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 Date1996 |
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 |
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 Health Status: healthy Age Group: 26.9 years (range: 18-51) years Sex: M 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 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 |
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: |
unhealthy Health Status: unhealthy Sources: |
Disc. AE: Headache... AEs leading to discontinuation/dose reduction: Headache (2 patients) Sources: |
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 |
| 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 |
| 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 |
| Dizziness | 3 patients | 800 mg single, oral Highest studied dose |
healthy, 26.9 years (range: 18-51) years Health Status: healthy Age Group: 26.9 years (range: 18-51) years Sex: M Sources: |
| Headache | 3 patients | 800 mg single, oral Highest studied dose |
healthy, 26.9 years (range: 18-51) years Health Status: healthy Age Group: 26.9 years (range: 18-51) years Sex: M Sources: |
| Tiredness | 3 patients | 800 mg single, oral Highest studied dose |
healthy, 26.9 years (range: 18-51) years Health Status: healthy Age Group: 26.9 years (range: 18-51) years Sex: M 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 |
| 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: |
unhealthy Health Status: unhealthy Sources: |
PubMed
| Title | Date | PubMed |
|---|---|---|
| The effects of acute doses of fexofenadine, promethazine, and placebo on cognitive and psychomotor function in healthy Japanese volunteers. | 2003-04 |
|
| Sedation and performance impairment of diphenhydramine and second-generation antihistamines: a meta-analysis. | 2003-04 |
|
| Fexofenadine is efficacious and safe in children (aged 6-11 years) with seasonal allergic rhinitis. | 2003-04 |
|
| Spectrophotometric determination of binary mixtures of pseudoephedrine with some histamine H1-receptor antagonists using derivative ratio spectrum method. | 2003-03-26 |
|
| Solar urticaria induced by infrared radiation. | 2003-03 |
|
| Decongestant effects of antihistamines: a class effect? | 2003-03 |
|
| The effects of single-dose fexofenadine, diphenhydramine, and placebo on cognitive performance in flight personnel. | 2003-02 |
|
| The effect of ketoconazole on the in vivo intestinal permeability of fexofenadine using a regional perfusion technique. | 2003-02 |
|
| Failure of cetirizine and fexofenadine to prevent motion sickness. | 2003-02 |
|
| Effect of fexofenadine hydrochloride on cedar pollinosis. | 2003-02 |
|
| [Effect of fexofenadine--selective antagonist of histamine receptor (H1) on histamine-induced bronchoconstriction]. | 2003-01 |
|
| Internal standard signal suppression by co-eluting analyte in isotope dilution LC-ESI-MS. | 2003-01 |
|
| Coordinate induction of both cytochrome P4503A and MDR1 by St John's wort in healthy subjects. | 2003-01 |
|
| Why aren't lower, effective, OTC doses available earlier by prescription? | 2003-01 |
|
| Chronic urticaria: a role for newer immunomodulatory drugs? | 2003 |
|
| Roles of histamine in regulation of arousal and cognition: functional neuroimaging of histamine H1 receptors in human brain. | 2002-12-20 |
|
| Comparative pharmacology of H1 antihistamines: clinical relevance. | 2002-12-16 |
|
| Treatment of allergic rhinitis. | 2002-12-16 |
|
| Role of histamine in the pathophysiology of asthma: immunomodulatory and anti-inflammatory activities of H1-receptor antagonists. | 2002-12-16 |
|
| Sea transport of animal and vegetable oils and its environmental consequences. | 2002-12 |
|
| Effect of fexofenadine, a mast cell blocker, in infertile men with significantly increased testicular mast cells. | 2002-12 |
|
| Effects of fexofenadine on the early response to nasal allergen challenge. | 2002-12 |
|
| Facial swelling and eosinophilia in a 44-year-old woman. | 2002-12 |
|
| Inhibitory effects of oral prednisolone and fexofenadine on skin responses by prick tests with histamine and compound 48/80. | 2002-12 |
|
| Clinical pharmacology of H1-antihistamines in the skin. | 2002-11 |
|
| Fexofenadine transport in Caco-2 cells: inhibition with verapamil and ritonavir. | 2002-11 |
|
| The antihistamine fexofenadine does not affect I(Kr) currents in a case report of drug-induced cardiac arrhythmia. | 2002-11 |
|
| Determination of some histamine H1-receptor antagonists in dosage forms. | 2002-10-15 |
|
| The use of handheld computers in clinical trials. | 2002-10 |
|
| Review of fexofenadine in the treatment of chronic idiopathic urticaria. | 2002-10 |
|
| Effects of fexofenadine and desloratadine on subjective and objective measures of nasal congestion in seasonal allergic rhinitis. | 2002-10 |
|
| 24-hour efficacy of once-daily desloratadine therapy in patients with seasonal allergic rhinitis [ISRCTN32042139]. | 2002-08-05 |
|
| Simultaneous determination of fexofenadine and its related compounds by HPLC. | 2002-07-20 |
|
| Chronic urticaria and angioedema. | 2002-07-18 |
|
| In vivo anti-inflammatory effects of fexofenadine in chronic idiopathic urticaria. | 2002-07 |
|
| 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. | 2002-07 |
|
| Onset of action, efficacy, and safety of fexofenadine 60 mg/pseudoephedrine 120 mg versus placebo in the Atlanta allergen exposure unit. | 2002-07 |
|
| Fexofenadine modulates T-cell function, preventing allergen-induced airway inflammation and hyperresponsiveness. | 2002-07 |
|
| Role of lung inflammatory mediators as a cause of exercise-induced arterial hypoxemia in young athletes. | 2002-07 |
|
| Pharmacological rescue of human K(+) channel long-QT2 mutations: human ether-a-go-go-related gene rescue without block. | 2002-06-18 |
|
| The Rx-to-OTC switch of Claritin, Allegra, and Zyrtec: an unprecedented FDA response to petitioners and the protection of public health. | 2002-06 |
|
| Effects of grapefruit juice and orange juice on the intestinal efflux of P-glycoprotein substrates. | 2002-06 |
|
| Effect of St John's wort on the pharmacokinetics of fexofenadine. | 2002-06 |
|
| Are herbal products dietary supplements or drugs? An important question for public safety. | 2002-06 |
|
| [Hay fever and asthma. Many of your patients have both]. | 2002-04-25 |
|
| The use of antihistamines in safety-critical jobs: a meeting report. | 2002 |
|
| Urticaria to cetirizine. | 2002 |
|
| Liquid chromatography/tandem mass spectrometric bioanalysis using normal-phase columns with aqueous/organic mobile phases - a novel approach of eliminating evaporation and reconstitution steps in 96-well SPE. | 2002 |
|
| H1-antihistamines in children. | 2002 |
|
| Potential cardiac toxicity of H1-antihistamines. | 2002 |
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
Wed Apr 02 07:29:38 GMT 2025
by
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| Record UNII |
E6582LOH6V
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| Record Status |
Validated (UNII)
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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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83799-24-0
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Fexofenadine
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7486
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FEXOFENADINE
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5050
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DB00950
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7469
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SALT/SOLVATE -> PARENT |
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TRANSPORTER -> INHIBITOR | |||
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TRANSPORTER -> SUBSTRATE | |||
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TRANSPORTER -> INHIBITOR | |||
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EXCRETED UNCHANGED |
FECAL
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EXCRETED UNCHANGED |
URINE
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TARGET -> INHIBITOR | |||
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PARENT -> METABOLITE ACTIVE |
MAJOR
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ACTIVE MOIETY |
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| 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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