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QuickView for Fexofenadine (compound)

Summary
General Info

PubChem

PubChem Compound 3348

Name:	fexofenadine
PubChem Compound ID:	3348
Molecular formula:	C₃₂H₃₉NO₄
Molecular weight:	501.656 g/mol
Synonyms:	KBioGR_000807; Fexofenadine hydrochloride; 159389-12-5; Spectrum3_001921; SPBio_001197; Benzeneacetic acid, 4-(1-hydroxy-4-(4-(hydroxydiphenylmethyl)-1-piperidinyl)butyl)-alpha,alpha-dimethyl-; KBio2_007585; KBioSS_002456; Terfenadine acid metabolite; MDL 16455. show more » KBioGR_000807; Fexofenadine hydrochloride; 159389-12-5; Spectrum3_001921; SPBio_001197; Benzeneacetic acid, 4-(1-hydroxy-4-(4-(hydroxydiphenylmethyl)-1-piperidinyl)butyl)-alpha,alpha-dimethyl-; KBio2_007585; KBioSS_002456; Terfenadine acid metabolite; MDL 16455; C06999; 4-(1-Hydroxy-4-(4-(hydroxydiphenylmethyl)-1-piperidinyl)butyl)-alpha,alpha-dimethylbenzeneacetic acid; Carboxyterfenadine; EU-0100488; Fexofenadine; KBio2_002449; Terfenadine carboxylate; Spectrum2_001179; Terfenadine-COOH; KBio3_002742; Spectrum4_000204; 76815-58-2; KBio2_005017; Spectrum_001914; 83799-24-0 show less «

DrugBank

Identification

Name:	fexofenadine
Name (isomeric):	DB00950
Drug Type:	small molecule
Synonyms:	Terfenadine acid metabolite; Fexofenadine hydrochloride; Carboxyterfenadine; Fexofendine; Terfenadine carboxylate; Terfenadine-COOH
Brand:	Allegra-D 12 Hour, Allegra, Allegra-D 24 Hour
Brand name mixture:	Allegra-D(Fexofenadine hydrochloride + Pseudoephedrine hydrochloride)
Category:	Antihistamines, Anti-Allergic Agents, Histamine H1 Antagonists, Non-Sedating
CAS number:	83799-24-0

Pharmacology

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 t... show more » 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. show less «
Mechanism of Action:	Like other H1-blockers, Fexofenadine competes with free histamine for binding at H1-receptors in the GI tract, large blood vessels, and bronchial smooth muscle. This blocks the action of endogenous histamine, which subsequently leads to temporary relief of the negative symptoms (eg. nasal congestion, watery eyes) brought on by histamine. Fexofenadi... show more » Like other H1-blockers, Fexofenadine competes with free histamine for binding at H1-receptors in the GI tract, large blood vessels, and bronchial smooth muscle. This blocks the action of endogenous histamine, which subsequently leads to temporary relief of the negative symptoms (eg. nasal congestion, watery eyes) brought on by histamine. Fexofenadine exhibits no anticholinergic, antidopaminergic, alpha1-adrenergic or beta-adrenergic-receptor blocking effects. show less «
Absorption:	33%
Protein binding:	60%-70%
Biotransformation:	Approximately 5% of the total dose is metabolized, by cytochrome P450 3A4 and by intestinal microflora.
Half Life:	14.4 hours
Toxicity:	Side effects include dizziness, drowsiness, and dry mouth.
Affected organisms:	Humans and other mammals

Interactions

Food interaction:

Grapefruit and grapefruit juice should be avoided throughout treatment as grapefruit can significantly decrease serum levels of this product.

Take without regard to meals.

Drug interaction:

Tacrine	The therapeutic effects of the central acetylcholinesterase inhibitor, Tacrine, and/or the anticholinergic, Fexofenadine, may be reduced due to antagonism. The interaction may be beneficial when the anticholinergic action is a side effect. Monitor for decreased efficacy of both agents.
Triprolidine	Triprolidine and Fexofenadine, two anticholinergics, may cause additive anticholinergic effects and enhance their adverse/toxic effects. Additive CNS depressant effects may also occur. Monitor for enhanced anticholinergic and CNS depressant effects.
Trimethobenzamide	Trimethobenzamide and Fexofenadine, two anticholinergics, may cause additive anticholinergic effects and enhance their adverse/toxic effects. Monitor for enhanced anticholinergic effects.
Trospium	Trospium and Fexofenadine, two anticholinergics, may cause additive anticholinergic effects and enhanced adverse/toxic effects. Monitor for enhanced anticholinergic effects.
Cisapride	Increased risk of cardiotoxicity and arrhythmias

Targets

Histamine H1 receptor

In peripheral tissues, the H1 subclass of histamine receptors mediates the contraction of smooth muscles, increase in capillary permeability due to contraction of terminal venules, and catecholamine release from adrenal medulla, as well as mediating neurotransmission in the central nervous system

UniProt ID:

P35367

Gene:

HRH1

Actions:

antagonist

References:

Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5.
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Amon U, Amon S, Gibbs BF: In vitro studies with fexofenadine, a new nonsedating histamine H1 receptor antagonist, on isolated human basophils. Inflamm Res. 2000 Apr;49 Suppl 1:S13-4.
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Abbas MN, Abdel Fattah AA, Zahran E: A novel membrane sensor for histamine H1-receptor antagonist "fexofenadine". Anal Sci. 2004 Aug;20(8):1137-42.
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Grzelewska-Rzymowska I, Kroczynska-Bednarek J, Pietrzkowicz M: [Effect of fexofenadine--selective antagonist of histamine receptor (H1) on histamine-induced bronchoconstriction] Pol Merkur Lekarski. 2003 Jan;14(79):43-6.
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Tashiro M, Sakurada Y, Iwabuchi K, Mochizuki H, Kato M, Aoki M, Funaki Y, Itoh M, Iwata R, Wong DF, Yanai K: Central effects of fexofenadine and cetirizine: measurement of psychomotor performance, subjective sleepiness, and brain histamine H1-receptor occupancy using 11C-doxepin positron emission tomography. J Clin Pharmacol. 2004 Aug;44(8):890-900.
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Cavero I, Mestre M, Guillon JM, Heuillet E, Roach AG: Preclinical in vitro cardiac electrophysiology: a method of predicting arrhythmogenic potential of antihistamines in humans? Drug Saf. 1999;21 Suppl 1:19-31; discussion 81-7.
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Devillier P, Roche N, Faisy C: Clinical pharmacokinetics and pharmacodynamics of desloratadine, fexofenadine and levocetirizine : a comparative review. Clin Pharmacokinet. 2008;47(4):217-30.
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Dhanya NB, Thasleem Z, Rai R, Srinivas CR: Comparative efficacy of levocetirizine, desloratidine and fexofenadine by histamine wheal suppression test. Indian J Dermatol Venereol Leprol. 2008 Jul-Aug;74(4):361-3.
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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.
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Markham A, Wagstaff AJ: Fexofenadine. Drugs. 1998 Feb;55(2):269-74; discussion 275-6.
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Enzymes

Cytochrome P450 2D6

Transporters

Multidrug resistance protein 1

Solute carrier organic anion transporter family member 2B1

Solute carrier organic anion transporter family member 1A2