Bilastine

Base Information

• Chemical Name: Bilastine
• CAS No.: 202189-78-4
• Molecular Formula: C₂₈H₃₇N₃O₃
• Molecular Weight: 463.62
• European Community (EC) Number: 824-988-5
• UNII: PA1123N395
• DSSTox Substance ID: DTXSID5057678
• Nikkaji Number: J3.277.525J
• Wikipedia: Bilastine
• Wikidata: Q2902977
• NCI Thesaurus Code: C73045
• Pharos Ligand ID: QGTVYQJRAHVZ
• Metabolomics Workbench ID: 152735
• ChEMBL ID: CHEMBL1742423
• Mol file: 202189-78-4.mol

Synonyms:bilastine

Chemical Property of Bilastine

Chemical Property:

• Vapor Pressure: 3.29E-17mmHg at 25°C
• Melting Point: 202 °C
• Boiling Point: 639.1°Cat760mmHg
• PKA: 4.40±0.10(Predicted)
• Flash Point: 340.3°C
• PSA: 67.59000
• Density: 1.16g/cm³
• LogP: 4.79500
• Storage Temp.: Sealed in dry,Room Temperature
• Water Solubility.: Insoluble in water
• XLogP3: 2.3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 10
• Exact Mass: 463.28349205
• Heavy Atom Count: 34
• Complexity: 641

Purity/Quality:

99% ^*data from raw suppliers

Bilastine >98.0%(HPLC)(T) ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOCCN1C2=CC=CC=C2N=C1C3CCN(CC3)CCC4=CC=C(C=C4)C(C)(C)C(=O)O
• Recent ClinicalTrials: Study to Assess the Safety, Tolerability and Efficacy of Bilastine Ophthalmic Solution 0.6% in Children
• Recent EU Clinical Trials: A multicentre, open-label clinical trial to assess plasma levels and safety of bilastine in children from 2 to 5 years of age with seasonal and/or perennial allergic rhinoconjunctivitis or urticaria
• Recent NIPH Clinical Trials: Efficacy of bilastine on switching treatment in patients with chronic spontaneous urticaria: A comparison study
• Description: Bilastine, a potent and selective histamine H1 receptor antagonist, was approved in Europe in 2010 for the treatment of allergic rhinoconjunctivitis (AR) and urticaria (hives or skin rash). The original synthesis of bilastine involves alkylation of 2-piperidinyl-1H-benzimidazole with a phenethyltosylate, the para position of which is substituted with a dimethyloxazoline moiety serving as a masked carboxylic acid group. Alkylation of the benzimidazole nitrogen with 2-chloroethyl ethyl ether followed by unmasking of the oxazoline moiety with sulfuric acid provided bilastine.In two major clinical trials, bilastine was effective at relieving allergic rhinitis as assessed by measuring the severity of nasal (obstruction, rhinorrhea, itching, sneezing) and nonnasal (ocular itching, tearing, ocular redness, itching of ears, and/or palate) symptoms. Bilastine is a histamine H1 receptor antagonist (IC50 = 180 nM). It is selective for the histamine H1 receptor in a panel of 30 receptors in vitro at 100 μM. Bilastine prevents microvascular extravasation (ED50 = 185 μg/kg, i.v.), bronchospasm (ED50 = 4.6 μg/kg, i.v.), and systemic anaphylaxis (ED50 = 0.2 μg/kg, p.o.) induced by subcutaneous histamine in guinea pigs. It prevents anaphylaxis induced by subcutaneous administration of ovalbumin or dinitrophenylated human albumin (DNP) in sensitized rats when administered at doses of 7.6 and 6.0 mg/kg, respectively. Formulations containing bilastine have been used in the treatment of urticaria and allergic rhinitis.
• Uses: Bilastine is a novel, nonsedating H1-antihistamine developed for symptomatic treatment of allergic rhinitis and chronic idiopathic urticaria. Labelled Bilastine. It is a novel, nonsedating H1-antihistamine developed for symptomatic treatment of allergic rhinitis and chronic idiopathic urticaria.
• Clinical Use: Bilastine is a selective histamine H1 antagonist approved for the treatment of allergic rhinoconjunctivitis and urticaria (hives). This drug, which has proven to be well tolerated in toxicology profiling, 46 was discovered by the Spainsh firm FAES Farma and was approved by the European Union in 2010.
• Drug interactions: Potentially hazardous interactions with other drugs Antivirals: concentration possibly increased by ritonavir. Grapefruit juice: concentration of bilastine reduced.

Technology Process of Bilastine

There total 70 articles about Bilastine 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: 99.65%

2-{4-[1-(4,4-dimethyl-4,5-dihydrooxazol-2-yl)-1-methylethyl]phenyl}ethyl p-toluenesulfonate (202189-76-2) + 1-(2-ethoxyethyl)-2-(piperidin-4-yl)-1H-benzo[d]imidazole dihydrochloride (1841081-72-8) → Bilastine (202189-78-4)

Guidance literature:

With potassium carbonate; In butanone; for 20h; Reflux;

Reference yield: 96.0%

4-[2-[4-[1-(2-ethoxyethyl)-1H-benzimidazol-2-yl]-1-piperidine]ethyl]-α,α-dimethylphenylacetic acid methyl ester (1181267-38-8) → Bilastine (202189-78-4)

Guidance literature:

With water; sodium hydroxide; In ethanol; for 16h; Reflux;

Reference yield: 95.0%

C31H41N3O3 → Bilastine (202189-78-4)

Guidance literature:

With methanol; sodium hydroxide; for 5h; Reflux;

upstream raw materials:

2-(2-(4-(2-(4-(1-(2-ethoxyethyl)-1H-benzo[d]imidazol-2-yl)piperidin-1-yl)ethyl)phenyl)propan-2-yl)-4,4-dimethyl-4,5-dihydrooxazole

4-[2-[4-[1-(2-ethoxyethyl)-1H-benzimidazol-2-yl]-1-piperidine]ethyl]-α,α-dimethylphenylacetic acid methyl ester

tert-butyl 4-(1H-benzo[d]imidazol-2-yl)piperidine-1-carboxylate

2-methyl-2-(4-(2-hydroxyethyl)phenyl)propionic acid methyl ester

Refernces

• 1、 -. "TITLE: PROCESS FOR THE PREPARATION OF BILASTINE". Paragraph 0131; 0141; 0143. . Retrieved 2020/05/12.
• 2、 -. "Preparation process of bilastine". Paragraph 0055-0060. . Retrieved 2020/05/02.