Details
Stereochemistry | RACEMIC |
Molecular Formula | C32H39NO4 |
Molecular Weight | 501.6564 |
Optical Activity | ( + / - ) |
Defined Stereocenters | 0 / 1 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
CC(C)(C(O)=O)C1=CC=C(C=C1)C(O)CCCN2CCC(CC2)C(O)(C3=CC=CC=C3)C4=CC=CC=C4
InChI
InChIKey=RWTNPBWLLIMQHL-UHFFFAOYSA-N
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)
Molecular Formula | C32H39NO4 |
Molecular Weight | 501.6564 |
Charge | 0 |
Count |
|
Stereochemistry | RACEMIC |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 1 |
E/Z Centers | 0 |
Optical Activity | ( + / - ) |
DescriptionCurator's Comment: Description was created based on several sources, including https://www.drugbank.ca/drugs/DB00950
Curator's Comment: Description was created based on several sources, including https://www.drugbank.ca/drugs/DB00950
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. Fexofenadine is sold under the trade name Allegra among others. ALLEGRA is indicated for the relief of symptoms associated with seasonal allergic
rhinitis in adults and children 2 years of age and older.
CNS Activity
Originator
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
246.0 nM [IC50] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | ALLEGRA Approved UseALLEGRA is indicated for the relief of symptoms associated with seasonal allergic
rhinitis in adults and children 2 years of age and older. Launch Date8.3825282E11 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
523.28 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/27151911 |
120 mg single, oral dose: 120 mg route of administration: Oral experiment type: SINGLE co-administered: |
FEXOFENADINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
AUC
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
3507.8 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/27151911 |
120 mg single, oral dose: 120 mg route of administration: Oral experiment type: SINGLE co-administered: |
FEXOFENADINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
9.26 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/27151911 |
120 mg single, oral dose: 120 mg route of administration: Oral experiment type: SINGLE co-administered: |
FEXOFENADINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
Doses
Dose | Population | Adverse events |
---|---|---|
690 mg 2 times / day multiple, oral Highest studied dose Dose: 690 mg, 2 times / day Route: oral Route: multiple Dose: 690 mg, 2 times / day Sources: |
healthy, 18-55 years n = 4 Health Status: healthy Age Group: 18-55 years Sex: M Population Size: 4 Sources: |
Other AEs: Headache, Tiredness... Other AEs: Headache (3 patients) Sources: Tiredness (3 patients) Dizziness (3 patients) |
800 mg single, oral Highest studied dose |
healthy, 26.9 years (range: 18-51) years n = 8 Health Status: healthy Age Group: 26.9 years (range: 18-51) years Sex: M Population Size: 8 Sources: |
Other AEs: Headache, Tiredness... Other AEs: Headache (3 patients) Sources: Tiredness (3 patients) Dizziness (3 patients) |
60 mg 2 times / day multiple, oral Highest studied dose Dose: 60 mg, 2 times / day Route: oral Route: multiple Dose: 60 mg, 2 times / day Sources: |
unhealthy, 6-11 years Health Status: unhealthy Condition: seasonal allergic rhinitis Age Group: 6-11 years Sex: M+F Sources: |
|
180 mg 1 times / day multiple, oral Dose: 180 mg, 1 times / day Route: oral Route: multiple Dose: 180 mg, 1 times / day Sources: |
unhealthy, 69 years n = 1 Health Status: unhealthy Age Group: 69 years Sex: M Population Size: 1 Sources: |
Disc. AE: Papular urticarial eruption... AEs leading to discontinuation/dose reduction: Papular urticarial eruption (1 patient) Sources: |
30 mg 1 times / day multiple, oral Recommended Dose: 30 mg, 1 times / day Route: oral Route: multiple Dose: 30 mg, 1 times / day Sources: Page: p. 22 |
unhealthy Health Status: unhealthy Sources: Page: p. 22 |
Disc. AE: Headache... AEs leading to discontinuation/dose reduction: Headache (2 patients) Sources: Page: p. 22 |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
Dizziness | 3 patients | 690 mg 2 times / day multiple, oral Highest studied dose Dose: 690 mg, 2 times / day Route: oral Route: multiple Dose: 690 mg, 2 times / day Sources: |
healthy, 18-55 years n = 4 Health Status: healthy Age Group: 18-55 years Sex: M Population Size: 4 Sources: |
Headache | 3 patients | 690 mg 2 times / day multiple, oral Highest studied dose Dose: 690 mg, 2 times / day Route: oral Route: multiple Dose: 690 mg, 2 times / day Sources: |
healthy, 18-55 years n = 4 Health Status: healthy Age Group: 18-55 years Sex: M Population Size: 4 Sources: |
Tiredness | 3 patients | 690 mg 2 times / day multiple, oral Highest studied dose Dose: 690 mg, 2 times / day Route: oral Route: multiple Dose: 690 mg, 2 times / day Sources: |
healthy, 18-55 years n = 4 Health Status: healthy Age Group: 18-55 years Sex: M Population Size: 4 Sources: |
Dizziness | 3 patients | 800 mg single, oral Highest studied dose |
healthy, 26.9 years (range: 18-51) years n = 8 Health Status: healthy Age Group: 26.9 years (range: 18-51) years Sex: M Population Size: 8 Sources: |
Headache | 3 patients | 800 mg single, oral Highest studied dose |
healthy, 26.9 years (range: 18-51) years n = 8 Health Status: healthy Age Group: 26.9 years (range: 18-51) years Sex: M Population Size: 8 Sources: |
Tiredness | 3 patients | 800 mg single, oral Highest studied dose |
healthy, 26.9 years (range: 18-51) years n = 8 Health Status: healthy Age Group: 26.9 years (range: 18-51) years Sex: M Population Size: 8 Sources: |
Papular urticarial eruption | 1 patient Disc. AE |
180 mg 1 times / day multiple, oral Dose: 180 mg, 1 times / day Route: oral Route: multiple Dose: 180 mg, 1 times / day Sources: |
unhealthy, 69 years n = 1 Health Status: unhealthy Age Group: 69 years Sex: M Population Size: 1 Sources: |
Headache | 2 patients Disc. AE |
30 mg 1 times / day multiple, oral Recommended Dose: 30 mg, 1 times / day Route: oral Route: multiple Dose: 30 mg, 1 times / day Sources: Page: p. 22 |
unhealthy Health Status: unhealthy Sources: Page: p. 22 |
PubMed
Title | Date | PubMed |
---|---|---|
Treatment of urticaria. An evidence-based evaluation of antihistamines. | 2001 |
|
Causality assessment of adverse effects: when is re-challenge ethically acceptable? | 2001 |
|
[The effect of second generation histamine antagonists on the heart]. | 2001 |
|
Newer antihistamines. | 2001 Apr 30 |
|
Uptake and efflux of the peptidic delta-opioid receptor agonist. | 2001 Apr 6 |
|
Identification of functionally variant MDR1 alleles among European Americans and African Americans. | 2001 Aug |
|
Ugly wait at the counter. Insurer pushes to make allergy drugs nonprescription. | 2001 Aug 6 |
|
Multicenter study of the efficacy and safety of fexofenadine 60 mg. twice daily in 108 Thai patients with chronic idiopathic urticaria. | 2001 Feb |
|
Histamine-induced activation of human lung macrophages. | 2001 Jan-Mar |
|
Evaluation of the safety of fexofenadine from experience gained in general practice use in England in 1997. | 2001 Jul |
|
Safety of fexofenadine in children treated for seasonal allergic rhinitis. | 2001 Jul |
|
Pharmacokinetic and safety profile of desloratadine and fexofenadine when coadministered with azithromycin: a randomized, placebo-controlled, parallel-group study. | 2001 Mar |
|
Fexofenadine hydrochloride--a new anti-histaminic drug. | 2001 Mar |
|
The effect of rifampin administration on the disposition of fexofenadine. | 2001 Mar |
|
Skin concentrations of H1-receptor antagonists. | 2001 Mar |
|
Histamine induces exocytosis and IL-6 production from human lung macrophages through interaction with H1 receptors. | 2001 Mar 15 |
|
A descriptive analysis of the use and cost of new-generation antihistamines in the treatment of allergic rhinitis: a retrospective database analysis. | 2001 May |
|
Controlled comparison of the efficacy and safety of cetirizine 10 mg o.d. and fexofenadine 120 mg o.d. in reducing symptoms of seasonal allergic rhinitis. | 2001 May |
|
Fexofenadine reduces nasal congestion in perennial allergic rhinitis. | 2001 Nov |
|
[Efficacy and safety of fexofenadine and cetirizine in the treatment of allergic rhinitis]. | 2001 Nov-Dec |
|
The costs of nonsedating antihistamine therapy for allergic rhinitis in managed care: an updated analysis. | 2001 Oct |
|
Urticaria to cetirizine. | 2002 |
|
Potential cardiac toxicity of H1-antihistamines. | 2002 |
|
[Comparative antihistamine and anti-allergic effects of various antihistamine preparations]. | 2002 |
|
Grapefruit juice reduces the oral bioavailability of fexofenadine but not desloratadine. | 2002 |
|
[Chronic idiopathic urticaria: effectiveness of fexofenadine. A double-blind, placebo controlled study with 21 patients]. | 2002 Apr 10 |
|
Sea transport of animal and vegetable oils and its environmental consequences. | 2002 Dec |
|
Effect of fexofenadine, a mast cell blocker, in infertile men with significantly increased testicular mast cells. | 2002 Dec |
|
A double-blind, randomized, single-dose, crossover comparison of levocetirizine with ebastine, fexofenadine, loratadine, mizolastine, and placebo: suppression of histamine-induced wheal-and-flare response during 24 hours in healthy male subjects. | 2002 Feb |
|
An evaluation of the effects of high-dose fexofenadine on the central nervous system: a double-blind, placebo-controlled study in healthy volunteers. | 2002 Jan |
|
A comparison of once daily fexofenadine versus the combination of montelukast plus loratadine on domiciliary nasal peak flow and symptoms in seasonal allergic rhinitis. | 2002 Jan |
|
Fruit juices inhibit organic anion transporting polypeptide-mediated drug uptake to decrease the oral availability of fexofenadine. | 2002 Jan |
|
Induction of multidrug resistance-1 and cytochrome P450 mRNAs in human mononuclear cells by rifampin. | 2002 Jan |
|
In vivo anti-inflammatory effects of fexofenadine in chronic idiopathic urticaria. | 2002 Jul |
|
Comparison of the efficacy of combined fluticasone propionate and olopatadine versus combined fluticasone propionate and fexofenadine for the treatment of allergic rhinoconjunctivitis induced by conjunctival allergen challenge. | 2002 Jul |
|
Fexofenadine modulates T-cell function, preventing allergen-induced airway inflammation and hyperresponsiveness. | 2002 Jul |
|
Role of lung inflammatory mediators as a cause of exercise-induced arterial hypoxemia in young athletes. | 2002 Jul |
|
Chronic urticaria and angioedema. | 2002 Jul 18 |
|
Simultaneous determination of fexofenadine and its related compounds by HPLC. | 2002 Jul 20 |
|
Effects of grapefruit juice and orange juice on the intestinal efflux of P-glycoprotein substrates. | 2002 Jun |
|
Effect of St John's wort on the pharmacokinetics of fexofenadine. | 2002 Jun |
|
Are herbal products dietary supplements or drugs? An important question for public safety. | 2002 Jun |
|
Evaluation of cytokines in nasal secretions after nasal antigen challenge: lack of influence of antihistamines. | 2002 May |
|
MDR1 gene polymorphisms and disposition of the P-glycoprotein substrate fexofenadine. | 2002 May |
|
Clinical pharmacology of H1-antihistamines in the skin. | 2002 Nov |
|
Effects of fexofenadine and desloratadine on subjective and objective measures of nasal congestion in seasonal allergic rhinitis. | 2002 Oct |
|
The effects of acute doses of fexofenadine, promethazine, and placebo on cognitive and psychomotor function in healthy Japanese volunteers. | 2003 Apr |
|
The effect of ketoconazole on the in vivo intestinal permeability of fexofenadine using a regional perfusion technique. | 2003 Feb |
|
Failure of cetirizine and fexofenadine to prevent motion sickness. | 2003 Feb |
|
Effect of fexofenadine hydrochloride on cedar pollinosis. | 2003 Feb |
Sample Use Guides
Seasonal Allergic Rhinitis and Chronic Idiopathic Urticaria
Adults and Children 12 Years and Older: The recommended dose of ALLEGRA (Fexofenadine)
tablets is 60 mg twice daily or 180 mg once daily with water. A dose of 60 mg once daily is
recommended as the starting dose in patients with decreased renal function
Route of Administration:
Oral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/24260772
The addition of fexofenadine at a dose of 10E-4 M elicited a significant relaxation response in isolated rat tracheas.
Substance Class |
Chemical
Created
by
admin
on
Edited
Sat Dec 16 16:12:51 UTC 2023
by
admin
on
Sat Dec 16 16:12:51 UTC 2023
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Record UNII |
E6582LOH6V
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Record Status |
Validated (UNII)
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Record Version |
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NDF-RT |
N0000000190
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WHO-ATC |
R06AX26
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NDF-RT |
N0000175587
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WHO-VATC |
QR06AX26
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LIVERTOX |
NBK548571
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NCI_THESAURUS |
C29578
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1170
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83799-24-0
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Fexofenadine
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C093230
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CHEMBL914
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7486
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FEXOFENADINE
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4819
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87636
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3348
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E6582LOH6V
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m5367
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1270363
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SUB13883MIG
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C61764
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DTXSID00861411
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100000078495
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5050
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DB00950
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7469
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E6582LOH6V
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SALT/SOLVATE -> PARENT | |||
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TRANSPORTER -> INHIBITOR | |||
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EXCRETED UNCHANGED |
FECAL
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EXCRETED UNCHANGED |
URINE
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PARENT -> METABOLITE ACTIVE |
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ACTIVE MOIETY |
Name | Property Type | Amount | Referenced Substance | Defining | Parameters | References |
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Biological Half-life | PHARMACOKINETIC |
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PROTEIN BINDING | PHARMACOKINETIC |
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Biological Half-life | PHARMACOKINETIC |
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Route of Elimination | PHARMACOKINETIC |
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Biological Half-life | PHARMACOKINETIC |
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Route of Elimination | PHARMACOKINETIC |
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Tmax | PHARMACOKINETIC |
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Biological Half-life | PHARMACOKINETIC |
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