KETOTIFEN FUMARATE

/static/temp/default.svg Search structure
Trade Names
Synonyms
Status
Molecule Category Mixture
UNII HBD503WORO
EPA CompTox DTXSID30892970

Structure

InChI Key YNQQEYBLVYAWNX-WLHGVMLRSA-N
Smiles CN1CCC(=C2c3ccccc3CC(=O)c3sccc32)CC1.O=C(O)/C=C/C(=O)O
InChI
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+

Physicochemical Descriptors

Property Name Value
Molecular Formula C23H23NO5S
Molecular Weight 425.51
AlogP 4.01
Hydrogen Bond Acceptor 3.0
Hydrogen Bond Donor 0.0
Number of Rotational Bond 0.0
Polar Surface Area 20.31
Molecular species NEUTRAL
Aromatic Rings 2.0
Heavy Atoms 22.0

Bioactivity

Mechanism of Action Action Reference
Histamine H1 receptor antagonist ANTAGONIST ISBN
Protein: Histamine H1 receptor
Description: Histamine H1 receptor
Organism : Homo sapiens
P35367 ENSG00000196639
Targets EC50(nM) IC50(nM) Kd(nM) Ki(nM) Inhibition(%)
Membrane receptor Family A G protein-coupled receptor Small molecule receptor (family A GPCR) Monoamine receptor Histamine receptor
- 1 - - -
Transporter Electrochemical transporter SLC superfamily of solute carriers SLC21/SLCO family of organic anion transporting polypeptides
- - - - 89
Assay Description Organism Bioactivity Reference
Displacement of [3H]pyrilamine from human recombinant histamine H1 receptor expressed in CHOK1 cells by scintillation counting Homo sapiens 1.0 nM
In vivo antihistaminic activity at histamine H1 receptor in ddY mouse assessed as inhibition of histamine-induced skin vascular permeability at 3 mg/kg, po administered 1 hr before histamine challenge measured after 30 mins by Evan's blue staining Mus musculus 98.0 %
Antiinflammatory activity in BALB/c mouse model assessed as inhibition of ovalbumin-induced ear swelling at 10 mg/kg, po administered 60 mins before ovalbumin challenge measured 1 hr after elicitation by immediate type reaction assay Mus musculus 119.0 %
Antiinflammatory activity in BALB/c mouse model assessed as inhibition of ovalbumin-induced ear swelling at 30 mg/kg, po administered 60 mins before ovalbumin challenge measured 1 hr after elicitation by immediate type reaction assay Mus musculus 106.0 %
Antiinflammatory activity in BALB/c mouse model assessed as inhibition of ovalbumin-induced ear swelling at 10 mg/kg, po administered 60 mins before ovalbumin challenge measured 24 hrs after elicitation by late type reaction assay Mus musculus 3.0 %
Antiinflammatory activity in BALB/c mouse model assessed as inhibition of ovalbumin-induced ear swelling at 30 mg/kg, po administered 60 mins before ovalbumin challenge measured 24 hrs after elicitation by late type reaction assay Mus musculus 4.0 %
Antiplasmodial activity against Plasmodium falciparum W2 after 72 hrs by SYBR green assay Plasmodium falciparum 794.33 nM
Inhibition of sodium fluorescein uptake in OATP1B1-transfected CHO cells at an equimolar substrate-inhibitor concentration of 10 uM Cricetulus griseus 94.79 %
Inhibition of sodium fluorescein uptake in OATP1B3-transfected CHO cells at an equimolar substrate-inhibitor concentration of 10 uM Cricetulus griseus 89.36 %
Antianaphylactic activity in ovalbumin sensitized albino guinea pig chopped lung assessed as inhibition of antigen-induced slow-reacting substance of anaphylaxis release at 10 ug/mL after 15 mins relative to control Cavia porcellus 38.0 %
Antianaphylactic activity in ovalbumin sensitized albino guinea pig chopped lung assessed as inhibition of antigen-induced histamine release at 10 ug/mL after 15 mins relative to control Cavia porcellus 37.0 %
Antibacterial activity against Staphylococcus aureus MRSA ATCC 43300 (CO-ADD:GP_020); MIC in CAMBH media, using NBS plates, by OD(600) Staphylococcus aureus subsp. aureus 6.88 %
Antibacterial activity against Escherichia coli ATCC 25922 (CO-ADD:GN_001); MIC in CAMBH media using NBS plates, by OD(600) Escherichia coli 3.55 %
Antibacterial activity against Klebsiella pneumoniae MDR ATCC 70063 (CO-ADD:GN_003); MIC in CAMBH media using NBS plates, by OD(600) Klebsiella pneumoniae 1.04 %
Antibacterial activity against Pseudomonas aeruginosa ATCC 27853 (CO-ADD:GN_042); MIC in CAMBH media using NBS plates, by OD(600) Pseudomonas aeruginosa 11.46 %
Antibacterial activity against Acinetobacter baumannii ATCC 19606 (CO-ADD:GN_034); MIC in CAMBH media using NBS plates, by OD600 Acinetobacter baumannii 11.38 %
Antifungal activity against Candida albicans ATCC 90028 (CO-ADD:FG_001); MIC in YNB media using NBS plates, by OD630 Candida albicans 3.18 %
Antifungal activity against Cryptococcus neoformans H99 ATCC 208821 (CO-ADD:FG_002); MIC in YNB media using NBS plates, by Resazurin OD(600-570) Cryptococcus neoformans -3.16 %
Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of Caco-2 cells at 10 uM after 48 hours by high content imaging Homo sapiens 2.84 %
SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate Severe acute respiratory syndrome coronavirus 2 17.19 %
Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of VERO-6 cells at 10 uM after 48 hours exposure to 0.01 MOI SARS CoV-2 virus by high content imaging Chlorocebus sabaeus 0.22 % Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of VERO-6 cells at 10 uM after 48 hours exposure to 0.01 MOI SARS CoV-2 virus by high content imaging Chlorocebus sabaeus 0.22 %

Cross References

Resources Reference
ChEBI 31750
ChEMBL CHEMBL1633
FDA SRS HBD503WORO
Guide to Pharmacology 7206
KEGG D08105
PubChem 5282408
SureChEMBL SCHEMBL8809
ZINC ZINC00004351
CONTENTS