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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
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
Severe cardiac arrhythmia on fexofenadine?
2000 Feb
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
Clinical prescribing of allergic rhinitis medication in the preschool and young school-age child: what are the options?
2001
Management of Peyronie's disease--a review.
2001 Aug
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
Suppression of the early and late cutaneous allergic responses using fexofenadine and montelukast.
2001 Jan
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
Fexofenadine hydrochloride--a new anti-histaminic drug.
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
Fexofenadine decreases sensitivity to and montelukast improves recovery from inhaled mannitol.
2001 May
Fexofenadine reduces nasal congestion in perennial allergic rhinitis.
2001 Nov
H1-antihistamines in children.
2002
[Comparative antihistamine and anti-allergic effects of various antihistamine preparations].
2002
Grapefruit juice reduces the oral bioavailability of fexofenadine but not desloratadine.
2002
Comparison of five new antihistamines (H1-receptor antagonists) in patients with allergic rhinitis using nasal provocation studies and skin tests.
2002 Apr
[Chronic idiopathic urticaria: effectiveness of fexofenadine. A double-blind, placebo controlled study with 21 patients].
2002 Apr 10
[Hay fever and asthma. Many of your patients have both].
2002 Apr 25
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
Effects of fexofenadine on the early response to nasal allergen challenge.
2002 Dec
Inhibitory effects of oral prednisolone and fexofenadine on skin responses by prick tests with histamine and compound 48/80.
2002 Dec
Comparative pharmacology of H1 antihistamines: clinical relevance.
2002 Dec 16
Treatment of allergic rhinitis.
2002 Dec 16
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
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
In vivo anti-inflammatory effects of fexofenadine in chronic idiopathic urticaria.
2002 Jul
Onset of action, efficacy, and safety of fexofenadine 60 mg/pseudoephedrine 120 mg versus placebo in the Atlanta allergen exposure unit.
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
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
Pharmacological rescue of human K(+) channel long-QT2 mutations: human ether-a-go-go-related gene rescue without block.
2002 Jun 18
MDR1 gene polymorphisms and disposition of the P-glycoprotein substrate fexofenadine.
2002 May
Transport of the sulfated, amidated bile acid, sulfolithocholyltaurine, into rat hepatocytes is mediated by Oatp1 and Oatp2.
2002 May
Fexofenadine transport in Caco-2 cells: inhibition with verapamil and ritonavir.
2002 Nov
The antihistamine fexofenadine does not affect I(Kr) currents in a case report of drug-induced cardiac arrhythmia.
2002 Nov
The use of handheld computers in clinical trials.
2002 Oct
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
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
Effect of fexofenadine hydrochloride on cedar pollinosis.
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 Dec 16 16:12:51 GMT 2023
Edited
by admin
on Sat Dec 16 16:12:51 GMT 2023
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 [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
TELFAST
Brand Name English
Classification Tree Code System Code
NDF-RT N0000000190
Created by admin on Sat Dec 16 16:12:53 GMT 2023 , Edited by admin on Sat Dec 16 16:12:53 GMT 2023
WHO-ATC R06AX26
Created by admin on Sat Dec 16 16:12:53 GMT 2023 , Edited by admin on Sat Dec 16 16:12:53 GMT 2023
NDF-RT N0000175587
Created by admin on Sat Dec 16 16:12:53 GMT 2023 , Edited by admin on Sat Dec 16 16:12:53 GMT 2023
WHO-VATC QR06AX26
Created by admin on Sat Dec 16 16:12:53 GMT 2023 , Edited by admin on Sat Dec 16 16:12:53 GMT 2023
LIVERTOX NBK548571
Created by admin on Sat Dec 16 16:12:53 GMT 2023 , Edited by admin on Sat Dec 16 16:12:53 GMT 2023
NCI_THESAURUS C29578
Created by admin on Sat Dec 16 16:12:53 GMT 2023 , Edited by admin on Sat Dec 16 16:12:53 GMT 2023
Code System Code Type Description
DRUG CENTRAL
1170
Created by admin on Sat Dec 16 16:12:53 GMT 2023 , Edited by admin on Sat Dec 16 16:12:53 GMT 2023
PRIMARY
CAS
83799-24-0
Created by admin on Sat Dec 16 16:12:53 GMT 2023 , Edited by admin on Sat Dec 16 16:12:53 GMT 2023
PRIMARY
LACTMED
Fexofenadine
Created by admin on Sat Dec 16 16:12:53 GMT 2023 , Edited by admin on Sat Dec 16 16:12:53 GMT 2023
PRIMARY
MESH
C093230
Created by admin on Sat Dec 16 16:12:53 GMT 2023 , Edited by admin on Sat Dec 16 16:12:53 GMT 2023
PRIMARY
ChEMBL
CHEMBL914
Created by admin on Sat Dec 16 16:12:53 GMT 2023 , Edited by admin on Sat Dec 16 16:12:53 GMT 2023
PRIMARY
HSDB
7486
Created by admin on Sat Dec 16 16:12:53 GMT 2023 , Edited by admin on Sat Dec 16 16:12:53 GMT 2023
PRIMARY
WIKIPEDIA
FEXOFENADINE
Created by admin on Sat Dec 16 16:12:53 GMT 2023 , Edited by admin on Sat Dec 16 16:12:53 GMT 2023
PRIMARY
IUPHAR
4819
Created by admin on Sat Dec 16 16:12:53 GMT 2023 , Edited by admin on Sat Dec 16 16:12:53 GMT 2023
PRIMARY
RXCUI
87636
Created by admin on Sat Dec 16 16:12:53 GMT 2023 , Edited by admin on Sat Dec 16 16:12:53 GMT 2023
PRIMARY RxNorm
PUBCHEM
3348
Created by admin on Sat Dec 16 16:12:53 GMT 2023 , Edited by admin on Sat Dec 16 16:12:53 GMT 2023
PRIMARY
FDA UNII
E6582LOH6V
Created by admin on Sat Dec 16 16:12:53 GMT 2023 , Edited by admin on Sat Dec 16 16:12:53 GMT 2023
PRIMARY
MERCK INDEX
m5367
Created by admin on Sat Dec 16 16:12:53 GMT 2023 , Edited by admin on Sat Dec 16 16:12:53 GMT 2023
PRIMARY Merck Index
RS_ITEM_NUM
1270363
Created by admin on Sat Dec 16 16:12:53 GMT 2023 , Edited by admin on Sat Dec 16 16:12:53 GMT 2023
PRIMARY
EVMPD
SUB13883MIG
Created by admin on Sat Dec 16 16:12:53 GMT 2023 , Edited by admin on Sat Dec 16 16:12:53 GMT 2023
PRIMARY
NCI_THESAURUS
C61764
Created by admin on Sat Dec 16 16:12:53 GMT 2023 , Edited by admin on Sat Dec 16 16:12:53 GMT 2023
PRIMARY
EPA CompTox
DTXSID00861411
Created by admin on Sat Dec 16 16:12:53 GMT 2023 , Edited by admin on Sat Dec 16 16:12:53 GMT 2023
PRIMARY
SMS_ID
100000078495
Created by admin on Sat Dec 16 16:12:53 GMT 2023 , Edited by admin on Sat Dec 16 16:12:53 GMT 2023
PRIMARY
CHEBI
5050
Created by admin on Sat Dec 16 16:12:53 GMT 2023 , Edited by admin on Sat Dec 16 16:12:53 GMT 2023
PRIMARY
DRUG BANK
DB00950
Created by admin on Sat Dec 16 16:12:53 GMT 2023 , Edited by admin on Sat Dec 16 16:12:53 GMT 2023
PRIMARY
INN
7469
Created by admin on Sat Dec 16 16:12:53 GMT 2023 , Edited by admin on Sat Dec 16 16:12:53 GMT 2023
PRIMARY
DAILYMED
E6582LOH6V
Created by admin on Sat Dec 16 16:12:53 GMT 2023 , Edited by admin on Sat Dec 16 16:12:53 GMT 2023
PRIMARY
Related Record Type Details
SALT/SOLVATE -> PARENT
TRANSPORTER -> INHIBITOR
TRANSPORTER -> SUBSTRATE
EXCRETED UNCHANGED
FECAL
TRANSPORTER -> SUBSTRATE
EXCRETED UNCHANGED
URINE
TRANSPORTER -> SUBSTRATE
TRANSPORTER -> SUBSTRATE
TRANSPORTER -> INHIBITOR
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