Details
Stereochemistry | ACHIRAL |
Molecular Formula | C32H39NO2 |
Molecular Weight | 469.6576 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
CC(C)(C)C1=CC=C(C=C1)C(=O)CCCN2CCC(CC2)OC(C3=CC=CC=C3)C4=CC=CC=C4
InChI
InChIKey=MJJALKDDGIKVBE-UHFFFAOYSA-N
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
Molecular Formula | C32H39NO2 |
Molecular Weight | 469.6576 |
Charge | 0 |
Count |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Optical Activity | NONE |
DescriptionSources: http://www.ncbi.nlm.nih.gov/pubmed/19032340
Sources: http://www.ncbi.nlm.nih.gov/pubmed/19032340
Ebastine is an antihistamine which blocks H1-receptors through its carboxylic acid metabolite. Ebastine is indicated for the treatment of allergic rhinitis and chronic idiopathic urticaria.
CNS Activity
Sources: http://www.ncbi.nlm.nih.gov/pubmed/11328664
Curator's Comment: Ebastine BBB transport was studied on rats, mice and bovine brain. Ebastine has shown limmited transport, while its active metabolite, carebastine, was effectively transported by P-gp.
Originator
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: P35367 Gene ID: 3269.0 Gene Symbol: HRH1 Target Organism: Homo sapiens (Human) Sources: http://www.ncbi.nlm.nih.gov/pubmed/19032340 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | EBATROL Approved UseUnknown |
|||
Primary | EBATROL Approved UseUnknown |
PubMed
Title | Date | PubMed |
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Inhibition of the histamine wheal by ebastine compared with cetirizine, fexofenadine and loratadine at steady state. | 2002 |
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Chronic urticaria: a role for newer immunomodulatory drugs? | 2003 |
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Implementation of guidelines for seasonal allergic rhinitis: a randomized controlled trial. | 2003 Aug |
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Rabbit aorta converts 15-HPETE to trihydroxyeicosatrienoic acids: potential role of cytochrome P450. | 2003 Dec 1 |
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In vitro inhibition of human small intestinal and liver microsomal astemizole O-demethylation: different contribution of CYP2J2 in the small intestine and liver. | 2003 Jun |
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[Effect of H1 histamine receptor antagonists on T cell functions]. | 2003 Nov |
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A study comparing the inhibitory effects of single and repeated oral doses of ebastine and fexofenadine against histamine-induced skin reactivity. | 2003 Nov |
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Ebastine inhibits T cell migration, production of Th2-type cytokines and proinflammatory cytokines. | 2003 Nov |
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Fixed drug eruption due to loratadine. | 2003 Sep-Oct |
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Cetirizine: a review of its use in allergic disorders. | 2004 |
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Pharmacokinetics and safety of ebastine in patients with impaired hepatic function compared with healthy volunteers: a phase I open-label study. | 2004 |
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Efficacy and safety of ebastine 20 mg compared to loratadine 10 mg once daily in the treatment of seasonal allergic rhinitis: a randomized, double-blind, placebo-controlled study. | 2004 Apr |
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A review of the second-generation antihistamine ebastine for the treatment of allergic disorders. | 2004 Aug |
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Human CYP4F12 genetic polymorphism: identification and functional characterization of seven variant allozymes. | 2004 Dec 15 |
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Anti-inflammatory activity of H1-receptor antagonists: review of recent experimental research. | 2004 Jan |
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Rupatadine 10 mg and ebastine 10 mg in seasonal allergic rhinitis: a comparison study. | 2004 Jul |
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Antihistamines and driving ability: evidence from on-the-road driving studies during normal traffic. | 2004 Mar |
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Microbial oxidation of terfenadine and ebastine into fexofenadine and carebastine. | 2004 Nov 1 |
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Management of persistent allergic rhinitis: evidence-based treatment with levocetirizine. | 2005 Dec |
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Meta-analysis of the efficacy of ebastine 20 mg compared to loratadine 10 mg and placebo in the symptomatic treatment of seasonal allergic rhinitis. | 2005 Dec |
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Collection of medical drug information in pharmacies: Drug Event Monitoring (DEM) in Japan. | 2005 Jul |
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[Cardiac arrest following treatment with non-cardiologic QT-interval-increasing medications]. | 2005 May 2 |
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Stimulating effects of H1-antagonists. | 2006 |
|
The effect of CYP2J2, CYP3A4, CYP3A5 and the MDR1 polymorphisms and gender on the urinary excretion of the metabolites of the H-receptor antihistamine ebastine: a pilot study. | 2006 Aug |
|
Long QT syndrome in a patient with allergic rhinoconjunctivitis and auto-immune diabetes: focus on the choice of anti-H1 drugs. | 2006 Dec |
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Inter-individual variation of cytochrome P4502J2 expression and catalytic activities in liver microsomes from Japanese and Caucasian populations. | 2006 Dec |
|
CYP4F enzymes are the major enzymes in human liver microsomes that catalyze the O-demethylation of the antiparasitic prodrug DB289 [2,5-bis(4-amidinophenyl)furan-bis-O-methylamidoxime]. | 2006 Dec |
|
[Comparison of clinical efficacy and cost-quality of antihistamines in early treatment for Japanese cedar pollinosis]. | 2006 May |
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Acceptance survey of a fast dissolving tablet pharmaceutical formulation in allergic patients. Satisfaction and expectancies. | 2006 May-Jun |
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Characterization of ebastine, hydroxyebastine, and carebastine metabolism by human liver microsomes and expressed cytochrome P450 enzymes: major roles for CYP2J2 and CYP3A. | 2006 Nov |
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Rupatadine: pharmacological profile and its use in the treatment of allergic disorders. | 2006 Oct |
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Desloratadine for chronic idiopathic urticaria: a review of clinical efficacy. | 2007 |
|
[Ebastine (kestine 20) in therapy of allergic rhinitis]. | 2007 |
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A comparison of ebastine 10 mg fast-dissolving tablet with oral desloratadine and placebo in inhibiting the cutaneous reaction to histamine in healthy adults. | 2007 |
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Pharmacokinetics and safety of ebastine in healthy subjects and patients with renal impairment. | 2007 |
|
Rupatadine: a review of its use in the management of allergic disorders. | 2007 |
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Selective, competitive and mechanism-based inhibitors of human cytochrome P450 2J2. | 2007 Aug 15 |
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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. | 2007 Dec |
|
Acquired cold urticaria symptoms can be safely prevented by ebastine. | 2007 Dec |
|
[New generation antihistamines as monotherapy or in combination. What is the relevance for daily clinical routine for allergic rhinoconjunctivitis]. | 2007 Jun |
|
Palmoplantar pityriasis rosea: two case reports. | 2007 Mar |
|
[Peripheral anticholinergic syndrome]. | 2007 Mar-Apr |
|
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. | 2007 May |
|
Human enteric microsomal CYP4F enzymes O-demethylate the antiparasitic prodrug pafuramidine. | 2007 Nov |
|
[Ebastine-induced hepatotoxicity]. | 2007 Oct |
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Ebastine improves nasal symptoms and airflow and affects response to decongestion test in patients with persistent allergic rhinitis: a pilot study. | 2007 Sep-Oct |
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Rupatadine in allergic rhinitis and chronic urticaria. | 2008 Apr |
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Granular parakeratosis presenting with facial keratotic papules. | 2008 Jan-Feb |
|
Probing ligand binding modes of human cytochrome P450 2J2 by homology modeling, molecular dynamics simulation, and flexible molecular docking. | 2008 May 1 |
|
Evaluation of efficacy and sedative profiles of H(1) antihistamines by large-scale surveillance using the visual analogue scale (VAS). | 2008 Sep |
Patents
Sample Use Guides
In Vitro Use Guide
Sources: http://www.ncbi.nlm.nih.gov/pubmed/21437146
In vitro, ebastine and carebastine were shown to block the release of anti-IgE-induced eicosanoids LTC4/D4 and PGD2. Ebastine inhibited release of the two mediators by 30% at clinically relevant concentrations (IC30 = 2.57–9.6 umol/L).
Substance Class |
Chemical
Created
by
admin
on
Edited
Wed Jul 05 23:10:35 UTC 2023
by
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on
Wed Jul 05 23:10:35 UTC 2023
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Record UNII |
TQD7Q784P1
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Record Status |
Validated (UNII)
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R06AX22
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QR06AX22
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C29578
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CHEMBL305660
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M4801
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90729-43-4
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Ebastine
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DB11742
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100000092562
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DTXSID6046472
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EBASTINE
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Y-98
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C058249
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C77437
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SUB06435MIG
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