Details
Stereochemistry | ACHIRAL |
Molecular Formula | C17H26N4O.2C4H4O4 |
Molecular Weight | 534.5589 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 2 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
OC(=O)\C=C\C(O)=O.OC(=O)\C=C\C(O)=O.CCOCCN1C2=CC=CC=C2N=C1N3CCCN(C)CC3
InChI
InChIKey=FWLKKPKZQYVAFR-LVEZLNDCSA-N
InChI=1S/C17H26N4O.2C4H4O4/c1-3-22-14-13-21-16-8-5-4-7-15(16)18-17(21)20-10-6-9-19(2)11-12-20;2*5-3(6)1-2-4(7)8/h4-5,7-8H,3,6,9-14H2,1-2H3;2*1-2H,(H,5,6)(H,7,8)/b;2*2-1+
Molecular Formula | C17H26N4O |
Molecular Weight | 302.4145 |
Charge | 0 |
Count |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Optical Activity | NONE |
Molecular Formula | C4H4O4 |
Molecular Weight | 116.0722 |
Charge | 0 |
Count |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 1 |
Optical Activity | NONE |
Emedastine is an antihistaminic agent, which was approved by FDA for the treatment of allergic conjunctivitis (Emadine brand name). The drug acts selectively on H1 receptors with lower affinity to H2 and H3 subtypes. Emedastine has a relatively unfavorable CNS effect profile. A small percentage of patients reported somnolence as an adverse effect after administration.
CNS Activity
Originator
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: P35367 Gene ID: 3269.0 Gene Symbol: HRH1 Target Organism: Homo sapiens (Human) |
1.3 nM [Ki] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | EMADINE Approved UseEMADINE (emedastine difumarate ophthalmic solution) 0.05% is indicated for the temporary relief of the signs and symptoms of allergic conjunctivitis. Launch Date1997 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
2 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/11317479 |
2 mg single, oral dose: 2 mg route of administration: Oral experiment type: SINGLE co-administered: |
EMEDASTINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
|
2.9 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/11317479 |
2 mg single, oral dose: 2 mg route of administration: Oral experiment type: SINGLE co-administered: |
EMEDASTINE plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
|
4 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/11317479 |
2 mg 2 times / day steady-state, oral dose: 2 mg route of administration: Oral experiment type: STEADY-STATE co-administered: |
EMEDASTINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
|
6 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/11317479 |
2 mg 2 times / day steady-state, oral dose: 2 mg route of administration: Oral experiment type: STEADY-STATE co-administered: |
EMEDASTINE plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
AUC
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
16.9 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/11317479 |
2 mg single, oral dose: 2 mg route of administration: Oral experiment type: SINGLE co-administered: |
EMEDASTINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
|
29.7 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/11317479 |
2 mg single, oral dose: 2 mg route of administration: Oral experiment type: SINGLE co-administered: |
EMEDASTINE plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
|
24.4 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/11317479 |
2 mg 2 times / day steady-state, oral dose: 2 mg route of administration: Oral experiment type: STEADY-STATE co-administered: |
EMEDASTINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
|
46.4 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/11317479 |
2 mg 2 times / day steady-state, oral dose: 2 mg route of administration: Oral experiment type: STEADY-STATE co-administered: |
EMEDASTINE plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
6.4 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/11317479 |
2 mg single, oral dose: 2 mg route of administration: Oral experiment type: SINGLE co-administered: |
EMEDASTINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
|
10.1 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/11317479 |
2 mg single, oral dose: 2 mg route of administration: Oral experiment type: SINGLE co-administered: |
EMEDASTINE plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
|
6.6 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/11317479 |
2 mg 2 times / day steady-state, oral dose: 2 mg route of administration: Oral experiment type: STEADY-STATE co-administered: |
EMEDASTINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
|
9.1 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/11317479 |
2 mg 2 times / day steady-state, oral dose: 2 mg route of administration: Oral experiment type: STEADY-STATE co-administered: |
EMEDASTINE plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
Doses
Dose | Population | Adverse events |
---|---|---|
4 mg 2 times / day steady, oral Studied dose Dose: 4 mg, 2 times / day Route: oral Route: steady Dose: 4 mg, 2 times / day Sources: |
healthy, 21 - 45 years n = 19 Health Status: healthy Condition: lower respiratory tract infections or sexually transmitted infections Age Group: 21 - 45 years Sex: M+F Population Size: 19 Sources: |
Other AEs: Impaired driving ability... |
0.05 % 1 times / day steady, ophthalmic Recommended Dose: 0.05 %, 1 times / day Route: ophthalmic Route: steady Dose: 0.05 %, 1 times / day Sources: |
healthy, 43 years n = 14 Health Status: healthy Condition: conjunctival allergen challenge model Age Group: 43 years Sex: M+F Population Size: 14 Sources: |
|
2 mg 2 times / day steady, oral Recommended Dose: 2 mg, 2 times / day Route: oral Route: steady Dose: 2 mg, 2 times / day Sources: |
unhealthy, adult n = 192 Health Status: unhealthy Condition: idiopathic chronic urticaria Age Group: adult Sex: unknown Population Size: 192 Sources: |
Other AEs: Sleepiness... |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
Impaired driving ability | 19 patients | 4 mg 2 times / day steady, oral Studied dose Dose: 4 mg, 2 times / day Route: oral Route: steady Dose: 4 mg, 2 times / day Sources: |
healthy, 21 - 45 years n = 19 Health Status: healthy Condition: lower respiratory tract infections or sexually transmitted infections Age Group: 21 - 45 years Sex: M+F Population Size: 19 Sources: |
Sleepiness | 7 patients | 2 mg 2 times / day steady, oral Recommended Dose: 2 mg, 2 times / day Route: oral Route: steady Dose: 2 mg, 2 times / day Sources: |
unhealthy, adult n = 192 Health Status: unhealthy Condition: idiopathic chronic urticaria Age Group: adult Sex: unknown Population Size: 192 Sources: |
Overview
CYP3A4 | CYP2C9 | CYP2D6 | hERG |
---|---|---|---|
OverviewOther
Other Inhibitor | Other Substrate | Other Inducer |
---|---|---|
Drug as victim
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
Page: 1.0 |
yes | |||
Page: 1.0 |
yes | |||
Page: 1.0 |
yes | weak (co-administration study) Comment: Emedastine steady state pharmacokinetics were slightly altered as a result of the ketoconazole co-treatment. AUCss rose by about 33% and total clearance decreased by about 30% Page: 1.0 |
PubMed
Title | Date | PubMed |
---|---|---|
Pharmacologic analysis of LY188695 (KB-2413), 1-(2-ethoxyethyl)-2-(4-methyl-1-homopiperazinyl)-benzimidazole difumarate, a potent histamine1 receptor antagonist. | 1987 Feb |
|
General pharmacology of 1-(2-ethoxyethyl)-2-(4-methyl-1-homopiperazinyl)benzimidazole difumarate. 1st communication: effects on the central nervous system. | 1988 Jan |
|
Effect of emedastine difumarate on CC chemokine-elicited eosinophil migration. | 2001 |
|
Cost effectiveness of emedastine versus levocabastine in the treatment of allergic conjunctivitis in 7 European countries. | 2001 |
|
Emedastine and allergic conjunctivitis: new preparation. Poor assessment. | 2001 Apr |
|
Clinical evaluation of twice-daily emedastine 0.05% eye drops (Emadine eye drops) versus levocabastine 0.05% eye drops in patients with allergic conjunctivitis. | 2001 Jun |
|
Emedastine-ketoconazole: pharmacokinetic and pharmacodynamic interactions in healthy volunteers. | 2001 Mar |
|
Pharmacokinetics of emedastine difumarate, a new anti-histaminic agent in patients with renal impairment. | 2001 Mar |
|
VUF-K-8788, a periphery-selective histamine H1 antagonist with anti-pruritic activities. | 2001 May |
|
Histamine-induced IL-6 and IL-8 production are differentially modulated by IFN-gamma and IL-4 in human keratinocytes. | 2002 Jan |
|
Comparison of emedastine 0.05% or nedocromil sodium 2% eye drops and placebo in controlling local reactions in subjects with allergic conjunctivitis. | 2002 Jul-Aug |
|
A randomized, double-blind, placebo-controlled comparison of emedastine 0.05% ophthalmic solution with loratadine 10 mg and their combination in the human conjunctival allergen challenge model. | 2002 Mar |
|
Randomized, double-masked, placebo-controlled comparison of the efficacy of emedastine difumarate 0.05% ophthalmic solution and ketotifen fumarate 0.025% ophthalmic solution in the human conjunctival allergen challenge model. | 2002 Mar |
|
Effects of emedastine and cetirizine, alone and with alcohol, on actual driving of males and females. | 2002 Mar |
|
Effect of antiallergic drugs on interleukin 5-induced eosinophil infiltration of rat airways. | 2002 Mar |
|
Search of antimicrobial activity of selected non-antibiotic drugs. | 2002 Nov-Dec |
|
Histamine-induced cytokine production and ICAM-1 expression in human conjunctival fibroblasts. | 2002 Sep |
|
Pharmacokinetic and mass balance study of unlabelled and (14)C-labelled emedastine difumarate in healthy volunteers. | 2002 Sep |
|
Onset and duration of action of ketotifen 0.025% and emedastine 0.05% in seasonal allergic conjunctivitis : efficacy after repeated pollen challenges in the vienna challenge chamber. | 2003 |
|
Acute allergy reaction after posterior sub-Tenon's triamcinolone injection in the treatment of intermediate uveitis in the asthmatic patient. | 2003 |
|
[In vitro effects of antiallergic eyedrops on complement activation induced by particulate matter]. | 2003 Apr |
|
[Effects of emedastine eyedrops on acute seasonal allergic conjunctivitis in children]. | 2003 Apr 6 |
|
Evaluation of the efficacy of antihistamines using human monocyte-derived dendritic cells stimulated with histamine. | 2003 Aug |
|
Interactions of olopatadine and selected antihistamines with model and natural membranes. | 2003 Dec |
|
The effect of ketotifen on inflammatory markers in allergic conjunctivitis: an open, uncontrolled study. | 2003 Jan 6 |
|
Development of a new dissolution test method for an oral controlled release preparation, the PVA swelling controlled release system (SCRS). | 2003 Jun 5 |
|
Epinastine inhibits eosinophil chemotaxis and adhesion molecules in atopic dermatitis. | 2003 Nov-Dec |
|
Suplatast tosilate inhibits eosinophil production and recruitment into the skin in murine contact sensitivity. | 2003 Sep |
|
Clinical study of the therapeutic efficacy and safety of emedastine difumarate versus cetirizine in the treatment of seasonal allergic rhinitis. | 2004 |
|
Clinical study of the therapeutic efficacy and safety of emedastine difumarate versus terfenadine in the treatment of seasonal allergic rhinitis. | 2004 |
|
[Topical H1 antihistaminics in the therapy of acute conjunctival allergic reactions]. | 2004 Jan |
|
Antihistamines and driving ability: evidence from on-the-road driving studies during normal traffic. | 2004 Mar |
|
Efficacy and tolerability of newer antihistamines in the treatment of allergic conjunctivitis. | 2005 |
|
Biopharmaceutical considerations on antihistamine effects of topically administered emedastine. | 2005 Jan |
|
Estimation of in vivo percutaneous absorption of emedastine from bile excretion data using a deconvolution method. | 2005 Oct |
|
Emedastine difumarate versus loratadine in chronic idiopathic urticaria: a randomized, double-blind, controlled European multicentre clinical trial. | 2006 Nov-Dec |
|
[The prompt effect of emedastine eye drop and the safety of its permanent use in children suffering from acute seasonal allergic conjunctivitis]. | 2007 Feb 11 |
|
High-performance liquid chromatography-electrospray ionization-mass spectrometric determination of emedastine difumarate in human plasma and its pharmacokinetics. | 2007 Mar |
|
Emedastine difumarate inhibits histamine-induced collagen synthesis in dermal fibroblasts. | 2008 |
|
Comparative efficacy of topical antihistamines in an animal model of early phase allergic conjunctivitis. | 2008 May |
|
(E)-1,1'-Bis[(E)-but-2-en-yl]-3,3'-(propane-1,3-di-yl)bis-(1H-benzimidazol-3-ium) dibromide monohydrate. | 2008 Oct 18 |
|
Emedastine difumarate: a review of its potential ameliorating effect for tissue remodeling in allergic diseases. | 2009 Aug |
|
Psychoactive medication and traffic safety. | 2009 Mar |
|
[Antihistamines in the treatment of allergic rhinitis--update 2008/2009]. | 2009 Sep |
|
Development of a list of potentially inappropriate drugs for the korean elderly using the delphi method. | 2010 Dec |
|
Chorea induced by antihistamine drugs. | 2010 Mar 15 |
|
Contribution of mast cells to cerebral aneurysm formation. | 2010 May |
Sample Use Guides
The recommended dose is one drop (0.05% solution) in the effected eye up to four times daily.
Route of Administration:
Other
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/7714409
Human trabecular meshwork cells were treated with emedastine and at concentration of 1.44 nM the drug antagonized histamine-induced phosphoinositide turnover by 50%.
Substance Class |
Chemical
Created
by
admin
on
Edited
Fri Dec 15 15:50:17 GMT 2023
by
admin
on
Fri Dec 15 15:50:17 GMT 2023
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Record UNII |
42MB94QOSM
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Record Status |
Validated (UNII)
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Record Version |
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Classification Tree | Code System | Code | ||
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NCI_THESAURUS |
C29578
Created by
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EMA ASSESSMENT REPORTS |
EMADINE (AUTHORIZED: CONJUNCTIVIS, ALLERGIC)
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m4884
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DBSALT002462
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II-46
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C61744
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