U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

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
Structure of FEXOFENADINE

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)

HIDE SMILES / InChI

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 ( + / - )

Description
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.

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
ALLEGRA

Approved Use

ALLEGRA is indicated for the relief of symptoms associated with seasonal allergic rhinitis in adults and children 2 years of age and older.

Launch Date

1996
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
523.28 ng/mL
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

AUC

ValueDoseCo-administeredAnalytePopulation
3507.8 ng × h/mL
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

T1/2

ValueDoseCo-administeredAnalytePopulation
9.26 h
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

Doses

DosePopulationAdverse 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
Health Status: healthy
Age Group: 18-55 years
Sex: M
Sources:
Other AEs: Headache, Tiredness...
Other AEs:
Headache (3 patients)
Tiredness (3 patients)
Dizziness (3 patients)
Sources:
800 mg single, oral
Highest studied dose
Dose: 800 mg
Route: oral
Route: single
Dose: 800 mg
Sources:
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)
Tiredness (3 patients)
Dizziness (3 patients)
Sources:
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
Health Status: unhealthy
Age Group: 69 years
Sex: M
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:
unhealthy
Disc. AE: Headache...
AEs leading to
discontinuation/dose reduction:
Headache (2 patients)
Sources:
AEs

AEs

AESignificanceDosePopulation
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
Health Status: healthy
Age Group: 18-55 years
Sex: M
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
Health Status: healthy
Age Group: 18-55 years
Sex: M
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
Health Status: healthy
Age Group: 18-55 years
Sex: M
Sources:
Dizziness 3 patients
800 mg single, oral
Highest studied dose
Dose: 800 mg
Route: oral
Route: single
Dose: 800 mg
Sources:
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
Dose: 800 mg
Route: oral
Route: single
Dose: 800 mg
Sources:
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
Dose: 800 mg
Route: oral
Route: single
Dose: 800 mg
Sources:
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
Health Status: unhealthy
Age Group: 69 years
Sex: M
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:
unhealthy
PubMed

PubMed

TitleDatePubMed
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
Patents

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
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 Wed Apr 02 07:29:38 GMT 2025
Edited
by admin
on Wed Apr 02 07:29:38 GMT 2025
Record UNII
E6582LOH6V
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
FEXOFENADINE
HSDB   INN   MI   VANDF   WHO-DD  
INN  
Official Name English
TELFAST
Preferred Name English
FEXOFENADINE [USP-RS]
Common Name English
Fexofenadine [WHO-DD]
Common Name English
FEXOFENADINE [VANDF]
Common Name English
fexofenadine [INN]
Common Name English
(±)-P-(1-HYDROXY-4-(4-(HYDROXYDIPHENYLMETHYL)PIPERIDINO)BUTYL)-.ALPHA.-METHYLHYDRATROPIC ACID
Common Name English
FEXOFENADINE [MI]
Common Name English
4-(1-HYDROXY-4-(4-(HYDROXYDIPHENYLMETHYL)-1-PIPERIDINYL)BUTYL)-ALPHA,ALPHA-DIMETHYLBENZENEACETIC ACID
Systematic Name English
BENZENEACETIC ACID, 4-(1-HYDROXY-4-(4-(HYDROXYDIPHENYLMETHYL)-1-PIPERIDINYL)BUTYL)-.ALPHA.,.ALPHA.-DIMETHYL-, (±)-
Common Name English
FEXOFENADINE [HSDB]
Common Name English
Classification Tree Code System Code
NDF-RT N0000000190
Created by admin on Wed Apr 02 07:29:38 GMT 2025 , Edited by admin on Wed Apr 02 07:29:38 GMT 2025
WHO-ATC R06AX26
Created by admin on Wed Apr 02 07:29:38 GMT 2025 , Edited by admin on Wed Apr 02 07:29:38 GMT 2025
NDF-RT N0000175587
Created by admin on Wed Apr 02 07:29:38 GMT 2025 , Edited by admin on Wed Apr 02 07:29:38 GMT 2025
WHO-VATC QR06AX26
Created by admin on Wed Apr 02 07:29:38 GMT 2025 , Edited by admin on Wed Apr 02 07:29:38 GMT 2025
LIVERTOX NBK548571
Created by admin on Wed Apr 02 07:29:38 GMT 2025 , Edited by admin on Wed Apr 02 07:29:38 GMT 2025
NCI_THESAURUS C29578
Created by admin on Wed Apr 02 07:29:38 GMT 2025 , Edited by admin on Wed Apr 02 07:29:38 GMT 2025
Code System Code Type Description
DRUG CENTRAL
1170
Created by admin on Wed Apr 02 07:29:38 GMT 2025 , Edited by admin on Wed Apr 02 07:29:38 GMT 2025
PRIMARY
CAS
83799-24-0
Created by admin on Wed Apr 02 07:29:38 GMT 2025 , Edited by admin on Wed Apr 02 07:29:38 GMT 2025
PRIMARY
LACTMED
Fexofenadine
Created by admin on Wed Apr 02 07:29:38 GMT 2025 , Edited by admin on Wed Apr 02 07:29:38 GMT 2025
PRIMARY
MESH
C093230
Created by admin on Wed Apr 02 07:29:38 GMT 2025 , Edited by admin on Wed Apr 02 07:29:38 GMT 2025
PRIMARY
ChEMBL
CHEMBL914
Created by admin on Wed Apr 02 07:29:38 GMT 2025 , Edited by admin on Wed Apr 02 07:29:38 GMT 2025
PRIMARY
HSDB
7486
Created by admin on Wed Apr 02 07:29:38 GMT 2025 , Edited by admin on Wed Apr 02 07:29:38 GMT 2025
PRIMARY
WIKIPEDIA
FEXOFENADINE
Created by admin on Wed Apr 02 07:29:38 GMT 2025 , Edited by admin on Wed Apr 02 07:29:38 GMT 2025
PRIMARY
IUPHAR
4819
Created by admin on Wed Apr 02 07:29:38 GMT 2025 , Edited by admin on Wed Apr 02 07:29:38 GMT 2025
PRIMARY
RXCUI
87636
Created by admin on Wed Apr 02 07:29:38 GMT 2025 , Edited by admin on Wed Apr 02 07:29:38 GMT 2025
PRIMARY RxNorm
PUBCHEM
3348
Created by admin on Wed Apr 02 07:29:38 GMT 2025 , Edited by admin on Wed Apr 02 07:29:38 GMT 2025
PRIMARY
FDA UNII
E6582LOH6V
Created by admin on Wed Apr 02 07:29:38 GMT 2025 , Edited by admin on Wed Apr 02 07:29:38 GMT 2025
PRIMARY
MERCK INDEX
m5367
Created by admin on Wed Apr 02 07:29:38 GMT 2025 , Edited by admin on Wed Apr 02 07:29:38 GMT 2025
PRIMARY Merck Index
RS_ITEM_NUM
1270363
Created by admin on Wed Apr 02 07:29:38 GMT 2025 , Edited by admin on Wed Apr 02 07:29:38 GMT 2025
PRIMARY
EVMPD
SUB13883MIG
Created by admin on Wed Apr 02 07:29:38 GMT 2025 , Edited by admin on Wed Apr 02 07:29:38 GMT 2025
PRIMARY
NCI_THESAURUS
C61764
Created by admin on Wed Apr 02 07:29:38 GMT 2025 , Edited by admin on Wed Apr 02 07:29:38 GMT 2025
PRIMARY
EPA CompTox
DTXSID00861411
Created by admin on Wed Apr 02 07:29:38 GMT 2025 , Edited by admin on Wed Apr 02 07:29:38 GMT 2025
PRIMARY
SMS_ID
100000078495
Created by admin on Wed Apr 02 07:29:38 GMT 2025 , Edited by admin on Wed Apr 02 07:29:38 GMT 2025
PRIMARY
CHEBI
5050
Created by admin on Wed Apr 02 07:29:38 GMT 2025 , Edited by admin on Wed Apr 02 07:29:38 GMT 2025
PRIMARY
DRUG BANK
DB00950
Created by admin on Wed Apr 02 07:29:38 GMT 2025 , Edited by admin on Wed Apr 02 07:29:38 GMT 2025
PRIMARY
INN
7469
Created by admin on Wed Apr 02 07:29:38 GMT 2025 , Edited by admin on Wed Apr 02 07:29:38 GMT 2025
PRIMARY
DAILYMED
E6582LOH6V
Created by admin on Wed Apr 02 07:29:38 GMT 2025 , Edited by admin on Wed Apr 02 07:29:38 GMT 2025
PRIMARY
Related Record Type Details
SALT/SOLVATE -> PARENT
TRANSPORTER -> INHIBITOR
TRANSPORTER -> SUBSTRATE
TRANSPORTER -> INHIBITOR
EXCRETED UNCHANGED
FECAL
TRANSPORTER -> SUBSTRATE
EXCRETED UNCHANGED
URINE
TRANSPORTER -> SUBSTRATE
TRANSPORTER -> SUBSTRATE
TARGET -> INHIBITOR
BINDER->LIGAND
Related Record Type Details
PARENT -> METABOLITE ACTIVE
MAJOR
Related Record Type Details
ACTIVE MOIETY
Name Property Type Amount Referenced Substance Defining Parameters References
Biological Half-life PHARMACOKINETIC
PROTEIN BINDING PHARMACOKINETIC
Biological Half-life PHARMACOKINETIC
Route of Elimination PHARMACOKINETIC
Biological Half-life PHARMACOKINETIC
Route of Elimination PHARMACOKINETIC
Tmax PHARMACOKINETIC
Biological Half-life PHARMACOKINETIC