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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 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under brand name Seldane was used for the treatment of allergic rhinitis and allergic skin disorders but was withdrawn because of the serious side effect, heart rhythm problems.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
406.9 ng/mL
120 mg single, oral
dose: 120 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
FEXOFENADINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
458.1 ng/mL
120 mg single, oral
dose: 120 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
FEXOFENADINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: HIGH-FAT
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
AUC

AUC

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

T1/2

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

Sourcing

Vendor/AggregatorIDURL
PubMed

PubMed

TitleDatePubMed
Mechanism of terfenadine block of ATP-sensitive K(+) channels.
2000 Aug
Loratadine blockade of K(+) channels in human heart: comparison with terfenadine under physiological conditions.
2000 Jan
Redox state dependency of HERGS631C channel pharmacology: relation to C-type inactivation.
2000 May 26
Effect of oxatomide, an antiallergic agent, on QT interval in dogs.
2001
Evaluation of drug-induced QT interval prolongation: implications for drug approval and labelling.
2001
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
Assessing the effect of intranasal steroids on growth.
2001 Jul
[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
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
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
Development and evaluation of high throughput functional assay methods for HERG potassium channel.
2001 Oct
[Comparative antihistamine and anti-allergic effects of various antihistamine preparations].
2002
Effects of antihistamines on leukotriene and cytokine release from dispersed nasal polyp cells.
2002
The relationship of clinical QT prolongation to outcome in the conscious dog using a beat-to-beat QT-RR interval assessment.
2002 Aug
Antihistamines in late-phase clinical development for allergic disease.
2002 Feb
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
Simultaneous determination of fexofenadine and its related compounds by HPLC.
2002 Jul 20
Drug eruption and liver injury caused by terfenadine and oxatomide.
2002 Jul-Aug
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
Patents

Sample Use Guides

Terfenadine 20 mg 3 times a day
Route of Administration: Oral
Substance Class Chemical
Created
by admin
on Mon Mar 31 18:25:30 GMT 2025
Edited
by admin
on Mon Mar 31 18:25:30 GMT 2025
Record UNII
7BA5G9Y06Q
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
SELDANE
Preferred Name English
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
TERFENADINE [EP MONOGRAPH]
Common Name English
TERFENADINE [MI]
Common Name English
TERFENADINE [JAN]
Common Name English
TERFENADINE [HSDB]
Common Name English
?-(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 Mon Mar 31 18:25:30 GMT 2025 , Edited by admin on Mon Mar 31 18:25:30 GMT 2025
WHO-ATC R06AX12
Created by admin on Mon Mar 31 18:25:30 GMT 2025 , Edited by admin on Mon Mar 31 18:25:30 GMT 2025
WHO-VATC QR06AX12
Created by admin on Mon Mar 31 18:25:30 GMT 2025 , Edited by admin on Mon Mar 31 18:25:30 GMT 2025
LIVERTOX 939
Created by admin on Mon Mar 31 18:25:30 GMT 2025 , Edited by admin on Mon Mar 31 18:25:30 GMT 2025
CFR 21 CFR 216.24
Created by admin on Mon Mar 31 18:25:30 GMT 2025 , Edited by admin on Mon Mar 31 18:25:30 GMT 2025
Code System Code Type Description
MESH
D016593
Created by admin on Mon Mar 31 18:25:30 GMT 2025 , Edited by admin on Mon Mar 31 18:25:30 GMT 2025
PRIMARY
ECHA (EC/EINECS)
256-710-8
Created by admin on Mon Mar 31 18:25:30 GMT 2025 , Edited by admin on Mon Mar 31 18:25:30 GMT 2025
PRIMARY
NSC
758627
Created by admin on Mon Mar 31 18:25:30 GMT 2025 , Edited by admin on Mon Mar 31 18:25:30 GMT 2025
PRIMARY
WIKIPEDIA
Terfenadine
Created by admin on Mon Mar 31 18:25:30 GMT 2025 , Edited by admin on Mon Mar 31 18:25:30 GMT 2025
PRIMARY
CAS
50679-08-8
Created by admin on Mon Mar 31 18:25:30 GMT 2025 , Edited by admin on Mon Mar 31 18:25:30 GMT 2025
PRIMARY
EVMPD
SUB10920MIG
Created by admin on Mon Mar 31 18:25:30 GMT 2025 , Edited by admin on Mon Mar 31 18:25:30 GMT 2025
PRIMARY
NCI_THESAURUS
C29494
Created by admin on Mon Mar 31 18:25:30 GMT 2025 , Edited by admin on Mon Mar 31 18:25:30 GMT 2025
PRIMARY
INN
3674
Created by admin on Mon Mar 31 18:25:30 GMT 2025 , Edited by admin on Mon Mar 31 18:25:30 GMT 2025
PRIMARY
FDA UNII
7BA5G9Y06Q
Created by admin on Mon Mar 31 18:25:30 GMT 2025 , Edited by admin on Mon Mar 31 18:25:30 GMT 2025
PRIMARY
RXCUI
42330
Created by admin on Mon Mar 31 18:25:30 GMT 2025 , Edited by admin on Mon Mar 31 18:25:30 GMT 2025
PRIMARY RxNorm
DRUG CENTRAL
2600
Created by admin on Mon Mar 31 18:25:30 GMT 2025 , Edited by admin on Mon Mar 31 18:25:30 GMT 2025
PRIMARY
ChEMBL
CHEMBL17157
Created by admin on Mon Mar 31 18:25:30 GMT 2025 , Edited by admin on Mon Mar 31 18:25:30 GMT 2025
PRIMARY
NSC
665802
Created by admin on Mon Mar 31 18:25:30 GMT 2025 , Edited by admin on Mon Mar 31 18:25:30 GMT 2025
PRIMARY
MERCK INDEX
m10576
Created by admin on Mon Mar 31 18:25:30 GMT 2025 , Edited by admin on Mon Mar 31 18:25:30 GMT 2025
PRIMARY Merck Index
SMS_ID
100000082708
Created by admin on Mon Mar 31 18:25:30 GMT 2025 , Edited by admin on Mon Mar 31 18:25:30 GMT 2025
PRIMARY
IUPHAR
2608
Created by admin on Mon Mar 31 18:25:30 GMT 2025 , Edited by admin on Mon Mar 31 18:25:30 GMT 2025
PRIMARY
PUBCHEM
5405
Created by admin on Mon Mar 31 18:25:30 GMT 2025 , Edited by admin on Mon Mar 31 18:25:30 GMT 2025
PRIMARY
EPA CompTox
DTXSID2023642
Created by admin on Mon Mar 31 18:25:30 GMT 2025 , Edited by admin on Mon Mar 31 18:25:30 GMT 2025
PRIMARY
DRUG BANK
DB00342
Created by admin on Mon Mar 31 18:25:30 GMT 2025 , Edited by admin on Mon Mar 31 18:25:30 GMT 2025
PRIMARY
HSDB
6508
Created by admin on Mon Mar 31 18:25:30 GMT 2025 , Edited by admin on Mon Mar 31 18:25:30 GMT 2025
PRIMARY
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