FEXOFENADINE

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 Search

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
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 313 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 2760		246.0 nM [IC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Seasonal allergic rhinitis 63 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2008/020872s018,021963s002lbl.pdf	Primary		Approved 8360	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

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
OATP and P-glycoprotein transporters mediate the cellular uptake and excretion of fexofenadine.	1999 Aug	10421612
Treatment of urticaria. An evidence-based evaluation of antihistamines.	2001	11702618
Clinical prescribing of allergic rhinitis medication in the preschool and young school-age child: what are the options?	2001	11520256
Newer antihistamines.	2001 Apr 30	11331439
Management of Peyronie's disease--a review.	2001 Aug	11550782
Multicenter study of the efficacy and safety of fexofenadine 60 mg. twice daily in 108 Thai patients with chronic idiopathic urticaria.	2001 Feb	11336071
Suppression of the early and late cutaneous allergic responses using fexofenadine and montelukast.	2001 Jan	11206237
Comparison of montelukast and fexofenadine for chronic idiopathic urticaria.	2001 Jan	11176678
Safety of fexofenadine in children treated for seasonal allergic rhinitis.	2001 Jul	11476456
A comprehensive account on the role of efflux transporters in the gastrointestinal absorption of 13 commonly used substrate drugs in humans.	2001 Mar	11396754
Skin concentrations of H1-receptor antagonists.	2001 Mar	11240955
Histamine induces exocytosis and IL-6 production from human lung macrophages through interaction with H1 receptors.	2001 Mar 15	11238657
A descriptive analysis of the use and cost of new-generation antihistamines in the treatment of allergic rhinitis: a retrospective database analysis.	2001 May	11392821
Fexofenadine reduces nasal congestion in perennial allergic rhinitis.	2001 Nov	11703220
[Efficacy and safety of fexofenadine and cetirizine in the treatment of allergic rhinitis].	2001 Nov-Dec	11802289
Urticaria to cetirizine.	2002	12371532
Potential cardiac toxicity of H1-antihistamines.	2002	12113224
Photosensitivity disorders: cause, effect and management.	2002	12010069
Comparison of five new antihistamines (H1-receptor antagonists) in patients with allergic rhinitis using nasal provocation studies and skin tests.	2002 Apr	11906367
24-hour efficacy of once-daily desloratadine therapy in patients with seasonal allergic rhinitis [ISRCTN32042139].	2002 Aug 5	12162793
Effect of fexofenadine, a mast cell blocker, in infertile men with significantly increased testicular mast cells.	2002 Dec	12508131
Effects of fexofenadine on the early response to nasal allergen challenge.	2002 Dec	12487223
Facial swelling and eosinophilia in a 44-year-old woman.	2002 Dec	12487220
Inhibitory effects of oral prednisolone and fexofenadine on skin responses by prick tests with histamine and compound 48/80.	2002 Dec	12443840
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
Are antihistamines useful in managing asthma?	2002 Feb	11964751
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
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	12002729
Induction of multidrug resistance-1 and cytochrome P450 mRNAs in human mononuclear cells by rifampin.	2002 Jan	11744607
Determination of fexofenadine in human plasma and urine by liquid chromatography-mass spectrometry.	2002 Jan 25	11824810
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	12182260
Onset of action, efficacy, and safety of fexofenadine 60 mg/pseudoephedrine 120 mg versus placebo in the Atlanta allergen exposure unit.	2002 Jul	12141718
Fexofenadine modulates T-cell function, preventing allergen-induced airway inflammation and hyperresponsiveness.	2002 Jul	12110826
Role of lung inflammatory mediators as a cause of exercise-induced arterial hypoxemia in young athletes.	2002 Jul	12070194
Simultaneous determination of fexofenadine and its related compounds by HPLC.	2002 Jul 20	12093497
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
The use of handheld computers in clinical trials.	2002 Oct	12392861
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
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
Why aren't lower, effective, OTC doses available earlier by prescription?	2003 Jan	12503949
Solar urticaria induced by infrared radiation.	2003 Mar	12653719

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.

Substance Class	Chemical Created by `admin` on `Thu Jul 06 21:43:37 UTC 2023` Edited by `admin` on `Thu Jul 06 21:43:37 UTC 2023`
Record UNII	E6582LOH6V
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

FEXOFENADINE

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