Ketotifen

Base Information

• Chemical Name: Ketotifen
• CAS No.: 34580-13-7
• Deprecated CAS: 116655-74-4
• Molecular Formula: C19H19NOS
• Molecular Weight: 309.432
• Hs Code.: 29349990
• European Community (EC) Number: 252-099-7
• UNII: X49220T18G
• DSSTox Substance ID: DTXSID701019837
• Nikkaji Number: J19.479D
• Wikipedia: Ketotifen
• Wikidata: Q2458673
• NCI Thesaurus Code: C61799
• RXCUI: 6146
• Pharos Ligand ID: GLYZCTF8JCY3
• Metabolomics Workbench ID: 43187
• ChEMBL ID: CHEMBL534
• Mol file: 34580-13-7.mol

Synonyms:4,9-Dihydro-4-(1-methyl-4-piperidylidene)-10H-benzo(4,5)-cyclohepta(1,2-b)thiophen-10-one;Fumarate, Ketotifen;Ketotifen;Ketotifen Fumarate;Ketotifene;Ketotiphen;Ketotiphene;Zaditen

Chemical Property of Ketotifen

Chemical Property:

• Melting Point: 152-153 °C
• Boiling Point: 488.9 °C at 760 mmHg
• PKA: 8.84±0.20(Predicted)
• Flash Point: 249.5 °C
• PSA: 48.55000
• Density: 1.236 g/cm³
• LogP: 3.95230
• Storage Temp.: Amber Vial, -20°C Freezer, Under inert atmosphere
• Solubility.: DMSO (Slightly, Heated), Methanol (Slightly)
• XLogP3: 3.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 0
• Exact Mass: 309.11873540
• Heavy Atom Count: 22
• Complexity: 476

Purity/Quality:

99% ^*data from raw suppliers

Ketotifen ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CN1CCC(=C2C3=C(C(=O)CC4=CC=CC=C42)SC=C3)CC1
• Recent ClinicalTrials: The Possible Protective Role of Ketotifen Against Oxaliplatin Induced Peripheral Neuropathy
• Recent EU Clinical Trials: Multicenter, randomised, double masked, controlled studies on the efficacy of Cyclosporine eye drop treatment in preventing Vernal Keratoconjunctivitis VKC relapses and in treating the acute phase.
• Recent NIPH Clinical Trials: Brain histamine H1 receptor occupancy of sedating OTC antihistamines: Time-course of receptor occupancy measured by PET in normal volunteers
• Uses: Anti-asthmatic. Ketotifen is an intermediate in the synthesis of Ketotifen N-Oxide Hydrochloride (K315410), which is a metabolite of Ketotifen (K315100) in humans; formed by human liver microsome. For the free base, see K315115.
• Therapeutic Function: Anti-asthmatic, Antihistaminic
• Clinical Use: Ketotifen is a potent, selective H1 antihistamine that also prevents release of transmitters from mast cells. It is approved in the United States for topical use to prevent itching of the eye because of allergic conjunctivitis, It is used as a systemic antiallergy agent in several countries outside the United States for the treatment of seasonal allergic rhinitis, hay fever, and asthma. Being structurally analogous to the cyproheptadine-like antihistamines, differences in activity of the two enantiomers (atropisomers) has been noted, being approximately six- to seven-fold in ligand displacement and rodent-based assays. Ketotifen has been shown to stabilize mast cells and to inhibit degranulation of eosinophils. Like olopatadine, it has been shown to interact with model membranes, stabilizing them by interaction with phospholipids monolayers.

Technology Process of Ketotifen

There total 23 articles about Ketotifen which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 97.0%

10-methoxy-4-(1-methyl-4-piperidyl)-4H-benzo<4,5>cyclohepta<1,2-b>thiopene-4-ol (59743-88-3,116655-77-7,116667-71-1) → ketotifen (34580-13-7)

Guidance literature:

With hydrogenchloride; In water; for 1h; Heating;

Reference yield: 97.0%

10-methoxy-4-(1-methyl-4-piperidyl)-4H-benzo<4,5>cyclohepta<1,2-b>thiopene-4-ol (59743-88-3,116655-77-7,116667-71-1) → Ketotifen (34580-13-7,116655-74-4,116655-75-5,116655-76-6)

Guidance literature:

With hydrogenchloride; In water; for 1h; Heating;

Reference yield: 97.0%

10-methoxy-4-(1-methyl-4-piperidyl)-4H-benzo<4,5>cyclohepta<1,2-b>thiopene-4-ol (59743-88-3,116655-77-7,116667-71-1) → (+)-(R)-4-(1-methyl-4-piperidylidene)-9,10-dihydro-4H-benzo<4,5>cyclohepta<1,2-b>thiopene-10-one (34580-13-7,116655-74-4,116655-75-5,116655-76-6)

Guidance literature:

With hydrogenchloride; In water; for 1h; Heating;

upstream raw materials:

10-methoxy-4-(1-methyl-4-piperidyl)-4H-benzo<4,5>cyclohepta<1,2-b>thiopene-4-ol

4-(10-bromo-benzo[4,5]cyclohepta[1,2-b]thiophen-4-ylidene)-1-methyl-piperidine

4-hydroxy-4-(1-methyl-4-piperidyl)-9,10-dihydro-4H-benzo<4,5>cyclohepta<1,2-b>thiopene-10-one

4-(10-oxo-9,10-dihydro-4H-benzo[4,5]cyclohepta[1,2-b]thiophen-4-ylidene)piperidine

Downstream raw materials:

4-(1-benzyl-piperidin-4-ylidene)-4,9-dihydro-benzo[4,5]cyclohepta[1,2-b]thiophen-10-one

4-(1-Methyl-4-piperidyliden)-4H-benzo<4,5>cyclohepta<1,2-b>thiophen-9,10-dion

9,10-Dihydro-4-(1-methyl-4-piperidyliden)-4H-benzo<4,5>cyclohepta<1,2-b>thiophen-10-ol

4-(1-methyl-1-oxy-piperidin-4-ylidene)-4,9-dihydro-benzo[4,5]cyclohepta[1,2-b]thiophen-10-one

Refernces

• 1、 Waldvogel,Schwarb,Bastian,Bourquin. "Synthetical pharmaceutics. 9 and 10 oxo derivatives of 9,10 dihydro 4H benzo [4,5] cyclohepta[1,2 b] thiophenes". . p. 866 - 877. Retrieved 2007/10/05.