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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 of KETOTIFEN FUMARATE

SMILES

OC(=O)\C=C\C(O)=O.CN1CCC(CC1)=C2C3=C(SC=C3)C(=O)CC4=C2C=CC=C4

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
MOL RATIO 1 MOL RATIO (average)
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
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description

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 TargetPharmacologyConditionPotency

Conditions

ConditionModalityTargetsHighest PhaseProduct
Palliative
ALAWAY

Cmax

ValueDoseCo-administeredAnalytePopulation
281 pg/mL
2 mg single, oral
KETOTIFEN plasma
Homo sapiens

AUC

ValueDoseCo-administeredAnalytePopulation
4703 pg × h/mL
2 mg single, oral
KETOTIFEN plasma
Homo sapiens

T1/2

ValueDoseCo-administeredAnalytePopulation
13.1 h
2 mg single, oral
KETOTIFEN plasma
Homo sapiens

Funbound

ValueDoseCo-administeredAnalytePopulation
25%
KETOTIFEN plasma
Homo sapiens

Doses

AEs

PubMed

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
Record UNII
HBD503WORO
Record Status Validated (UNII)
Record Version