Details
Stereochemistry | ACHIRAL |
Molecular Formula | C17H26N4O.C4H4O4 |
Molecular Weight | 418.4867 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 1 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
OC(=O)\C=C\C(O)=O.CCOCCN1C2=CC=CC=C2N=C1N3CCCN(C)CC3
InChI
InChIKey=FGFODSDYSQTNOS-WLHGVMLRSA-N
InChI=1S/C17H26N4O.C4H4O4/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;5-3(6)1-2-4(7)8/h4-5,7-8H,3,6,9-14H2,1-2H3;1-2H,(H,5,6)(H,7,8)/b;2-1+
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 |
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 |
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 |
---|---|---|
General pharmacology of 1-(2-ethoxyethyl)-2-(4-methyl-1-homopiperazinyl)benzimidazole difumarate. 1st communication: effects on the central nervous system. | 1988 Jan |
|
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 |
|
Acute allergy reaction after posterior sub-Tenon's triamcinolone injection in the treatment of intermediate uveitis in the asthmatic patient. | 2003 |
|
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 |
|
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 |
|
Emedastine difumarate: a review of its potential ameliorating effect for tissue remodeling in allergic diseases. | 2009 Aug |
|
Psychoactive medication and traffic safety. | 2009 Mar |
|
Development of a list of potentially inappropriate drugs for the korean elderly using the delphi method. | 2010 Dec |
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
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admin
on
Edited
Fri Dec 15 20:11:21 GMT 2023
by
admin
on
Fri Dec 15 20:11:21 GMT 2023
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Record UNII |
1P089Y932J
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Record Status |
Validated (UNII)
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Record Version |
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