Identification

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

Fexofenadine hydrochloride (Allegra) is an antihistamine drug used in the treatment of hayfever and similar allergy symptoms. It was developed as a successor of and alternative to terfenadine. Fexofenadine, like other second and third-generation antihistamines, does not readily pass through the blood-brain barrier, and so causes less drowsiness than first-generation histamine-receptor antagonists.

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
Product Ingredients
IngredientUNIICASInChI Key
Fexofenadine hydrochloride2S068B75ZU153439-40-8RRJFVPUCXDGFJB-UHFFFAOYSA-N
Product Images
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
AllegraTablet, film coated60 mg/1OralSanofi Aventis2000-02-252012-08-31Us
AllegraCapsule60 mg/1OralAventis Pharmaceuticals Inc.2007-01-182007-02-16Us
AllegraSuspension6 mg/1mLOralSanofi Aventis2006-10-16Not applicableUs
AllegraTablet, film coated60 mg/1OralPhysicians Total Care, Inc.2002-06-042011-06-30Us
AllegraTablet, orally disintegrating30 mg/1OralSanofi Aventis2007-07-262013-06-30Us
AllegraTablet, film coated180 mg/1OralSanofi-Synthelabo Limited2010-03-13Not applicableUs
AllegraTablet, film coated180 mg/1OralSanofi Aventis2000-02-252013-02-28Us
AllegraTablet, film coated180 mg/1OralPhysicians Total Care, Inc.2000-11-272011-06-30Us
AllegraTablet, film coated30 mg/1OralSanofi Aventis2000-02-252008-09-19Us
Fexofenadine HydrochlorideTablet, film coated60 mg/1OralNCS HealthCare of KY, Inc dba Vangard Labs2000-02-25Not applicableUs66993 0107 02 nlmimage10 3a239d7c
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Fexofenadine HydrochlorideTablet60 mg/1OralRemedy Repack2011-08-222012-08-23Us
Fexofenadine HydrochlorideTablet60 mg/1OralLake Erie Medical Dba Quality Care Produts Llc2009-12-092014-06-01Us55111 0193 01 nlmimage10 f007f83f
Fexofenadine HydrochlorideTablet180 mg/1OralRebel Distributors2009-12-09Not applicableUs
Fexofenadine HydrochlorideTablet, film coated30 mg/1OralDr Reddy's Laboratories2006-04-122011-01-25Us
Fexofenadine HydrochlorideTablet, film coated30 mg/1OralBarr Laboratories2006-11-172012-05-22Us
Fexofenadine HydrochlorideTablet, film coated60 mg/1OralMylan Institutional2006-06-302012-09-30Us
Fexofenadine HydrochlorideTablet, film coated60 mg/1OralPhysicians Total Care, Inc.2006-08-07Not applicableUs54868 541720180907 15195 1pvc33g
Fexofenadine HydrochlorideTablet, film coated30 mg/1OralMajor2009-06-10Not applicableUs
Fexofenadine HydrochlorideTablet60 mg/1OralAmerincan Health Packaging2009-12-092013-03-31Us
Fexofenadine HydrochlorideTablet, film coated30 mg/1OralPrasco, Laboratories2005-09-012013-01-31Us
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 Eleven2014-04-17Not applicableUs
Allegra 12 HourTablet60 mgOralSanofi Aventis1997-07-10Not applicableCanada
Allegra 24 Hour (120mg)Tablet120 mgOralSanofi Aventis2001-01-09Not applicableCanada
Allegra AllergyTablet, film coated180 mg/1OralA-S Medication Solutions2011-03-03Not applicableUs
Allegra AllergyTablet180 mg/1OralNavajo Manuracturing Company2015-05-12Not applicableUs
Allegra AllergyTablet, film coated60 mg/1OralChattem, Inc.2011-03-03Not applicableUs
Allegra AllergyTablet, film coated180 mg/1OralChattem, Inc.2011-03-03Not applicableUs
Allegra AllergyTablet180 mg/1OralLil' Drug Store Products, Inc2014-09-01Not applicableUs
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
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 releaseOralCaremark L.L.C.2007-12-172011-04-30Us
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 releaseOralLake Erie Medical &Surgical Supply Dba Quality Care Products Llc2001-01-012012-05-10Us
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 24 HourFexofenadine hydrochloride (180 mg/1) + Pseudoephedrine hydrochloride (240 mg/1)Tablet, film coatedOralSanofi Aventis2004-10-192018-09-25Us
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-DFexofenadine hydrochloride (60 mg) + Pseudoephedrine hydrochloride (120 mg)Tablet, extended releaseOralSanofi Aventis1999-04-29Not applicableCanada
Allegra-DFexofenadine (60 mg/1) + Pseudoephedrine (60 mg/1)Tablet, extended releaseOralbryant ranch prepack2009-03-042018-09-21Us
Allegra-D 24 HourFexofenadine hydrochloride (180 mg/1) + Pseudoephedrine hydrochloride (240 mg/1)Tablet, film coatedOralStat Rx USA2004-10-19Not applicableUs
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

For management of Seasonal allergic rhinitis

Associated Conditions
Pharmacodynamics

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.

Mechanism of action

Like other H1-blockers, Fexofenadine competes with free histamine for binding at H1-receptors in the GI tract, large blood vessels, and bronchial smooth muscle. This blocks the action of endogenous histamine, which subsequently leads to temporary relief of the negative symptoms (eg. nasal congestion, watery eyes) brought on by histamine. Fexofenadine exhibits no anticholinergic, antidopaminergic, alpha1-adrenergic or beta-adrenergic-receptor blocking effects.

TargetActionsOrganism
AHistamine H1 receptor
antagonist
Human
Absorption

33%

Volume of distribution
Not Available
Protein binding

60%-70%

Metabolism

Approximately 5% of the total dose is metabolized, by cytochrome P450 3A4 and by intestinal microflora.

Route of elimination
Not Available
Half life

14.4 hours

Clearance
Not Available
Toxicity

Side effects include dizziness, drowsiness, and dry mouth.

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

Interactions

Drug Interactions
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.
3,4-Methylenedioxyamphetamine3,4-Methylenedioxyamphetamine 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.
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.
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]
External Links
Human Metabolome Database
HMDB0005030
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
1CompletedTreatmentAllergic Rhinitis (AR)1
1CompletedTreatmentDrug Drug Interaction (DDI)1
1CompletedTreatmentDrug Interaction Potentiation1
1CompletedTreatmentHealthy Volunteers5
1RecruitingBasic ScienceChronic Obstructive Pulmonary Disease (COPD) / Heart Failure, Unspecified / High Blood Pressure (Hypertension) / Pulmonary Arterial Hypertension (PAH)1
1TerminatedTreatmentHealthy Volunteers1
2CompletedSupportive CareItching1
2CompletedTreatmentAllergic Rhinitis (AR)2
2CompletedTreatmentEdema1
2CompletedTreatmentSeasonal Allergic Rhinitis (SAR)1
2RecruitingTreatmentReflux, Gastroesophageal1
2, 3CompletedTreatmentAtopic Dermatitis (AD)1
2, 3CompletedTreatmentRhinitis Perennial1
3CompletedTreatmentAsthma Bronchial2
3CompletedTreatmentPerennial Allergic Rhinitis (PAR)1
3CompletedTreatmentSeasonal Rhinitis1
3RecruitingTreatmentSeasonal Rhinitis1
4CompletedNot AvailableSeasonal Allergic Rhinitis (SAR)2
4CompletedOtherSeasonal Allergic Rhinitis (SAR)1
4CompletedTreatmentAllergic Rhinitis (AR)5
4CompletedTreatmentCat Induced Allergic Rhinitis1
4CompletedTreatmentPruritus1
4CompletedTreatmentRhinitis1
4CompletedTreatmentRhinitis, Allergic, Perennial1
4CompletedTreatmentRhinitis, Allergic, Seasonal2
4CompletedTreatmentSeasonal Allergic Rhinitis (SAR)4
4CompletedTreatmentUrticarias1
4RecruitingBasic ScienceHemodialysis Treatment1
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
TabletOral60 mg
TabletOral120 mg
Tablet, film coatedOral
Tablet, extended releaseOral
Tablet, coatedOral180 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

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)142.5 °CPhysProp
water solubilitySlightly solubleNot Available
logP5.6Not Available
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
Human
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. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352]
  2. Amon U, Amon S, Gibbs BF: In vitro studies with fexofenadine, a new nonsedating histamine H1 receptor antagonist, on isolated human basophils. Inflamm Res. 2000 Apr;49 Suppl 1:S13-4. [PubMed:10864400]
  3. Abbas MN, Abdel Fattah AA, Zahran E: A novel membrane sensor for histamine H1-receptor antagonist "fexofenadine". Anal Sci. 2004 Aug;20(8):1137-42. [PubMed:15352500]
  4. Grzelewska-Rzymowska I, Kroczynska-Bednarek J, Pietrzkowicz M: [Effect of fexofenadine--selective antagonist of histamine receptor (H1) on histamine-induced bronchoconstriction]. Pol Merkur Lekarski. 2003 Jan;14(79):43-6. [PubMed:12712828]
  5. Tashiro M, Sakurada Y, Iwabuchi K, Mochizuki H, Kato M, Aoki M, Funaki Y, Itoh M, Iwata R, Wong DF, Yanai K: Central effects of fexofenadine and cetirizine: measurement of psychomotor performance, subjective sleepiness, and brain histamine H1-receptor occupancy using 11C-doxepin positron emission tomography. J Clin Pharmacol. 2004 Aug;44(8):890-900. [PubMed:15286093]
  6. Cavero I, Mestre M, Guillon JM, Heuillet E, Roach AG: Preclinical in vitro cardiac electrophysiology: a method of predicting arrhythmogenic potential of antihistamines in humans? Drug Saf. 1999;21 Suppl 1:19-31; discussion 81-7. [PubMed:10597865]
  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. Dhanya NB, Thasleem Z, Rai R, Srinivas CR: Comparative efficacy of levocetirizine, desloratidine and fexofenadine by histamine wheal suppression test. Indian J Dermatol Venereol Leprol. 2008 Jul-Aug;74(4):361-3. [PubMed:18797058]
  9. 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]
  10. Markham A, Wagstaff AJ: Fexofenadine. Drugs. 1998 Feb;55(2):269-74; discussion 275-6. [PubMed:9506246]

Transporters

Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
Inhibitor
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]
Kind
Protein
Organism
Human
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. Nozawa T, Imai K, Nezu J, Tsuji A, Tamai I: Functional characterization of pH-sensitive organic anion transporting polypeptide OATP-B in human. J Pharmacol Exp Ther. 2004 Feb;308(2):438-45. Epub 2003 Nov 10. [PubMed:14610227]
Kind
Protein
Organism
Human
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]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
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]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
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]
Kind
Protein
Organism
Human
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 December 12, 2018 07:10