90729-43-4 Usage
Description
Ebastine is a second-generation histamine H1 receptor antagonist that effectively blocks the H1 receptor in peripheral tissue without penetrating the blood-brain barrier. This property allows it to prevent side effects such as sedation and drowsiness. It is primarily used for treating allergic conditions and acts as an alternative decongestant. Upon entering the human body, it is converted to its active carboxylic acid metabolite, carebastine, through the action of hepatic cytochrome P450 3A4. Ebastine exhibits high safety, without causing cognitive or psychomotor impairment, but may cause side effects such as inflammation of the nasal air-cavities, sore throat, indigestion, nausea, headache, and abdominal pain.
Uses
Used in Pharmaceutical Industry:
Ebastine is used as a once-daily histamine H1-receptor antagonist for the treatment of allergic rhinitis and chronic idiopathic urticaria. It is available in various forms, including 10 and 20 mg tablets, fast-dissolving tablets, and pediatric syrup, with a recommended flexible daily dose of 10 or 20 mg depending on the severity of the disease.
Used in Allergy Treatment:
Ebastine is used as a nonsedating antihistamine to alleviate symptoms of hay fever, perennial rhinitis, and urticaria. Its antihistamine activity is attributed to its metabolite, carebastine, which helps in reducing inflammation and other allergic reactions.
Used in Decongestant Alternatives:
Ebastine serves as an alternative decongestant, providing relief from nasal congestion without causing sedation or other central nervous system side effects. This makes it a suitable option for individuals who require decongestant effects without the associated sedative properties.
References
https://pubchem.ncbi.nlm.nih.gov/compound/3191#section=Top
http://www.tabletwise.com/medicine/ebastine/side-effects
http://www.druginfosys.com/drug.aspx?drugcode=897&type=1
Manufacturing Process
(a) A mixture of 4-hydroxypiperidine (40.4 g; 0.4 moles), p-tert-butyl-ω-
chlorobutyrophenone (105 g, 0.44 moles), sodium bicarbonate (67.2 g; 0.8
moles) and a crystal of potassium iodide in methyl isobutyl ketone (1 liter)
was boiled under reflux for 24 hours. After cooling, the reaction mixture waswashed with water, dried (Na2SO4) and the solvent removed in vacuum. The
residue was salified with the stoichiometric amount of fumaric acid in a
mixture of acetone and ethanol to give 1-[3-(4-tert-butylbenzoyl)propyl]-4-
hydroxypiperidine fumarate (148 g), melting point 163-165°C. This compound
was converted into the free base, and 1-[3-(4-tert-butylbenzoyl)propyl]-4-
hydroxypiperidine was obtained and recrystallized from a mixture of diethyl
ether and petroleum ether (boiling point 50-70°C). 102 g were obtained (yield
84%), melting point 63-65°C.(b) A mixture of 1-[3-(tert-butylbenzoyl)propyl]-4-hydroxypiperidine (60.68 g;
0.2 moles) and sodium carbonate (42.4 g; 0.4 moles) in methyl isobutyl
ketone (500 ml) was heated to the boiling point and a solution of
diphenylmethyl bromide (49.42 g; 0.2 moles) in methyl isobutyl ketone (75
ml) was slowly added in 1.5 hours. The resulting mixture was boiled under
reflux for another 12 hours, and then another solution of diphenylmethyl
bromide (24.71 g; 0.1 moles) in methyl isobutyl ketone (50 ml) was added
and the mixture boiled under reflux again for 12 hours. Another solution of
diphenylmethyl bromide in the same quantity was added and after refluxing
for 12 additional hours the reaction mixture was cooled, washed with water,
dried (Na2SO4) and the solvent removed in vacuum.The residual oil was treated with the stoichiometric amount of fumaric acid in
ethanol and 4-diphenylmethoxy-1-[3-(4-tert-butylbenzoyl)propyl]piperidine
fumarate crystallized. After recrystallisation from ethanol the pure compound
was obtained (88 g; yield 75%), melting point 197-198°C.
Therapeutic Function
Antihistaminic, Antiallergic, Calcium entry blocker
Biochem/physiol Actions
Ebastine is a non-sedating histamine H1 receptor antagonist, which inhibits allergen-induced bronchospasm in conscious guinea pigs. Unlike other compounds in this category, ebastine does not prolong the QT interval at up to five times the recommended therapeutic dose.
Check Digit Verification of cas no
The CAS Registry Mumber 90729-43-4 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 9,0,7,2 and 9 respectively; the second part has 2 digits, 4 and 3 respectively.
Calculate Digit Verification of CAS Registry Number 90729-43:
(7*9)+(6*0)+(5*7)+(4*2)+(3*9)+(2*4)+(1*3)=144
144 % 10 = 4
So 90729-43-4 is a valid CAS Registry Number.
InChI:InChI=1/C32H39NO2/c1-32(2,3)28-18-16-25(17-19-28)30(34)15-10-22-33-23-20-29(21-24-33)35-31(26-11-6-4-7-12-26)27-13-8-5-9-14-27/h4-9,11-14,16-19,29,31H,10,15,20-24H2,1-3H3
90729-43-4Relevant articles and documents
Method for preparing ebastine
-
Paragraph 0052-0064, (2019/04/27)
The invention provides a method for preparing ebastine. The method comprises the following steps: condensing an initial raw material benzophenone and 4-hydroxypiperidine to obtain 4-benzhydryloxypiperidine; condensing with 4-chloro-1-(4-tert-butylphenyl)-1-butanone to obtain ebastine. According to the method, benzophenone with low price is used as the initial raw material, has low cost and is simple and convenient to operate, only one reaction kettle is used, alkaline washing and rinsing are performed in the middle process, and the final product can be obtained by freezing and crystallizing with alcohol. The method has the advantages of good economic benefit, high safety, high yield, good purity and the like, and is suitable for industrial production.
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 30, (2011/10/13)
The present invention describes processes for the preparation of 1-[4-(1,1-dimethylethyl)phenyl]-4-[4-(diphenylmethoxy)-1-piperidinyl]-1-butanone and acid addition salts thereof.
PROCESS OF PREPARING EBASTINE
-
Page/Page column 11, (2010/01/30)
The present invention relates to a novel process for preparing ebastine from 1-[4-(1,1-dimethylethyl) phenyl]-4-(4-hydroxy piperidin-1-yl) butan-1-one and diphenyl methanol, which is easily reproducible on an industrial scale. A process for preparation of 1-[4-(1,1-dimethylethyl) phenyl]-4-(4-hydroxy piperidin-1-yl) butan-1-one.
