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

Details

Stereochemistry RACEMIC
Molecular Formula C32H39NO4.ClH
Molecular Weight 538.117
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of FEXOFENADINE HYDROCHLORIDE

SMILES

Cl.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=RRJFVPUCXDGFJB-UHFFFAOYSA-N
InChI=1S/C32H39NO4.ClH/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);1H

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 ( + / - )

Molecular Formula ClH
Molecular Weight 36.461
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

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
QT lengthening and life-threatening arrhythmias associated with fexofenadine.
1999 Mar 20
Fexofenadine and prolonged QT intervals.
1999 Sep
Severe cardiac arrhythmia on fexofenadine?
2000 Feb
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
Safety of antihistamines in children.
2001
Twenty-four hours of activity of cetirizine and fexofenadine in the skin.
2001 Apr
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
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
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
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
Urticaria to cetirizine.
2002
H1-antihistamines in children.
2002
Potential cardiac toxicity of H1-antihistamines.
2002
[Comparative antihistamine and anti-allergic effects of various antihistamine preparations].
2002
[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
24-hour efficacy of once-daily desloratadine therapy in patients with seasonal allergic rhinitis [ISRCTN32042139].
2002 Aug 5
Sea transport of animal and vegetable oils and its environmental consequences.
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
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
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
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
Chronic urticaria and angioedema.
2002 Jul 18
Simultaneous determination of fexofenadine and its related compounds by HPLC.
2002 Jul 20
The Rx-to-OTC switch of Claritin, Allegra, and Zyrtec: an unprecedented FDA response to petitioners and the protection of public health.
2002 Jun
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
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
Transport of the sulfated, amidated bile acid, sulfolithocholyltaurine, into rat hepatocytes is mediated by Oatp1 and Oatp2.
2002 May
The antihistamine fexofenadine does not affect I(Kr) currents in a case report of drug-induced cardiac arrhythmia.
2002 Nov
The effects of acute doses of fexofenadine, promethazine, and placebo on cognitive and psychomotor function in healthy Japanese volunteers.
2003 Apr
The effects of single-dose fexofenadine, diphenhydramine, and placebo on cognitive performance in flight personnel.
2003 Feb
[Effect of fexofenadine--selective antagonist of histamine receptor (H1) on histamine-induced bronchoconstriction].
2003 Jan
Spectrophotometric determination of binary mixtures of pseudoephedrine with some histamine H1-receptor antagonists using derivative ratio spectrum method.
2003 Mar 26
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 Fri Dec 15 16:49:24 GMT 2023
Edited
by admin
on Fri Dec 15 16:49:24 GMT 2023
Record UNII
2S068B75ZU
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
FEXOFENADINE HYDROCHLORIDE
EP   JAN   MART.   MI   ORANGE BOOK   USAN   USP   USP-RS   VANDF   WHO-DD  
USAN  
Official Name English
MDL-16455A
Code English
FEXOFENADINE HYDROCHLORIDE [USP MONOGRAPH]
Common Name English
FEXOFENADINE HYDROCHLORIDE [MART.]
Common Name English
FEXOFENADINE HYDROCHLORIDE COMPONENT OF ALLEGRA-D
Common Name English
ALLEGRA
Brand Name English
FEXOFENADINE HYDROCHLORIDE [VANDF]
Common Name English
FEXOFENADINE HCL
Common Name English
FEXOFENADINE HYDROCHLORIDE [MI]
Common Name English
Fexofenadine hydrochloride [WHO-DD]
Common Name English
FEXOFENADINE HYDROCHLORIDE [JAN]
Common Name English
FEXOFENADINE HYDROCHLORIDE [USP IMPURITY]
Common Name English
FEXOFENADINE HYDROCHLORIDE [USP-RS]
Common Name English
FEXOFENADINE HYDROCHLORIDE [USAN]
Common Name English
FEXOFENADINE HYDROCHLORIDE [ORANGE BOOK]
Common Name English
ALLEGRA-D COMPONENT FEXOFENADINE HYDROCHLORIDE
Common Name English
MDL 16,455A
Code English
(±)-P-(1-HYDROXY-4-(4-(HYDROXYDIPHENYLMETHYL)PIPERIDINO)BUTYL)-.ALPHA.-METHYLHYDRATROPIC ACID, HYDROCHLORIDE
Common Name English
FEXOFENADINE HYDROCHLORIDE [EP MONOGRAPH]
Common Name English
BENZENEACETIC ACID, 4-(1-HYDROXY-4-(4-(HYDROXYDIPHENYLMETHYL)-1-PIPERIDINYL)BUTYL)-.ALPHA.,.ALPHA.-DIMETHYL-, HYDROCHLORIDE, (±)-
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C29578
Created by admin on Fri Dec 15 16:49:24 GMT 2023 , Edited by admin on Fri Dec 15 16:49:24 GMT 2023
Code System Code Type Description
EPA CompTox
DTXSID5048716
Created by admin on Fri Dec 15 16:49:24 GMT 2023 , Edited by admin on Fri Dec 15 16:49:24 GMT 2023
PRIMARY
RXCUI
236474
Created by admin on Fri Dec 15 16:49:24 GMT 2023 , Edited by admin on Fri Dec 15 16:49:24 GMT 2023
PRIMARY RxNorm
EVMPD
SUB13884MIG
Created by admin on Fri Dec 15 16:49:24 GMT 2023 , Edited by admin on Fri Dec 15 16:49:24 GMT 2023
PRIMARY
CAS
153439-40-8
Created by admin on Fri Dec 15 16:49:24 GMT 2023 , Edited by admin on Fri Dec 15 16:49:24 GMT 2023
PRIMARY
NCI_THESAURUS
C29050
Created by admin on Fri Dec 15 16:49:24 GMT 2023 , Edited by admin on Fri Dec 15 16:49:24 GMT 2023
PRIMARY
USAN
FF-73
Created by admin on Fri Dec 15 16:49:24 GMT 2023 , Edited by admin on Fri Dec 15 16:49:24 GMT 2023
PRIMARY
RS_ITEM_NUM
1270377
Created by admin on Fri Dec 15 16:49:24 GMT 2023 , Edited by admin on Fri Dec 15 16:49:24 GMT 2023
PRIMARY
SMS_ID
100000092281
Created by admin on Fri Dec 15 16:49:24 GMT 2023 , Edited by admin on Fri Dec 15 16:49:24 GMT 2023
PRIMARY
PUBCHEM
63002
Created by admin on Fri Dec 15 16:49:24 GMT 2023 , Edited by admin on Fri Dec 15 16:49:24 GMT 2023
PRIMARY
MERCK INDEX
m5367
Created by admin on Fri Dec 15 16:49:24 GMT 2023 , Edited by admin on Fri Dec 15 16:49:24 GMT 2023
PRIMARY Merck Index
ChEMBL
CHEMBL914
Created by admin on Fri Dec 15 16:49:24 GMT 2023 , Edited by admin on Fri Dec 15 16:49:24 GMT 2023
PRIMARY
DRUG BANK
DBSALT001227
Created by admin on Fri Dec 15 16:49:24 GMT 2023 , Edited by admin on Fri Dec 15 16:49:24 GMT 2023
PRIMARY
DAILYMED
2S068B75ZU
Created by admin on Fri Dec 15 16:49:24 GMT 2023 , Edited by admin on Fri Dec 15 16:49:24 GMT 2023
PRIMARY
FDA UNII
2S068B75ZU
Created by admin on Fri Dec 15 16:49:24 GMT 2023 , Edited by admin on Fri Dec 15 16:49:24 GMT 2023
PRIMARY
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