FEXOFENADINE HYDROCHLORIDE

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 Search

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

Description
Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2008/020872s018,021963s002lbl.pdf
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
Histamine H1 receptor 315 Target ID: CHEMBL231 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2008/020872s018,021963s002lbl.pdf \| https://www.ncbi.nlm.nih.gov/pubmed/16274260	Antagonist 2778		246.0 nM [IC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Seasonal allergic rhinitis 64 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2008/020872s018,021963s002lbl.pdf	Primary		Approved 8429	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

C_max

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

T_1/2

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: https://pubmed.ncbi.nlm.nih.gov/9871426	healthy, 18-55 years n = 4 Health Status: healthy Age Group: 18-55 years Sex: M Population Size: 4 Sources: https://pubmed.ncbi.nlm.nih.gov/9871426	Other AEs: Headache, Tiredness... Other AEs: Headache (3 patients) Tiredness (3 patients) Dizziness (3 patients) Sources: https://pubmed.ncbi.nlm.nih.gov/9871426
800 mg single, oral Highest studied dose Dose: 800 mg Route: oral Route: single Dose: 800 mg Sources: https://pubmed.ncbi.nlm.nih.gov/9871426	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: https://pubmed.ncbi.nlm.nih.gov/9871426	Other AEs: Headache, Tiredness... Other AEs: Headache (3 patients) Tiredness (3 patients) Dizziness (3 patients) Sources: https://pubmed.ncbi.nlm.nih.gov/9871426
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: https://pubmed.ncbi.nlm.nih.gov/15209959	unhealthy, 6-11 years Health Status: unhealthy Condition: seasonal allergic rhinitis Age Group: 6-11 years Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/15209959	Sources: https://pubmed.ncbi.nlm.nih.gov/15209959
180 mg 1 times / day multiple, oral Dose: 180 mg, 1 times / day Route: oral Route: multiple Dose: 180 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/22346270	unhealthy, 69 years n = 1 Health Status: unhealthy Age Group: 69 years Sex: M Population Size: 1 Sources: https://pubmed.ncbi.nlm.nih.gov/22346270	Disc. AE: Papular urticarial eruption... AEs leading to discontinuation/dose reduction: Papular urticarial eruption (1 patient) Sources: https://pubmed.ncbi.nlm.nih.gov/22346270
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: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2007/021909s000_MedR.pdf Page: p. 22	unhealthy Health Status: unhealthy Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2007/021909s000_MedR.pdf Page: p. 22	Disc. AE: Headache... AEs leading to discontinuation/dose reduction: Headache (2 patients) Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2007/021909s000_MedR.pdf Page: p. 22

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: https://pubmed.ncbi.nlm.nih.gov/9871426	healthy, 18-55 years n = 4 Health Status: healthy Age Group: 18-55 years Sex: M Population Size: 4 Sources: https://pubmed.ncbi.nlm.nih.gov/9871426
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: https://pubmed.ncbi.nlm.nih.gov/9871426	healthy, 18-55 years n = 4 Health Status: healthy Age Group: 18-55 years Sex: M Population Size: 4 Sources: https://pubmed.ncbi.nlm.nih.gov/9871426
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: https://pubmed.ncbi.nlm.nih.gov/9871426	healthy, 18-55 years n = 4 Health Status: healthy Age Group: 18-55 years Sex: M Population Size: 4 Sources: https://pubmed.ncbi.nlm.nih.gov/9871426
Dizziness	3 patients	800 mg single, oral Highest studied dose Dose: 800 mg Route: oral Route: single Dose: 800 mg Sources: https://pubmed.ncbi.nlm.nih.gov/9871426	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: https://pubmed.ncbi.nlm.nih.gov/9871426
Headache	3 patients	800 mg single, oral Highest studied dose Dose: 800 mg Route: oral Route: single Dose: 800 mg Sources: https://pubmed.ncbi.nlm.nih.gov/9871426	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: https://pubmed.ncbi.nlm.nih.gov/9871426
Tiredness	3 patients	800 mg single, oral Highest studied dose Dose: 800 mg Route: oral Route: single Dose: 800 mg Sources: https://pubmed.ncbi.nlm.nih.gov/9871426	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: https://pubmed.ncbi.nlm.nih.gov/9871426
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: https://pubmed.ncbi.nlm.nih.gov/22346270	unhealthy, 69 years n = 1 Health Status: unhealthy Age Group: 69 years Sex: M Population Size: 1 Sources: https://pubmed.ncbi.nlm.nih.gov/22346270
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: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2007/021909s000_MedR.pdf Page: p. 22	unhealthy Health Status: unhealthy Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2007/021909s000_MedR.pdf Page: p. 22

Sourcing

Vendor/Aggregator	ID	URL
ChEBI	CHEBI:5050	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:5050
ChemicalBook	CB5473513	https://www.chemicalbook.com/ChemicalProductProperty_EN_CB5473513
MolPort	MolPort-002-508-207	https://www.molport.com/shop/molecule-link/MolPort-002-508-207
eMolecules	901886	https://www.emolecules.com/cgi-bin/more?vid=901886

PubMed

Title	Date	PubMed
Treatment of urticaria. An evidence-based evaluation of antihistamines.	2001	11702618
Causality assessment of adverse effects: when is re-challenge ethically acceptable?	2001	11665867
Fexofenadine reduces nasal congestion in perennial allergic rhinitis.	2001 Nov	11703220
The costs of nonsedating antihistamine therapy for allergic rhinitis in managed care: an updated analysis.	2001 Oct	11680261
Urticaria to cetirizine.	2002	12371532
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	12362389
Photosensitivity disorders: cause, effect and management.	2002	12010069
Grapefruit juice reduces the oral bioavailability of fexofenadine but not desloratadine.	2002	11978146
[Hay fever and asthma. Many of your patients have both].	2002 Apr 25	12048855
24-hour efficacy of once-daily desloratadine therapy in patients with seasonal allergic rhinitis [ISRCTN32042139].	2002 Aug 5	12162793
Sea transport of animal and vegetable oils and its environmental consequences.	2002 Dec	12523544
Effect of fexofenadine, a mast cell blocker, in infertile men with significantly increased testicular mast cells.	2002 Dec	12508131
Inhibitory effects of oral prednisolone and fexofenadine on skin responses by prick tests with histamine and compound 48/80.	2002 Dec	12443840
Comparative pharmacology of H1 antihistamines: clinical relevance.	2002 Dec 16	12517581
Treatment of allergic rhinitis.	2002 Dec 16	12517578
Role of histamine in the pathophysiology of asthma: immunomodulatory and anti-inflammatory activities of H1-receptor antagonists.	2002 Dec 16	12517576
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	11868924
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	12002730
Fruit juices inhibit organic anion transporting polypeptide-mediated drug uptake to decrease the oral availability of fexofenadine.	2002 Jan	11823753
Determination of fexofenadine in human plasma and urine by liquid chromatography-mass spectrometry.	2002 Jan 25	11824810
In vivo anti-inflammatory effects of fexofenadine in chronic idiopathic urticaria.	2002 Jul	12224713
Onset of action, efficacy, and safety of fexofenadine 60 mg/pseudoephedrine 120 mg versus placebo in the Atlanta allergen exposure unit.	2002 Jul	12141718
Role of lung inflammatory mediators as a cause of exercise-induced arterial hypoxemia in young athletes.	2002 Jul	12070194
Chronic urticaria and angioedema.	2002 Jul 18	12124416
Simultaneous determination of fexofenadine and its related compounds by HPLC.	2002 Jul 20	12093497
Effects of grapefruit juice and orange juice on the intestinal efflux of P-glycoprotein substrates.	2002 Jun	12134950
Effect of St John's wort on the pharmacokinetics of fexofenadine.	2002 Jun	12087344
Are herbal products dietary supplements or drugs? An important question for public safety.	2002 Jun	12087343
Evaluation of cytokines in nasal secretions after nasal antigen challenge: lack of influence of antihistamines.	2002 May	12027065
MDR1 gene polymorphisms and disposition of the P-glycoprotein substrate fexofenadine.	2002 May	11994059
Transport of the sulfated, amidated bile acid, sulfolithocholyltaurine, into rat hepatocytes is mediated by Oatp1 and Oatp2.	2002 May	11981753
Clinical pharmacology of H1-antihistamines in the skin.	2002 Nov	12417888
The antihistamine fexofenadine does not affect I(Kr) currents in a case report of drug-induced cardiac arrhythmia.	2002 Nov	12411421
Review of fexofenadine in the treatment of chronic idiopathic urticaria.	2002 Oct	12390200
Effects of fexofenadine and desloratadine on subjective and objective measures of nasal congestion in seasonal allergic rhinitis.	2002 Oct	12372132
Determination of some histamine H1-receptor antagonists in dosage forms.	2002 Oct 15	12367712
Chronic urticaria: a role for newer immunomodulatory drugs?	2003	12688835
The effects of acute doses of fexofenadine, promethazine, and placebo on cognitive and psychomotor function in healthy Japanese volunteers.	2003 Apr	12722962
Sedation and performance impairment of diphenhydramine and second-generation antihistamines: a meta-analysis.	2003 Apr	12704356
Fexofenadine is efficacious and safe in children (aged 6-11 years) with seasonal allergic rhinitis.	2003 Apr	12704355
The effect of ketoconazole on the in vivo intestinal permeability of fexofenadine using a regional perfusion technique.	2003 Feb	12580990
Failure of cetirizine and fexofenadine to prevent motion sickness.	2003 Feb	12549941
Effect of fexofenadine hydrochloride on cedar pollinosis.	2003 Feb	12543163
[Effect of fexofenadine--selective antagonist of histamine receptor (H1) on histamine-induced bronchoconstriction].	2003 Jan	12712828
Internal standard signal suppression by co-eluting analyte in isotope dilution LC-ESI-MS.	2003 Jan	12572803
Coordinate induction of both cytochrome P4503A and MDR1 by St John's wort in healthy subjects.	2003 Jan	12545142
Why aren't lower, effective, OTC doses available earlier by prescription?	2003 Jan	12503949
Solar urticaria induced by infrared radiation.	2003 Mar	12653719
Decongestant effects of antihistamines: a class effect?	2003 Mar	12642858
Spectrophotometric determination of binary mixtures of pseudoephedrine with some histamine H1-receptor antagonists using derivative ratio spectrum method.	2003 Mar 26	12644207

Patents

Sample Use Guides

In Vivo Use Guide

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

The addition of fexofenadine at a dose of 10E-4 M elicited a significant relaxation response in isolated rat tracheas.

Name

Type

Language

FEXOFENADINE HYDROCHLORIDE

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