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Details

Stereochemistry RACEMIC
Molecular Formula C32H39NO4
Molecular Weight 501.6576
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of FEXOFENADINE

SMILES

CC(C)(c1ccc(cc1)C(CCCN2CCC(CC2)C(c3ccccc3)(c4ccccc4)O)O)C(=O)O

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 501.6576
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

8.3825282E11
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
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)
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
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)
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
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
Disc. AE: Headache...
AEs leading to
discontinuation/dose reduction:
Headache (2 patients)
Sources: Page: p. 22
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
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
Dose: 800 mg
Route: oral
Route: single
Dose: 800 mg
Sources:
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
Dose: 800 mg
Route: oral
Route: single
Dose: 800 mg
Sources:
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
Dose: 800 mg
Route: oral
Route: single
Dose: 800 mg
Sources:
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
PubMed

PubMed

TitleDatePubMed
Fexofenadine and prolonged QT intervals.
1999 Sep
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
Safety of antihistamines in children.
2001
Newer antihistamines.
2001 Apr 30
Uptake and efflux of the peptidic delta-opioid receptor agonist.
2001 Apr 6
Ugly wait at the counter. Insurer pushes to make allergy drugs nonprescription.
2001 Aug 6
Suppression of the early and late cutaneous allergic responses using fexofenadine and montelukast.
2001 Jan
Comparison of montelukast and fexofenadine for chronic idiopathic urticaria.
2001 Jan
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
A comprehensive account on the role of efflux transporters in the gastrointestinal absorption of 13 commonly used substrate drugs in humans.
2001 Mar
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
[Seasonal allergic rhinitis. Nasal obstruction can also beh improved].
2001 May 3
[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
The use of antihistamines in safety-critical jobs: a meeting report.
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
[Hay fever and asthma. Many of your patients have both].
2002 Apr 25
Effect of fexofenadine, a mast cell blocker, in infertile men with significantly increased testicular mast cells.
2002 Dec
Effects of fexofenadine on the early response to nasal allergen challenge.
2002 Dec
Facial swelling and eosinophilia in a 44-year-old woman.
2002 Dec
Inhibitory effects of oral prednisolone and fexofenadine on skin responses by prick tests with histamine and compound 48/80.
2002 Dec
Roles of histamine in regulation of arousal and cognition: functional neuroimaging of histamine H1 receptors in human brain.
2002 Dec 20
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
Induction of multidrug resistance-1 and cytochrome P450 mRNAs in human mononuclear cells by rifampin.
2002 Jan
Determination of fexofenadine in human plasma and urine by liquid chromatography-mass spectrometry.
2002 Jan 25
The Rx-to-OTC switch of Claritin, Allegra, and Zyrtec: an unprecedented FDA response to petitioners and the protection of public health.
2002 Jun
Are herbal products dietary supplements or drugs? An important question for public safety.
2002 Jun
Pharmacological rescue of human K(+) channel long-QT2 mutations: human ether-a-go-go-related gene rescue without block.
2002 Jun 18
Transport of the sulfated, amidated bile acid, sulfolithocholyltaurine, into rat hepatocytes is mediated by Oatp1 and Oatp2.
2002 May
Clinical pharmacology of H1-antihistamines in the skin.
2002 Nov
Fexofenadine transport in Caco-2 cells: inhibition with verapamil and ritonavir.
2002 Nov
Chronic urticaria: a role for newer immunomodulatory drugs?
2003
The effects of acute doses of fexofenadine, promethazine, and placebo on cognitive and psychomotor function in healthy Japanese volunteers.
2003 Apr
Sedation and performance impairment of diphenhydramine and second-generation antihistamines: a meta-analysis.
2003 Apr
Fexofenadine is efficacious and safe in children (aged 6-11 years) with seasonal allergic rhinitis.
2003 Apr
The effect of ketoconazole on the in vivo intestinal permeability of fexofenadine using a regional perfusion technique.
2003 Feb
[Effect of fexofenadine--selective antagonist of histamine receptor (H1) on histamine-induced bronchoconstriction].
2003 Jan
Why aren't lower, effective, OTC doses available earlier by prescription?
2003 Jan
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 Sat Jun 26 03:45:45 UTC 2021
Edited
by admin
on Sat Jun 26 03:45:45 UTC 2021
Record UNII
E6582LOH6V
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
FEXOFENADINE
HSDB   INN   MI   VANDF   WHO-DD  
INN  
Official Name English
FEXOFENADINE [USP-RS]
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 [WHO-DD]
Common Name English
FEXOFENADINE [HSDB]
Common Name English
TELFAST
Brand Name English
Classification Tree Code System Code
NDF-RT N0000000190
Created by admin on Sat Jun 26 03:45:45 UTC 2021 , Edited by admin on Sat Jun 26 03:45:45 UTC 2021
WHO-ATC R06AX26
Created by admin on Sat Jun 26 03:45:45 UTC 2021 , Edited by admin on Sat Jun 26 03:45:45 UTC 2021
NDF-RT N0000175587
Created by admin on Sat Jun 26 03:45:45 UTC 2021 , Edited by admin on Sat Jun 26 03:45:45 UTC 2021
WHO-VATC QR06AX26
Created by admin on Sat Jun 26 03:45:45 UTC 2021 , Edited by admin on Sat Jun 26 03:45:45 UTC 2021
LIVERTOX 408
Created by admin on Sat Jun 26 03:45:45 UTC 2021 , Edited by admin on Sat Jun 26 03:45:45 UTC 2021
NCI_THESAURUS C29578
Created by admin on Sat Jun 26 03:45:45 UTC 2021 , Edited by admin on Sat Jun 26 03:45:45 UTC 2021
Code System Code Type Description
DRUG CENTRAL
1170
Created by admin on Sat Jun 26 03:45:45 UTC 2021 , Edited by admin on Sat Jun 26 03:45:45 UTC 2021
PRIMARY
CAS
83799-24-0
Created by admin on Sat Jun 26 03:45:45 UTC 2021 , Edited by admin on Sat Jun 26 03:45:45 UTC 2021
PRIMARY
LACTMED
Fexofenadine
Created by admin on Sat Jun 26 03:45:45 UTC 2021 , Edited by admin on Sat Jun 26 03:45:45 UTC 2021
PRIMARY
MESH
C093230
Created by admin on Sat Jun 26 03:45:45 UTC 2021 , Edited by admin on Sat Jun 26 03:45:45 UTC 2021
PRIMARY
ChEMBL
CHEMBL914
Created by admin on Sat Jun 26 03:45:45 UTC 2021 , Edited by admin on Sat Jun 26 03:45:45 UTC 2021
PRIMARY
HSDB
7486
Created by admin on Sat Jun 26 03:45:45 UTC 2021 , Edited by admin on Sat Jun 26 03:45:45 UTC 2021
PRIMARY
WIKIPEDIA
FEXOFENADINE
Created by admin on Sat Jun 26 03:45:45 UTC 2021 , Edited by admin on Sat Jun 26 03:45:45 UTC 2021
PRIMARY
IUPHAR
4819
Created by admin on Sat Jun 26 03:45:45 UTC 2021 , Edited by admin on Sat Jun 26 03:45:45 UTC 2021
PRIMARY
RXCUI
87636
Created by admin on Sat Jun 26 03:45:45 UTC 2021 , Edited by admin on Sat Jun 26 03:45:45 UTC 2021
PRIMARY RxNorm
PUBCHEM
3348
Created by admin on Sat Jun 26 03:45:45 UTC 2021 , Edited by admin on Sat Jun 26 03:45:45 UTC 2021
PRIMARY
FDA UNII
E6582LOH6V
Created by admin on Sat Jun 26 03:45:45 UTC 2021 , Edited by admin on Sat Jun 26 03:45:45 UTC 2021
PRIMARY
MERCK INDEX
M5367
Created by admin on Sat Jun 26 03:45:45 UTC 2021 , Edited by admin on Sat Jun 26 03:45:45 UTC 2021
PRIMARY Merck Index
USP_CATALOG
1270363
Created by admin on Sat Jun 26 03:45:45 UTC 2021 , Edited by admin on Sat Jun 26 03:45:45 UTC 2021
PRIMARY USP-RS
EVMPD
SUB13883MIG
Created by admin on Sat Jun 26 03:45:45 UTC 2021 , Edited by admin on Sat Jun 26 03:45:45 UTC 2021
PRIMARY
NCI_THESAURUS
C61764
Created by admin on Sat Jun 26 03:45:45 UTC 2021 , Edited by admin on Sat Jun 26 03:45:45 UTC 2021
PRIMARY
DRUG BANK
DB00950
Created by admin on Sat Jun 26 03:45:45 UTC 2021 , Edited by admin on Sat Jun 26 03:45:45 UTC 2021
PRIMARY
INN
7469
Created by admin on Sat Jun 26 03:45:45 UTC 2021 , Edited by admin on Sat Jun 26 03:45:45 UTC 2021
PRIMARY
Related Record Type Details
TRANSPORTER -> INHIBITOR
SALT/SOLVATE -> PARENT
TRANSPORTER -> SUBSTRATE
EXCRETED UNCHANGED
FECAL
EXCRETED UNCHANGED
URINE
TRANSPORTER -> INHIBITOR
TRANSPORTER -> SUBSTRATE
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