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
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
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 | ( + / - ) |
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL231 Sources: https://www.ncbi.nlm.nih.gov/pubmed/19660947 |
40.0 nM [Ki] |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
1.544 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/6113858/ |
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 EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/6113858/ |
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 EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1576325/ |
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 EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1576325/ |
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
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
11.864 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/6113858/ |
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 EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/6113858/ |
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 EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1576325/ |
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 EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1576325/ |
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
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
11.6 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1576325/ |
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 EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1576325/ |
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
Dose | Population | Adverse 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%) Sources: Page: p.462Headache (2.4%) |
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... |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
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
CYP3A4 | CYP2C9 | CYP2D6 | hERG |
---|---|---|---|
Drug as perpetrator
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
Sources: https://pubmed.ncbi.nlm.nih.gov/15133245/ Page: 6.0 |
yes [IC50 23 uM] | |||
Sources: https://pubmed.ncbi.nlm.nih.gov/21612343/ Page: 17.0 |
yes [IC50 41 uM] | |||
Page: 2.0 |
yes [IC50 <10 uM] | |||
Sources: https://pubmed.ncbi.nlm.nih.gov/16495056/ Page: 1.0 |
yes [Ki 0.16 uM] | |||
yes [Ki 3.6 uM] | ||||
yes [Ki 5 uM] |
Drug as victim
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
yes | ||||
Sources: https://pubmed.ncbi.nlm.nih.gov/17180728/ Page: 8.0 |
yes | |||
Page: 1.0 |
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
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
PubMed
Title | Date | PubMed |
---|---|---|
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
In Vivo Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/6129869
Terfenadine 20 mg 3 times a day
Route of Administration:
Oral
Substance Class |
Chemical
Created
by
admin
on
Edited
Wed Jul 05 23:47:08 UTC 2023
by
admin
on
Wed Jul 05 23:47:08 UTC 2023
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Record UNII |
7BA5G9Y06Q
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Record Status |
Validated (UNII)
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Record Version |
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-
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NCI_THESAURUS |
C29578
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WHO-ATC |
R06AX12
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WHO-VATC |
QR06AX12
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LIVERTOX |
939
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D016593
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256-710-8
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758627
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Terfenadine
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50679-08-8
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SUB10920MIG
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C29494
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3674
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7BA5G9Y06Q
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42330
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2600
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CHEMBL17157
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665802
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M10576
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100000082708
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2608
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5405
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DTXSID2023642
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DB00342
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6508
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Related Record | Type | Details | ||
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METABOLIC ENZYME -> INHIBITOR |
IC50
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METABOLIC ENZYME -> SUBSTRATE | |||
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TRANSPORTER -> INHIBITOR | |||
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BINDER->LIGAND |
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METABOLIC ENZYME -> SUBSTRATE | |||
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METABOLIC ENZYME -> SUBSTRATE |
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METABOLITE -> PARENT |
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METABOLITE -> PARENT |
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IMPURITY -> PARENT |
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IMPURITY -> PARENT |
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
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IMPURITY -> PARENT |
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ACTIVE MOIETY |