Ebastine

"Aleva" redirects here. For the pepper called "aleva", see Cayenne pepper.

Ebastine

Systematic (IUPAC) name
4-(4-benzhydryloxy-1-piperidyl)-1-(4-tert-butylphenyl)butan-1-one
Clinical data
AHFS/Drugs.com	International Drug Names
Routes of administration	Oral
Pharmacokinetic data
Protein binding	Greater than 95%
Metabolism	Hepatic (CYP3A4-mediated), to carebastine
Biological half-life	15 to 19 hours (carebastine)
Identifiers
CAS Number	90729-43-4 Y
ATC code	R06AX22 (WHO)
PubChem	CID: 3191
ChemSpider	3079 Y
UNII	TQD7Q784P1 Y
ChEMBL	CHEMBL305660 Y
Chemical data
Formula	C32H39NO2
Molecular mass	469.658 g/mol
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
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Ebastine (trade names Evastin, Kestine, Ebastel, Aleva, Ebatrol) is a H₁ antihistamine 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.

Uses and availability

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.

Pharmacokinetic profile

After oral administration, ebastine undergoes extensive first-pass metabolism by hepatic cytochrome P450 3A4 into its active carboxylic acid metabolite, carebastine. This conversion is practically complete.

Carebastine, the active metabolite

Efficacy

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.

Safety

Ebastine has shown overall safety and tolerability profile with no cognitive/psychomotor impairment and no sedation worse than placebo, and cardiac safety, that is, no QT prolongation. The incidence of most commonly reported adverse events was comparable between the ebastine and placebo groups, which confirms that ebastine has a favourable safety profile.

While experiments in pregnant animals showed no risk for the unborn, no such data are available in humans. It is not known whether ebastine passes into the breast milk.