Ebastine: Difference between revisions

{{Short description|Antihistamine drug}}

{{cs1 config|name-list-style=vanc}}

{{Redirect|Aleva|the pepper called "aleva"|Cayenne pepper}}

{{

| verifiedrevid = 439227374

| IUPAC_name = 4-(4-benzhydryloxy-1-piperidyl)-1-(4-tert-butylphenyl)butan-1-one

| =

<!--Clinical data-->

| tradename =

| Drugs.com = {{drugs.com|international|ebastine}}

| pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X -->

| pregnancy_US = <!-- A / B / C / D / X -->

| pregnancy_category =

| legal_AU = <!-- Unscheduled / S2 / S3 / S4 / S5 / S6 / S7 / S8 / S9 -->

| legal_CA = <!-- / Schedule I, II, III, IV, V, VI, VII, VIII -->

| legal_UK = <!-- GSL / P / POM / CD / Class A, B, C -->

| legal_US = <!-- OTC / Rx-only / Schedule I, II, III, IV, V -->

| legal_status =

| routes_of_administration = Oral

<!--Pharmacokinetic data-->

| bioavailability =

| protein_bound = Greater than 95%

| metabolism = [[Liver|Hepatic]] ([[CYP3A4]]-mediated), to [[carebastine]]

| elimination_half-life = 15 to 19 hours (carebastine)

| excretion =

<!--Identifiers-->

| CAS_number_Ref = {{cascite|correct|??}}

| CAS_number = 90729-43-4

| ATC_prefix = R06

| ATC_suffix = AX22

| PubChem = 3191

| DrugBank_Ref = {{drugbankcite|correct|drugbank}}

| DrugBank =

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = TQD7Q784P1

<!--Chemical data-->

| C=32 | H=39 | N=1 | O=2

| smiles = O=C(c1ccc(cc1)C(C)(C)C)CCCN4CCC(OC(c2ccccc2)c3ccccc3)CC4

<!-- Definition and medical uses -->

'''Ebastine''' is a H₁ [[antihistamine]] with low potential for causing drowsiness.

<!-- Side effects and mechanisms -->

It does not penetrate the [[blood–brain barrier]] to a significant amount and thus combines an effective block of the [[histamine H1 receptor|H₁ receptor]] in peripheral [[biological tissue|tissue]] with a low incidence of central side effects, i.e. seldom causing sedation or drowsiness.<ref name="Tagawa 2001" /><ref name="Arzneistoff-Profile" /><ref name="Bousquet 1999" />

<!-- Society and culture -->

It was patented in 1983 by Almirall S.A and came into medical use in 1990.<ref name=Fis2006>{{cite book | vauthors = Fischer J, Ganellin CR |title=Analogue-based Drug Discovery |date=2006 |publisher=John Wiley & Sons |isbn=9783527607495 |page=549 |url=https://books.google.com/books?id=FjKfqkaKkAAC&pg=PA549 |language=en}}</ref> The substance is often provided in [[micronise]]d form due to poor water solubility.

==Uses==

Ebastine is a second-generation H1 receptor antagonist that is indicated mainly for allergic [[rhinitis]] and [[chronic idiopathic urticaria]].<ref name="Van Cauwenberge 2004" /> It is available in 10 and 20&nbsp;mg tablets<ref name="Sastre 2008" /> and as fast-dissolving tablets,<ref name="pmid 17697901" /> as well as in pediatric syrup. It has a recommended flexible daily dose of 10 or 20&nbsp;mg, depending on disease severity.

Data from over 8,000 patients in more than 40 clinical trials{{failed verification|date=March 2014}} and studies<ref name="Bousquet 1999" /><ref name="Van Cauwenberge 2004" /><ref name="Sastre 2008" /><ref name="Ratner 2005" /><ref name="pmid 17563125" /><ref name="Gehanno 1996" /> 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<ref name="Sastre 2008" /> and no sedation<ref name="Sastre 2008" /> worse than [[placebo]],<ref name="Arzneistoff-Profile" /> and cardiac safety, that is, no [[QT prolongation]].<ref name="Sastre 2008" /> 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.

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

[[File:Carebastine skeletal.svg|thumb|left|Carebastine, the active metabolite]]

{{clear left}}

====

Ebastine is available in different formulations (tablets, fast dissolving tablets and syrup) and commercialized under different brand names around the world, Ebast, Ebatin, Ebatin Fast, Ebatrol, Atmos, Ebet, Ebastel FLAS, Kestine, KestineLIO, KestinLYO, EstivanLYO, Evastel Z, Eteen (EURO Pharma Ltd.), Tebast (SQUARE), Ebasten (ACI),etc.{{medcn|date=February 2024}}

====

* [[Desloratadine]]

==References==

{{reflist|32em|refs=

Gehanno P, Bremard-Oury C, Zeisser P Comparison of ebastine to cetirizine in seasonal allergic rhinitis in adults Annals of Allergy, Asthma 76 6 .

Bousquet J, Gaudaño EM, Carlos AG A 12-week, placebo-controlled study of the efficacy and safety ebastine, 10 and 20mg once daily, in the treatment of perennial allergic rhinitis. Allergy 1999 -.

Tagawa M, Kano M, Okamura N, Neuroimaging of histamine H1-receptor occupancy in human brain by positron emission tomography (PET): a comparative study of ebastine, a second-generation antihistamine, and (+)-, a classical antihistamine 52-.

Van Cauwenberge P, Belder T, Sys L A review of the second-generation antihistamine ebastine for the treatment of allergic disorders 200458.

Ratner P, Falqués M, Chuecos F Meta-analysis of the efficacy of ebastine 20mg compared to loratadine 10mg and placebo in the symptomatic treatment of seasonal allergic rhinitis Allergy 138.

Antonijoan RM, García-Gea C Puntes A comparison of ebastine 10mg fast-dissolving tablet with oral desloratadine and placebo in inhibiting the cutaneous reaction to histamine in healthy adults Drug 277.

Antonijoan R, García-Gea C, Puntes M Comparison of inhibition of cutaneous histamine reaction of ebastine fast-dissolving tablet (20mg) versus desloratadine (5mg): a randomized, double-blind, double-dummy, placebo-controlled, threeperiod crossover study in healthy, nonatopic adults 295.

<ref name="Sastre 2008">{{cite journal | vauthors = Sastre J | title = Ebastine in allergic rhinitis and chronic idiopathic urticaria | journal = Allergy | volume = 63 | issue = Suppl 89 | pages = 1–20 | date = December 2008 | pmid = 19032340 | doi = 10.1111/j.1398-9995.2008.01897.x | s2cid = 12474747 | doi-access = free }}</ref>

<ref name="Arzneistoff-Profile">{{cite book|title=Arzneistoff-Profile|editor1=Dinnendahl, V |editor2=Fricke, U |publisher=Govi Pharmazeutischer Verlag|location=Eschborn, Germany|year=2010|edition=23|volume=4|isbn=978-3-7741-98-46-3|language=German}}</ref>}}

* {{cite thesis |url=https://dspace.bracu.ac.bd/xmlui/handle/10361/13923 |title=Comparative in vitro quality evaluation of different brands of Ebastine 10 mg tablets commercially available in Bangladesh |publisher=Brac University |date=2019 |access-date=2024-07-14}}

==External links==

*{{cite web | url = http://home.intekom.com/pharm/lennon/kestine.html | title = KESTINE Package Insert | date = 1997-10-24 | = 2007-04-01 | publisher = [[South Africa]]n Electronic Package Inserts}}

{{Antihistamines}}

[[Category:]]

[[Category:Peripherally selective drugs]]