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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 of FEXOFENADINE

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

Description

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

Targets

Primary TargetPharmacologyConditionPotency
246.0 nM [IC50]
Conditions
PubMed

PubMed

TitleDatePubMed
Clinical prescribing of allergic rhinitis medication in the preschool and young school-age child: what are the options?
2001
A comprehensive account on the role of efflux transporters in the gastrointestinal absorption of 13 commonly used substrate drugs in humans.
2001 Mar
24-hour efficacy of once-daily desloratadine therapy in patients with seasonal allergic rhinitis [ISRCTN32042139].
2002 Aug 5
Chronic urticaria: a role for newer immunomodulatory drugs?
2003
The effects of acute doses of fexofenadine, promethazine, and placebo on cognitive and psychomotor function in healthy Japanese volunteers.
2003 Apr
Sedation and performance impairment of diphenhydramine and second-generation antihistamines: a meta-analysis.
2003 Apr
Fexofenadine is efficacious and safe in children (aged 6-11 years) with seasonal allergic rhinitis.
2003 Apr
The effects of single-dose fexofenadine, diphenhydramine, and placebo on cognitive performance in flight personnel.
2003 Feb
The effect of ketoconazole on the in vivo intestinal permeability of fexofenadine using a regional perfusion technique.
2003 Feb
[Effect of fexofenadine--selective antagonist of histamine receptor (H1) on histamine-induced bronchoconstriction].
2003 Jan
Solar urticaria induced by infrared radiation.
2003 Mar
Decongestant effects of antihistamines: a class effect?
2003 Mar
Spectrophotometric determination of binary mixtures of pseudoephedrine with some histamine H1-receptor antagonists using derivative ratio spectrum method.
2003 Mar 26
Patents

Sample Use Guides

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
HSDB   INN   MI   VANDF   WHO-DD  
INN  
Official 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
BENZENEACETIC ACID, 4-(1-HYDROXY-4-(4-(HYDROXYDIPHENYLMETHYL)-1-PIPERIDINYL)BUTYL)-.ALPHA.,.ALPHA.-DIMETHYL-, (+/-)-
Common Name English
FEXOFENADINE [WHO-DD]
Common Name English
FEXOFENADINE [HSDB]
Common Name English
TELFAST
Brand Name English
Classification Tree Code System Code
NDF-RT N0000000190
Created by admin on Tue Mar 06 11:22:53 UTC 2018 , Edited by admin on Tue Mar 06 11:22:53 UTC 2018
WHO-ATC R06AX26
Created by admin on Tue Mar 06 11:22:53 UTC 2018 , Edited by admin on Tue Mar 06 11:22:53 UTC 2018
NDF-RT N0000175587
Created by admin on Tue Mar 06 11:22:53 UTC 2018 , Edited by admin on Tue Mar 06 11:22:53 UTC 2018
WHO-VATC QR06AX26
Created by admin on Tue Mar 06 11:22:53 UTC 2018 , Edited by admin on Tue Mar 06 11:22:53 UTC 2018
LIVERTOX 408
Created by admin on Tue Mar 06 11:22:53 UTC 2018 , Edited by admin on Tue Mar 06 11:22:53 UTC 2018
Code System Code Type Description
CAS
83799-24-0
Created by admin on Tue Mar 06 11:22:53 UTC 2018 , Edited by admin on Tue Mar 06 11:22:53 UTC 2018
PRIMARY
LactMed
83799-24-0
Created by admin on Tue Mar 06 11:22:53 UTC 2018 , Edited by admin on Tue Mar 06 11:22:53 UTC 2018
PRIMARY
MESH
C093230
Created by admin on Tue Mar 06 11:22:53 UTC 2018 , Edited by admin on Tue Mar 06 11:22:53 UTC 2018
PRIMARY
ChEMBL
CHEMBL914
Created by admin on Tue Mar 06 11:22:53 UTC 2018 , Edited by admin on Tue Mar 06 11:22:53 UTC 2018
PRIMARY
HSDB
83799-24-0
Created by admin on Tue Mar 06 11:22:53 UTC 2018 , Edited by admin on Tue Mar 06 11:22:53 UTC 2018
PRIMARY
WIKIPEDIA
FEXOFENADINE
Created by admin on Tue Mar 06 11:22:53 UTC 2018 , Edited by admin on Tue Mar 06 11:22:53 UTC 2018
PRIMARY
IUPHAR
4819
Created by admin on Tue Mar 06 11:22:53 UTC 2018 , Edited by admin on Tue Mar 06 11:22:53 UTC 2018
PRIMARY
RXCUI
87636
Created by admin on Tue Mar 06 11:22:53 UTC 2018 , Edited by admin on Tue Mar 06 11:22:53 UTC 2018
PRIMARY RxNorm
PUBCHEM
3348
Created by admin on Tue Mar 06 11:22:53 UTC 2018 , Edited by admin on Tue Mar 06 11:22:53 UTC 2018
PRIMARY SWITZERF
MERCK INDEX
M5367
Created by admin on Tue Mar 06 11:22:53 UTC 2018 , Edited by admin on Tue Mar 06 11:22:53 UTC 2018
PRIMARY Merck Index
EVMPD
SUB13883MIG
Created by admin on Tue Mar 06 11:22:53 UTC 2018 , Edited by admin on Tue Mar 06 11:22:53 UTC 2018
PRIMARY
NCI_THESAURUS
C61764
Created by admin on Tue Mar 06 11:22:53 UTC 2018 , Edited by admin on Tue Mar 06 11:22:53 UTC 2018
PRIMARY
DRUG BANK
DB00950
Created by admin on Tue Mar 06 11:22:53 UTC 2018 , Edited by admin on Tue Mar 06 11:22:53 UTC 2018
PRIMARY
INN
7469
Created by admin on Tue Mar 06 11:22:53 UTC 2018 , Edited by admin on Tue Mar 06 11:22:53 UTC 2018
PRIMARY