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under brand name Seldane was used for the treatment of allergic rhinitis and allergic skin disorders but was withdrawn because of the serious side effect, heart rhythm problems.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
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
The relationship of clinical QT prolongation to outcome in the conscious dog using a beat-to-beat QT-RR interval assessment.
2002-08
Simultaneous determination of fexofenadine and its related compounds by HPLC.
2002-07-20
Chronic urticaria and angioedema.
2002-07-18
Drug eruption and liver injury caused by terfenadine and oxatomide.
2002-07-04
Fexofenadine modulates T-cell function, preventing allergen-induced airway inflammation and hyperresponsiveness.
2002-07
Role of lung inflammatory mediators as a cause of exercise-induced arterial hypoxemia in young athletes.
2002-07
Pharmacological rescue of human K(+) channel long-QT2 mutations: human ether-a-go-go-related gene rescue without block.
2002-06-18
Antihistamines and the torsade de point in children with allergic rhinitis.
2002-06-18
Effect of St John's wort on the pharmacokinetics of fexofenadine.
2002-06
Are herbal products dietary supplements or drugs? An important question for public safety.
2002-06
Next generation antihistamines: therapeutic rationale, accomplishments and advances.
2002-06
Delineation of the protective action of zinc sulfate on ulcerative colitis in rats.
2002-05-17
Evaluation of cytokines in nasal secretions after nasal antigen challenge: lack of influence of antihistamines.
2002-05
MDR1 gene polymorphisms and disposition of the P-glycoprotein substrate fexofenadine.
2002-05
Three-dimensional quantitative structure-activity relationship for inhibition of human ether-a-go-go-related gene potassium channel.
2002-05
[Hay fever and asthma. Many of your patients have both].
2002-04-25
[Chronic idiopathic urticaria: effectiveness of fexofenadine. A double-blind, placebo controlled study with 21 patients].
2002-04-10
Intradermal cholinergic agonists induce itch-associated response via M3 muscarinic acetylcholine receptors in mice.
2002-03
Cardiotoxicity of new antihistamines and cisapride.
2002-02-28
Are antihistamines useful in managing asthma?
2002-02
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.
2002-02
Proarrhythmic potential of halofantrine, terfenadine and clofilium in a modified in vivo model of torsade de pointes.
2002-02
Antihistamines in late-phase clinical development for allergic disease.
2002-02
Determination of fexofenadine in human plasma and urine by liquid chromatography-mass spectrometry.
2002-01-25
[Efficacy and safety of fexofenadine and cetirizine in the treatment of allergic rhinitis].
2002-01-23
An evaluation of the effects of high-dose fexofenadine on the central nervous system: a double-blind, placebo-controlled study in healthy volunteers.
2002-01
A comparison of once daily fexofenadine versus the combination of montelukast plus loratadine on domiciliary nasal peak flow and symptoms in seasonal allergic rhinitis.
2002-01
Fruit juices inhibit organic anion transporting polypeptide-mediated drug uptake to decrease the oral availability of fexofenadine.
2002-01
Induction of multidrug resistance-1 and cytochrome P450 mRNAs in human mononuclear cells by rifampin.
2002-01
Potential cardiac toxicity of H1-antihistamines.
2002
Do standard doses of frequently prescribed drugs cause preventable adverse effects in women?
2002
[Comparative antihistamine and anti-allergic effects of various antihistamine preparations].
2002
Grapefruit juice reduces the oral bioavailability of fexofenadine but not desloratadine.
2002
Pharmacokinetic profile of zafirlukast.
2002
Effects of antihistamines on leukotriene and cytokine release from dispersed nasal polyp cells.
2002
Second generation antihistamines in the treatment of seasonal allergic rhinitis due to Parietaria and cypress pollen.
2001-12
pH-metric solubility. 3. Dissolution titration template method for solubility determination.
2001-12
Dissociable effects of histamine H1 antagonists on reaction-time performance in rats.
2001-11-10
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).
2001-11-01
Fexofenadine reduces nasal congestion in perennial allergic rhinitis.
2001-11
[3H]dofetilide binding to HERG transfected membranes: a potential high throughput preclinical screen.
2001-10-26
An amino acid residue whose change by mutation affects drug binding to the HERG channel.
2001-10-12
Development and evaluation of high throughput functional assay methods for HERG potassium channel.
2001-10
The costs of nonsedating antihistamine therapy for allergic rhinitis in managed care: an updated analysis.
2001-10
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).
2001-10
Terfenadine-beta-Cyclodextrin inclusion complex with antihistaminic activity enhancement.
2001-09
Pharmacological characterization of the leukocyte kinetics after intranasal antigen challenge in a guinea pig model of allergic rhinitis.
2001-09
Involvement of thromboxane A2 and peptide leukotrienes in early and late phase nasal blockage in a guinea pig model of allergic rhinitis.
2001-09
Effect of oxatomide, an antiallergic agent, on QT interval in dogs.
2001
Impact of rhinitis on airway inflammation: biological and therapeutic implications.
2001
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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