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Details

Stereochemistry RACEMIC
Molecular Formula C32H41NO2
Molecular Weight 471.6734
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of TERFENADINE

SMILES

CC(C)(C)C1=CC=C(C=C1)C(O)CCCN2CCC(CC2)C(O)(C3=CC=CC=C3)C4=CC=CC=C4

InChI

InChIKey=GUGOEEXESWIERI-UHFFFAOYSA-N
InChI=1S/C32H41NO2/c1-31(2,3)26-18-16-25(17-19-26)30(34)15-10-22-33-23-20-29(21-24-33)32(35,27-11-6-4-7-12-27)28-13-8-5-9-14-28/h4-9,11-14,16-19,29-30,34-35H,10,15,20-24H2,1-3H3

HIDE SMILES / InChI

Molecular Formula C32H41NO2
Molecular Weight 471.6734
Charge 0
Count
Stereochemistry RACEMIC
Additional Stereochemistry
Defined Stereocenters 0 / 1
E/Z Centers 0
Optical Activity ( + / - )

Description

Terfenadine under brand name Seldane was used for the treatment of allergic rhinitis and allergic skin disorders but was withdrawn because of the serious side effect, heart rhythm problems. Terfenadine is a potent antagonist of histamine H1-receptor-mediated responses.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
40.0 nM [Ki]
PubMed

PubMed

TitleDatePubMed
Interplay between CYP3A-mediated metabolism and polarized efflux of terfenadine and its metabolites in intestinal epithelial Caco-2 (TC7) cell monolayers.
1999 May
Mechanism of terfenadine block of ATP-sensitive K(+) channels.
2000 Aug
Impact of rhinitis on airway inflammation: biological and therapeutic implications.
2001
Evaluation of drug-induced QT interval prolongation: implications for drug approval and labelling.
2001
Saquinavir soft gelatin capsule: a comparative safety review.
2001
Problems of heart rate correction in assessment of drug-induced QT interval prolongation.
2001 Apr
Newer antihistamines.
2001 Apr 30
Uptake and efflux of the peptidic delta-opioid receptor agonist.
2001 Apr 6
Second generation antihistamines in the treatment of seasonal allergic rhinitis due to Parietaria and cypress pollen.
2001 Dec
Multicenter study of the efficacy and safety of fexofenadine 60 mg. twice daily in 108 Thai patients with chronic idiopathic urticaria.
2001 Feb
Assessing the effect of intranasal steroids on growth.
2001 Jul
Antihistamines and the torsade de point in children with allergic rhinitis.
2001 Jul-Aug
Delusion of worm infestation associated with clarithromycin in a patient on peritoneal dialysis.
2001 Jul-Aug
[Effect of olopatadine hydrochloride, a novel antiallergic agent, on the QT interval in dogs].
2001 Jun
The effect of rifampin administration on the disposition of fexofenadine.
2001 Mar
Cooperativity of alpha-naphthoflavone in cytochrome P450 3A-dependent drug oxidation activities in hepatic and intestinal microsomes from mouse and human.
2001 May
Roles of mast cells and histamine in mosquito bite-induced allergic itch-associated responses in mice.
2001 May
A descriptive analysis of the use and cost of new-generation antihistamines in the treatment of allergic rhinitis: a retrospective database analysis.
2001 May
Controlled comparison of the efficacy and safety of cetirizine 10 mg o.d. and fexofenadine 120 mg o.d. in reducing symptoms of seasonal allergic rhinitis.
2001 May
Fexofenadine decreases sensitivity to and montelukast improves recovery from inhaled mannitol.
2001 May
The canine Purkinje fiber: an in vitro model system for acquired long QT syndrome and drug-induced arrhythmogenesis.
2001 May
[Seasonal allergic rhinitis. Nasal obstruction can also beh improved].
2001 May 3
Fexofenadine reduces nasal congestion in perennial allergic rhinitis.
2001 Nov
Assay of terfenadine in pharmaceutical formulation and human plasma by adsorptive stripping voltammetry.
2001 Nov
[Efficacy and safety of fexofenadine and cetirizine in the treatment of allergic rhinitis].
2001 Nov-Dec
Effects of a new antiallergic drug, VUF-K-8788, on infiltration of lung parenchyma by eosinophils in guinea pigs and eosinophil-adhesion to human umbilical vein endothelial cells (HUVEC).
2001 Oct
An amino acid residue whose change by mutation affects drug binding to the HERG channel.
2001 Oct 12
Dissociable effects of histamine H1 antagonists on reaction-time performance in rats.
2001 Oct-Nov
Terfenadine-beta-Cyclodextrin inclusion complex with antihistaminic activity enhancement.
2001 Sep
Potential cardiac toxicity of H1-antihistamines.
2002
[Comparative antihistamine and anti-allergic effects of various antihistamine preparations].
2002
[Chronic idiopathic urticaria: effectiveness of fexofenadine. A double-blind, placebo controlled study with 21 patients].
2002 Apr 10
The relationship of clinical QT prolongation to outcome in the conscious dog using a beat-to-beat QT-RR interval assessment.
2002 Aug
Are antihistamines useful in managing asthma?
2002 Feb
Cardiotoxicity of new antihistamines and cisapride.
2002 Feb 28
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
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
Determination of fexofenadine in human plasma and urine by liquid chromatography-mass spectrometry.
2002 Jan 25
Fexofenadine modulates T-cell function, preventing allergen-induced airway inflammation and hyperresponsiveness.
2002 Jul
Role of lung inflammatory mediators as a cause of exercise-induced arterial hypoxemia in young athletes.
2002 Jul
Chronic urticaria and angioedema.
2002 Jul 18
Simultaneous determination of fexofenadine and its related compounds by HPLC.
2002 Jul 20
Are herbal products dietary supplements or drugs? An important question for public safety.
2002 Jun
Next generation antihistamines: therapeutic rationale, accomplishments and advances.
2002 Jun
Intradermal cholinergic agonists induce itch-associated response via M3 muscarinic acetylcholine receptors in mice.
2002 Mar
Patents

Sample Use Guides

In Vivo Use Guide
Terfenadine 20 mg 3 times a day
Route of Administration: Oral
Substance Class Chemical
Created
by admin
on Mon Oct 21 20:19:39 UTC 2019
Edited
by admin
on Mon Oct 21 20:19:39 UTC 2019
Record UNII
7BA5G9Y06Q
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
TERFENADINE
EP   HSDB   INN   JAN   MART.   MI   USAN   USP-RS   VANDF   WHO-DD  
INN   USAN  
Official Name English
TERFENADINE [EP]
Common Name English
TERFENADINE [WHO-DD]
Common Name English
TERFENADINE [MART.]
Common Name English
SELDANE
Brand Name English
TERFENADINE [MI]
Common Name English
TERFENADINE [JAN]
Common Name English
TERFENADINE [HSDB]
Common Name English
.ALPHA.-(P-TERT-BUTYLPHENYL)-4-(HYDROXYDIPHENYLMETHYL)-1-PIPERIDINEBUTANOL
Common Name English
TERFENADINE [USAN]
Common Name English
RMI 9918
Code English
RMI-9918
Code English
TERFENADINE [INN]
Common Name English
TERFENADINE [USP-RS]
Common Name English
TERFENADINE [VANDF]
Common Name English
1-PIPERIDINEBUTANOL, .ALPHA.-(4-(1,1-DIMETHYLETHYL)PHENYL)-4-(HYDROXYDIPHENYLMETHYL)-
Systematic Name English
Classification Tree Code System Code
NCI_THESAURUS C29578
Created by admin on Mon Oct 21 20:19:39 UTC 2019 , Edited by admin on Mon Oct 21 20:19:39 UTC 2019
WHO-ATC R06AX12
Created by admin on Mon Oct 21 20:19:39 UTC 2019 , Edited by admin on Mon Oct 21 20:19:39 UTC 2019
WHO-VATC QR06AX12
Created by admin on Mon Oct 21 20:19:39 UTC 2019 , Edited by admin on Mon Oct 21 20:19:39 UTC 2019
LIVERTOX 939
Created by admin on Mon Oct 21 20:19:39 UTC 2019 , Edited by admin on Mon Oct 21 20:19:39 UTC 2019
Code System Code Type Description
MESH
D016593
Created by admin on Mon Oct 21 20:19:39 UTC 2019 , Edited by admin on Mon Oct 21 20:19:39 UTC 2019
PRIMARY
ECHA (EC/EINECS)
256-710-8
Created by admin on Mon Oct 21 20:19:39 UTC 2019 , Edited by admin on Mon Oct 21 20:19:39 UTC 2019
PRIMARY
WIKIPEDIA
Terfenadine
Created by admin on Mon Oct 21 20:19:39 UTC 2019 , Edited by admin on Mon Oct 21 20:19:39 UTC 2019
PRIMARY
CAS
50679-08-8
Created by admin on Mon Oct 21 20:19:39 UTC 2019 , Edited by admin on Mon Oct 21 20:19:39 UTC 2019
PRIMARY
EVMPD
SUB10920MIG
Created by admin on Mon Oct 21 20:19:39 UTC 2019 , Edited by admin on Mon Oct 21 20:19:39 UTC 2019
PRIMARY
NCI_THESAURUS
C29494
Created by admin on Mon Oct 21 20:19:39 UTC 2019 , Edited by admin on Mon Oct 21 20:19:39 UTC 2019
PRIMARY
INN
3674
Created by admin on Mon Oct 21 20:19:39 UTC 2019 , Edited by admin on Mon Oct 21 20:19:39 UTC 2019
PRIMARY
RXCUI
42330
Created by admin on Mon Oct 21 20:19:39 UTC 2019 , Edited by admin on Mon Oct 21 20:19:39 UTC 2019
PRIMARY RxNorm
ChEMBL
CHEMBL17157
Created by admin on Mon Oct 21 20:19:39 UTC 2019 , Edited by admin on Mon Oct 21 20:19:39 UTC 2019
PRIMARY
MERCK INDEX
M10576
Created by admin on Mon Oct 21 20:19:39 UTC 2019 , Edited by admin on Mon Oct 21 20:19:39 UTC 2019
PRIMARY Merck Index
IUPHAR
2608
Created by admin on Mon Oct 21 20:19:39 UTC 2019 , Edited by admin on Mon Oct 21 20:19:39 UTC 2019
PRIMARY
PUBCHEM
5405
Created by admin on Mon Oct 21 20:19:39 UTC 2019 , Edited by admin on Mon Oct 21 20:19:39 UTC 2019
PRIMARY
EPA CompTox
50679-08-8
Created by admin on Mon Oct 21 20:19:39 UTC 2019 , Edited by admin on Mon Oct 21 20:19:39 UTC 2019
PRIMARY
HSDB
50679-08-8
Created by admin on Mon Oct 21 20:19:39 UTC 2019 , Edited by admin on Mon Oct 21 20:19:39 UTC 2019
PRIMARY
Related Record Type Details
TRANSPORTER -> INHIBITOR
METABOLIC ENZYME -> SUBSTRATE
BINDER->LIGAND
METABOLIC ENZYME -> SUBSTRATE
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METABOLITE ACTIVE -> PARENT
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IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
Related Record Type Details
ACTIVE MOIETY