Ebastine

Last updated

Ebastine
Ebastine.svg
Clinical data
AHFS/Drugs.com International Drug Names
Routes of
administration 		Oral
ATC code
Pharmacokinetic data
Protein binding Greater than 95%
Metabolism Hepatic (CYP3A4-mediated), to carebastine
Elimination half-life 15 to 19 hours (carebastine)
Identifiers
  • 4-(4-benzhydryloxy-1-piperidyl)-1-(4-tert-butylphenyl)butan-1-one
CAS Number
PubChem CID
ChemSpider
UNII
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard 100.106.831 OOjs UI icon edit-ltr-progressive.svg
Chemical and physical data
Formula C32H39NO2
Molar mass 469.669 g·mol−1
3D model (JSmol)
  • O=C(c1ccc(cc1)C(C)(C)C)CCCN4CCC(OC(c2ccccc2)c3ccccc3)CC4
  • 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 Yes check.svgY
  • Key:MJJALKDDGIKVBE-UHFFFAOYSA-N Yes check.svgY
   (verify)

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

Contents

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. [1] [2] [3]

It was patented in 1983 by Almirall S.A and came into medical use in 1990. [4] The substance is often provided in micronised 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. [5] It is available in 10 and 20 mg tablets [6] and as fast-dissolving tablets, [7] as well as in pediatric syrup. It has a recommended flexible daily dose of 10 or 20 mg, depending on disease severity.

Data from over 8,000 patients in more than 40 clinical trials[ failed verification ] and studies [3] [5] [6] [8] [9] [10] 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 [6] and no sedation [6] worse than placebo, [2] and cardiac safety, that is, no QT prolongation. [6] 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.

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 Carebastine skeletal.svg
Carebastine, the active metabolite

Brand names

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.[ medical citation needed ]

See also

Related Research Articles

H1 antagonists, also called H1 blockers, are a class of medications that block the action of histamine at the H1 receptor, helping to relieve allergic reactions. Agents where the main therapeutic effect is mediated by negative modulation of histamine receptors are termed antihistamines; other agents may have antihistaminergic action but are not true antihistamines.

<span class="mw-page-title-main">Allergic rhinitis</span> Nasal inflammation due to allergens in the air

Allergic rhinitis, of which the seasonal type is called hay fever, is a type of inflammation in the nose that occurs when the immune system overreacts to allergens in the air. It is classified as a type I hypersensitivity reaction. Signs and symptoms include a runny or stuffy nose, sneezing, red, itchy, and watery eyes, and swelling around the eyes. The fluid from the nose is usually clear. Symptom onset is often within minutes following allergen exposure, and can affect sleep and the ability to work or study. Some people may develop symptoms only during specific times of the year, often as a result of pollen exposure. Many people with allergic rhinitis also have asthma, allergic conjunctivitis, or atopic dermatitis.

<span class="mw-page-title-main">Loratadine</span> Antihistamine medication

Loratadine, sold under the brand name Claritin among others, is a medication used to treat allergies. This includes allergic rhinitis and hives. It is also available in drug combinations such as loratadine/pseudoephedrine, in which it is combined with pseudoephedrine, a nasal decongestant. It is taken orally.

<span class="mw-page-title-main">Hydroxyzine</span> Antihistamine drug

Hydroxyzine, sold under the brand names Atarax and Vistaril among others, is an antihistamine medication. It is used in the treatment of itchiness, anxiety, insomnia, and nausea. It is used either by mouth or injection into a muscle.

<span class="mw-page-title-main">Desloratadine</span> Allergy medication

Desloratadine sold under the brand name Clarinex among others, is a tricyclic H1 inverse agonist that is used to treat allergies. It is an active metabolite of loratadine.

<span class="mw-page-title-main">Hives</span> Skin disease characterized by red, raised, and itchy bumps

Hives, also known as urticaria, is a kind of skin rash with red, raised, itchy bumps. Hives may burn or sting. The patches of rash may appear on different body parts, with variable duration from minutes to days, and does not leave any long-lasting skin change. Fewer than 5% of cases last for more than six weeks. The condition frequently recurs.

<span class="mw-page-title-main">Cetirizine</span> Antihistamine medication

Cetirizine is a second-generation antihistamine used to treat allergic rhinitis, dermatitis, and urticaria (hives). It is taken by mouth. Effects generally begin within thirty minutes and last for about a day. The degree of benefit is similar to other antihistamines such as diphenhydramine, which is a first-generation antihistamine.

<span class="mw-page-title-main">Fexofenadine</span> Antihistamine medication

Fexofenadine, sold under the brand name Allegra among others, is an antihistamine pharmaceutical drug used in the treatment of allergy symptoms, such as hay fever and urticaria.

<span class="mw-page-title-main">Allergic conjunctivitis</span> Medical condition

Allergic conjunctivitis (AC) is inflammation of the conjunctiva due to allergy. Although allergens differ among patients, the most common cause is hay fever. Symptoms consist of redness, edema (swelling) of the conjunctiva, itching, and increased lacrimation. If this is combined with rhinitis, the condition is termed allergic rhinoconjunctivitis (ARC).

<span class="mw-page-title-main">Dermatographic urticaria</span> Skin disorder

Dermatographic urticaria is a skin disorder and one of the most common types of urticaria, affecting 2–5% of the population.

<span class="mw-page-title-main">Levocetirizine</span> Antihistamine drug

Levocetirizine, sold under the brand name Xyzal, among others, is a second-generation antihistamine used for the treatment of allergic rhinitis and long-term hives of unclear cause. It is less sedating than older antihistamines. It is taken by mouth.

<span class="mw-page-title-main">Ketotifen</span> Antihistamine medication

Ketotifen is an antihistamine medication and a mast cell stabilizer used to treat allergic conditions such as conjunctivitis, asthma, and urticaria (hives). Ketotifen is available in ophthalmic and oral forms: the ophthalmic form relieves eye itchiness and irritation associated with seasonal allergies, while the oral form helps prevent systemic conditions such as asthma attacks and allergic reactions. In addition to treating allergies, ketotifen has shown efficacy in managing systemic mast cell diseases such as mastocytosis and mast cell activation syndrome (MCAS), which involve abnormal accumulation or activation of mast cells throughout the body. Ketotifen is also used for other allergic-type conditions like atopic dermatitis (eczema) and food allergies.

Histamine H<sub>1</sub> receptor Histamine receptor

The H1 receptor is a histamine receptor belonging to the family of rhodopsin-like G-protein-coupled receptors. This receptor is activated by the biogenic amine histamine. It is expressed in smooth muscles, on vascular endothelial cells, in the heart, and in the central nervous system. The H1 receptor is linked to an intracellular G-protein (Gq) that activates phospholipase C and the inositol triphosphate (IP3) signalling pathway. Antihistamines, which act on this receptor, are used as anti-allergy drugs. The crystal structure of the receptor has been determined (shown on the right/below) and used to discover new histamine H1 receptor ligands in structure-based virtual screening studies.

<span class="mw-page-title-main">Azelastine</span> Chemical compound

Azelastine, sold under the brand name Astelin among others, is a H1 receptor-blocking medication primarily used as a nasal spray to treat allergic rhinitis (hay fever) and as eye drops for allergic conjunctivitis. Other uses may include asthma and skin rashes for which it is taken by mouth. Onset of effects is within minutes when used in the eyes and within an hour when used in the nose. Effects last for up to 12 hours.

<span class="mw-page-title-main">Acrivastine</span> Chemical compound

Acrivastine is a medication used for the treatment of allergies and hay fever. It is a second-generation H1-receptor antagonist antihistamine and works by blocking histamine H1 receptors.

<span class="mw-page-title-main">Mequitazine</span> Chemical compound

Mequitazine (trade name Primalan) is an H1 antagonist and anticholinergic of the phenothiazine chemical class. It is used to treat allergies and rhinitis.

<span class="mw-page-title-main">Rupatadine</span> Second generation H1-antihistamine

Rupatadine is a second generation antihistamine and platelet-activating factor antagonist used to treat allergies. It was discovered and developed by Uriach and is marketed as Rupafin and under several other trade names.

<span class="mw-page-title-main">Antihistamine</span> Drug that blocks histamine or histamine agonists

Antihistamines are drugs which treat allergic rhinitis, common cold, influenza, and other allergies. Typically, people take antihistamines as an inexpensive, generic drug that can be bought without a prescription and provides relief from nasal congestion, sneezing, or hives caused by pollen, dust mites, or animal allergy with few side effects. Antihistamines are usually for short-term treatment. Chronic allergies increase the risk of health problems which antihistamines might not treat, including asthma, sinusitis, and lower respiratory tract infection. Consultation of a medical professional is recommended for those who intend to take antihistamines for longer-term use.

<span class="mw-page-title-main">Bilastine</span> Antihistamine medication

Bilastine is an antihistamine medication used to treat hives (urticaria), allergic rhinitis and itchy inflamed eyes (allergic conjunctivitis) caused by an allergy. It is a second-generation antihistamine and takes effect by selectively inhibiting the histamine H1 receptor, preventing these allergic reactions. Bilastine has an effectiveness similar to cetirizine, fexofenadine, and desloratadine.

<span class="mw-page-title-main">Ze339</span> Brand of herbal extracts

Ze339 brand herbal extracts are taken from the leaves of a unique variety (Petzell) of the butterbur plant. Petzell is grown on GAP-managed farms in Europe.

References

  1. ↑ Tagawa M, Kano M, Okamura N, Higuchi M, Matsuda M, Mizuki Y, et al. (November 2001). "Neuroimaging of histamine H1-receptor occupancy in human brain by positron emission tomography (PET): a comparative study of ebastine, a second-generation antihistamine, and (+)-chlorpheniramine, a classical antihistamine". British Journal of Clinical Pharmacology. 52 (5): 501–509. doi:10.1046/j.1365-2125.2001.01471.x. PMC   2014616 . PMID   11736858. Open Access logo PLoS transparent.svg
  2. 1 2 Dinnendahl, V, Fricke, U, eds. (2010). Arzneistoff-Profile (in German). Vol. 4 (23 ed.). Eschborn, Germany: Govi Pharmazeutischer Verlag. ISBN   978-3-7741-98-46-3.
  3. 1 2 Bousquet J, Gaudaño EM, Palma Carlos AG, Staudinger H (June 1999). "A 12-week, placebo-controlled study of the efficacy and safety of ebastine, 10 and 20 mg once daily, in the treatment of perennial allergic rhinitis. Multicentre Study Group". Allergy. 54 (6): 562–568. doi:10.1034/j.1398-9995.1999.00984.x. PMID   10435469. S2CID   24186838.
  4. ↑ Fischer J, Ganellin CR (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 549. ISBN   9783527607495.
  5. 1 2 Van Cauwenberge P, De Belder T, Sys L (August 2004). "A review of the second-generation antihistamine ebastine for the treatment of allergic disorders". Expert Opinion on Pharmacotherapy. 5 (8): 1807–1813. doi:10.1517/14656566.5.8.1807. PMID   15264995. S2CID   24967427.
  6. 1 2 3 4 5 Sastre J (December 2008). "Ebastine in allergic rhinitis and chronic idiopathic urticaria". Allergy. 63 (Suppl 89): 1–20. doi: 10.1111/j.1398-9995.2008.01897.x . PMID   19032340. S2CID   12474747.
  7. ↑ Antonijoan R, García-Gea C, Puntes M, Pérez J, Esbrí R, Serra C, et al. (May 2007). "Comparison of inhibition of cutaneous histamine reaction of ebastine fast-dissolving tablet (20 mg) versus desloratadine capsule (5 mg): a randomized, double-blind, double-dummy, placebo-controlled, three-period crossover study in healthy, nonatopic adults". Clinical Therapeutics. 29 (5): 814–822. doi:10.1016/j.clinthera.2007.05.001. PMID   17697901.
  8. ↑ Ratner P, Falqués M, Chuecos F, Esbrí R, Gispert J, Peris F, et al. (December 2005). "Meta-analysis of the efficacy of ebastine 20 mg compared to loratadine 10 mg and placebo in the symptomatic treatment of seasonal allergic rhinitis". International Archives of Allergy and Immunology. 138 (4): 312–318. doi:10.1159/000088869. PMID   16224195. S2CID   4126940.
  9. ↑ Antonijoan RM, García-Gea C, Puntes M, Valle M, Esbri R, Fortea J, Barbanoj MJ (2007). "A comparison of ebastine 10 mg fast-dissolving tablet with oral desloratadine and placebo in inhibiting the cutaneous reaction to histamine in healthy adults". Clinical Drug Investigation. 27 (7): 453–461. doi:10.2165/00044011-200727070-00002. PMID   17563125. S2CID   23324628.
  10. ↑ Gehanno P, Bremard-Oury C, Zeisser P (June 1996). "Comparison of ebastine to cetirizine in seasonal allergic rhinitis in adults". Annals of Allergy, Asthma & Immunology. 76 (6): 507–512. doi:10.1016/S1081-1206(10)63269-3. PMID   8673684.
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