Ketotifen fumarateProduct ingredient for Ketotifen
- Name
- Ketotifen fumarate
- Drug Entry
- Ketotifen
Ketotifen is a benzocycloheptathiophene derivative3 with potent antihistaminic and mast cell stabilizing properties. It has a similar structure to some other first-generation antihistamines such as cyproheptadine and azatadine.3
Ketotifen was first developed in Switzerland in 1970 by Sandoz Pharmaceuticals and was initially marketed for the treatment of anaphylaxis.3 In the US, it is now used in an over-the-counter ophthalmic formulation for the treatment of itchy eyes associated with allergies,6 and in Canada a prescription-only oral formulation is available and indicated as an add-on therapy for children with atopic asthma.7 In addition, oral ketotifen is used in Mexico and across Europe for the treatment of various allergic symptoms and disorders,3 including urticaria, mastocytosis, and food allergy.
- Accession Number
- DBSALT001856
- Structure
Structure for Ketotifen fumarate (DBSALT001856)
- Synonyms
- 10H-BENZO(4,5)CYCLOHEPTA(1,2-B)THIOPHEN-10-ONE, 4,9-DIHYDRO-4-(1-METHYL-4-PIPERIDINYLIDENE)-, (E)-2-BUTENEDIOATE (1:1) / 4,9-Dihydro-4-(1-methyl-4-piperidylidene)-10H-benzo[4,5]cyclohepta[1,2-b]thiophen-10-one fumarate (1:1) / HC 20,511 FUMARATE / HC-20511 FUMARATE / Ketotifen (as fumarate) / Ketotifen hydrogen fumarate
- External IDs
- NSC-757415
- UNII
- HBD503WORO
- CAS Number
- 34580-14-8
- Weight
- Average: 425.5
Monoisotopic: 425.129694019 - Chemical Formula
- C23H23NO5S
- InChI Key
- YNQQEYBLVYAWNX-WLHGVMLRSA-N
- 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+
- IUPAC Name
- (2E)-but-2-enedioic acid; 2-(1-methylpiperidin-4-ylidene)-6-thiatricyclo[8.4.0.0³,⁷]tetradeca-1(10),3(7),4,11,13-pentaen-8-one
- SMILES
- OC(=O)\C=C\C(O)=O.CN1CCC(CC1)=C1C2=C(SC=C2)C(=O)CC2=C1C=CC=C2
- External Links
- ChemSpider
- 4445563
- ChEBI
- 31750
- ChEMBL
- CHEMBL1633
- Wikipedia
- Ketotifen
- 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 2 Chemaxon Refractivity 101.73 m3·mol-1 Chemaxon Polarizability 34.5 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