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
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 |
|||
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 |
---|---|---|
Effects of mast-cell stabilization in cerulein-induced acute pancreatitis in rats. | 2001 |
|
Role of histamine in aggravation of gastric acid back-diffusion and vascular permeability in septic rats. | 2001 Dec 31 |
|
Adsorption of allopurinol and ketotifen by chitosan. | 2001 Jan 18 |
|
Long-term management of asthma. | 2001 Sep |
|
Purging of contaminating breast cancer cells from hematopoietic progenitor cell preparations using activation enhanced cell death. | 2002 Apr |
|
Oral administration of ketotifen in a patient with eosinophilic colitis and severe osteoporosis. | 2002 Apr |
|
Pharmacokinetics of ketotifen fumarate after intravenous, intranasal, oral and rectal administration in rabbits. | 2002 Dec |
|
The comparison of the efficacy and safety of cetirizine, oxatomide, ketotifen, and a placebo for the treatment of childhood perennial allergic rhinitis. | 2002 Dec |
|
Inhibition of allergic dermal inflammation by the novel imidazopyridazine derivative TAK-427 in a guinea pig experimental model of eczema. | 2002 Dec |
|
[Stem cell factor production from cultured nasal epithelial cells--effect on SCF production by drugs]. | 2002 Feb |
|
Evaluation of inflammatory parameters in physical urticarias and effects of an anti-inflammatory/antiallergic treatment. | 2002 Jul |
|
Gateways to clinical trials. | 2002 Jul-Aug |
|
[Anti-allergic drugs inhibit the proliferation of human Tenon's capsule fibroblast and maintain the experimental filtering blebs on rabbit eyes]. | 2002 Jun |
|
Role of Rho-associated protein kinase and histamine in lysophosphatidic acid-induced airway hyperresponsiveness in guinea pigs. | 2002 Mar |
|
Development and validation of a HPLC method for the determination of cetirizine in pharmaceutical dosage forms. | 2002 May |
|
Delineation of the protective action of zinc sulfate on ulcerative colitis in rats. | 2002 May 17 |
|
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 |
|
Rhinitis (allergic and nonallergic) in an atopic pediatric referral population in the grasslands of inland South Africa. | 2002 Nov |
|
Sensitivity of myeloid leukemia cells to calcium influx blockade: application to bone marrow purging. | 2002 Oct |
|
[Correction with zaditen of impaired activity of pancreatic digestive enzymes in sensitization and anaphylactic shock]. | 2002 Sep-Oct |
|
Determination of ketotifen and its conjugated metabolite in human plasma by liquid chromatography/tandem mass spectrometry: application to a pharmacokinetic study. | 2003 |
|
High-frequency oscillation in the hippocampus of the behaving rat and its modulation by the histaminergic system. | 2003 |
|
[In vitro effects of antiallergic eyedrops on complement activation induced by particulate matter]. | 2003 Apr |
|
[Effectiveness and impact in the quality of life of ketotifen ophthalmic solution. Results of zeta study in patients with seasonal allergic conjunctivitis]. | 2003 Aug |
|
Role of mast cells and pro-inflammatory mediators on the intestinal secretion induced by cholera toxin. | 2003 Aug |
|
Effects of TAK-427 on acute nasal symptoms and nasal obstruction in guinea pig model of experimental allergic rhinitis. | 2003 Aug 29 |
|
Effects of nonsteroidal anti-inflammatory drugs on experimental allergic conjunctivitis in Guinea pigs. | 2003 Dec |
|
Interactions of olopatadine and selected antihistamines with model and natural membranes. | 2003 Dec |
|
Release of TNF-alpha during myocardial reperfusion depends on oxidative stress and is prevented by mast cell stabilizers. | 2003 Dec 1 |
|
In vitro inhibition of human conjunctival mast-cell degranulation by ketotifen. | 2003 Feb |
|
Alteration of CCK-induced satiety in post-Nippostrongylus brasiliensis-infected rats. | 2003 Feb |
|
Montelukast reduces peripheral blood eosinophilia but not tissue eosinophilia or symptoms in a patient with eosinophilic gastroenteritis and esophageal stricture. | 2003 Jan |
|
The effect of ketotifen on inflammatory markers in allergic conjunctivitis: an open, uncontrolled study. | 2003 Jan 6 |
|
Effects of second-generation histamine H1 receptor antagonists on the active avoidance response in rats. | 2003 Jan-Feb |
|
Use of anti-asthmatic medications in elderly Taiwanese patients. | 2003 Jun |
|
Resident cardiac mast cells and ischemia-reperfusion injury. | 2003 Jun |
|
Activation of mast cells induced by agonists of proteinase-activated receptors under normal conditions and during acute inflammation in rats. | 2003 Jun 20 |
|
A randomized comparison of chloroquine and chloroquine plus ketotifen in the treatment of acute, uncomplicated, Plasmodium falciparum malaria in children. | 2003 Mar |
|
The use of anti-asthmatic medications among pediatric patients in Taiwan. | 2003 Mar |
|
Disposition kinetics of ketotifen from liposomal dry powder for inhalation in rat lung. | 2003 Mar |
|
Ketotifen fumarate and olopatadine hydrochloride in the treatment of allergic conjunctivitis: a real-world comparison of efficacy and ocular comfort. | 2003 Mar-Apr |
|
[Treatment of chronic idiopathic urticaria unresponsive to type 1 antihistamines in monotherapy]. | 2003 May |
|
Effect of dehydroleucodine on histamine and serotonin release from mast cells in the isolated mouse jejunum. | 2003 May |
|
Efficacy of ketotifen fumarate 0.025% ophthalmic solution compared with placebo in the conjunctival allergen challenge model. | 2003 May |
|
Ketotifen reverses MDR1-mediated multidrug resistance in human breast cancer cells in vitro and alleviates cardiotoxicity induced by doxorubicin in vivo. | 2003 May |
|
Antiasthmatic property of polyherbal preparation E-721 B. | 2003 Nov |
|
Effect of ketotifen on the production of reactive oxygen species from human eosinophils primed by eotaxin. | 2003 Nov |
|
Epileptogenic activity induced by histamine H(1) antagonists in amygdala-kindled rats. | 2003 Nov 21 |
|
Efficacy and safety of ketotifen eye drops in the treatment of seasonal allergic conjunctivitis. | 2003 Oct |
|
Plasmodium falciparum gametocytaemia in Nigerian children: before, during and after treatment with antimalarial drugs. | 2003 Sep |
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).
Name | Type | Language | ||
---|---|---|---|---|
|
Official Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English |
Classification Tree | Code System | Code | ||
---|---|---|---|---|
|
NDF-RT |
N0000000190
Created by
admin on Fri Dec 15 15:25:22 GMT 2023 , Edited by admin on Fri Dec 15 15:25:22 GMT 2023
|
||
|
NCI_THESAURUS |
C29578
Created by
admin on Fri Dec 15 15:25:22 GMT 2023 , Edited by admin on Fri Dec 15 15:25:22 GMT 2023
|
||
|
WHO-VATC |
QR06AX17
Created by
admin on Fri Dec 15 15:25:22 GMT 2023 , Edited by admin on Fri Dec 15 15:25:22 GMT 2023
|
||
|
FDA ORPHAN DRUG |
464714
Created by
admin on Fri Dec 15 15:25:22 GMT 2023 , Edited by admin on Fri Dec 15 15:25:22 GMT 2023
|
||
|
NDF-RT |
N0000175519
Created by
admin on Fri Dec 15 15:25:22 GMT 2023 , Edited by admin on Fri Dec 15 15:25:22 GMT 2023
|
||
|
WHO-ATC |
S01GX08
Created by
admin on Fri Dec 15 15:25:22 GMT 2023 , Edited by admin on Fri Dec 15 15:25:22 GMT 2023
|
||
|
WHO-ATC |
R06AX17
Created by
admin on Fri Dec 15 15:25:22 GMT 2023 , Edited by admin on Fri Dec 15 15:25:22 GMT 2023
|
||
|
WHO-VATC |
QS01GX08
Created by
admin on Fri Dec 15 15:25:22 GMT 2023 , Edited by admin on Fri Dec 15 15:25:22 GMT 2023
|
Code System | Code | Type | Description | ||
---|---|---|---|---|---|
|
92511
Created by
admin on Fri Dec 15 15:25:22 GMT 2023 , Edited by admin on Fri Dec 15 15:25:22 GMT 2023
|
PRIMARY | |||
|
34580-13-7
Created by
admin on Fri Dec 15 15:25:22 GMT 2023 , Edited by admin on Fri Dec 15 15:25:22 GMT 2023
|
PRIMARY | |||
|
SUB08377MIG
Created by
admin on Fri Dec 15 15:25:22 GMT 2023 , Edited by admin on Fri Dec 15 15:25:22 GMT 2023
|
PRIMARY | |||
|
Ketotifen
Created by
admin on Fri Dec 15 15:25:22 GMT 2023 , Edited by admin on Fri Dec 15 15:25:22 GMT 2023
|
PRIMARY | |||
|
KETOTIFEN
Created by
admin on Fri Dec 15 15:25:22 GMT 2023 , Edited by admin on Fri Dec 15 15:25:22 GMT 2023
|
PRIMARY | |||
|
DB00920
Created by
admin on Fri Dec 15 15:25:22 GMT 2023 , Edited by admin on Fri Dec 15 15:25:22 GMT 2023
|
PRIMARY | |||
|
D007665
Created by
admin on Fri Dec 15 15:25:22 GMT 2023 , Edited by admin on Fri Dec 15 15:25:22 GMT 2023
|
PRIMARY | |||
|
3993
Created by
admin on Fri Dec 15 15:25:22 GMT 2023 , Edited by admin on Fri Dec 15 15:25:22 GMT 2023
|
PRIMARY | |||
|
X49220T18G
Created by
admin on Fri Dec 15 15:25:22 GMT 2023 , Edited by admin on Fri Dec 15 15:25:22 GMT 2023
|
PRIMARY | |||
|
X49220T18G
Created by
admin on Fri Dec 15 15:25:22 GMT 2023 , Edited by admin on Fri Dec 15 15:25:22 GMT 2023
|
PRIMARY | |||
|
3827
Created by
admin on Fri Dec 15 15:25:22 GMT 2023 , Edited by admin on Fri Dec 15 15:25:22 GMT 2023
|
PRIMARY | |||
|
7206
Created by
admin on Fri Dec 15 15:25:22 GMT 2023 , Edited by admin on Fri Dec 15 15:25:22 GMT 2023
|
PRIMARY | |||
|
C61799
Created by
admin on Fri Dec 15 15:25:22 GMT 2023 , Edited by admin on Fri Dec 15 15:25:22 GMT 2023
|
PRIMARY | |||
|
252-099-7
Created by
admin on Fri Dec 15 15:25:22 GMT 2023 , Edited by admin on Fri Dec 15 15:25:22 GMT 2023
|
PRIMARY | |||
|
7283
Created by
admin on Fri Dec 15 15:25:22 GMT 2023 , Edited by admin on Fri Dec 15 15:25:22 GMT 2023
|
PRIMARY | |||
|
CHEMBL534
Created by
admin on Fri Dec 15 15:25:22 GMT 2023 , Edited by admin on Fri Dec 15 15:25:22 GMT 2023
|
PRIMARY | |||
|
m6624
Created by
admin on Fri Dec 15 15:25:22 GMT 2023 , Edited by admin on Fri Dec 15 15:25:22 GMT 2023
|
PRIMARY | Merck Index | ||
|
1530
Created by
admin on Fri Dec 15 15:25:22 GMT 2023 , Edited by admin on Fri Dec 15 15:25:22 GMT 2023
|
PRIMARY | |||
|
100000092111
Created by
admin on Fri Dec 15 15:25:22 GMT 2023 , Edited by admin on Fri Dec 15 15:25:22 GMT 2023
|
PRIMARY | |||
|
6146
Created by
admin on Fri Dec 15 15:25:22 GMT 2023 , Edited by admin on Fri Dec 15 15:25:22 GMT 2023
|
PRIMARY | RxNorm |
ACTIVE MOIETY
SALT/SOLVATE (PARENT)