Details
Stereochemistry | ACHIRAL |
Molecular Formula | C19H19NOS |
Molecular Weight | 309.425 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
CN1CCC(CC1)=C2C3=C(SC=C3)C(=O)CC4=C2C=CC=C4
InChI
InChIKey=ZCVMWBYGMWKGHF-UHFFFAOYSA-N
InChI=1S/C19H19NOS/c1-20-9-6-13(7-10-20)18-15-5-3-2-4-14(15)12-17(21)19-16(18)8-11-22-19/h2-5,8,11H,6-7,9-10,12H2,1H3
Molecular Formula | C19H19NOS |
Molecular Weight | 309.425 |
Charge | 0 |
Count |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Optical Activity | NONE |
DescriptionCurator's Comment: description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/?term=24267353
Curator's Comment: description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/?term=24267353
Ketotifen is a cycloheptathiophene blocker of histamine H1 receptors and release of inflammatory mediators. It has been proposed for the treatment of asthma, rhinitis, skin allergies, and anaphylaxis. Ketotifen was developed in 1970 by Sandoz Pharmaceuticals of Switzerland. It is a benzocycloheptathiophene derivative and was initially marketed as an inhibitor of anaphylaxis. The pharmacodynamic properties of ketotifen are many, because it is an inhibitor of the release and/or activity of mast cell and basophil mediators, including histamine, neutrophil, and eosinophil chemotactic factors, arachidonic acid metabolites, prostaglandins, and leukotrienes. Properties of ketotifen which may contribute to its antiallergic activity and its ability to affect the underlying pathology of asthma include inhibition of the development of airway hyper-reactivity associated with activation of platelets by PAF (Platelet Activating Factor), inhibition of PAF-induced accumulation of eosinophils and platelets in the airways, suppression of the priming of eosinophils by human recombinant cytokines and antagonism of bronchoconstriction due to leukotrienes. Ketotifen is marketed under many brand names worldwide. Ketotifen inhibits the release of mediators from mast cells involved in hypersensitivity reactions. Decreased chemotaxis and activation of eosinophils have also been demonstrated. Ketotifen also inhibits cAMP phosphodiesterase.
CNS Activity
Sources: https://www.ncbi.nlm.nih.gov/pubmed/16390347
Curator's Comment: First-generation antihistamines, such as ketotifen and d-chlorpheniramine, can easily penetrate the blood–brain barrier, and tend to occupy a large proportion of postsynaptic H1Rs (>50%)
Originator
Sources: https://www.ncbi.nlm.nih.gov/pubmed/?term=24267353
Curator's Comment: in 1970 by Sandoz Pharmaceuticals of Switzerland
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL2111411 Sources: https://www.ncbi.nlm.nih.gov/pubmed/1702263 |
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Target ID: CHEMBL231 Sources: https://www.ncbi.nlm.nih.gov/pubmed/8101246 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Palliative | ALAWAY Approved UseUses Temporarily relieves itchy eyes due to pollen, ragweed, grass, animal hair and dander. Launch Date2006 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
281 pg/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/1600111 |
2 mg single, oral dose: 2 mg route of administration: Oral experiment type: SINGLE co-administered: |
KETOTIFEN plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
AUC
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
4703 pg × h/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/1600111 |
2 mg single, oral dose: 2 mg route of administration: Oral experiment type: SINGLE co-administered: |
KETOTIFEN plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
13.1 h EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/1600111 |
2 mg single, oral dose: 2 mg route of administration: Oral experiment type: SINGLE co-administered: |
KETOTIFEN plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
Funbound
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
25% |
KETOTIFEN plasma | Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN |
Doses
Dose | Population | Adverse events |
---|---|---|
120 mg single, oral Overdose |
unhealthy, 21 years n = 1 Health Status: unhealthy Age Group: 21 years Sex: F Population Size: 1 Sources: |
Other AEs: Abdominal pain, Headache... Other AEs: Abdominal pain (mild, 1 patient) Sources: Headache (1 patient) |
1.5 mg 1 times / day multiple, oral Overdose Dose: 1.5 mg, 1 times / day Route: oral Route: multiple Dose: 1.5 mg, 1 times / day Sources: |
unhealthy, 4 months n = 1 Health Status: unhealthy Condition: atopic dermatitis Age Group: 4 months Sex: M Population Size: 1 Sources: |
Disc. AE: Irritability, Drowsiness... AEs leading to discontinuation/dose reduction: Irritability (1 patient) Sources: Drowsiness (1 patient) Encephalopathy toxic (1 patient) |
0.05 mg/mL 1 times / day multiple, ophthalmic Dose: 0.05 mg/mL, 1 times / day Route: ophthalmic Route: multiple Dose: 0.05 mg/mL, 1 times / day Sources: |
unhealthy, 69 years n = 1 Health Status: unhealthy Condition: seasonal allergic conjunctivitis Age Group: 69 years Sex: F Population Size: 1 Sources: |
Disc. AE: Allergic contact dermatitis... AEs leading to discontinuation/dose reduction: Allergic contact dermatitis (1 patient) Sources: |
2 mg 2 times / day multiple, oral Highest studied dose Dose: 2 mg, 2 times / day Route: oral Route: multiple Dose: 2 mg, 2 times / day Sources: |
unhealthy, adult n = 1 Health Status: unhealthy Age Group: adult Population Size: 1 Sources: |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
Headache | 1 patient | 120 mg single, oral Overdose |
unhealthy, 21 years n = 1 Health Status: unhealthy Age Group: 21 years Sex: F Population Size: 1 Sources: |
Abdominal pain | mild, 1 patient | 120 mg single, oral Overdose |
unhealthy, 21 years n = 1 Health Status: unhealthy Age Group: 21 years Sex: F Population Size: 1 Sources: |
Drowsiness | 1 patient Disc. AE |
1.5 mg 1 times / day multiple, oral Overdose Dose: 1.5 mg, 1 times / day Route: oral Route: multiple Dose: 1.5 mg, 1 times / day Sources: |
unhealthy, 4 months n = 1 Health Status: unhealthy Condition: atopic dermatitis Age Group: 4 months Sex: M Population Size: 1 Sources: |
Encephalopathy toxic | 1 patient Disc. AE |
1.5 mg 1 times / day multiple, oral Overdose Dose: 1.5 mg, 1 times / day Route: oral Route: multiple Dose: 1.5 mg, 1 times / day Sources: |
unhealthy, 4 months n = 1 Health Status: unhealthy Condition: atopic dermatitis Age Group: 4 months Sex: M Population Size: 1 Sources: |
Irritability | 1 patient Disc. AE |
1.5 mg 1 times / day multiple, oral Overdose Dose: 1.5 mg, 1 times / day Route: oral Route: multiple Dose: 1.5 mg, 1 times / day Sources: |
unhealthy, 4 months n = 1 Health Status: unhealthy Condition: atopic dermatitis Age Group: 4 months Sex: M Population Size: 1 Sources: |
Allergic contact dermatitis | 1 patient Disc. AE |
0.05 mg/mL 1 times / day multiple, ophthalmic Dose: 0.05 mg/mL, 1 times / day Route: ophthalmic Route: multiple Dose: 0.05 mg/mL, 1 times / day Sources: |
unhealthy, 69 years n = 1 Health Status: unhealthy Condition: seasonal allergic conjunctivitis Age Group: 69 years Sex: F Population Size: 1 Sources: |
PubMed
Title | Date | PubMed |
---|---|---|
Adsorption of allopurinol and ketotifen by chitosan. | 2001 Jan 18 |
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Pharmacokinetics of ketotifen fumarate after intravenous, intranasal, oral and rectal administration in rabbits. | 2002 Dec |
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A comparison of the relative clinical efficacy of a single dose of ketotifen fumarate 0.025% ophthalmic solution versus placebo in inhibiting the signs and symptoms of allergic rhinoconjunctivitis as induced by the conjunctival allergen challenge model. | 2002 Nov |
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[Correction with zaditen of impaired activity of pancreatic digestive enzymes in sensitization and anaphylactic shock]. | 2002 Sep-Oct |
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Determination of ketotifen and its conjugated metabolite in human plasma by liquid chromatography/tandem mass spectrometry: application to a pharmacokinetic study. | 2003 |
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High-frequency oscillation in the hippocampus of the behaving rat and its modulation by the histaminergic system. | 2003 |
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[In vitro effects of antiallergic eyedrops on complement activation induced by particulate matter]. | 2003 Apr |
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Effects of ketotifen 0.025% and lodoxamide 0.1% on eosinophil infiltration into the guinea pig conjunctiva in a model of allergic conjunctivitis. | 2003 Apr |
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Role of mast cells in gastrointestinal mucosal defense. | 2003 Aug |
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The role of platelet activating factor and the efficacy of apafant ophthalmic solution in experimental allergic conjunctivitis. | 2003 Aug |
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[Effectiveness and impact in the quality of life of ketotifen ophthalmic solution. Results of zeta study in patients with seasonal allergic conjunctivitis]. | 2003 Aug |
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Role of mast cells and pro-inflammatory mediators on the intestinal secretion induced by cholera toxin. | 2003 Aug |
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Evaluation of the efficacy of antihistamines using human monocyte-derived dendritic cells stimulated with histamine. | 2003 Aug |
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Effects of TAK-427 on acute nasal symptoms and nasal obstruction in guinea pig model of experimental allergic rhinitis. | 2003 Aug 29 |
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Effects of nonsteroidal anti-inflammatory drugs on experimental allergic conjunctivitis in Guinea pigs. | 2003 Dec |
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Interactions of olopatadine and selected antihistamines with model and natural membranes. | 2003 Dec |
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Efficacy and safety of ketotifen fumarate 0.025% in the conjunctival antigen challenge model of ocular allergic conjunctivitis. | 2003 Dec |
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Release of TNF-alpha during myocardial reperfusion depends on oxidative stress and is prevented by mast cell stabilizers. | 2003 Dec 1 |
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In vitro inhibition of human conjunctival mast-cell degranulation by ketotifen. | 2003 Feb |
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Alteration of CCK-induced satiety in post-Nippostrongylus brasiliensis-infected rats. | 2003 Feb |
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Montelukast reduces peripheral blood eosinophilia but not tissue eosinophilia or symptoms in a patient with eosinophilic gastroenteritis and esophageal stricture. | 2003 Jan |
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The effect of ketotifen on inflammatory markers in allergic conjunctivitis: an open, uncontrolled study. | 2003 Jan 6 |
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Effects of second-generation histamine H1 receptor antagonists on the active avoidance response in rats. | 2003 Jan-Feb |
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A placebo-controlled comparison of ketotifen fumarate and nedocromil sodium ophthalmic solutions for the prevention of ocular itching with the conjunctival allergen challenge model. | 2003 Jul |
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Comparison of ketotifen fumarate ophthalmic solution alone, desloratadine alone, and their combination for inhibition of the signs and symptoms of seasonal allergic rhinoconjunctivitis in the conjunctival allergen challenge model: a double-masked, placebo- and active-controlled trial. | 2003 Jul |
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Forsythia fructus inhibits the mast-cell-mediated allergic inflammatory reactions. | 2003 Jun |
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Use of anti-asthmatic medications in elderly Taiwanese patients. | 2003 Jun |
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Resident cardiac mast cells and ischemia-reperfusion injury. | 2003 Jun |
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Activation of mast cells induced by agonists of proteinase-activated receptors under normal conditions and during acute inflammation in rats. | 2003 Jun 20 |
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Analysis of the spontaneous scratching behavior by NC/Nga mice: a possible approach to evaluate antipruritics for subjects with atopic dermatitis. | 2003 Jun 27 |
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A randomized comparison of chloroquine and chloroquine plus ketotifen in the treatment of acute, uncomplicated, Plasmodium falciparum malaria in children. | 2003 Mar |
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The anti-allergic effects of a cromolyn sodium-chlorpheniramine combination compared to ketotifen in the conjunctival allergen challenge model. | 2003 Mar |
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The use of anti-asthmatic medications among pediatric patients in Taiwan. | 2003 Mar |
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Disposition kinetics of ketotifen from liposomal dry powder for inhalation in rat lung. | 2003 Mar |
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Ketotifen fumarate and olopatadine hydrochloride in the treatment of allergic conjunctivitis: a real-world comparison of efficacy and ocular comfort. | 2003 Mar-Apr |
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[Treatment of chronic idiopathic urticaria unresponsive to type 1 antihistamines in monotherapy]. | 2003 May |
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Effect of dehydroleucodine on histamine and serotonin release from mast cells in the isolated mouse jejunum. | 2003 May |
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Inhibitory effects of ketotifen on eotaxin-dependent activation of eosinophils: consequences for allergic eye diseases. | 2003 May |
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Efficacy of ketotifen fumarate 0.025% ophthalmic solution compared with placebo in the conjunctival allergen challenge model. | 2003 May |
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In vitro uptake and release studies of ocular pharmaceutical agents by silicon-containing and p-HEMA hydrogel contact lens materials. | 2003 May 12 |
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Ebastine inhibits T cell migration, production of Th2-type cytokines and proinflammatory cytokines. | 2003 Nov |
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Antiasthmatic property of polyherbal preparation E-721 B. | 2003 Nov |
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Effect of ketotifen on the production of reactive oxygen species from human eosinophils primed by eotaxin. | 2003 Nov |
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Epileptogenic activity induced by histamine H(1) antagonists in amygdala-kindled rats. | 2003 Nov 21 |
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Epinastine inhibits eosinophil chemotaxis and adhesion molecules in atopic dermatitis. | 2003 Nov-Dec |
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Coincidental increase of leukotriene B4 between cerebral cortex and lung tissue of sensitized rats. | 2003 Oct |
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Enhanced skin permeation of cationic drug ketotifen through excised guinea pig dorsal skin by surfactants with different electric charges. | 2003 Oct |
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Efficacy and safety of ketotifen eye drops in the treatment of seasonal allergic conjunctivitis. | 2003 Oct |
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Plasmodium falciparum gametocytaemia in Nigerian children: before, during and after treatment with antimalarial drugs. | 2003 Sep |
|
Involvement of central mu-opioid system in the scratching behavior in mice, and the suppression of it by the activation of kappa-opioid system. | 2003 Sep 5 |
Sample Use Guides
1 drop in the affected eye twice daily, every 8-12 hours, not more than twice per day
Route of Administration:
Other
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/12648306
Ketotifen at concentrations of approximately 10(-11) to 10(-4) M inhibited mast-cell histamine release by 90% or more. Similarly, ketotifen at approximately 10(-10) to 10(-4) M inhibited tryptase release by 90% or more (apart from a single anomalous reading).
Substance Class |
Chemical
Created
by
admin
on
Edited
Fri Dec 15 15:25:22 GMT 2023
by
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on
Fri Dec 15 15:25:22 GMT 2023
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Record UNII |
X49220T18G
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Record Status |
Validated (UNII)
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Record Version |
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NDF-RT |
N0000000190
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NCI_THESAURUS |
C29578
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QR06AX17
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FDA ORPHAN DRUG |
464714
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NDF-RT |
N0000175519
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S01GX08
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R06AX17
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QS01GX08
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34580-13-7
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SUB08377MIG
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Ketotifen
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KETOTIFEN
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DB00920
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CHEMBL534
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m6624
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100000092111
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6146
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PRIMARY | RxNorm |
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BINDER->LIGAND |
BINDING
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SALT/SOLVATE -> PARENT |
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Related Record | Type | Details | ||
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PARENT -> IMPURITY |
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ACTIVE MOIETY |
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Name | Property Type | Amount | Referenced Substance | Defining | Parameters | References |
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Biological Half-life | PHARMACOKINETIC |
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