KETOTIFEN FUMARATE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C19H19NOS.C4H4O4
Molecular Weight	425.497
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	1
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

OC(=O)\C=C\C(O)=O.CN1CCC(CC1)=C2C3=C(SC=C3)C(=O)CC4=CC=CC=C24

InChI

InChIKey=YNQQEYBLVYAWNX-WLHGVMLRSA-N

InChI=1S/C19H19NOS.C4H4O4/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;5-3(6)1-2-4(7)8/h2-5,8,11H,6-7,9-10,12H2,1H3;1-2H,(H,5,6)(H,7,8)/b;2-1+

HIDE SMILES / InChI

Molecular Formula	C4H4O4
Molecular Weight	116.0722
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	1
Optical Activity	NONE

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

Description
Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2015/021996Orig1s008lbl.pdf
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

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Phosphodiesterase 7 2 Target ID: CHEMBL2111411 Sources: https://www.ncbi.nlm.nih.gov/pubmed/1702263	Inhibitor 8504
Histamine H1 receptor 316 Target ID: CHEMBL231 Sources: https://www.ncbi.nlm.nih.gov/pubmed/8101246	Antagonist 2849

Conditions

Condition	Modality	Targets	Highest Phase	Product
Allergic conjunctivitis 101 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2015/021996Orig1s008lbl.pdf	Palliative		Approved 8583	ALAWAY Approved Use Uses Temporarily relieves itchy eyes due to pollen, ragweed, grass, animal hair and dander. Launch Date 2006

C_max

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

T_1/2

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

F_unbound

Value	Dose	Co-administered	Analyte	Population
25% DRUG LABEL https://www.drugs.com/mmx/ketotifen-fumarate.html			KETOTIFEN plasma	Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN

Doses

Dose	Population	Adverse events
120 mg single, oral Overdose Dose: 120 mg Route: oral Route: single Dose: 120 mg Sources: https://pubmed.ncbi.nlm.nih.gov/6113023	unhealthy, 21 years Health Status: unhealthy Age Group: 21 years Sex: F Sources: https://pubmed.ncbi.nlm.nih.gov/6113023	Other AEs: Abdominal pain, Headache... Other AEs: Abdominal pain (mild, 1 patient) Headache (1 patient) Sources: https://pubmed.ncbi.nlm.nih.gov/6113023
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: https://pubmed.ncbi.nlm.nih.gov/23279031	unhealthy, 4 months Health Status: unhealthy Age Group: 4 months Sex: M Sources: https://pubmed.ncbi.nlm.nih.gov/23279031	Disc. AE: Irritability, Drowsiness... AEs leading to discontinuation/dose reduction: Irritability (1 patient) Drowsiness (1 patient) Encephalopathy toxic (1 patient) Sources: https://pubmed.ncbi.nlm.nih.gov/23279031
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: https://pubmed.ncbi.nlm.nih.gov/32064627	unhealthy, 69 years Health Status: unhealthy Age Group: 69 years Sex: F Sources: https://pubmed.ncbi.nlm.nih.gov/32064627	Disc. AE: Allergic contact dermatitis... AEs leading to discontinuation/dose reduction: Allergic contact dermatitis (1 patient) Sources: https://pubmed.ncbi.nlm.nih.gov/32064627
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: https://pubmed.ncbi.nlm.nih.gov/25031584	unhealthy, adult Health Status: unhealthy Age Group: adult Sources: https://pubmed.ncbi.nlm.nih.gov/25031584	Sources: https://pubmed.ncbi.nlm.nih.gov/25031584

AEs

AE	Significance	Dose	Population
Headache	1 patient	120 mg single, oral Overdose Dose: 120 mg Route: oral Route: single Dose: 120 mg Sources: https://pubmed.ncbi.nlm.nih.gov/6113023	unhealthy, 21 years Health Status: unhealthy Age Group: 21 years Sex: F Sources: https://pubmed.ncbi.nlm.nih.gov/6113023
Abdominal pain	mild, 1 patient	120 mg single, oral Overdose Dose: 120 mg Route: oral Route: single Dose: 120 mg Sources: https://pubmed.ncbi.nlm.nih.gov/6113023	unhealthy, 21 years Health Status: unhealthy Age Group: 21 years Sex: F Sources: https://pubmed.ncbi.nlm.nih.gov/6113023
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: https://pubmed.ncbi.nlm.nih.gov/23279031	unhealthy, 4 months Health Status: unhealthy Age Group: 4 months Sex: M Sources: https://pubmed.ncbi.nlm.nih.gov/23279031
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: https://pubmed.ncbi.nlm.nih.gov/23279031	unhealthy, 4 months Health Status: unhealthy Age Group: 4 months Sex: M Sources: https://pubmed.ncbi.nlm.nih.gov/23279031
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: https://pubmed.ncbi.nlm.nih.gov/23279031	unhealthy, 4 months Health Status: unhealthy Age Group: 4 months Sex: M Sources: https://pubmed.ncbi.nlm.nih.gov/23279031
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: https://pubmed.ncbi.nlm.nih.gov/32064627	unhealthy, 69 years Health Status: unhealthy Age Group: 69 years Sex: F Sources: https://pubmed.ncbi.nlm.nih.gov/32064627

Sourcing

Vendor/Aggregator	ID	URL
ChEBI	CHEBI:92511	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:92511
ChemicalBook	CB9249738	https://www.chemicalbook.com/ChemicalProductProperty_EN_CB9249738
eMolecules	626322	https://www.emolecules.com/cgi-bin/more?vid=626322
MolPort	MolPort-001-933-278	https://www.molport.com/shop/molecule-link/MolPort-001-933-278
ZINC	ZINC000000004351	http://zinc15.docking.org/substances/ZINC000000004351

PubMed

Title	Date	PubMed
Release of TNF-alpha during myocardial reperfusion depends on oxidative stress and is prevented by mast cell stabilizers.	2003-12-01	14659806
Effects of nonsteroidal anti-inflammatory drugs on experimental allergic conjunctivitis in Guinea pigs.	2003-12	14733714
Interactions of olopatadine and selected antihistamines with model and natural membranes.	2003-12	14704897
Efficacy and safety of ketotifen fumarate 0.025% in the conjunctival antigen challenge model of ocular allergic conjunctivitis.	2003-12	14644221
Epileptogenic activity induced by histamine H(1) antagonists in amygdala-kindled rats.	2003-11-21	14575901
Ebastine inhibits T cell migration, production of Th2-type cytokines and proinflammatory cytokines.	2003-11	14616867
Antiasthmatic property of polyherbal preparation E-721 B.	2003-11	14595594
Effect of ketotifen on the production of reactive oxygen species from human eosinophils primed by eotaxin.	2003-11	14512700
Coincidental increase of leukotriene B4 between cerebral cortex and lung tissue of sensitized rats.	2003-10	14531949
Enhanced skin permeation of cationic drug ketotifen through excised guinea pig dorsal skin by surfactants with different electric charges.	2003-10	14519926
Efficacy and safety of ketotifen eye drops in the treatment of seasonal allergic conjunctivitis.	2003-10	14507747
Involvement of central mu-opioid system in the scratching behavior in mice, and the suppression of it by the activation of kappa-opioid system.	2003-09-05	14512095
Plasmodium falciparum gametocytaemia in Nigerian children: before, during and after treatment with antimalarial drugs.	2003-09	12950664
Effects of TAK-427 on acute nasal symptoms and nasal obstruction in guinea pig model of experimental allergic rhinitis.	2003-08-29	12969771
Role of mast cells in gastrointestinal mucosal defense.	2003-08	14510234
The role of platelet activating factor and the efficacy of apafant ophthalmic solution in experimental allergic conjunctivitis.	2003-08	12964956
[Effectiveness and impact in the quality of life of ketotifen ophthalmic solution. Results of zeta study in patients with seasonal allergic conjunctivitis].	2003-08	12955623
Role of mast cells and pro-inflammatory mediators on the intestinal secretion induced by cholera toxin.	2003-08	12906889
Evaluation of the efficacy of antihistamines using human monocyte-derived dendritic cells stimulated with histamine.	2003-08	12894071
Ketotifen fumarate and olopatadine hydrochloride in the treatment of allergic conjunctivitis: a real-world comparison of efficacy and ocular comfort.	2003-07-03	12836808
A placebo-controlled comparison of ketotifen fumarate and nedocromil sodium ophthalmic solutions for the prevention of ocular itching with the conjunctival allergen challenge model.	2003-07	12946546
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.	2003-07	12946545
Analysis of the spontaneous scratching behavior by NC/Nga mice: a possible approach to evaluate antipruritics for subjects with atopic dermatitis.	2003-06-27	12826242
Activation of mast cells induced by agonists of proteinase-activated receptors under normal conditions and during acute inflammation in rats.	2003-06-20	12818702
Forsythia fructus inhibits the mast-cell-mediated allergic inflammatory reactions.	2003-06	12875366
Use of anti-asthmatic medications in elderly Taiwanese patients.	2003-06	12873039
Resident cardiac mast cells and ischemia-reperfusion injury.	2003-06	12808487
In vitro uptake and release studies of ocular pharmaceutical agents by silicon-containing and p-HEMA hydrogel contact lens materials.	2003-05-12	12711169
[Treatment of chronic idiopathic urticaria unresponsive to type 1 antihistamines in monotherapy].	2003-05	12843818
Effect of dehydroleucodine on histamine and serotonin release from mast cells in the isolated mouse jejunum.	2003-05	12813624
Inhibitory effects of ketotifen on eotaxin-dependent activation of eosinophils: consequences for allergic eye diseases.	2003-05	12752326
Efficacy of ketotifen fumarate 0.025% ophthalmic solution compared with placebo in the conjunctival allergen challenge model.	2003-05	12742839
Ketotifen reverses MDR1-mediated multidrug resistance in human breast cancer cells in vitro and alleviates cardiotoxicity induced by doxorubicin in vivo.	2003-05	12687290
[In vitro effects of antiallergic eyedrops on complement activation induced by particulate matter].	2003-04	12843888
Effects of ketotifen 0.025% and lodoxamide 0.1% on eosinophil infiltration into the guinea pig conjunctiva in a model of allergic conjunctivitis.	2003-04	12804060
A randomized comparison of chloroquine and chloroquine plus ketotifen in the treatment of acute, uncomplicated, Plasmodium falciparum malaria in children.	2003-03	12803865
The anti-allergic effects of a cromolyn sodium-chlorpheniramine combination compared to ketotifen in the conjunctival allergen challenge model.	2003-03	12696630
The use of anti-asthmatic medications among pediatric patients in Taiwan.	2003-03	12642976
Disposition kinetics of ketotifen from liposomal dry powder for inhalation in rat lung.	2003-03	12603343
[Correction with zaditen of impaired activity of pancreatic digestive enzymes in sensitization and anaphylactic shock].	2003-02-25	12596514
In vitro inhibition of human conjunctival mast-cell degranulation by ketotifen.	2003-02	12648306
Alteration of CCK-induced satiety in post-Nippostrongylus brasiliensis-infected rats.	2003-02	12615048
Effects of second-generation histamine H1 receptor antagonists on the active avoidance response in rats.	2003-01-25	12542455
The effect of ketotifen on inflammatory markers in allergic conjunctivitis: an open, uncontrolled study.	2003-01-06	12515585
Montelukast reduces peripheral blood eosinophilia but not tissue eosinophilia or symptoms in a patient with eosinophilic gastroenteritis and esophageal stricture.	2003-01	12546333
Determination of ketotifen and its conjugated metabolite in human plasma by liquid chromatography/tandem mass spectrometry: application to a pharmacokinetic study.	2003	14608613
High-frequency oscillation in the hippocampus of the behaving rat and its modulation by the histaminergic system.	2003	12699334
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.	2002-11	12501875
Epinastine inhibits eosinophil chemotaxis and adhesion molecules in atopic dermatitis.	2001-03-19	14528065
Adsorption of allopurinol and ketotifen by chitosan.	2001-01-18	14727888

Patents

Sample Use Guides

In Vivo Use Guide

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

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 `Mon Mar 31 17:51:24 GMT 2025` Edited by `admin` on `Mon Mar 31 17:51:24 GMT 2025`
Record UNII	HBD503WORO
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

ZADITEN

Preferred Name

English

KETOTIFEN FUMARATE

Official Name

English

HC-20511 FUMARATE

Code

English

Ketotifen fumarate [WHO-DD]

Common Name

English

KETOTIFEN FUMARATE [JAN]

Common Name

English

4,9-Dihydro-4-(1-methyl-4-piperidylidene)-10H-benzo[4,5]cyclohepta[1,2-b]thiophen-10-one fumarate (1:1)

Systematic Name

English

ZADITOR

Brand Name

English

HC 20,511 FUMARATE

Code

English

KETOTIFEN FUMARATE [ORANGE BOOK]

Common Name

English

NSC-757415

Code

English

KETOTIFEN FUMARATE [MART.]

Common Name

English

KETOTIFEN FUMARATE [USAN]

Common Name

English

ALAWAY

Brand Name

English

KETOTIFEN FUMARATE [VANDF]

Common Name

English

KETOTIFEN HYDROGEN FUMARATE

Common Name

English

KETOTIFEN FUMARATE [MI]

Common Name

English

KETOTIFEN (AS FUMARATE)

Common Name

English

10H-BENZO(4,5)CYCLOHEPTA(1,2-B)THIOPHEN-10-ONE, 4,9-DIHYDRO-4-(1-METHYL-4-PIPERIDINYLIDENE)-, (E)-2-BUTENEDIOATE (1:1)

Systematic Name

English

KETOTIFEN HYDROGEN FUMARATE [EP MONOGRAPH]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C29578