(2E)-but-2-enedioic acid; 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: 73233
• Molecular Formular: C23H23NO5S
• Molecular Mass: 425.49742
• Monoisotopic Mass: 425.12969384
• SMILES: c12C(=O)Cc3c(C(=C4CCN(CC4)C)c1ccs2)cccc3.C(=O)(/C=C/C(=O)O)O
• Canonical SMILES: CN1CCC(=C2c3ccccc3CC(=O)c3c2ccs3)CC1.OC(=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+
• InChIKey: YNQQEYBLVYAWNX-WLHGVMLRSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2E)-but-2-enedioic acid; 2-(1-methylpiperidin-4-ylidene)-6-thiatricyclo[8.4.0.0^{3,7}]tetradeca-1(10),3(7),4,11,13-pentaen-8-one; (2E)-but-2-enedioic acid; 2-(1-methylpiperidin-4-ylidene)-6-thiatricyclo[8.4.0.0^3,^7]tetradeca-1(14),3(7),4,10,12-pentaen-8-one; (2E)-but-2-enedioic acid; 2-(1-methylpiperidin-4-ylidene)-6-thiatricyclo[8.4.0.0^3,^7]tetradeca-1(10),3(7),4,11,13-pentaen-8-one; 2-(1-methylpiperidin-4-ylidene)-6-thiatricyclo[8.4.0.0^{3,7}]tetradeca-1(10),3(7),4,11,13-pentaen-8-one; but-2-enedioic acid
• IUPAC Traditional name: fumaric acid; ketotifen; butenedioic acid; ketotifen
• Synonyms: Zaditor; Ketotifen fumarate; Ketotifen fumarate salt; 4,9-Dihydro-4-(1-methyl-4-piperidinylidene)-10H-benzo[4,5]cyclohepta[1,2-b]thiophen-10-one (2E)-2-Butenedioate; Ketotifen Hydrogen Fumarate; Totifen; Zaditen; Zasten; KETOTIFEN

Database IDs

• CAS Number: 34580-14-8
• EC Number: 252-100-0
• MDL Number: MFCD00079394
• PubChem SID: 24278506; 162038153
• PubChem CID: 5282408

CALCULATED PROPERTIES

• 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: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol
• Apperance: Off-White Solid
• Melting Point: 188-190°C (dec.)

Safety Information

• Storage Condition: -20°C; Refrigerator; Room Temperature (15-30°C)
• RTECS: DE8260000
• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 22; R:22
• Safety Statements: 36; S:36/37/39
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H302
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Faceshields, Gloves

Pharmacology Properties

• Target: histamine
• Gene Information: human ... HRH1(3269), PDE7B(27115)

Product Information

• Salt Data: fumarate

DETAILS

MP Biomedicals - 02155155

Fumarate Salt An H1 Histamine receptor antagonist that inhibits the anaphylactic release of histamine.

Selleck Chemicals - S2024

Biological Activity:
Ketotifen fumarate (Zaditor) is a fumarate acid salt of ketotifen which is a H1-antihistamine and mast cell stabilizer. In its ophthalmic form, ketotifen fumarate is used to treat allergic conjunctivitis, or the itchy red eyes caused by allergies. In its oral form, Ketotifen fumarate (Zaditor) is used to inhibit asthma attacks. Side effects of ketotifen fumarate include drowsiness, weight gain, dry mouth, irritability, and increased nosebleeds. [1]References on Ketotifen fumarate (Zaditor)[1] http://en.wikipedia.org/wiki/Ketotifen, ,

Sigma Aldrich - K2628

Biochem/physiol Actions
H1 histamine receptor antagonist.

Toronto Research Chemicals - K315100

Ketotifen is used as an antiasthmatic. Ketotifen is an antiallergic agent.

REFERENCES

• http://en.wikipedia.org/wiki/Ketotifen
• Tsuji, F., et al.: Biol. Pharm. Bull., 33, 1050 (2010)
• Al O., et al.: J., Mol., Liq., 155, 103 (2010)
• Uccello-Barretta, G., et al.: Int. J. Pharm., 395, 122 (2010)