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

Details

Stereochemistry RACEMIC
Molecular Formula C32H41NO2
Molecular Weight 471.6734
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 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under brand name Seldane was used for the treatment of allergic rhinitis and allergic skin disorders but was withdrawn because of the serious side effect, heart rhythm problems.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
40.0 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: Page: p.203
healthy, 18-40
n = 24
Health Status: healthy
Age Group: 18-40
Sex: M
Population Size: 24
Sources: Page: p.203
Other AEs: Electrocardiogram QTc interval prolonged...
Other AEs:
Electrocardiogram QTc interval prolonged (12.5%)
Sources: Page: p.203
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: Page: p.69
unhealthy, 18-45
n = 24
Health Status: unhealthy
Condition: Seasonal allergic rhinitis
Age Group: 18-45
Sex: M
Population Size: 24
Sources: Page: p.69
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: Page: p.69
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: Page: p.462
unhealthy, 19-66
n = 41
Health Status: unhealthy
Condition: Adverse reactions to specific immunotherapy with Hymenoptera venom
Age Group: 19-66
Sex: M+F
Population Size: 41
Sources: Page: p.462
Disc. AE: Nausea, Headache...
AEs leading to
discontinuation/dose reduction:
Nausea (2.4%)
Headache (2.4%)
Sources: Page: p.462
60 mg single, oral
Recommended
Dose: 60 mg
Route: oral
Route: single
Dose: 60 mg
Sources: Page: p.406
healthy, 23-40
n = 12
Health Status: healthy
Age Group: 23-40
Sex: M
Population Size: 12
Sources: Page: p.406
240 mg single, oral
Highest studied dose
Dose: 240 mg
Route: oral
Route: single
Dose: 240 mg
Sources: Page: p.610
healthy, 23-47
n = 12
Health Status: healthy
Age Group: 23-47
Sex: F
Population Size: 12
Sources: Page: p.610
Other AEs: Driving ability disturbed...
Other AEs:
Driving ability disturbed
Sources: Page: p.610
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: Page: p.203
healthy, 18-40
n = 24
Health Status: healthy
Age Group: 18-40
Sex: M
Population Size: 24
Sources: Page: p.203
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: Page: p.69
unhealthy, 18-45
n = 24
Health Status: unhealthy
Condition: Seasonal allergic rhinitis
Age Group: 18-45
Sex: M
Population Size: 24
Sources: Page: p.69
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: Page: p.69
unhealthy, 18-45
n = 24
Health Status: unhealthy
Condition: Seasonal allergic rhinitis
Age Group: 18-45
Sex: M
Population Size: 24
Sources: Page: p.69
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: Page: p.462
unhealthy, 19-66
n = 41
Health Status: unhealthy
Condition: Adverse reactions to specific immunotherapy with Hymenoptera venom
Age Group: 19-66
Sex: M+F
Population Size: 41
Sources: Page: p.462
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: Page: p.462
unhealthy, 19-66
n = 41
Health Status: unhealthy
Condition: Adverse reactions to specific immunotherapy with Hymenoptera venom
Age Group: 19-66
Sex: M+F
Population Size: 41
Sources: Page: p.462
Driving ability disturbed
240 mg single, oral
Highest studied dose
Dose: 240 mg
Route: oral
Route: single
Dose: 240 mg
Sources: Page: p.610
healthy, 23-47
n = 12
Health Status: healthy
Age Group: 23-47
Sex: F
Population Size: 12
Sources: Page: p.610
Overview

OverviewOther

Other InhibitorOther SubstrateOther Inducer





Drug as perpetrator​

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: 1.0
Tox targets

Tox targets

TargetModalityActivityMetaboliteClinical evidence
Sourcing

Sourcing

Vendor/AggregatorIDURL
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
Antiallergic effects of H1-receptor antagonists.
2000
Redox state dependency of HERGS631C channel pharmacology: relation to C-type inactivation.
2000 May 26
A structural basis for drug-induced long QT syndrome.
2000 Oct 24
Impact of rhinitis on airway inflammation: biological and therapeutic implications.
2001
Saquinavir soft gelatin capsule: a comparative safety review.
2001
Drug-induced cholestasis.
2001 Apr
Uptake and efflux of the peptidic delta-opioid receptor agonist.
2001 Apr 6
Effects of supratherapeutic doses of ebastine and terfenadine on the QT interval.
2001 Aug
Second generation antihistamines in the treatment of seasonal allergic rhinitis due to Parietaria and cypress pollen.
2001 Dec
Involvement of multiple human cytochromes P450 in the liver microsomal metabolism of astemizole and a comparison with terfenadine.
2001 Feb
Fixed solar urticaria to visible light successfully treated with fexofenadine.
2001 Feb
Suppression of the early and late cutaneous allergic responses using fexofenadine and montelukast.
2001 Jan
Premedication with antihistamines may enhance efficacy of specific-allergen immunotherapy.
2001 Jan
Role of mast cells in antigen-induced airway inflammation and bronchial hyperresponsiveness in rats.
2001 Mar
Fexofenadine hydrochloride--a new anti-histaminic drug.
2001 Mar
Effect of hydroxyzine on the transport of etoposide in rat small intestine.
2001 Mar
Loratadine and terfenadine interaction with nefazodone: Both antihistamines are associated with QTc prolongation.
2001 Mar
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
Development and evaluation of high throughput functional assay methods for HERG potassium channel.
2001 Oct
The costs of nonsedating antihistamine therapy for allergic rhinitis in managed care: an updated analysis.
2001 Oct
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
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
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
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
Are herbal products dietary supplements or drugs? An important question for public safety.
2002 Jun
Pharmacological rescue of human K(+) channel long-QT2 mutations: human ether-a-go-go-related gene rescue without block.
2002 Jun 18
Evaluation of cytokines in nasal secretions after nasal antigen challenge: lack of influence of antihistamines.
2002 May
Patents

Sample Use Guides

Terfenadine 20 mg 3 times a day
Route of Administration: Oral
Substance Class Chemical
Created
by admin
on Wed Jul 05 23:47:08 UTC 2023
Edited
by admin
on Wed Jul 05 23:47:08 UTC 2023
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 [MART.]
Common Name English
NSC-758627
Code English
Terfenadine [WHO-DD]
Common Name 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
α-(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
TERFENADINE [EP IMPURITY]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C29578
Created by admin on Wed Jul 05 23:47:08 UTC 2023 , Edited by admin on Wed Jul 05 23:47:08 UTC 2023
WHO-ATC R06AX12
Created by admin on Wed Jul 05 23:47:08 UTC 2023 , Edited by admin on Wed Jul 05 23:47:08 UTC 2023
WHO-VATC QR06AX12
Created by admin on Wed Jul 05 23:47:08 UTC 2023 , Edited by admin on Wed Jul 05 23:47:08 UTC 2023
LIVERTOX 939
Created by admin on Wed Jul 05 23:47:08 UTC 2023 , Edited by admin on Wed Jul 05 23:47:08 UTC 2023
Code System Code Type Description
MESH
D016593
Created by admin on Wed Jul 05 23:47:08 UTC 2023 , Edited by admin on Wed Jul 05 23:47:08 UTC 2023
PRIMARY
ECHA (EC/EINECS)
256-710-8
Created by admin on Wed Jul 05 23:47:08 UTC 2023 , Edited by admin on Wed Jul 05 23:47:08 UTC 2023
PRIMARY
NSC
758627
Created by admin on Wed Jul 05 23:47:08 UTC 2023 , Edited by admin on Wed Jul 05 23:47:08 UTC 2023
PRIMARY
WIKIPEDIA
Terfenadine
Created by admin on Wed Jul 05 23:47:08 UTC 2023 , Edited by admin on Wed Jul 05 23:47:08 UTC 2023
PRIMARY
CAS
50679-08-8
Created by admin on Wed Jul 05 23:47:08 UTC 2023 , Edited by admin on Wed Jul 05 23:47:08 UTC 2023
PRIMARY
EVMPD
SUB10920MIG
Created by admin on Wed Jul 05 23:47:08 UTC 2023 , Edited by admin on Wed Jul 05 23:47:08 UTC 2023
PRIMARY
NCI_THESAURUS
C29494
Created by admin on Wed Jul 05 23:47:08 UTC 2023 , Edited by admin on Wed Jul 05 23:47:08 UTC 2023
PRIMARY
INN
3674
Created by admin on Wed Jul 05 23:47:08 UTC 2023 , Edited by admin on Wed Jul 05 23:47:08 UTC 2023
PRIMARY
FDA UNII
7BA5G9Y06Q
Created by admin on Wed Jul 05 23:47:08 UTC 2023 , Edited by admin on Wed Jul 05 23:47:08 UTC 2023
PRIMARY
RXCUI
42330
Created by admin on Wed Jul 05 23:47:08 UTC 2023 , Edited by admin on Wed Jul 05 23:47:08 UTC 2023
PRIMARY RxNorm
DRUG CENTRAL
2600
Created by admin on Wed Jul 05 23:47:08 UTC 2023 , Edited by admin on Wed Jul 05 23:47:08 UTC 2023
PRIMARY
ChEMBL
CHEMBL17157
Created by admin on Wed Jul 05 23:47:08 UTC 2023 , Edited by admin on Wed Jul 05 23:47:08 UTC 2023
PRIMARY
NSC
665802
Created by admin on Wed Jul 05 23:47:08 UTC 2023 , Edited by admin on Wed Jul 05 23:47:08 UTC 2023
PRIMARY
MERCK INDEX
M10576
Created by admin on Wed Jul 05 23:47:08 UTC 2023 , Edited by admin on Wed Jul 05 23:47:08 UTC 2023
PRIMARY Merck Index
SMS_ID
100000082708
Created by admin on Wed Jul 05 23:47:08 UTC 2023 , Edited by admin on Wed Jul 05 23:47:08 UTC 2023
PRIMARY
IUPHAR
2608
Created by admin on Wed Jul 05 23:47:08 UTC 2023 , Edited by admin on Wed Jul 05 23:47:08 UTC 2023
PRIMARY
PUBCHEM
5405
Created by admin on Wed Jul 05 23:47:08 UTC 2023 , Edited by admin on Wed Jul 05 23:47:08 UTC 2023
PRIMARY
EPA CompTox
DTXSID2023642
Created by admin on Wed Jul 05 23:47:08 UTC 2023 , Edited by admin on Wed Jul 05 23:47:08 UTC 2023
PRIMARY
DRUG BANK
DB00342
Created by admin on Wed Jul 05 23:47:08 UTC 2023 , Edited by admin on Wed Jul 05 23:47:08 UTC 2023
PRIMARY
HSDB
6508
Created by admin on Wed Jul 05 23:47:08 UTC 2023 , Edited by admin on Wed Jul 05 23:47:08 UTC 2023
PRIMARY
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