Ebastine

Base Information

• Chemical Name: Ebastine
• CAS No.: 90729-43-4
• Molecular Formula: C32H39NO2
• Molecular Weight: 469.667
• European Community (EC) Number: 635-609-6
• UNII: TQD7Q784P1
• DSSTox Substance ID: DTXSID6046472
• Nikkaji Number: J22.761G
• Wikipedia: Ebastine
• Wikidata: Q2327739
• NCI Thesaurus Code: C77437
• Pharos Ligand ID: Z4PMKLF1FYC7
• Metabolomics Workbench ID: 152848
• ChEMBL ID: CHEMBL305660
• Mol file: 90729-43-4.mol

Synonyms:4-diphenylmethoxy-1-(3-(4-tert-butylbenzoyl)propyl)piperidine;Bactil;Busidril;Ebastel;ebastine;Evastel;Kestin;Kestine;LAS W-090

Chemical Property of Ebastine

Chemical Property:

• Appearance/Colour: White to off-white powder
• Vapor Pressure: 3.47E-14mmHg at 25°C
• Melting Point: 80-82 °C
• Refractive Index: 1.59
• Boiling Point: 596.3 °C at 760 mmHg
• PKA: 8.19±0.10(Predicted)
• Flash Point: 314.5 °C
• PSA: 29.54000
• Density: 1.09 g/cm³
• LogP: 7.15550
• Storage Temp.: Room temp
• Solubility.: Slightly soluble in chloroform, methanol.
• XLogP3: 7.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 10
• Exact Mass: 469.298079487
• Heavy Atom Count: 35
• Complexity: 594

Purity/Quality:

98%min ^*data from raw suppliers

Ebastine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)C1=CC=C(C=C1)C(=O)CCCN2CCC(CC2)OC(C3=CC=CC=C3)C4=CC=CC=C4
• Recent ClinicalTrials: Ebastine Versus Mebeverine in IBS Patients
• Recent EU Clinical Trials: Ebastine in combination with docetaxel as a treatment for castration-resistant metastatic prostate cancer
• Recent NIPH Clinical Trials: Effects of ebastine on up-regulation of histamine H1 receptor mRNA in the nasal mucosa induced by artificial exposure of Japanese cedar pollen in patients with allergic rhinitis to cedar pollen.
• Description: Ebastine belongs to an effective second generation histamine H1 receptor antagonist. One important property of it is that it doesn’t penetrate the blood brain barrier. Therefore, it is capable of blocking the H1 receptor in peripheral tissue without having some specific side effects such as sedation and drowsiness. Ebastine is mainly applied for the treatment of allergic rhinitis, pruritus as well as acting as an alternative drug in Decongestant. Upon entering into the human body, it can subject to the action of hepatic cytochrome P450 3A4 to be converted to an active carboxylic acid metabolite, carebastine. The later one is the major active form in vivo. Under certain range, it can inhibit T cell proliferation and the production of Th2-type pro-inflammatory cytokines through macrophages. Ebastine generally has a high safety property without causing cognitive/psychomotor impairment and sedation, like placebo. However, it can cause side effects such as inflammation of the air-cavities around nose, sore throat, indigestion, nausea, headache, and abdominal pain. Ebastine is a new once-daily histamine Hl-receptor antagonist with no sedative effects or autonomic impairment at therapeutic doses. It is reported to be effective in the treatment of hay fever, perennial rhinitis, and uticaria. Ebastine's antihistamine activity is attributed to its carboxylic acid metabolite carebastine.
• Uses: Ebastine is a second-generation H1 receptor antagonist that is indicated mainly for allergic rhinitis and chronic idiopathic urticaria. It is available in 10 and 20 mg tablets and as fast-dissolving tablets, as well as in pediatric syrup. It has a recommended flexible daily dose of 10 or 20 mg, depending on disease severity. A nonsedating type histamine H1-receptor antagonist. Antihistaminic
• Therapeutic Function: Antihistaminic, Antiallergic, Calcium entry blocker

Technology Process of Ebastine

There total 15 articles about Ebastine 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: 96.75%

1-[4-(1,1-dimethylethyl)phenyl]-4-[4-(diphenylmethoxy)-1-piperidinyl]-1-butanone oxalate → ebastine (90729-43-4)

Guidance literature:

With potassium carbonate; In water; ethyl acetate; Product distribution / selectivity;

Reference yield: 96.75%

1-[4-(1,1-dimethylethyl)phenyl]-4-[4-(diphenylmethoxy)-1-piperidinyl]-1-butanone oxalate → ebastine (90729-43-4)

Guidance literature:

With potassium carbonate; In water; ethyl acetate; Product distribution / selectivity;

Reference yield: 91.13%

1-[4-(1,1-dimethylethyl)phenyl]-4-[4-(diphenylmethoxy)-1-piperidinyl]-1-butanone phosphate → ebastine (90729-43-4)

Guidance literature:

With potassium hydroxide; In water; toluene; for 2.16667h; Product distribution / selectivity;

upstream raw materials:

4-diphenylmethoxypiperidine

4'-tert-butyl-4-chlorobutyrophenone

4-HYDROXYPIPERIDINE

4-(diphenylmethoxy)piperidine hydrochloride

Downstream raw materials:

1-(4-tert-butylphenyl)-4-(4-(benzhydryloxy)piperidin-1-yl)butan-1-ol

Hydroxyebastine

1-[4-(1,1-dimethylethyl)phenyl]-4-[4-(diphenylmethoxy)-1-piperidinyl]-1-butanone tosylate

ebastine N-oxide

Refernces

• 1、 -. "PROCESS OF PREPARING EBASTINE". Page/Page column 10. . Retrieved 2012/06/30.
• 2、 -. "Process for the preparation of 1-[4-(1,1-dimethylethyl)phenyl]-4-[4-(diphenylmethoxy)-1-piperidinyl]-1-butanone and acid addition salts thereof". Page/Page column 28. . Retrieved 2011/10/13.