Ketotifen - DrugBank

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ID Pharmacology Interactions References Trials Economics Properties Spectra Taxonomy Targets (2)Comments

Targets (2)Biointeractions (2)

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

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

Synonyms

Ketotifene

Ketotifeno

Ketotifenum

External IDs

Not Available

Product Ingredients

Ingredient	UNII	CAS	InChI Key	Details
Ketotifen fumarate	HBD503WORO	34580-14-8	YNQQEYBLVYAWNX-WLHGVMLRSA-N	Details

Approved Prescription Products

Name	Dosage	Strength	Route	Labeller	Marketing Start	Marketing End
Ketotifen Ophthalmic Solution	Solution	0.25 mg	Ophthalmic	Sterimax Inc	2013-03-07	Not applicable	Canada
Novo-ketotifen - Syr 1mg/5ml	Syrup	1 mg	Oral	Novopharm Limited	1995-12-31	2015-10-26	Canada
Novo-ketotifen Tab 1mg	Tablet	1 mg	Oral	Novopharm Limited	1997-07-29	2013-02-11	Canada
Nu-ketotifen Syrup - 1mg/5ml	Syrup	1 mg	Oral	Nu Pharm Inc	1996-12-09	2012-09-04	Canada
PMS-ketotifen	Syrup	1 mg	Oral	Pharmascience Inc	1998-08-31	2013-02-07	Canada
PMS-ketotifen	Tablet	1 mg	Oral	Pharmascience Inc	1998-08-31	2013-02-07	Canada
Zaditen	Tablet	1 mg	Oral	Teva	1990-12-31	Not applicable	Canada
Zaditen	Syrup	1 mg	Oral	Teva	1990-12-31	Not applicable	Canada
Zaditen - Dps 1mg/ml	Solution / drops	1 mg	Oral	Novartis	Not applicable	Not applicable	Canada
Zaditor	Solution	0.25 mg	Ophthalmic	Laboratoires Thea	2000-08-01	Not applicable	Canada
Zaditor	Solution	0.25 mg	Ophthalmic	Novartis	2006-08-03	2012-01-17	Canada

Approved Generic Prescription Products

Name	Dosage	Strength	Route	Labeller	Marketing Start	Marketing End
Apo-ketotifen - Syr 1mg/5ml	Syrup	1 mg	Oral	Apotex Corporation	1996-11-07	Not applicable	Canada

Approved Over the Counter Products

Name	Dosage	Strength	Route	Labeller	Marketing Start	Marketing End
Alaway	Solution / drops	.25 mg/mL	Ophthalmic	Bauch & Lomb Incorporated	2006-12-01	Not applicable	US
Alaway	Kit			Bauch & Lomb Incorporated	2006-12-01	Not applicable	US
Allergy Eye	Solution / drops	.25 mg/mL	Ophthalmic	H.E.B.	2010-09-15	Not applicable	US
Allergy Eye	Solution / drops	.25 mg/mL	Ophthalmic	Cvs Health	2011-01-07	Not applicable	US
Allergy Eye Drops	Solution / drops	.35 mg/mL	Ophthalmic	Advanced Vision Research (Subsidiary of Akorn, Inc.)	2013-11-14	Not applicable	US
Allergy Eye Drops	Solution / drops	.35 mg/mL	Ophthalmic	H.E.B.	2014-02-25	Not applicable	US
Allergy Eye Drops	Solution / drops	.35 mg/mL	Ophthalmic	Cardinal Health	2014-01-13	Not applicable	US
Allergy Eye Original Prescription Strength	Solution / drops	.25 mg/mL	Ophthalmic	Meijer Distribution	1995-12-12	Not applicable	US
Allergy Relief Eye	Solution / drops	.25 mg/mL	Ophthalmic	Western Family Foods	2011-05-25	Not applicable	US
Allergy Relief Eye Drops	Solution / drops	.35 mg/mL	Ophthalmic	Kinray	2014-03-18	Not applicable	US
Antihistamine Eye	Solution	.25 mg/mL	Ophthalmic	Cvs Health	2010-10-19	Not applicable	US
Care One Allergy Eye	Solution / drops	.25 mg/mL	Ophthalmic	American Sales Company	2010-08-30	Not applicable	US
Care One Eye Itch Relief	Solution	.25 mg/mL	Ophthalmic	American Sales Company	2010-08-30	Not applicable	US
Equaline Eye Itch Relief	Solution	.25 mg/mL	Ophthalmic	Supervalu	2010-10-15	Not applicable	US
Equate Eye Itch Relief	Solution	.25 mg/mL	Ophthalmic	Walmart Stores	2010-07-08	Not applicable	US
Equate Itchy Eye	Solution	.25 mg/mL	Ophthalmic	Walmart Stores	2010-09-09	Not applicable	US
Eye Itch	Solution / drops	.35 mg/mL	Ophthalmic	Kroger	2014-01-22	Not applicable	US
Eye Itch	Solution / drops	.35 mg/mL	Ophthalmic	Meijer Distribution	2014-01-23	Not applicable	US
Eye Itch	Solution	.25 mg/mL	Ophthalmic	Kroger	2010-10-16	Not applicable	US
Eye Itch Relief	Solution	.25 mg/mL	Ophthalmic	Walgreen	2010-08-13	Not applicable	US
Eye Itch Relief	Solution / drops	.35 mg/mL	Ophthalmic	Cvs Health	2014-02-07	Not applicable	US
Eye Itch Relief	Solution / drops	.35 mg/mL	Ophthalmic	Good Sense	2014-06-20	Not applicable	US
Eye Itch Relief	Solution / drops	.35 mg/mL	Ophthalmic	Mc Kesson	2014-02-07	Not applicable	US
Eye Itch Relief	Solution / drops	.35 mg/mL	Ophthalmic	Rite Aid	2013-12-06	Not applicable	US
Eye Itch Relief	Solution / drops	.35 mg/mL	Ophthalmic	Cvs Health	2014-02-07	Not applicable	US
Eye Itch Relief	Solution / drops	.35 mg/mL	Ophthalmic	Mc Kesson Corporation Valu Rite	2014-02-07	Not applicable	US
Eye Itch Relief	Solution / drops	.35 mg/mL	Ophthalmic	Chain Drug Consortium	2014-01-10	Not applicable	US
Eye Itch Relief	Solution / drops	.35 mg/mL	Ophthalmic	Rite Aid	2013-12-06	Not applicable	US
Eye Itch Relief	Solution	.25 g/mL	Ophthalmic	Cvs Health	2010-09-14	Not applicable	US
Eye Itch Relief	Solution / drops	.35 mg/mL	Ophthalmic	Cardinal Health	2017-01-18	Not applicable	US
Eye Itch Relief	Solution	.25 mg/mL	Ophthalmic	Safeway	2014-08-20	Not applicable	US
Eye Itch Relief	Solution / drops	.35 mg/mL	Ophthalmic	H.E.B.	2014-02-25	Not applicable	US
Eye Itch Relief	Solution / drops	.35 mg/mL	Ophthalmic	Kinray	2014-03-18	Not applicable	US
Eye Itch Relief	Solution / drops	.25 mg/mL	Ophthalmic	Walgreens	2012-05-01	Not applicable	US
Eye Itch Relief	Solution / drops	.35 mg/mL	Ophthalmic	Amerisource Bergen	2013-12-06	Not applicable	US
Eye Itch Relief	Solution / drops	.35 mg/mL	Ophthalmic	Cardinal Health	2014-01-13	Not applicable	US
Eye Itch Relief	Solution	.25 mg/mL	Ophthalmic	H.E.B.	2010-09-10	Not applicable	US
Eye Itch Relief	Solution	.25 mg/mL	Ophthalmic	Meijer Distribution	2010-08-23	Not applicable	US
Eye Itch Relief	Solution	.25 mg/mL	Ophthalmic	Rite Aid	2010-10-06	Not applicable	US
Eye Itch Relief	Solution / drops	.35 mg/mL	Ophthalmic	Rugby	2016-01-20	Not applicable	US
Good Neighbor Pharmacy Eye Itch Relief	Solution	.25 mg/mL	Ophthalmic	Dispensing Solutions, Inc.	2010-11-13	Not applicable	US
Good Neighbor Pharmacy Eye Itch Relief	Solution	.25 mg/mL	Ophthalmic	Amerisource Bergen	2010-11-13	Not applicable	US
Good Neighbor Pharmacy Itchy Eye	Solution	.25 mg/mL	Ophthalmic	Amerisource Bergen	2010-10-07	Not applicable	US
Good Sense Allergy Eye	Solution / drops	.25 mg/mL	Ophthalmic	L. Perrigo Company	1997-11-18	Not applicable	US
Good Sense Eye Itch Relief	Solution	.25 mg/mL	Ophthalmic	L. Perrigo Company	2010-09-15	Not applicable	US
Good Sense Itchy Eye Original Prescription Strength	Solution	.25 mg/mL	Ophthalmic	L. Perrigo Company	1997-10-28	Not applicable	US
Health Mart Eye Itch Relief	Solution	.25 mg/mL	Ophthalmic	Mc Kesson	2012-02-03	Not applicable	US
Itchy Eye	Solution	.25 mg/mL	Ophthalmic	Kroger	2011-05-27	Not applicable	US
Itchy Eye	Solution	.25 mg/mL	Ophthalmic	H.E.B.	2010-09-15	Not applicable	US
Itchy Eye	Solution	.25 mg/mL	Ophthalmic	Major	2010-11-16	Not applicable	US
Itchy Eye	Solution / drops	.35 mg/mL	Ophthalmic	Kroger	2014-01-22	Not applicable	US
Itchy Eye	Solution / drops	.35 mg/mL	Ophthalmic	Meijer Distribution	2016-01-26	Not applicable	US
Itchy Eye	Solution / drops	.35 mg/mL	Ophthalmic	Meijer Distribution	2014-01-23	Not applicable	US
Itchy Eye Drops	Solution / drops	.35 mg/mL	Ophthalmic	Good Sense	2014-06-20	Not applicable	US
Itchy Eye Drops	Solution / drops	.35 mg/mL	Ophthalmic	Amerisource Bergen	2013-12-06	Not applicable	US
Itchy Eye Original Prescription Strength	Solution	.25 mg/mL	Ophthalmic	Meijer Distribution	2010-08-23	Not applicable	US
Itchy Eye Relief	Solution	.25 mg/mL	Ophthalmic	Western Family Foods	2011-05-25	Not applicable	US
Ketotifen Fumarate	Solution	.35 mg/mL	Ophthalmic	Advanced Vision Research (Subsidiary of Akorn, Inc.)	2012-03-15	Not applicable	US
Ketotifen Fumarate	Solution / drops	.35 mg/mL	Ophthalmic	Remedy Repack	2016-09-12	2017-03-08	US
Ketotifen Fumarate	Solution / drops	.25 mg/mL	Ophthalmic	Walgreens	2013-01-25	Not applicable	US
Ketotifen Fumarate	Solution / drops	.35 mg/mL	Ophthalmic	Cvs Health	2013-02-21	Not applicable	US
Ketotifen Fumarate	Solution / drops	.35 mg/mL	Ophthalmic	A S Medication Solutions	2007-10-01	Not applicable	US
Ketotifen Fumarate	Solution / drops	.35 mg/mL	Ophthalmic	Akorn	2007-10-01	Not applicable	US
Ketotifen Fumarate	Solution / drops	.35 mg/mL	Ophthalmic	Cvs Health	2013-11-08	Not applicable	US
Leader Allergy Eye	Solution	.25 mg/mL	Ophthalmic	Cardinal Health	2010-09-22	Not applicable	US
Leader Eye Itch Relief Drops	Solution / drops	.345 mg/mL	Ophthalmic	HANLIM PHARM. CO., LTD.	2010-04-21	Not applicable	US
Smart Sense Allergy	Solution / drops	.25 mg/mL	Ophthalmic	Kmart Corporation	2010-08-27	Not applicable	US
Sunmark Eye Itch Relief	Solution	.25 mg/mL	Ophthalmic	Mc Kesson	2012-02-21	Not applicable	US
Topcare Eye Itch Relief	Solution	.25 mg/mL	Ophthalmic	Topco Associates	2013-02-08	2016-10-29	US
Up and Up Eye Itch Relief	Solution	.25 mg/mL	Ophthalmic	Target Corporation.	2010-09-03	Not applicable	US
Wal Zyr	Solution	.25 mg/mL	Ophthalmic	Walgreen	2010-03-12	Not applicable	US
Zaditor	Solution	.35 mg/mL	Ophthalmic	Alcon, Inc.	2012-12-21	Not applicable	US
Zaditor	Solution	.35 mg/mL	Ophthalmic	A S Medication Solutions	2012-12-21	Not applicable	US

Unapproved/Other Products

Not Available

International Brands

Name	Company
Totifen	Patron
Zasten	Novartis

Brand mixtures

Not Available

Categories

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).

Structured Indications

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	Kind	Pharmacological action	Actions	Organism	UniProt ID
Histamine H1 receptor	Protein	yes	antagonist	Human	P35367	details
6-phosphogluconate dehydrogenase, decarboxylating	Protein	unknown	inhibitor	Human	P52209	details

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.

Substrate	Enzymes	Product
Ketotifen	Not Available	Ketotifen-N-glucuronide	Details
Ketotifen	Not Available	10-alpha-hydroxyl Ketotifen	Details
Ketotifen	Not Available	Nor-ketotifen	Details

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

Not Available

Pharmacogenomic Effects/ADRs

Not Available

Interactions

Drug Interactions

Drug	Interaction	Drug group
2,5-Dimethoxy-4-ethylamphetamine	2,5-Dimethoxy-4-ethylamphetamine may decrease the sedative activities of Ketotifen.	Experimental, Illicit
3,4-Methylenedioxyamphetamine	3,4-Methylenedioxyamphetamine may decrease the sedative activities of Ketotifen.	Experimental, Illicit
3,4-Methylenedioxymethamphetamine	3,4-Methylenedioxymethamphetamine may decrease the sedative activities of Ketotifen.	Experimental, Illicit
4-Bromo-2,5-dimethoxyamphetamine	4-Bromo-2,5-dimethoxyamphetamine may decrease the sedative activities of Ketotifen.	Experimental, Illicit
Amphetamine	Amphetamine may decrease the sedative activities of Ketotifen.	Approved, Illicit
Benzphetamine	Benzphetamine may decrease the sedative activities of Ketotifen.	Approved, Illicit
Benzylpenicilloyl Polylysine	Ketotifen may decrease effectiveness of Benzylpenicilloyl Polylysine as a diagnostic agent.	Approved
Betahistine	The therapeutic efficacy of Betahistine can be decreased when used in combination with Ketotifen.	Approved
Chlorphentermine	Chlorphentermine may decrease the sedative activities of Ketotifen.	Illicit, Withdrawn
Dextroamphetamine	Dextroamphetamine may decrease the sedative activities of Ketotifen.	Approved, Illicit
Diethylpropion	Diethylpropion may decrease the sedative activities of Ketotifen.	Approved, Illicit
Hyaluronidase	The therapeutic efficacy of Hyaluronidase can be decreased when used in combination with Ketotifen.	Approved, Investigational
Hydroxyamphetamine	Hydroxyamphetamine hydrobromide may decrease the sedative activities of Ketotifen.	Approved
Lisdexamfetamine	Lisdexamfetamine may decrease the sedative activities of Ketotifen.	Approved, Investigational
Mephentermine	Mephentermine may decrease the sedative activities of Ketotifen.	Approved
Methamphetamine	Methamphetamine may decrease the sedative activities of Ketotifen.	Approved, Illicit
MMDA	MMDA may decrease the sedative activities of Ketotifen.	Experimental, Illicit
Phentermine	Phentermine may decrease the sedative activities of Ketotifen.	Approved, Illicit
Pseudoephedrine	Pseudoephedrine may decrease the sedative activities of Ketotifen.	Approved

Food Interactions

Take without regard to meals.

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

Resource	Link
Human Metabolome Database (HMDB)	HMDB15056
KEGG Drug	D01332
PubChem Compound	3827
PubChem Substance	46508921
ChemSpider	3695
BindingDB	94597
ChEBI	92511
ChEMBL	CHEMBL534
Therapeutic Targets Database	DAP000329
PharmGKB	PA450152
Drug Product Database	11175
RxList	http://www.rxlist.com/cgi/generic/ketotifen.htm
Drugs.com	http://www.drugs.com/cdi/ketotifen-drops.html
PDRhealth	http://www.pdrhealth.com/drug_info/rxdrugprofiles/drugs/zad1598.shtml
Wikipedia	Ketotifen

ATC Codes

S01GX08

R06AX17

AHFS Codes

04:00.00
04:92.00
52:02.00

PDB Entries

Not Available

FDA label

Download (9.05 KB)

MSDS

Not Available

Clinical Trials

Phase	Status	Purpose	Conditions	Count
1	Completed	Not Available	Conjunctivitis, Seasonal Allergic	1
1, 2	Recruiting	Treatment	Widespread Chronic Pain	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	Basic Science	Fibromyalgia	1
3	Completed	Treatment	Atopics / Dermatitis	1
3	Completed	Treatment	Conjunctivitis, Seasonal Allergic	2
3	Completed	Treatment	Rhinitis, Allergic, Perennial	1
3	Not Yet Recruiting	Treatment	Functional Dyspepsia	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

Dosage forms

Form	Route	Strength
Kit
Solution	Ophthalmic	.25 g/mL
Solution / drops	Ophthalmic	.35 mg/mL
Solution / drops	Ophthalmic	.25 mg/mL
Solution	Ophthalmic	.25 mg/mL
Solution / drops	Ophthalmic	.345 mg/mL
Syrup	Oral	1 mg
Tablet	Oral	1 mg
Solution / drops	Oral	1 mg
Solution	Ophthalmic	.35 mg/mL
Solution	Ophthalmic	0.25 mg

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	Yes	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

ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )

Spectra

Mass Spec (NIST)

Not Available

Spectra

Spectrum Type	Description	Splash Key
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	Not Available
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	Not Available
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	Not Available
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	Not Available
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	Not Available
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	Not Available

Taxonomy

Description

This compound belongs to the class of chemical entities 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

Chemical entities

Super Class

Organic compounds

Class

Organoheterocyclic compounds

Sub Class

Cycloheptathiophenes

Direct Parent

Cycloheptathiophenes

Alternative Parents

Substituents

Cycloheptathiophene
Aryl alkyl ketone
Aryl ketone
Piperidine
Benzenoid
Thiophene
Heteroaromatic compound
Ketone
Tertiary amine
Tertiary aliphatic amine
Azacycle
Amine
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organooxygen compound
Organonitrogen compound
Organic oxygen compound
Organic nitrogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Targets

Details

1. Histamine H1 receptor

Kind: Protein
Organism: Human
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 catecholamine release from adrenal medulla, as well as mediating neurotransmission in the central nervous system.
Gene Name:: HRH1
Uniprot ID:: P35367
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 ]

Details

2. 6-phosphogluconate dehydrogenase, decarboxylating

Kind: Protein
Organism: Human
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
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 ]

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Drug created on June 13, 2005 07:24 / Updated on May 19, 2017 16:43

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Structure for DB00920 (Ketotifen)

Targets

References

References