2):269-74; discussion 275-6. Pubmed