Identification

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Name
Fexofenadine
Accession Number
DB00950  (APRD00349)
Type
Small Molecule
Groups
Approved, Investigational
Description

Fexofenadine is an over-the-counter second-generation antihistamine used in the treatment of various allergic symptoms.10 It is selective for the H1 receptor, carries little-to-no activity at off-targets, and does not cross the blood-brain barrier9 - this is in contrast to previous first-generation antihistamines, such as diphenhydramine, which readily bind to off-targets that contribute to side effects such as sedation.1 Fexofenadine is the major active metabolite of terfenadine7 and is administered as a racemic mixture in which both enantiomers display approximately equivalent antihistamine activity.9

Structure
Thumb
Synonyms
  • 4-(1-Hydroxy-4-(4-(hydroxydiphenylmethyl)-1-piperidinyl)butyl)-alpha,alpha-dimethylbenzeneacetic acid
  • Carboxyterfenadine
  • Fexofenadina
  • Fexofenadine
  • Terfenadine acid metabolite
  • Terfenadine carboxylate
  • Terfenadine-COOH
External IDs
MDL 16455
Product Ingredients
IngredientUNIICASInChI Key
Fexofenadine hydrochloride2S068B75ZU153439-40-8RRJFVPUCXDGFJB-UHFFFAOYSA-N
Product Images
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
AllegraTablet, film coated180 mg/1OralSanofi-Synthelabo Limited2010-03-13Not applicableUs
AllegraTablet, film coated60 mg/1OralSanofi Aventis2000-02-252012-08-31Us
AllegraTablet, film coated30 mg/1OralSanofi Aventis2000-02-252008-09-19Us
AllegraCapsule60 mg/1OralAventis Pharmaceuticals Inc.2007-01-182007-02-16Us
AllegraTablet, orally disintegrating30 mg/1OralSanofi Aventis2007-07-262013-06-30Us
AllegraTablet, film coated180 mg/1OralPhysicians Total Care, Inc.2000-11-272011-06-30Us
AllegraSuspension6 mg/1mLOralSanofi Aventis2006-10-16Not applicableUs
AllegraTablet, film coated60 mg/1OralPhysicians Total Care, Inc.2002-06-042011-06-30Us
AllegraTablet, film coated180 mg/1OralSanofi Aventis2000-02-252013-02-28Us
Fexofenadine HydrochlorideTablet, film coated180 mg/1OralNCS HealthCare of KY, Inc dba Vangard Labs2000-02-25Not applicableUs
Additional Data Available
  • Application Number
    Application Number

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  • Product Code
    Product Code

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Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Fexofenadine HydrochlorideTablet, film coated60 mg/1OralNcs Health Care Of Ky, Inc Dba Vangard Labs2010-07-01Not applicableUs
Fexofenadine HydrochlorideTablet, film coated30 mg/1OralTEVA Pharmaceutical Industries Ltd.2010-09-172013-12-26Us
Fexofenadine HydrochlorideTablet, film coated60 mg/1OralMylan Pharmaceuticals2010-05-212012-12-31Us
Fexofenadine HydrochlorideTablet, film coated60 mg/1OralMajor2009-06-10Not applicableUs
Fexofenadine HydrochlorideTablet, film coated180 mg/1Oralbryant ranch prepack2006-04-12Not applicableUs
Fexofenadine HydrochlorideTablet, film coated60 mg/1OralPhysicians Total Care, Inc.2006-08-07Not applicableUs54868 541720180907 15195 1pvc33g
Fexofenadine HydrochlorideTablet60 mg/1OralRebel Distributors2009-12-09Not applicableUs
Fexofenadine HydrochlorideTablet60 mg/1OralLake Erie Medical Dba Quality Care Produts Llc2009-12-092014-06-01Us55111 0193 01 nlmimage10 f007f83f
Fexofenadine HydrochlorideTablet, film coated30 mg/1OralPhysicians Total Care, Inc.2005-11-09Not applicableUs
Fexofenadine HydrochlorideTablet180 mg/1OralAmerincan Health Packaging2009-12-092013-03-31Us
Additional Data Available
  • Application Number
    Application Number

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  • Product Code
    Product Code

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Over the Counter Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
24 Hour AllergyTablet180 mg/1OralLIVE BETTER (The Great Atlantic & Pacific Tea Company)2013-03-20Not applicableUs
24HR Allergy ReliefTablet180 mg/1OralCardinal Health2018-04-27Not applicableUs
7 Select Allergy ReliefTablet, film coated180 mg/1Oral7-Eleven2014-04-172020-07-31Us
Allegra 12 HourTabletOralSanofi Consumer Health Inc Sanofi Sante Grand Public Inc1997-07-10Not applicableCanada
Allegra 24 HourTabletOralSanofi Consumer Health Inc Sanofi Sante Grand Public Inc2001-01-09Not applicableCanada
Allegra AllergyTablet, film coated180 mg/1OralChattem, Inc.2011-03-03Not applicableUs
Allegra AllergyTablet180 mg/1OralNavajo Manuracturing Company2016-09-23Not applicableUs
Allegra AllergyTablet, coated180 mg/1OralChattem, Inc.2014-12-17Not applicableUs
Allegra AllergyTablet, film coated180 mg/1OralA-S Medication Solutions2011-03-03Not applicableUs
Allegra AllergyTablet, film coated60 mg/1OralA-S Medication Solutions2011-03-032016-12-07Us
Additional Data Available
  • Application Number
    Application Number

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  • Product Code
    Product Code

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Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
12HR Allergy and Congestion ReliefFexofenadine hydrochloride (60 mg/1) + Pseudoephedrine hydrochloride (120 mg/1)Tablet, extended releaseOralCardinal Health2019-10-08Not applicableUs
Allegra D 12 Hour Allergy and CongestionFexofenadine hydrochloride (60 mg/1) + Pseudoephedrine hydrochloride (120 mg/1)Tablet, film coated, extended releaseOralRebel Distributors2011-03-03Not applicableUs
Allegra D-12 HourFexofenadine hydrochloride (60 mg/1) + Pseudoephedrine hydrochloride (120 mg/1)Tablet, extended releaseOralSanofi Aventis1997-12-242018-09-26Us00088 1090 47 nlmimage10 d503eadf
Allegra D-12 HourFexofenadine hydrochloride (60 mg/1) + Pseudoephedrine hydrochloride (120 mg/1)Tablet, extended releaseOralCaremark L.L.C.2007-12-172011-04-30Us
Allegra D-12 HourFexofenadine hydrochloride (60 mg/1) + Pseudoephedrine hydrochloride (120 mg/1)Tablet, extended releaseOralPhysicians Total Care, Inc.2000-09-18Not applicableUs54868 425820180907 15195 hfy01t
Allegra D-12 HourFexofenadine hydrochloride (60 mg/1) + Pseudoephedrine hydrochloride (120 mg/1)Tablet, extended releaseOralLake Erie Medical &Surgical Supply Dba Quality Care Products Llc2001-01-012012-05-10Us
Allegra--D 24 HourFexofenadine hydrochloride (180 mg/1) + Pseudoephedrine hydrochloride (240 mg/1)Tablet, film coated, extended releaseOralPhysicians Total Care, Inc.2005-09-14Not applicableUs
Allegra--D 24 HourFexofenadine hydrochloride (180 mg/1) + Pseudoephedrine hydrochloride (240 mg/1)Tablet, film coatedOralSanofi Aventis2004-10-192018-09-25Us
Allegra-DFexofenadine hydrochloride (60 mg) + Pseudoephedrine hydrochloride (120 mg)Tablet, multilayer, extended releaseOralSanofi Aventis1999-04-29Not applicableCanada
Allegra-DFexofenadine (60 mg/1) + Pseudoephedrine (60 mg/1)Tablet, extended releaseOralbryant ranch prepack2009-03-042018-09-21Us
International/Other Brands
Fastofen / Fexidine / Telfast / Vifas
Categories
UNII
E6582LOH6V
CAS number
83799-24-0
Weight
Average: 501.6564
Monoisotopic: 501.287908741
Chemical Formula
C32H39NO4
InChI Key
RWTNPBWLLIMQHL-UHFFFAOYSA-N
InChI
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)
IUPAC Name
2-(4-{1-hydroxy-4-[4-(hydroxydiphenylmethyl)piperidin-1-yl]butyl}phenyl)-2-methylpropanoic acid
SMILES
CC(C)(C(O)=O)C1=CC=C(C=C1)C(O)CCCN1CCC(CC1)C(O)(C1=CC=CC=C1)C1=CC=CC=C1

Pharmacology

Indication

In the United States, fexofenadine is indicated for the symptomatic treatment of allergic rhinitis in patients ≥2 years old and chronic idiopathic urticaria in patients ≥6 months old.10 In Canada, fexofenadine carries the same indications but is approved only for patients ≥12 years old.9 Fexofenadine is also available in combination with pseudoephedrine for the symptomatic treatment of season allergic rhinitis in patients ≥12 years old.11

Associated Conditions
Pharmacodynamics

Fexofenadine relieves allergy symptoms by antagonizing the actions of histamine, an endogenous compound predominantly responsible for allergic symptomatology.10 The relatively long duration of action of fexofenadine (approximately 24 hours)7 allows for once or twice daily dosing, and its rapid absorption allows for an onset of action within 1-3 hours. Fexofenadine should not be taken with fruit juice, as this may impair its absorption.10

Mechanism of action

The H1 histamine receptor is responsible for mediating hypersensitivity and allergic reactions. Exposure to an allergen results in degranulation of mast cells and basophils, which then release histamine and other inflammatory mediators. Histamine binds to, and activates, H1 receptors, which results in the further release of pro-inflammatory cytokines, such as interleukins, from basophils and mast cells. These downstream effects of histamine binding are responsible for a wide variety of allergic symptoms, such as pruritus, rhinorrhea, and watery eyes.7

Fexofenadine is considered an “inverse agonist” of the H1 receptor because it binds to and stabilizes the inactive form of the receptor, preventing its activation and subsequent downstream effects.7 It has a potent and selective affinity for H1 receptors, and there is no evidence that it carries antidopaminergic, antiserotonergic, anticholinergic, sedative, or adrenergic blocking activity.9 Fexofenadine does not cross the blood-brain barrier and thus is unlikely to cause significant CNS effects.9

TargetActionsOrganism
AHistamine H1 receptor
antagonist
Humans
Additional Data Available
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Contraindications

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Absorption

Fexofenadine is rapidly absorbed following oral administration and its absolute bioavailability is approximately 33%.9 The Tmax following oral administration is approximately 1-3 hours.9,7 The steady-state AUCss(0-12h) and Cmax following twice daily dosing of 60mg are 1367 ng/mL.h and 299 ng/mL, respectively.9

Fexofenadine AUC is decreased by >20% when coadministered with fruit juices (e.g. apple, orange, grapefruit) due to their inhibition of OATP transporters - for this reason, prescribing information recommends administering fexofenadine only with water.8 Similarly, coadministration of fexofenadine with a high-fat meal appears to decrease AUC and Cmax by >20%.10

Volume of distribution

The volume of distribution is approximately 5.4-5.8 L/kg.7

Protein binding

Fexofenadine is 60-70% bound to plasma proteins,10 primarily to albumin and α1-acid glycoprotein. The extent of protein binding is decreased to 56-68% and 56-75% in patients with renal and hepatic impairment, respectively.9

Metabolism

Fexofenadine is very minimally metabolized, with only 5% of an ingested dose undergoing hepatic metabolism.10,7 The only identified metabolites are a methyl ester of fexofenadine (3.6% of the total dose) and MDL 4829 (1.5% of the total dose).9 The enzymes responsible for this metabolism have not been elucidated.

Route of elimination

Approximately 80% of an ingested dose is eliminated in the feces, likely largely unchanged due to fexofenadine's limited metabolism, and 11% is eliminated in the urine.7 The principal pathways of fexofenadine elimination are biliary and renal.9

Half life

The terminal elimination half-life is approximately 11-15 hours.9,7

Clearance

The oral clearance of fexofenadine is approximately 50.6 L/h and the renal clearance is approximately 4.32 L/h.9

Toxicity

No deaths were observed following the oral administration of up to 5000 mg/kg in both mice and rats (equivalent to approximately 100-200x the recommended human dose). Single doses of up to 800 mg and chronic exposure of up to 690 mg twice daily for 1 month in humans did not result in clinically significant adverse events. Symptoms of overdosage are consistent with fexofenadine's adverse effect profile and are likely to include dizziness, drowsiness, and dry mouth.10

If overdosage occurs, employ symptomatic and supportive treatment. Hemodialysis does not effectively remove fexofenadine from the blood and is therefore of no benefit.10

Affected organisms
  • Humans and other mammals
Pathways
PathwayCategory
Fexofenadine H1-Antihistamine ActionDrug action
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
2,5-Dimethoxy-4-ethylamphetamine2,5-Dimethoxy-4-ethylamphetamine may decrease the sedative and stimulatory activities of Fexofenadine.
2,5-Dimethoxy-4-ethylthioamphetamine2,5-Dimethoxy-4-ethylthioamphetamine may decrease the sedative and stimulatory activities of Fexofenadine.
4-Bromo-2,5-dimethoxyamphetamine4-Bromo-2,5-dimethoxyamphetamine may decrease the sedative and stimulatory activities of Fexofenadine.
4-MethoxyamphetamineThe risk or severity of adverse effects can be increased when Fexofenadine is combined with 4-Methoxyamphetamine.
5-methoxy-N,N-dimethyltryptamineThe risk or severity of adverse effects can be increased when Fexofenadine is combined with 5-methoxy-N,N-dimethyltryptamine.
7-NitroindazoleThe risk or severity of adverse effects can be increased when Fexofenadine is combined with 7-Nitroindazole.
7,8-Dichloro-1,2,3,4-tetrahydroisoquinolineThe risk or severity of adverse effects can be increased when Fexofenadine is combined with 7,8-Dichloro-1,2,3,4-tetrahydroisoquinoline.
AbemaciclibThe serum concentration of Abemaciclib can be increased when it is combined with Fexofenadine.
AbexinostatThe risk or severity of QTc prolongation can be increased when Fexofenadine is combined with Abexinostat.
AcebutololThe serum concentration of Acebutolol can be increased when it is combined with Fexofenadine.
Additional Data Available
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Food Interactions
  • Grapefruit and grapefruit juice should be avoided throughout treatment as grapefruit can significantly decrease serum levels of this product.
  • Take without regard to meals.

References

Synthesis Reference

Federico Milla, "Processes for the production of fexofenadine." U.S. Patent US20030166682, issued September 04, 2003.

US20030166682
General References
  1. Smith SM, Gums JG: Fexofenadine: biochemical, pharmacokinetic and pharmacodynamic properties and its unique role in allergic disorders. Expert Opin Drug Metab Toxicol. 2009 Jul;5(7):813-22. doi: 10.1517/17425250903044967. [PubMed:19545214]
  2. Bachert C: A review of the efficacy of desloratadine, fexofenadine, and levocetirizine in the treatment of nasal congestion in patients with allergic rhinitis. Clin Ther. 2009 May;31(5):921-44. doi: 10.1016/j.clinthera.2009.05.017. [PubMed:19539095]
  3. Markham A, Wagstaff AJ: Fexofenadine. Drugs. 1998 Feb;55(2):269-74; discussion 275-6. [PubMed:9506246]
  4. Golightly LK, Greos LS: Second-generation antihistamines: actions and efficacy in the management of allergic disorders. Drugs. 2005;65(3):341-84. [PubMed:15669879]
  5. Molimard M, Diquet B, Benedetti MS: Comparison of pharmacokinetics and metabolism of desloratadine, fexofenadine, levocetirizine and mizolastine in humans. Fundam Clin Pharmacol. 2004 Aug;18(4):399-411. [PubMed:15312146]
  6. Akamine Y, Miura M: An update on the clinical pharmacokinetics of fexofenadine enantiomers. Expert Opin Drug Metab Toxicol. 2018 Apr;14(4):429-434. doi: 10.1080/17425255.2018.1459565. Epub 2018 Apr 11. [PubMed:29635947]
  7. Devillier P, Roche N, Faisy C: Clinical pharmacokinetics and pharmacodynamics of desloratadine, fexofenadine and levocetirizine : a comparative review. Clin Pharmacokinet. 2008;47(4):217-30. [PubMed:18336052]
  8. Yu J, Zhou Z, Tay-Sontheimer J, Levy RH, Ragueneau-Majlessi I: Intestinal Drug Interactions Mediated by OATPs: A Systematic Review of Preclinical and Clinical Findings. J Pharm Sci. 2017 Sep;106(9):2312-2325. doi: 10.1016/j.xphs.2017.04.004. Epub 2017 Apr 13. [PubMed:28414144]
  9. DPD Approved Drugs: Allegra® oral tablets [Link]
  10. Allegra (Fexofenadine Hydrochloride) FDA Label [Link]
  11. FDA Approved Drug Products: Allegra-D® extended-release tablets [Link]
External Links
Human Metabolome Database
HMDB0005030
KEGG Drug
D07958
KEGG Compound
C06999
PubChem Compound
3348
PubChem Substance
46504676
ChemSpider
3231
BindingDB
22874
ChEBI
5050
ChEMBL
CHEMBL914
Therapeutic Targets Database
DAP000330
PharmGKB
PA449621
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
Wikipedia
Fexofenadine
ATC Codes
R06AX26 — Fexofenadine
AHFS Codes
  • 04:08.00 — Second Generation Antihistamines
FDA label
Download (43.7 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
1Active Not RecruitingTreatmentLung Cancer Non-Small Cell Cancer (NSCLC)1
1CompletedNot AvailableHealthy Volunteers5
1CompletedBasic ScienceAdministration, Oral / Magnetic Resonance Imaging (MRI) / Pharmacokinetics1
1CompletedDiagnosticDrug Drug Interaction (DDI)1
1CompletedDiagnosticHealthy Volunteers1
1CompletedTreatmentDrug Drug Interaction (DDI)1
1CompletedTreatmentDrug Interaction Potentiation1
1CompletedTreatmentHealthy Volunteers5
1RecruitingBasic ScienceChronic Obstructive Pulmonary Disease (COPD) / Heart Failure / High Blood Pressure (Hypertension) / Pulmonary Arterial Hypertension (PAH)1
1TerminatedBasic ScienceHealthy Volunteers1
1TerminatedTreatmentHealthy Volunteers1
2CompletedSupportive CareItching1
2CompletedTreatmentAllergic Rhinitis (AR)2
2CompletedTreatmentEdema1
2CompletedTreatmentSeasonal Allergic Rhinitis (SAR)1
2RecruitingTreatmentGastroesophageal Reflux1
2, 3CompletedTreatmentAtopic Dermatitis (AD)1
2, 3CompletedTreatmentRhinitis Perennial1
3CompletedTreatmentAsthma3
3CompletedTreatmentPerennial Allergic Rhinitis (PAR)1
3CompletedTreatmentSeasonal Rhinitis2
4CompletedNot AvailableSeasonal Allergic Rhinitis (SAR)2
4CompletedOtherSeasonal Allergic Rhinitis (SAR)1
4CompletedTreatmentAllergic Rhinitis (AR)5
4CompletedTreatmentAllergic Rhinitis (AR) / Chronic Urticaria / Pruritus1
4CompletedTreatmentAllergies1
4CompletedTreatmentCat Induced Allergic Rhinitis1
4CompletedTreatmentPruritus1
4CompletedTreatmentRhinitis1
4CompletedTreatmentRhinitis, Allergic, Perennial1
4CompletedTreatmentRhinitis, Allergic, Seasonal2
4CompletedTreatmentSeasonal Allergic Rhinitis (SAR)4
4CompletedTreatmentUrticaria1
4RecruitingBasic ScienceHemodialysis Treatment1
4RecruitingTreatmentDiabetic Kidney Disease1
4RecruitingTreatmentGout Flares1
4Unknown StatusTreatmentUremic Pruritus1
Not AvailableCompletedNot AvailableFood-Drug Interactions1
Not AvailableCompletedNot AvailableHealthy Volunteers1
Not AvailableRecruitingNot AvailableDepression1

Pharmacoeconomics

Manufacturers
  • Sanofi aventis us llc
  • Barr laboratories inc
  • Dr reddys laboratories ltd
  • Mylan pharmaceuticals inc
  • Teva pharmaceuticals usa inc
  • Sanofi-Aventis
Packagers
  • Amerisource Health Services Corp.
  • Apotheca Inc.
  • A-S Medication Solutions LLC
  • Cardinal Health
  • Caremark LLC
  • Cima Laboratories Inc.
  • DHHS Program Support Center Supply Service Center
  • Direct Dispensing Inc.
  • Direct Pharmaceuticals Inc.
  • Dispensing Solutions
  • Diversified Healthcare Services Inc.
  • Doctor Reddys Laboratories Ltd.
  • H.J. Harkins Co. Inc.
  • Heartland Repack Services LLC
  • Kaiser Foundation Hospital
  • Lake Erie Medical and Surgical Supply
  • Liberty Pharmaceuticals
  • Major Pharmaceuticals
  • Mckesson Corp.
  • Murfreesboro Pharmaceutical Nursing Supply
  • Mylan
  • Novopharm Ltd.
  • Nucare Pharmaceuticals Inc.
  • Palmetto Pharmaceuticals Inc.
  • PCA LLC
  • PD-Rx Pharmaceuticals Inc.
  • Physicians Total Care Inc.
  • Prasco Labs
  • Prepackage Specialists
  • Prepak Systems Inc.
  • Rebel Distributors Corp.
  • Redpharm Drug
  • Resource Optimization and Innovation LLC
  • Sanofi-Aventis Inc.
  • Southwood Pharmaceuticals
  • St Mary's Medical Park Pharmacy
  • Stat Rx Usa
  • Teva Pharmaceutical Industries Ltd.
  • UDL Laboratories
  • Va Cmop Dallas
  • Vangard Labs Inc.
Dosage forms
FormRouteStrength
CapsuleOral60 mg/1
SuspensionOral6 mg/1mL
Tablet, orally disintegratingOral30 mg/1
TabletOral
Tablet, extended releaseOral
Tablet, film coatedOral
Tablet, coatedOral180 mg/1
Tablet, coatedOral60 mg/1
TabletOral30 mg/1
SuspensionOral30 mg/5mL
TabletOral180 mg/1
TabletOral60 mg/1
Tablet, film coatedOral180 mg/1
Tablet, film coatedOral30 mg/1
Tablet, film coatedOral60 mg/1
Tablet, film coated, extended releaseOral
Tablet, multilayer, extended releaseOral
Prices
Unit descriptionCostUnit
Allegra ODT 60 30 mg Dispersible Tablet Box126.0USD box
Allegra-D 24 Hour 180-240 mg 24 Hour tablet5.01USD tablet
Allegra-d 24 hour tablet4.98USD tablet
Allegra 180 mg tablet2.89USD tablet
Allegra-D 12 Hour 60-120 mg 12 Hour tablet2.72USD tablet
Allegra-d 12 hour tablet2.49USD tablet
Fexofenadine hcl 180 mg tablet2.47USD tablet
Allegra odt 30 mg tablet1.98USD tablet
Allegra 60 mg tablet1.64USD tablet
Fexofenadine hcl 60 mg tablet1.43USD tablet
Allegra 30 mg tablet0.81USD tablet
Fexofenadine hcl 30 mg tablet0.71USD tablet
Allegra 30 mg/5ml Suspension0.25USD ml
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)
US5178878No1993-01-122010-01-12Us
CA2301267No2004-07-132018-07-21Canada
CA2134211No1999-06-292013-04-06Canada
US6037353Yes2000-03-142017-09-14Us
US6039974No2000-03-212018-07-31Us
US6723348No2004-04-202021-11-26Us
US6613357No2003-09-022020-12-25Us
USRE39069No2006-04-182018-05-29Us
US8933097No2015-01-132032-08-16Us
US6113942Yes2000-09-052015-08-28Us
US5855912Yes1999-01-052015-08-28Us
US5932247Yes1999-08-032015-08-28Us
US5738872Yes1998-04-142015-08-28Us
Additional Data Available
  • Filed On
    Filed On

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Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)142.5 °CPhysProp
water solubilitySlightly solubleCanadian Label
Predicted Properties
PropertyValueSource
Water Solubility0.00266 mg/mLALOGPS
logP5.02ALOGPS
logP2.94ChemAxon
logS-5.3ALOGPS
pKa (Strongest Acidic)4.04ChemAxon
pKa (Strongest Basic)9.01ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area81 Å2ChemAxon
Rotatable Bond Count10ChemAxon
Refractivity147.98 m3·mol-1ChemAxon
Polarizability57.42 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.7881
Blood Brain Barrier-0.8574
Caco-2 permeable+0.5
P-glycoprotein substrateSubstrate0.8641
P-glycoprotein inhibitor INon-inhibitor0.6791
P-glycoprotein inhibitor IINon-inhibitor0.8779
Renal organic cation transporterNon-inhibitor0.5166
CYP450 2C9 substrateNon-substrate0.836
CYP450 2D6 substrateNon-substrate0.9116
CYP450 3A4 substrateSubstrate0.6458
CYP450 1A2 substrateNon-inhibitor0.9046
CYP450 2C9 inhibitorNon-inhibitor0.9162
CYP450 2D6 inhibitorNon-inhibitor0.9231
CYP450 2C19 inhibitorNon-inhibitor0.9026
CYP450 3A4 inhibitorNon-inhibitor0.8421
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9756
Ames testNon AMES toxic0.9122
CarcinogenicityNon-carcinogens0.9163
BiodegradationNot ready biodegradable0.8428
Rat acute toxicity2.3481 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.8469
hERG inhibition (predictor II)Inhibitor0.6258
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-QFT , negativeLC-MS/MSsplash10-0a6r-0005900000-17ae091cc3d9ba9c62f3
LC-MS/MS Spectrum - LC-ESI-QFT , negativeLC-MS/MSsplash10-0a6r-0396000000-be2d6fedab983b50c280
LC-MS/MS Spectrum - LC-ESI-QFT , negativeLC-MS/MSsplash10-0a4i-1970000000-c78b1c745afc54f58e01
LC-MS/MS Spectrum - LC-ESI-QFT , negativeLC-MS/MSsplash10-0a4r-0920000000-9ad3dc88e743866c23ca
LC-MS/MS Spectrum - LC-ESI-QFT , negativeLC-MS/MSsplash10-0btj-0900000000-66a31911b29382b93745
LC-MS/MS Spectrum - LC-ESI-QFT , negativeLC-MS/MSsplash10-0a4i-1900000000-ce2d00bbddc284806cb0
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-0udi-0000090000-2622c1f2ddb4bff3f93d
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-0159-0000910000-0afa1079fbe9a822e35c
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-00xr-1920200000-1163d721ce08480aea71
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-00di-1910000000-c593678096415da5efb2
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-002f-2900000000-01de1f32826ab5569301
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-002f-3900000000-72f624b2d6e05d29cb72

Taxonomy

Description
This compound belongs to the class of organic compounds known as diphenylmethanes. These are compounds containing a diphenylmethane moiety, which consists of a methane wherein two hydrogen atoms are replaced by two phenyl groups.
Kingdom
Organic compounds
Super Class
Benzenoids
Class
Benzene and substituted derivatives
Sub Class
Diphenylmethanes
Direct Parent
Diphenylmethanes
Alternative Parents
Phenylbutylamines / Phenylpropanes / Aralkylamines / Piperidines / Tertiary alcohols / Trialkylamines / Secondary alcohols / Amino acids / Monocarboxylic acids and derivatives / Azacyclic compounds
show 6 more
Substituents
Diphenylmethane / Phenylbutylamine / Phenylpropane / Aralkylamine / Piperidine / Tertiary alcohol / Amino acid or derivatives / Secondary alcohol / Amino acid / Tertiary amine
show 18 more
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
piperidines, tertiary amine (CHEBI:5050)

Targets

Details
1. Histamine H1 receptor
Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Antagonist
General Function
Histamine receptor activity
Specific Function
In peripheral tissues, the H1 subclass of histamine receptors mediates the contraction of smooth muscles, increase in capillary permeability due to contraction of terminal venules, and catecholamin...
Gene Name
HRH1
Uniprot ID
P35367
Uniprot Name
Histamine H1 receptor
Molecular Weight
55783.61 Da
References
  1. Devillier P, Roche N, Faisy C: Clinical pharmacokinetics and pharmacodynamics of desloratadine, fexofenadine and levocetirizine : a comparative review. Clin Pharmacokinet. 2008;47(4):217-30. [PubMed:18336052]
  2. Smith SM, Gums JG: Fexofenadine: biochemical, pharmacokinetic and pharmacodynamic properties and its unique role in allergic disorders. Expert Opin Drug Metab Toxicol. 2009 Jul;5(7):813-22. doi: 10.1517/17425250903044967. [PubMed:19545214]
  3. Allegra (Fexofenadine Hydrochloride) FDA Label [Link]
  4. DPD Approved Drugs: Allegra® oral tablets [Link]

Carriers

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Toxic substance binding
Specific Function
Serum albumin, the main protein of plasma, has a good binding capacity for water, Ca(2+), Na(+), K(+), fatty acids, hormones, bilirubin and drugs. Its main function is the regulation of the colloid...
Gene Name
ALB
Uniprot ID
P02768
Uniprot Name
Serum albumin
Molecular Weight
69365.94 Da
References
  1. Allegra (Fexofenadine Hydrochloride) FDA Label [Link]
  2. DPD Approved Drugs: Allegra® oral tablets [Link]
Kind
Protein group
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Not Available
Specific Function
Functions as transport protein in the blood stream. Binds various ligands in the interior of its beta-barrel domain. Also binds synthetic drugs and influences their distribution and availability in...

Components:
References
  1. Allegra (Fexofenadine Hydrochloride) FDA Label [Link]
  2. DPD Approved Drugs: Allegra® oral tablets [Link]

Transporters

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Xenobiotic-transporting atpase activity
Specific Function
Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells.
Gene Name
ABCB1
Uniprot ID
P08183
Uniprot Name
Multidrug resistance protein 1
Molecular Weight
141477.255 Da
References
  1. Cvetkovic M, Leake B, Fromm MF, Wilkinson GR, Kim RB: OATP and P-glycoprotein transporters mediate the cellular uptake and excretion of fexofenadine. Drug Metab Dispos. 1999 Aug;27(8):866-71. [PubMed:10421612]
  2. Soldner A, Christians U, Susanto M, Wacher VJ, Silverman JA, Benet LZ: Grapefruit juice activates P-glycoprotein-mediated drug transport. Pharm Res. 1999 Apr;16(4):478-85. [PubMed:10227700]
  3. Petri N, Tannergren C, Rungstad D, Lennernas H: Transport characteristics of fexofenadine in the Caco-2 cell model. Pharm Res. 2004 Aug;21(8):1398-404. [PubMed:15359574]
  4. FDA Drug Development and Drug Interactions: Table of Substrates, Inhibitors and Inducers [Link]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Sodium-independent organic anion transmembrane transporter activity
Specific Function
Mediates the Na(+)-independent uptake of organic anions such as pravastatin, taurocholate, methotrexate, dehydroepiandrosterone sulfate, 17-beta-glucuronosyl estradiol, estrone sulfate, prostagland...
Gene Name
SLCO1B1
Uniprot ID
Q9Y6L6
Uniprot Name
Solute carrier organic anion transporter family member 1B1
Molecular Weight
76447.99 Da
References
  1. Cvetkovic M, Leake B, Fromm MF, Wilkinson GR, Kim RB: OATP and P-glycoprotein transporters mediate the cellular uptake and excretion of fexofenadine. Drug Metab Dispos. 1999 Aug;27(8):866-71. [PubMed:10421612]
  2. FDA Drug Development and Drug Interactions: Table of Substrates, Inhibitors and Inducers [Link]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Sodium-independent organic anion transmembrane transporter activity
Specific Function
Mediates the Na(+)-independent uptake of organic anions such as 17-beta-glucuronosyl estradiol, taurocholate, triiodothyronine (T3), leukotriene C4, dehydroepiandrosterone sulfate (DHEAS), methotre...
Gene Name
SLCO1B3
Uniprot ID
Q9NPD5
Uniprot Name
Solute carrier organic anion transporter family member 1B3
Molecular Weight
77402.175 Da
References
  1. Shimizu M, Fuse K, Okudaira K, Nishigaki R, Maeda K, Kusuhara H, Sugiyama Y: Contribution of OATP (organic anion-transporting polypeptide) family transporters to the hepatic uptake of fexofenadine in humans. Drug Metab Dispos. 2005 Oct;33(10):1477-81. Epub 2005 Jul 13. [PubMed:16014768]
  2. FDA Drug Development and Drug Interactions: Table of Substrates, Inhibitors and Inducers [Link]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Sodium-independent organic anion transmembrane transporter activity
Specific Function
Mediates the Na(+)-independent transport of organic anions such as taurocholate, the prostaglandins PGD2, PGE1, PGE2, leukotriene C4, thromboxane B2 and iloprost.
Gene Name
SLCO2B1
Uniprot ID
O94956
Uniprot Name
Solute carrier organic anion transporter family member 2B1
Molecular Weight
76709.98 Da
References
  1. Yu J, Zhou Z, Tay-Sontheimer J, Levy RH, Ragueneau-Majlessi I: Intestinal Drug Interactions Mediated by OATPs: A Systematic Review of Preclinical and Clinical Findings. J Pharm Sci. 2017 Sep;106(9):2312-2325. doi: 10.1016/j.xphs.2017.04.004. Epub 2017 Apr 13. [PubMed:28414144]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Sodium-independent organic anion transmembrane transporter activity
Specific Function
Mediates the Na(+)-independent transport of organic anions such as sulfobromophthalein (BSP) and conjugated (taurocholate) and unconjugated (cholate) bile acids (By similarity). Selectively inhibit...
Gene Name
SLCO1A2
Uniprot ID
P46721
Uniprot Name
Solute carrier organic anion transporter family member 1A2
Molecular Weight
74144.105 Da
References
  1. Cvetkovic M, Leake B, Fromm MF, Wilkinson GR, Kim RB: OATP and P-glycoprotein transporters mediate the cellular uptake and excretion of fexofenadine. Drug Metab Dispos. 1999 Aug;27(8):866-71. [PubMed:10421612]
  2. Yu J, Zhou Z, Tay-Sontheimer J, Levy RH, Ragueneau-Majlessi I: Intestinal Drug Interactions Mediated by OATPs: A Systematic Review of Preclinical and Clinical Findings. J Pharm Sci. 2017 Sep;106(9):2312-2325. doi: 10.1016/j.xphs.2017.04.004. Epub 2017 Apr 13. [PubMed:28414144]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Organic anion transmembrane transporter activity
Specific Function
Mediates hepatobiliary excretion of numerous organic anions. May function as a cellular cisplatin transporter.
Gene Name
ABCC2
Uniprot ID
Q92887
Uniprot Name
Canalicular multispecific organic anion transporter 1
Molecular Weight
174205.64 Da
References
  1. FDA Drug Development and Drug Interactions: Table of Substrates, Inhibitors and Inducers [Link]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Organic anion transmembrane transporter activity
Specific Function
May act as an inducible transporter in the biliary and intestinal excretion of organic anions. Acts as an alternative route for the export of bile acids and glucuronides from cholestatic hepatocyte...
Gene Name
ABCC3
Uniprot ID
O15438
Uniprot Name
Canalicular multispecific organic anion transporter 2
Molecular Weight
169341.14 Da
References
  1. FDA Drug Development and Drug Interactions: Table of Substrates, Inhibitors and Inducers [Link]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
Curator comments
Substrate profile was investigated in vitro using human OAT3 expressed on HEK293 cells. Reported Km was 70.2 ± 2.7 μM.
General Function
Sodium-independent organic anion transmembrane transporter activity
Specific Function
Plays an important role in the excretion/detoxification of endogenous and exogenous organic anions, especially from the brain and kidney. Involved in the transport basolateral of steviol, fexofenad...
Gene Name
SLC22A8
Uniprot ID
Q8TCC7
Uniprot Name
Solute carrier family 22 member 8
Molecular Weight
59855.585 Da
References
  1. VanWert AL, Gionfriddo MR, Sweet DH: Organic anion transporters: discovery, pharmacology, regulation and roles in pathophysiology. Biopharm Drug Dispos. 2010 Jan;31(1):1-71. doi: 10.1002/bdd.693. [PubMed:19953504]

Drug created on June 13, 2005 07:24 / Updated on January 21, 2020 16:20