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+
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 |
|
Histamine-induced IL-6 and IL-8 production are differentially modulated by IFN-gamma and IL-4 in human keratinocytes. | 2002 Jan |
|
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 |
|
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 |
|
Interactions of olopatadine and selected antihistamines with model and natural membranes. | 2003 Dec |
|
Suplatast tosilate inhibits eosinophil production and recruitment into the skin in murine contact sensitivity. | 2003 Sep |
|
[Topical H1 antihistaminics in the therapy of acute conjunctival allergic reactions]. | 2004 Jan |
|
Emedastine difumarate versus loratadine in chronic idiopathic urticaria: a randomized, double-blind, controlled European multicentre clinical trial. | 2006 Nov-Dec |
|
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 |
|
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%.
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PARENT (SALT/SOLVATE)
PARENT (SALT/SOLVATE)
SUBSTANCE RECORD