2-(1-methylpiperidin-4-ylidene)-6-thiatricyclo[8.4.0.0^{3,7}]tetradeca-1(10),3(7),4,11,13-pentaen-8-one

• ChemBase ID: 796
• Molecular Formular: C19H19NOS
• Molecular Mass: 309.42526
• Monoisotopic Mass: 309.11873523
• SMILES: s1c2c(C(=C3CCN(CC3)C)c3c(CC2=O)cccc3)cc1
• Canonical SMILES: CN1CCC(=C2c3ccccc3CC(=O)c3c2ccs3)CC1
• 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
• InChIKey: ZCVMWBYGMWKGHF-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-(1-methylpiperidin-4-ylidene)-6-thiatricyclo[8.4.0.0^{3,7}]tetradeca-1(10),3(7),4,11,13-pentaen-8-one
• IUPAC Traditional name: ketotifen
• Brand Name: Ketotifen; Zaditor
• Synonyms: Ketotifene [INN-French]; Ketotifeno [INN-Spanish]; Ketotifenum [INN-Latin]; Ketotifene fumarate; Ketotifen Fumarate; Ketotifen

Database IDs

• CAS Number: 34580-14-8
• PubChem SID: 160964259; 46508921
• PubChem CID: 3827

CALCULATED PROPERTIES

JChem

• Acid pKa: 12.299357
• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): 1.6982583
• LogD (pH = 7.4): 3.1556277
• Log P: 3.3478694
• Molar Refractivity: 101.734 cm^3
• Polarizability: 35.112392 Å^3
• Polar Surface Area: 20.31 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 3.49
• LOG S: -4.59
• Solubility (Water): 7.87e-03 g/l

PROPERTIES

Physical Property

• Hydrophobicity(logP): 2.2

DETAILS

DrugBank - DB00920

• Drug 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. [PubChem]
• 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).
• Pharmacology: 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).
• Toxicity: Adverse reactions include headaches, conjunctival injection and rhinitis.
• Affected Organisms: Humans and other mammals
• Biotransformation: 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.
• Absorption: Following oral administration absorption is at least 60%
• Half Life: 21 hours (for elimination)
• Protein Binding: 75%
• External Links: Wikipedia; RxList; PDRhealth; Drugs.com