Ebastine

Ebastine

Clinical data
AHFS/Drugs.com	International Drug Names
Routes of administration	Oral
ATC code	R06AX22 (WHO)
Pharmacokinetic data
Protein binding	Greater than 95%
Metabolism	Hepatic (CYP3A4-mediated), to carebastine
Biological half-life	15 to 19 hours (carebastine)
Identifiers
IUPAC name 4-(4-benzhydryloxy-1-piperidyl)-1-(4-tert-butylphenyl)butan-1-one
CAS Number	90729-43-4 Y
PubChem CID	3191
ChemSpider	3079 Y
UNII	TQD7Q784P1
ChEMBL	CHEMBL305660 Y
ECHA InfoCard	100.106.831
Chemical and physical data
Formula	C32H39NO2
Molar mass	469.658 g/mol
3D model (Jmol)	Interactive image
SMILES O=C(c1ccc(cc1)C(C)(C)C)CCCN4CCC(OC(c2ccccc2)c3ccccc3)CC4
InChI InChI=1S/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 Y Key:MJJALKDDGIKVBE-UHFFFAOYSA-N Y

Ebastine (trade names Evastin, Kestine, Ebastel, Aleva, Ebatrol) is a H₁antihistamine with low potential for causing drowsiness.

It does not penetrate the blood–brain barrier to a significant amount and thus combines an effective block of the H₁ receptor in peripheral tissue with a low incidence of central side effects, i.e. seldom causing sedation or drowsiness.

The patent in which the structure of ebastine is first mentioned is EP 134124  in Europe and US 4550116  in the US. The substance is often provided in micronised form due to poor water solubility.

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.

Ebastine is available in different formulations (tablets, fast dissolving tablets and syrup) and commercialized under different brand names around the world,Ebatrol, Ebet, Ebastel FLAS, Kestine, KestineLIO, KestinLYO, EstivanLYO, Evastel Z, etc.

After oral administration, ebastine undergoes extensive first-pass metabolism by hepatic into its active carboxylic acid metabolite, carebastine. This conversion is practically complete.

Data from over 8,000 patients in more than 40 clinical trials and studies suggest efficacy of ebastine in the treatment of intermittent allergic rhinitis, persistent allergic rhinitis and other indications.