U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry RACEMIC
Molecular Formula C32H41NO2
Molecular Weight 471.6746
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of TERFENADINE

SMILES

CC(C)(C)c1ccc(cc1)C(CCCN2CCC(CC2)C(c3ccccc3)(c4ccccc4)O)O

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 471.6746
Charge 0
Count
Stereochemistry RACEMIC
Additional Stereochemistry No
Defined Stereocenters 0 / 1
E/Z Centers 0
Optical Activity ( + / - )

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under brand name Seldane was used for the treatment of allergic rhinitis and allergic skin disorders but was withdrawn because of the serious side effect, heart rhythm problems.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 nM [Ki]
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
1.544 ng/mL
60 mg single, oral
dose: 60 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
TERFENADINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
4.519 ng/mL
180 mg single, oral
dose: 180 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
TERFENADINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
458.1 ng/mL
120 mg single, oral
dose: 120 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
TERFENADINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: HIGH-FAT
406.9 ng/mL
120 mg single, oral
dose: 120 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
TERFENADINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
11.864 ng × h/mL
60 mg single, oral
dose: 60 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
TERFENADINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
44.341 ng × h/mL
180 mg single, oral
dose: 180 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
TERFENADINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
2712.1 ng × h/mL
120 mg single, oral
dose: 120 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
TERFENADINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: HIGH-FAT
2720.1 ng × h/mL
120 mg single, oral
dose: 120 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
TERFENADINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
11.6 h
120 mg single, oral
dose: 120 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
TERFENADINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: HIGH-FAT
12.6 h
120 mg single, oral
dose: 120 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
TERFENADINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
Doses

Doses

DosePopulationAdverse events​
180 mg 2 times / day multiple, oral
Highest studied dose
Dose: 180 mg, 2 times / day
Route: oral
Route: multiple
Dose: 180 mg, 2 times / day
Sources:
healthy, 18-40
Health Status: healthy
Age Group: 18-40
Sex: M
Sources:
Other AEs: Electrocardiogram QTc interval prolonged...
Other AEs:
Electrocardiogram QTc interval prolonged (12.5%)
Sources:
60 mg 2 times / day multiple, oral
Recommended
Dose: 60 mg, 2 times / day
Route: oral
Route: multiple
Dose: 60 mg, 2 times / day
Sources:
unhealthy, 18-45
Health Status: unhealthy
Age Group: 18-45
Sex: M
Sources:
Disc. AE: Headache...
Other AEs: Somnolence...
AEs leading to
discontinuation/dose reduction:
Headache (grade 2-3, 8.3%)
Other AEs:
Somnolence (grade 1, 4.15%)
Sources:
120 mg 1 times / day multiple, oral
Recommended
Dose: 120 mg, 1 times / day
Route: oral
Route: multiple
Dose: 120 mg, 1 times / day
Sources:
unhealthy, 19-66
Health Status: unhealthy
Age Group: 19-66
Sex: M+F
Sources:
Disc. AE: Nausea, Headache...
AEs leading to
discontinuation/dose reduction:
Nausea (2.4%)
Headache (2.4%)
Sources:
60 mg single, oral
Recommended
Dose: 60 mg
Route: oral
Route: single
Dose: 60 mg
Sources:
healthy, 23-40
Health Status: healthy
Age Group: 23-40
Sex: M
Sources:
240 mg single, oral
Highest studied dose
Dose: 240 mg
Route: oral
Route: single
Dose: 240 mg
Sources:
healthy, 23-47
Health Status: healthy
Age Group: 23-47
Sex: F
Sources:
Other AEs: Driving ability disturbed...
Other AEs:
Driving ability disturbed
Sources:
AEs

AEs

AESignificanceDosePopulation
Electrocardiogram QTc interval prolonged 12.5%
180 mg 2 times / day multiple, oral
Highest studied dose
Dose: 180 mg, 2 times / day
Route: oral
Route: multiple
Dose: 180 mg, 2 times / day
Sources:
healthy, 18-40
Health Status: healthy
Age Group: 18-40
Sex: M
Sources:
Somnolence grade 1, 4.15%
60 mg 2 times / day multiple, oral
Recommended
Dose: 60 mg, 2 times / day
Route: oral
Route: multiple
Dose: 60 mg, 2 times / day
Sources:
unhealthy, 18-45
Health Status: unhealthy
Age Group: 18-45
Sex: M
Sources:
Headache grade 2-3, 8.3%
Disc. AE
60 mg 2 times / day multiple, oral
Recommended
Dose: 60 mg, 2 times / day
Route: oral
Route: multiple
Dose: 60 mg, 2 times / day
Sources:
unhealthy, 18-45
Health Status: unhealthy
Age Group: 18-45
Sex: M
Sources:
Headache 2.4%
Disc. AE
120 mg 1 times / day multiple, oral
Recommended
Dose: 120 mg, 1 times / day
Route: oral
Route: multiple
Dose: 120 mg, 1 times / day
Sources:
unhealthy, 19-66
Health Status: unhealthy
Age Group: 19-66
Sex: M+F
Sources:
Nausea 2.4%
Disc. AE
120 mg 1 times / day multiple, oral
Recommended
Dose: 120 mg, 1 times / day
Route: oral
Route: multiple
Dose: 120 mg, 1 times / day
Sources:
unhealthy, 19-66
Health Status: unhealthy
Age Group: 19-66
Sex: M+F
Sources:
Driving ability disturbed
240 mg single, oral
Highest studied dose
Dose: 240 mg
Route: oral
Route: single
Dose: 240 mg
Sources:
healthy, 23-47
Health Status: healthy
Age Group: 23-47
Sex: F
Sources:
Overview

OverviewOther

Other InhibitorOther SubstrateOther Inducer





Drug as perpetrator​Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
yes
yes
yes
likely (co-administration study)
Comment: From abstract: a drug interaction between terfenadine and ketoconazole resulted in the elevated terfenadine levels in plasma and in the cardiotoxicity previously seen only in cases of terfenadine overdose.
Page: 1
Tox targets

Tox targets

TargetModalityActivityMetaboliteClinical evidence
PubMed

PubMed

TitleDatePubMed
Effect of oxatomide, an antiallergic agent, on QT interval in dogs.
2001
[The effect of second generation histamine antagonists on the heart].
2001
Evaluation of drug-induced QT interval prolongation: implications for drug approval and labelling.
2001
Identification of functionally variant MDR1 alleles among European Americans and African Americans.
2001 Aug
Effects of supratherapeutic doses of ebastine and terfenadine on the QT interval.
2001 Aug
Ugly wait at the counter. Insurer pushes to make allergy drugs nonprescription.
2001 Aug 6
Pharmacokinetic/pharmacodynamic assessment of the effects of E4031, cisapride, terfenadine and terodiline on monophasic action potential duration in dog.
2001 Aug-Sep
pH-metric solubility. 3. Dissolution titration template method for solubility determination.
2001 Dec
Evaluation of the safety of fexofenadine from experience gained in general practice use in England in 1997.
2001 Jul
Safety of fexofenadine in children treated for seasonal allergic rhinitis.
2001 Jul
Assessing the effect of intranasal steroids on growth.
2001 Jul
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
Inhibition of human CYP1A2 activity in vitro by methylxanthines: potent competitive inhibition by 8-phenyltheophylline.
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
VUF-K-8788, a periphery-selective histamine H1 antagonist with anti-pruritic activities.
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
Assay of terfenadine in pharmaceutical formulation and human plasma by adsorptive stripping voltammetry.
2001 Nov
Inhibition of depolarization-induced [3H]noradrenaline release from SH-SY5Y human neuroblastoma cells by some second-generation H(1) receptor antagonists through blockade of store-operated Ca(2+) channels (SOCs).
2001 Nov 1
[Efficacy and safety of fexofenadine and cetirizine in the treatment of allergic rhinitis].
2001 Nov-Dec
The costs of nonsedating antihistamine therapy for allergic rhinitis in managed care: an updated analysis.
2001 Oct
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
[3H]dofetilide binding to HERG transfected membranes: a potential high throughput preclinical screen.
2001 Oct 26
Terfenadine-beta-Cyclodextrin inclusion complex with antihistaminic activity enhancement.
2001 Sep
Pharmacological characterization of the leukocyte kinetics after intranasal antigen challenge in a guinea pig model of allergic rhinitis.
2001 Sep
Involvement of thromboxane A2 and peptide leukotrienes in early and late phase nasal blockage in a guinea pig model of allergic rhinitis.
2001 Sep
Pharmacokinetic profile of zafirlukast.
2002
Effects of antihistamines on leukotriene and cytokine release from dispersed nasal polyp cells.
2002
[Hay fever and asthma. Many of your patients have both].
2002 Apr 25
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
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
Proarrhythmic potential of halofantrine, terfenadine and clofilium in a modified in vivo model of torsade de pointes.
2002 Feb
Antihistamines in late-phase clinical development for allergic disease.
2002 Feb
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
Fruit juices inhibit organic anion transporting polypeptide-mediated drug uptake to decrease the oral availability of fexofenadine.
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
Effect of St John's wort on the pharmacokinetics of fexofenadine.
2002 Jun
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
Pharmacological rescue of human K(+) channel long-QT2 mutations: human ether-a-go-go-related gene rescue without block.
2002 Jun 18
Intradermal cholinergic agonists induce itch-associated response via M3 muscarinic acetylcholine receptors in mice.
2002 Mar
MDR1 gene polymorphisms and disposition of the P-glycoprotein substrate fexofenadine.
2002 May
Three-dimensional quantitative structure-activity relationship for inhibition of human ether-a-go-go-related gene potassium channel.
2002 May
Patents

Sample Use Guides

Terfenadine 20 mg 3 times a day
Route of Administration: Oral
Substance Class Chemical
Created
by admin
on Fri Jun 25 21:10:44 UTC 2021
Edited
by admin
on Fri Jun 25 21:10:44 UTC 2021
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
NSC-758627
Code English
SELDANE
Brand Name English
TERFENADINE [EP MONOGRAPH]
Common 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
NSC-665802
Code English
TERFENADINE [INN]
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 Fri Jun 25 21:10:45 UTC 2021 , Edited by admin on Fri Jun 25 21:10:45 UTC 2021
WHO-ATC R06AX12
Created by admin on Fri Jun 25 21:10:45 UTC 2021 , Edited by admin on Fri Jun 25 21:10:45 UTC 2021
WHO-VATC QR06AX12
Created by admin on Fri Jun 25 21:10:45 UTC 2021 , Edited by admin on Fri Jun 25 21:10:45 UTC 2021
LIVERTOX 939
Created by admin on Fri Jun 25 21:10:45 UTC 2021 , Edited by admin on Fri Jun 25 21:10:45 UTC 2021
Code System Code Type Description
MESH
D016593
Created by admin on Fri Jun 25 21:10:45 UTC 2021 , Edited by admin on Fri Jun 25 21:10:45 UTC 2021
PRIMARY
ECHA (EC/EINECS)
256-710-8
Created by admin on Fri Jun 25 21:10:45 UTC 2021 , Edited by admin on Fri Jun 25 21:10:45 UTC 2021
PRIMARY
WIKIPEDIA
Terfenadine
Created by admin on Fri Jun 25 21:10:45 UTC 2021 , Edited by admin on Fri Jun 25 21:10:45 UTC 2021
PRIMARY
CAS
50679-08-8
Created by admin on Fri Jun 25 21:10:45 UTC 2021 , Edited by admin on Fri Jun 25 21:10:45 UTC 2021
PRIMARY
EVMPD
SUB10920MIG
Created by admin on Fri Jun 25 21:10:45 UTC 2021 , Edited by admin on Fri Jun 25 21:10:45 UTC 2021
PRIMARY
NCI_THESAURUS
C29494
Created by admin on Fri Jun 25 21:10:45 UTC 2021 , Edited by admin on Fri Jun 25 21:10:45 UTC 2021
PRIMARY
INN
3674
Created by admin on Fri Jun 25 21:10:45 UTC 2021 , Edited by admin on Fri Jun 25 21:10:45 UTC 2021
PRIMARY
FDA UNII
7BA5G9Y06Q
Created by admin on Fri Jun 25 21:10:45 UTC 2021 , Edited by admin on Fri Jun 25 21:10:45 UTC 2021
PRIMARY
RXCUI
42330
Created by admin on Fri Jun 25 21:10:45 UTC 2021 , Edited by admin on Fri Jun 25 21:10:45 UTC 2021
PRIMARY RxNorm
DRUG CENTRAL
2600
Created by admin on Fri Jun 25 21:10:45 UTC 2021 , Edited by admin on Fri Jun 25 21:10:45 UTC 2021
PRIMARY
ChEMBL
CHEMBL17157
Created by admin on Fri Jun 25 21:10:45 UTC 2021 , Edited by admin on Fri Jun 25 21:10:45 UTC 2021
PRIMARY
MERCK INDEX
M10576
Created by admin on Fri Jun 25 21:10:45 UTC 2021 , Edited by admin on Fri Jun 25 21:10:45 UTC 2021
PRIMARY Merck Index
IUPHAR
2608
Created by admin on Fri Jun 25 21:10:45 UTC 2021 , Edited by admin on Fri Jun 25 21:10:45 UTC 2021
PRIMARY
PUBCHEM
5405
Created by admin on Fri Jun 25 21:10:45 UTC 2021 , Edited by admin on Fri Jun 25 21:10:45 UTC 2021
PRIMARY
EPA CompTox
50679-08-8
Created by admin on Fri Jun 25 21:10:45 UTC 2021 , Edited by admin on Fri Jun 25 21:10:45 UTC 2021
PRIMARY
DRUG BANK
DB00342
Created by admin on Fri Jun 25 21:10:45 UTC 2021 , Edited by admin on Fri Jun 25 21:10:45 UTC 2021
PRIMARY
HSDB
6508
Created by admin on Fri Jun 25 21:10:45 UTC 2021 , Edited by admin on Fri Jun 25 21:10:45 UTC 2021
PRIMARY
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