Ebastine

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Ebastine

Systematic (IUPAC) name
4-(4-benzhydryloxy-1-piperidyl)-1-(4-tert-butylphenyl)butan-1-one
Clinical data
AHFS/Drugs.com	International Drug Names
Legal status	?
Routes	Oral
Pharmacokinetic data
Protein binding	Greater than 95%
Metabolism	Hepatic (CYP3A4-mediated), to carebastine
Half-life	15 to 19 hours (carebastine)
Identifiers
CAS number	90729-43-4^Y
ATC code	R06AX22
PubChem	CID 3191
ChemSpider	3079^Y
UNII	TQD7Q784P1^Y
ChEMBL	CHEMBL305660^Y
Chemical data
Formula	C₃₂H₃₉N O₂
Mol. 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
Y (what is this?) (verify)

Ebastine (trade names Evastin, Kestine, Ebastel, Aleva, Ebatrol) is a non-sedating H₁ antihistamine.

It does not penetrate the blood–brain barrier and thus allows an effective block of the H₁ receptor in peripheral tissue without a central side effect, i.e. not causing sedation or drowsiness.

The basic patent for ebastine in Europe is EP-B-134124. It is often provided in micronised form, due to poor water solubility.

Introduction

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, Ebet, Ebastel FLAS, Kestine, KestineLIO, KestinLYO, EstivanLYO, Evastel Z, Ebatrol-Delta Pharma Bangladesh, ETC.

Pharmacokinetic profile

The structure differs from other second generation antihistamines. After oral administration, ebastine undergoes extensive first-pass metabolism by hepatic cytochrome P450 3A4 into its active carboxylic acid metabolite, carebastine. This reaction has a conversion rate of 100%.

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.it also considered type 2 antihistamine

Safety

Ebastine has shown overall safety and tolerability profile with no cognitive/psychomotor impairment, no sedation and cardiac safety. 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. It should not be used by pregnant women without consulting a doctor.

References

Peyri J, Vidal J, Marrón J et al.Ebastine in chronic urticaria: a double-blind placebo controlled study J Dermatol Treat 1991;2:51-3.
Gehanno P, Bremard-Oury C, Zeisser P. Comparison of ebastine to cetirizine in seasonal allergic rhinitis in adults. Annals of Allergy, Asthma and Immunol 1996;76 (6): 507-12.
Bousquet J, Gaudaño EM, Palama Carlos AG et al. A 12-week, placebo-controlled study of the efficacy and safety opf ebastine, 10 and 20 mg once daily, in the treatment of perennial allergic rhinitis. Allergy 1999;S4: S62-S68.
Tagawa M, Kano M, Okamura N, et al.Neuroimaging of histamine H1-receptor occupancy in human brain by positron emission tomography (PET): a comparative study of ebastine, a second-generation antihistamine, and (+)-clorphrniramine, a classical antihistamine.Br J Clin Pharmacl 2001;52:501-509.
Van Cauwenberge P, de Belder T, Sys L. A review of the second-generation antihistamine ebastine for the treatment of allergic disorders. Exp Rew Pharmacother 2004;5(8):1807-13.
Ratner P, Falqués M, Chuecos F et al. Meta-analysis of the efficacy of ebastine 20 mg compared to loratadine 10 mg and placebo in the symptomatic treatment of seasonal allergic rhinitis.Int Arch Allergy Immunol 2005;138:312-8.
Antonijoan RM, García- Gea C; Puntes Met al. A comparison of ebastine 10 mg fast-dissolving tablet with oral desloratadine and placebo in inhibiting the cutaneous reaction to histamine in healthy adults.Clin Drug Invest 2007;27(7):453-61.
Antonijoan R, García-Gea C, Puntes M et al.Comparison of inhibition of cutaneous histamine reaction of ebastine fast-dissolving tablet (20 mg) versus desloratadine capsules (5 mg): a randomized, double-blind, double-dummy, placebo-controlled, three period crossover study in healthy, nonatopic adults. Clin Ther 2007;29(5):814-22.
Salvà M, Carreño B, Pintos M et al. Phase I, single dose, open label, randomized, crossover bioequivalence studies of ebastine 10 mg and 20 mg regular tablets vs 10 and 20 mg fast-dissolving tablets in healthy male volunteers. J Invest Allergol Clin Immunol 2004;14(4) (Suppl 1): S5.
J Sastre. Ebastine in allergic rhinitis and chronic idiopathic urticaria. Allergy 2008;63( Suppl 89):1-20.

External links

"KESTINE Package Insert". South African Electronic Package Inserts. 1997-10-24. Retrieved 2007-04-01.

v t e Antihistamines (R06)

Aminoalkyl ethers	Bromazine (bromodiphenhydramine) Carbinoxamine Clemastine Chlorphenoxamine Diphenylpyraline Diphenhydramine Doxylamine Orphenadrine Phenyltoloxamine

Substituted alkylamines	Brompheniramine Chlorphenamine Dexbrompheniramine (+pseudoephedrine) Dexchlorpheniramine (+betamethasone) Dimetindene Pheniramine Talastine

Substituted ethylenediamines	Chloropyramine Histapyrrodine Mepyramine Methapyrilene Tripelennamine (pyribenzamine)

Phenothiazine derivatives	Alimemazine Hydroxyethylpromethazine Isothipendyl Mequitazine Methdilazine Oxomemazine Promethazine

Piperazine derivatives	Buclizine Cetirizine Chlorcyclizine Cinnarizine Cyclizine Hydroxyzine Levocetirizine Meclizine Niaprazine Oxatomide

Others for systemic use	Antazoline Azatadine Bamipine Cyproheptadine Deptropine Ebastine Emedastine Epinastine Ketotifen Latrepirdine Mebhydrolin Mizolastine Olopatadine Phenindamine Pimethixene Pyrrobutamine Quifenadine Rupatadine Triprolidine selective (Acrivastine Astemizole Azelastine Bilastine Desloratadine Fexofenadine Loratadine Terfenadine)

For topical use	Bamipine Chloropyramine Chlorphenoxamine Clemastine Dimetindene Diphenhydramine Isothipendyl Mepyramine Promethazine Thenalidine

Histaminergics

Receptor

H₁	Agonists: 2-Pyridylethylamine Betahistine Histamine HTMT UR-AK49 Antagonists: 1st generation: 4-Methyldiphenhydramine Alimemazine Antazoline Azatadine Bamipine Benzatropine/Benztropine Bepotastine Bromazine Brompheniramine Buclizine Captodiame Carbinoxamine Chlorcyclizine Chloropyramine Chlorothen Chlorphenamine Chlorphenoxamine Cinnarizine Clemastine Clobenzepam Clocinizine Cyclizine Cyproheptadine Dacemazine Deptropine Dexbrompheniramine Dexchlorpheniramine Dimenhydrinate Dimetindene Diphenhydramine Diphenylpyraline Doxylamine Embramine Etodroxizine Etybenzatropine/Ethylbenztropine Etymemazine Flunarizine Histapyrrodine Homochlorcyclizine Hydroxyethylpromethazine Hydroxyzine Isopromethazine Isothipendyl Meclozine Mepyramine/Pyrilamine Mequitazine Methafurylene Methapyrilene Methdilazine Moxastine Niaprazine Orphenadrine Oxatomide Oxomemazine Phenindamine Pheniramine Phenyltoloxamine Pimethixene Piperoxan Pipoxizine Promethazine Propiomazine Pyrrobutamine Talastine Thenalidine Thenyldiamine Thiazinamium Thonzylamine Tolpropamine Tripelennamine Triprolidine 2nd generation: Acrivastine Alinastine Astemizole Azelastine Bamirastine Barmastine Bepiastine Bepotastine Bilastine Cabastinen Carebastine Cetirizine Clemastine Clemizole Clobenztropine Dorastine Ebastine Emedastine Epinastine Flezelastine Ketotifen Latrepirdine Levocabastine Linetastine Loratadine Mapinastine Mebhydrolin Mizolastine Moxastine Noberastine Octastine Olopatadine Perastine Piclopastine Rocastine Rupatadine Setastine Talastine Temelastine Terfenadine Zepastine 3rd generation: Desloratadine Fexofenadine Levocetirizine Ungrouped: Belarizine Efletirizine Elbanizine Flotrenizine Medrylamine Napactadine Pibaxizine Tagorizine Trelnarizine Trenizine Vapitadine Miscellaneous: Tricyclic antidepressants (amitriptyline, doxepin, trimipramine, etc) Tetracyclic antidepressants (mianserin, mirtazapine, etc) Typical antipsychotics (chlorpromazine, thioridazine, etc) Atypical antipsychotics (clozapine, olanzapine, quetiapine, etc)

H₂	Agonists: Amthamine Betazole Dimaprit Histamine HTMT Impromidine UR-AK49 Antagonists: Bisfentidine Burimamide Cimetidine Dalcotidine Donetidine Ebrotidine Etintidine Famotidine Lafutidine Lamtidine Lavoltidine/Loxtidine Lupitidine Metiamide Mifentidine Niperotidine Nizatidine Osutidine Oxmetidine Pibutidine Quisultazine/Quisultidine Ramixotidine Ranitidine Roxatidine Sufotidine Tiotidine Tuvatidine Venritidine Xaltidine

H₃	Agonists: α-Methylhistamine Cipralisant Histamine Imetit Immepip Immethridine Methimepip Proxyfan Antagonists: A-349,821 A-423,579 ABT-239 Betahistine Burimamide Ciproxifan Clobenpropit Conessine GSK-189,254 Impentamine Iodophenpropit JNJ-5,207,852 MK-0249 NNC-38-1,049 PF-03654746 Pitolisant SCH-79,687 Thioperamide VUF-5,681

H₄	Agonists: 4-Methylhistamine Histamine VUF-8,430 Antagonists: JNJ-7,777,120 Thioperamide VUF-6,002

Transporter

VMAT	Inhibitors: Ibogaine Reserpine Tetrabenazine

Enzyme

HDC	Inhibitors: Catechin Meciadanol Naringenin Tritoqualine

HNMT	Inhibitors: Amodiaquine Diphenhydramine Harmaline Metoprine Quinacrine SKF-91,488 Tacrine

DAO	Inhibitors: Aminoguanidine

Others

Endogenous	Histamine; Precursors: L-Histidine; Cofactors: Vitamin B6

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