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IdentificationPharmacologyInteractionsReferencesTrialsEconomicsPropertiesSpectraTaxonomyKetotifen
Identification
- Name
- Ketotifen
- Accession Number
- DB00920 (APRD01061)
- Type
- Small Molecule
- Groups
- Approved
- Description
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.
- Structure
Structure for Ketotifen (DB00920)
- Synonyms
- Ketotifen
- Ketotifene
- Ketotifeno
- Ketotifenum
- Product Ingredients
Ingredient UNII CAS InChI Key Ketotifen fumarate HBD503WORO 34580-14-8 YNQQEYBLVYAWNX-WLHGVMLRSA-N - Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Unlock Additional DataKetotifen Ophthalmic Solution Solution Ophthalmic Sterimax Inc 2013-03-07 Not applicable Canada 
Zaditen Syrup Oral TEVA Canada Limited 1990-12-31 Not applicable Canada Zaditen Tablet Oral TEVA Canada Limited 1990-12-31 Not applicable Canada Zaditen - Dps 1mg/ml Solution / drops Oral Novartis Not applicable Not applicable Canada Zaditor Solution 0.25 mg Ophthalmic Novartis 2006-08-03 2012-01-17 Canada Zaditor Solution 0.25 mg Ophthalmic Laboratoires Thea 2000-08-01 Not applicable Canada Zaditor Solution 0.345 mg/1mL Ophthalmic Novartis Ophthalmics 1999-07-02 2008-10-31 US 
Zaditor Solution 0.345 mg/1mL Ophthalmic Physicians Total Care, Inc. 2002-11-04 2010-12-29 US Additional Data Available- Application NumberApplication Number
A unique ID assigned by the FDA when a product is submitted for approval by the labeller.
Learn more - Product CodeProduct Code
A governmentally-recognized ID which uniquely identifies the product within its regulatory market.
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- Generic Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Unlock Additional DataApo-ketotifen - Syr 1mg/5ml Syrup Oral Apotex Corporation 1996-11-07 2019-01-16 Canada Jamp-ketotifen Solution Ophthalmic Jamp Pharma Corporation Not applicable Not applicable Canada Novo-ketotifen - Syr 1mg/5ml Syrup Oral Novopharm Limited 1995-12-31 2015-10-26 Canada Novo-ketotifen Tab 1mg Tablet Oral Novopharm Limited 1997-07-29 2013-02-11 Canada Nu-ketotifen Syrup - 1mg/5ml Syrup Oral Nu Pharm Inc 1996-12-09 2012-09-04 Canada PMS-ketotifen Tablet Oral Pharmascience Inc 1998-08-31 2013-02-07 Canada PMS-ketotifen Syrup Oral Pharmascience Inc 1998-08-31 2013-02-07 Canada Additional Data Available- Application NumberApplication Number
A unique ID assigned by the FDA when a product is submitted for approval by the labeller.
Learn more - Product CodeProduct Code
A governmentally-recognized ID which uniquely identifies the product within its regulatory market.
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- Over the Counter Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Unlock Additional DataAlaway Solution / drops 0.25 mg/1mL Ophthalmic Bausch & Lomb Incorporated 2006-12-01 Not applicable US Allergy Eye Solution / drops 0.25 mg/1mL Ophthalmic H.E.B. 2010-09-15 2015-05-01 US Allergy Eye Solution / drops 0.25 mg/1mL Ophthalmic CVS Health 2011-01-07 2014-07-01 US Allergy Eye Drops Solution / drops 0.35 mg/1mL Ophthalmic H E B 2014-02-25 Not applicable US Allergy Eye Drops Solution / drops 0.35 mg/1mL Ophthalmic Advanced Vision Research (Subsidiary of Akorn, Inc.) 2013-11-14 Not applicable US Allergy Eye Drops Solution / drops 0.35 mg/1mL Ophthalmic Cardinal Health 2014-01-13 Not applicable US Allergy Eye Original Prescription Strength Solution / drops 0.25 mg/1mL Ophthalmic Meijer Distribution 1995-12-12 2015-01-01 US Allergy Relief Eye Solution / drops 0.25 mg/1mL Ophthalmic Western Family Foods 2011-05-25 2015-06-01 US Allergy Relief Eye Drops Solution / drops 0.35 mg/1mL Ophthalmic Kinray 2014-03-18 Not applicable US Antihistamine Eye Solution 0.25 mg/1mL Ophthalmic CVS Health 2010-10-19 2015-06-01 US Additional Data Available- Application NumberApplication Number
A unique ID assigned by the FDA when a product is submitted for approval by the labeller.
Learn more - Product CodeProduct Code
A governmentally-recognized ID which uniquely identifies the product within its regulatory market.
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- Mixture Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Alaway Ketotifen fumarate (0.25 mg/1mL) + Ketotifen fumarate (0.25 mg/1mL) Ophthalmic Bausch & Lomb Incorporated 2006-12-01 Not applicable US Alaway Ketotifen fumarate (0.25 mg/1mL) + Ketotifen fumarate (0.25 mg/1mL) Ophthalmic Bausch & Lomb Incorporated 2006-12-01 Not applicable US - Unapproved/Other Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Zaditor Ketotifen fumarate (0.345 mg/1mL) Solution Ophthalmic Physicians Total Care, Inc. 2002-11-04 2010-12-29 US - International/Other Brands
- Totifen (Patron) / Zasten (Novartis)
- Categories
- Anti-Allergic Agents
- Antihistamine Drugs
- Antihistamines for Systemic Use
- Antipruritics
- Decongestants and Antiallergics
- Dermatologicals
- Histamine Agents
- Histamine Antagonists
- Histamine H1 Antagonists
- Histamine H1 Inhibitors
- Neurotransmitter Agents
- Ophthalmologicals
- Other Antihistamines
- Piperidines
- Potential QTc-Prolonging Agents
- QTc Prolonging Agents
- Sensory Organs
- Sulfur Compounds
- Thiophenes
- UNII
- X49220T18G
- CAS number
- 34580-13-7
- Weight
- Average: 309.425
Monoisotopic: 309.118734925 - Chemical Formula
- C19H19NOS
- InChI Key
- ZCVMWBYGMWKGHF-UHFFFAOYSA-N
- InChI
- 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
- IUPAC Name
- 2-(1-methylpiperidin-4-ylidene)-6-thiatricyclo[8.4.0.0³,⁷]tetradeca-1(14),3(7),4,10,12-pentaen-8-one
- SMILES
- CN1CCC(CC1)=C1C2=C(SC=C2)C(=O)CC2=CC=CC=C12
Pharmacology
- Indication
Indicated as an add-on or prophylactic oral medication in the chronic treatment of mild atopic asthmatic children. Also used as self-medication for the temporary relief of itching of the eye due to allergic conjunctivitis (ophthalmic).
- Associated Conditions
- Pharmacodynamics
Ketotifen is a fast acting non-competitive histamine antagonist. It inhibits the release of mediators from mast cells. It is a non-bronchodilator antiasthmatic drug (when taken orally).
- Mechanism of action
Ketotifen is a relatively selective, non-competitive histamine antagonist (H1-receptor) and mast cell stabilizer. 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. 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 inhibits of the release of allergic mediators such as histamine, leukotrienes C4 and D4(SRS-A) and PAF.
Target Actions Organism AHistamine H1 receptor antagonistHumans U6-phosphogluconate dehydrogenase, decarboxylating inhibitorHumans - Absorption
Following oral administration absorption is at least 60%
- Volume of distribution
- Not Available
- Protein binding
75%
- Metabolism
Primarily hepatic. The main metabolite found in both plasma and urine is the inactive ketotifen-N-glucuronide. Nor-ketotifen, the N-demethylated metabolite, and the 10-alpha-hydroxyl derivative are the only other metabolites detectable in human urine.
- Route of elimination
- Not Available
- Half life
21 hours (for elimination)
- Clearance
- Not Available
- Toxicity
Adverse reactions include headaches, conjunctival injection and rhinitis.
- Affected organisms
- Humans and other mammals
- Pathways
Pathway Category Ketotifen H1-Antihistamine Action Drug action - Pharmacogenomic Effects/ADRs
- Not Available
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Additional Data Available
Adverse Effects
Comprehensive structured data on known drug adverse effects with statistical prevalence. MedDRA and ICD10 ids are provided for adverse effect conditions and symptoms.
Learn more Additional Data Available
Contraindications
Structured data covering drug contraindications. Each contraindication describes a scenario in which the drug is not to be used. Includes restrictions on co-administration, contraindicated populations, and more.
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Blackbox Warnings
Structured data representing warnings from the black box section of drug labels. These warnings cover important and dangerous risks, contraindications, or adverse effects.
Learn moreInteractions
- Drug Interactions
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Drug Interaction Unlock Additional Data2,5-Dimethoxy-4-ethylamphetamine 2,5-Dimethoxy-4-ethylamphetamine may decrease the sedative and stimulatory activities of Ketotifen. 2,5-Dimethoxy-4-ethylthioamphetamine 2,5-Dimethoxy-4-ethylthioamphetamine may decrease the sedative and stimulatory activities of Ketotifen. 4-Bromo-2,5-dimethoxyamphetamine 4-Bromo-2,5-dimethoxyamphetamine may decrease the sedative and stimulatory activities of Ketotifen. Abexinostat The risk or severity of QTc prolongation can be increased when Ketotifen is combined with Abexinostat. Acebutolol The risk or severity of QTc prolongation can be increased when Ketotifen is combined with Acebutolol. Aceprometazine The risk or severity of QTc prolongation can be increased when Ketotifen is combined with Aceprometazine. Acetyldigoxin The risk or severity of QTc prolongation can be increased when Ketotifen is combined with Acetyldigoxin. Acrivastine The risk or severity of QTc prolongation can be increased when Ketotifen is combined with Acrivastine. Adenosine The risk or severity of QTc prolongation can be increased when Ketotifen is combined with Adenosine. Ajmaline The risk or severity of QTc prolongation can be increased when Ketotifen is combined with Ajmaline. Additional Data Available- Extended DescriptionExtended Description
Extended description of the mechanism of action and particular properties of each drug interaction.
Learn more - Severity
- Evidence Level
- ActionAction
An effect category for each drug interaction. Know how this interaction affects the subject drug.
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- Food Interactions
- Take with or without food. The absorption is unaffected by food.
References
- Synthesis Reference
Roy W. Bryant, Ravi Parihar, Thomas Rowe, Susan Caballa, "Methods of Making and Using Stable Pharmaceutical Compositions Comprising Ketotifen and Naphazoline." U.S. Patent US20110312998, issued December 22, 2011.
US20110312998- General References
- Not Available
- External Links
- Human Metabolome Database
- HMDB0015056
- KEGG Drug
- D01332
- PubChem Compound
- 3827
- PubChem Substance
- 46508921
- ChemSpider
- 3695
- BindingDB
- 94597
- RxNav
- 6146
- ChEBI
- 92511
- ChEMBL
- CHEMBL534
- ZINC
- ZINC000000004351
- Therapeutic Targets Database
- DAP000329
- PharmGKB
- PA450152
- RxList
- RxList Drug Page
- Drugs.com
- Drugs.com Drug Page
- PDRhealth
- PDRhealth Drug Page
- Wikipedia
- Ketotifen
- ATC Codes
- S01GX08 — Ketotifen
- S01GX — Other antiallergics
- S01G — DECONGESTANTS AND ANTIALLERGICS
- S01 — OPHTHALMOLOGICALS
- S — SENSORY ORGANS
- AHFS Codes
- 52:02.00 — Antiallergic Agents
- 04:00.00 — Antihistamine Drugs
- 04:92.00 — Other Antihistamines
- FDA label
- Download (9.05 KB)
Clinical Trials
- Clinical Trials
Phase Status Purpose Conditions Count 1 Completed Not Available Conjunctivitis, Seasonal Allergic 1 2 Completed Treatment Conjunctivitis, Seasonal Allergic 1 2 Unknown Status Treatment Peanut Allergies in Children 1 2 Withdrawn Not Available Conjunctivitis, Seasonal Allergic 1 3 Active Not Recruiting Prevention Joint Contractures 1 3 Completed Not Available Conjunctivitis, Seasonal Allergic 1 3 Completed Basic Science Fibromyalgia 1 3 Completed Treatment Atopic Dermatitis (AD) / Dermatitis atopic 1 3 Completed Treatment Atopics / Skin Inflammation 1 3 Completed Treatment Conjunctivitis, Seasonal Allergic 5 3 Completed Treatment Rhinitis, Allergic, Perennial 2 3 Completed Treatment Vernal Keratoconjunctivitis 1 3 Completed Treatment Widespread Chronic Pain 1 3 Recruiting Prevention Elbow Dislocation / Elbow Fractures / Elbow Injury 1 3 Recruiting Treatment Functional Dyspepsia 1 4 Completed Treatment Asthma 1 4 Completed Treatment Conjunctivitis, Seasonal Allergic 1 4 Recruiting Treatment Dengue Fever / Pleural Effusions 1
Pharmacoeconomics
- Manufacturers
- Bausch and lomb inc
- Akorn inc
- Alcon inc
- Apotex inc etobicoke site
- Novartis pharmaceuticals corp
- Packagers
- Akorn Inc.
- Allergan Inc.
- Apotex Inc.
- Bausch & Lomb Inc.
- Ciba Vision Canada Inc.
- Novartis AG
- Physicians Total Care Inc.
- Spectrum Pharmaceuticals
- Dosage forms
Form Route Strength Solution / drops Ophthalmic 0.35 mg/1mL Solution Ophthalmic 0.25 g/1mL Solution Ophthalmic 0.25 mg/1mL Solution Ophthalmic 0.35 mg/1mL Solution Ophthalmic Solution / drops Ophthalmic 0.345 mg/1mL Solution Ophthalmic .25 mg/1mL Syrup Oral Tablet Oral Solution / drops Oral Solution Ophthalmic .35 mg/1mL Solution Ophthalmic 0.25 mg Solution Ophthalmic 0.345 mg/1mL Solution / drops Ophthalmic 0.25 mg/1mL - Prices
Unit description Cost Unit Ketotifen fumarate powder 926.63USD g Zaditor 0.025% Solution 5ml Bottle 74.96USD bottle Ketotifen fum 0.025% eye drops 2.44USD ml Refresh 0.025% eye drops 2.2USD ml Zaditor 0.025% eye drops 2.15USD ml Alaway 0.025% eye drops 0.96USD ml Zaditen 1 mg Tablet 0.83USD tablet Novo-Ketotifen 1 mg Tablet 0.66USD tablet Novo-Ketotifen 0.2 mg/ml Syrup 0.14USD ml DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 152-153 U.S. Patents 3,682,930; 3,770,728; and 3,960,894 logP 2.2 Not Available pKa 8.43 Not Available - Predicted Properties
Property Value Source Water Solubility 0.00787 mg/mL ALOGPS logP 3.49 ALOGPS logP 3.35 ChemAxon logS -4.6 ALOGPS pKa (Strongest Acidic) 12.3 ChemAxon pKa (Strongest Basic) 7.15 ChemAxon Physiological Charge 1 ChemAxon Hydrogen Acceptor Count 2 ChemAxon Hydrogen Donor Count 0 ChemAxon Polar Surface Area 20.31 Å2 ChemAxon Rotatable Bond Count 0 ChemAxon Refractivity 101.73 m3·mol-1 ChemAxon Polarizability 34.61 Å3 ChemAxon Number of Rings 4 ChemAxon Bioavailability 1 ChemAxon Rule of Five Yes ChemAxon Ghose Filter Yes ChemAxon Veber's Rule Yes ChemAxon MDDR-like Rule No ChemAxon - Predicted ADMET features
Property Value Probability Human Intestinal Absorption + 1.0 Blood Brain Barrier + 0.9923 Caco-2 permeable + 0.8867 P-glycoprotein substrate Substrate 0.87 P-glycoprotein inhibitor I Inhibitor 0.8564 P-glycoprotein inhibitor II Non-inhibitor 0.7474 Renal organic cation transporter Inhibitor 0.8198 CYP450 2C9 substrate Non-substrate 0.7542 CYP450 2D6 substrate Non-substrate 0.5638 CYP450 3A4 substrate Substrate 0.6984 CYP450 1A2 substrate Non-inhibitor 0.9045 CYP450 2C9 inhibitor Non-inhibitor 0.9071 CYP450 2D6 inhibitor Inhibitor 0.8931 CYP450 2C19 inhibitor Non-inhibitor 0.9026 CYP450 3A4 inhibitor Non-inhibitor 0.8607 CYP450 inhibitory promiscuity High CYP Inhibitory Promiscuity 0.6414 Ames test Non AMES toxic 0.7576 Carcinogenicity Non-carcinogens 0.9649 Biodegradation Not ready biodegradable 0.9547 Rat acute toxicity 2.7979 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.6336 hERG inhibition (predictor II) Non-inhibitor 0.5145
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted GC-MS Spectrum - GC-MS Predicted GC-MS Not Available Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS Not Available
Taxonomy
- Description
- This compound belongs to the class of organic compounds known as cycloheptathiophenes. These are polycyclic compounds containing a thiophene ring fused to a 7 member carbocyclic moiety. Thiophene is 5-membered ring consisting of four carbon atoms and one sulfur atom.
- Kingdom
- Organic compounds
- Super Class
- Organoheterocyclic compounds
- Class
- Cycloheptathiophenes
- Sub Class
- Not Available
- Direct Parent
- Cycloheptathiophenes
- Alternative Parents
- Aryl alkyl ketones / Piperidines / Benzenoids / Thiophenes / Heteroaromatic compounds / Trialkylamines / Azacyclic compounds / Organopnictogen compounds / Organic oxides / Hydrocarbon derivatives
- Substituents
- Cycloheptathiophene / Aryl alkyl ketone / Aryl ketone / Piperidine / Benzenoid / Thiophene / Heteroaromatic compound / Ketone / Tertiary amine / Tertiary aliphatic amine
- Molecular Framework
- Aromatic heteropolycyclic compounds
- External Descriptors
- Not Available
Targets
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Antagonist
- General Function
- Histamine receptor activity
- Specific Function
- In peripheral tissues, the H1 subclass of histamine receptors mediates the contraction of smooth muscles, increase in capillary permeability due to contraction of terminal venules, and catecholamin...
- Gene Name
- HRH1
- Uniprot ID
- P35367
- Uniprot Name
- Histamine H1 receptor
- Molecular Weight
- 55783.61 Da
References
- Mita H, Shida T: Comparison of anti-allergic activities of the histamine H1 receptor antagonists epinastine, ketotifen and oxatomide in human leukocytes. Arzneimittelforschung. 1995 Jan;45(1):36-40. [PubMed:7893266]
- Okabe S, Nakaji S, Tachibana M: Effect of ketotifen on acute gastric lesions and gastric secretion in rats. Jpn J Pharmacol. 1992 Jun;59(2):251-4. [PubMed:1434122]
- Hashimoto T, Ohata H, Honda K: Lysophosphatidic acid (LPA) induces plasma exudation and histamine release in mice via LPA receptors. J Pharmacol Sci. 2006 Jan;100(1):82-7. Epub 2006 Jan 11. [PubMed:16404130]
- Ito K, Sakamoto T, Hayashi Y, Morishita M, Shibata E, Sakai K, Takeuchi Y, Torii S: Role of tachykinin and bradykinin receptors and mast cells in gaseous formaldehyde-induced airway microvascular leakage in rats. Eur J Pharmacol. 1996 Jul 4;307(3):291-8. [PubMed:8836617]
- Yokoyama H, Iinuma K, Yanai K, Watanabe T, Sakurai E, Onodera K: Proconvulsant effect of ketotifen, a histamine H1 antagonist, confirmed by the use of d-chlorpheniramine with monitoring electroencephalography. Methods Find Exp Clin Pharmacol. 1993 Apr;15(3):183-8. [PubMed:8101246]
- Werner-Klein M, Goggel R, Westhof A, Erb KJ: Development and characterisation of a novel and rapid lung eosinophil influx model in the rat. Pulm Pharmacol Ther. 2008 Aug;21(4):648-56. doi: 10.1016/j.pupt.2008.03.002. Epub 2008 Apr 7. [PubMed:18490184]
- Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- Phosphogluconate dehydrogenase (decarboxylating) activity
- Specific Function
- Catalyzes the oxidative decarboxylation of 6-phosphogluconate to ribulose 5-phosphate and CO(2), with concomitant reduction of NADP to NADPH.
- Gene Name
- PGD
- Uniprot ID
- P52209
- Uniprot Name
- 6-phosphogluconate dehydrogenase, decarboxylating
- Molecular Weight
- 53139.56 Da
References
- Akkemik E, Budak H, Ciftci M: Effects of some drugs on human erythrocyte 6-phosphogluconate dehydrogenase: an in vitro study. J Enzyme Inhib Med Chem. 2010 Aug;25(4):476-9. doi: 10.3109/14756360903257900. [PubMed:20235752]
- Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [PubMed:10592235]
Drug created on June 13, 2005 07:24 / Updated on April 02, 2020 01:52
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