Product Name

Fexofenadine Hydrochloride

CAS Number

153439-40-8

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Product Name:
Fexofenadine Hydrochloride
CAS Number:
153439-40-8
Indication:
For management of Seasonal allergic rhinitis
Mode 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. Fexofenadine exhibits no anticholinergic, antidopaminergic, alpha1-adrenergic or beta-adrenergic-receptor blocking effects.

Pharmacodynamics:

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.

Metabolism:

Approximately 5% of the total dose is metabolized, by cytochrome P450 3A4 and by intestinal microflora.

Toxicity:

Side effects include dizziness, drowsiness, and dry mouth.

IUPAC:
Benzeneacetic acid, 4-(1-hydroxy-4-(4-(hydroxydiphenylmethyl)-1-piperidinyl)butyl)-alpha, alpha-dimethyl-, hydrochloride
ATC:
R06AX26
PubChem:
3348
DrugBank:
DB00950 (APRD00349)
Formula:
C32-H39-N-O4.Cl-H
Molecular Mass:
538.124
Synonyms:
(+-)-p-(1-Hydroxy-4-(4-(hydroxydiphenylmethyl)piperidino)butyl)-alpha-methylhydratropic acid hydrochloride, Allegra, Allegra Allergy, Allegra Hives, Benzeneacetic acid, 4-(1-hydroxy-4-(4-(hydroxydiphenylmethyl)-1-piperidinyl)butyl)-alpha,alpha-dimethyl-, hydrochloride, (+-)-, Carboxyterfenadine hydrochloride, Children's Allegra Allergy, Children's Allegra Hives, Fexofenadine, Fexofenadine HCl, Fexofenadine hydrochloride, MDL 16,455A, Telfast, Terfenadine carboxylate hydrochloride, UNII-2S068B75ZU
SMILES:
CC(C)(c1ccc(cc1)C(CCCN2CCC(CC2)C(c3ccccc3)(c4ccccc4)O)O)C(=O)O.Cl
AHFS Code:
04:08.0
InChi:
1S/C32H39NO4.ClH/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);1H
General Reference:
General Reference:

 

  1. 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
  2. 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
  3. Markham A, Wagstaff AJ: Fexofenadine. Drugs. 1998 Feb;55(2):269-74; discussion 275-6. Pubmed
  4. Golightly LK, Greos LS: Second-generation antihistamines: actions and efficacy in the management of allergic disorders. Drugs. 2005;65(3):341-84. Pubmed
  5. 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

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