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{{Short description|Chemical compound}}
{{Drugbox
{{Infobox drug
| verifiedrevid = 461093245
⚫
| CAS_number_Ref = {{cascite|correct|CAS}}
⚫
| IUPAC_name = 1-(2-ethoxyethyl)-2- (4-methyl-1,4-diazepan-1-yl)- benzoimidazole
⚫
| CAS_number = 87233-61-2
⚫
| UNII_Ref = {{fdacite|correct|FDA}}
⚫
| UNII = 9J1H7Y9OJV
⚫
| IUPAC_name = 1-(2-Ethoxyethyl)-2-(hexahydro-4-methyl-1H-1,4-diazepin-1-yl)-1H-benzimidazole
| chemical_formula = C<sub>17</sub> H<sub>26</sub> N<sub>4</sub> O
| image = Emedastine.png
| image = Emedastine.png
⚫
}}


[[FILE:Emedastine.jpg|thumb|upright=1|Eye drop of emedastine]]
<!--Clinical data-->
'''Emedastine''' (trade name '''Emadine''') is a second generation [[antihistamine]] used in [[eye drop]]s to alleviate the symptoms of [[allergic conjunctivitis]].<ref name="AHFS2020">{{cite web|title= Emedastine (Ophthalmic)|url= https://www.drugs.com/ppa/emedastine-ophthalmic.html|publisher= The American Society of Health-System Pharmacists|access-date= 11 February 2020|archive-date= 6 August 2019|archive-url= https://web.archive.org/web/20190806171738/https://www.drugs.com/ppa/emedastine-ophthalmic.html|url-status= dead}}</ref> It acts as a [[H1 receptor antagonist|H<sub>1</sub> receptor antagonist]]. It works by blocking the action of [[histamine]] that causes allergic symptoms. It is used in form of the di[[fumarate]].<ref>{{cite journal | vauthors = Bielory L, Lien KW, Bigelsen S | title = Efficacy and tolerability of newer antihistamines in the treatment of allergic conjunctivitis | journal = Drugs | volume = 65 | issue = 2 | pages = 215–28 | year = 2005 | pmid = 15631542 | doi = 10.2165/00003495-200565020-00004 | s2cid = 46791611 }}</ref>
| tradename = Emadine
The emedastine difumarate is a white, crystalline, water-soluble fine powder. Emedastine eye drops is usually applied twice a day to the affected eye. When the patients with allergic conjunctivitis were treated with 0.05% emedastine difumarate ophthalmic solution for six weeks, the signs and symptoms such as redness, itching and swelling of the eyes were relieved. Emedastine appears to be devoid of effects on adrenergic, dopaminergic and serotonin receptors. This drug was developed by [[Alcon]], which is global medical company specializing in eye care products.
| Drugs.com = {{drugs.com|monograph|emadine}}
| pregnancy_category =
| legal_status =
| routes_of_administration =


== Pharmacodynamics ==
<!--Pharmacokinetic data-->
⚫
Emedastine is significantly selective to H<sub>1</sub> histamine receptors ([[Dissociation constant|K<sub>i</sub>]] = 1.3 nM), whereas its affinities for other histamine receptors were low (H<sub>2</sub>: K<sub>i</sub> = 49067 nM and H<sub>3</sub>: K<sub>i</sub> = 12430 nM) ub ''in vitro'' study. Topical ocular administration of emedastine inhibits histamine-stimulated vascular permeability in the conjunctiva as a concentration-dependent manner in ''in vitro'' study.
| bioavailability =
| protein_bound =
| metabolism =
| elimination_half-life =


== Pharmacokinetics ==
<!--Identifiers-->
⚫
The human oral bioavailability is approximately 50% and maximum plasma concentration was achieved within 1–2 hours after dosing. Emedastine is mainly metabolized by the liver. There are two primary metabolites: 5-hydroxyemedastine and 6-hydroxyemedastine. They are excreted in the urine as both free and conjugated forms. The 5'-oxoanalogs of 5-hydroxyemedastine, 6-hydroxyemedastine and the ''N''-oxide are also formed as minor metabolites. The elimination half-life of oral emedastine in plasma is 3–4 hours, whereas that of topical emedastine is 10 hours. Approximately 44% of the oral dose is recovered in the urine over 24 hours with only 3.6% of the dose excreted as parent drug.<ref name = "PI">{{cite web|title=Emadine (emedastine difumarate ophthalmic solution) 0.05%. Full Prescribing Information|url=http://ecatalog.alcon.com/PI/Emadine_us_en.pdf|publisher=Alcon Laboratories, Inc. 6201 South Freeway Fort Worth, Texas 76134, USA|access-date=5 January 2016}}</ref>
| CASNo_Ref = {{cascite|correct|CAS}}
⚫
| CAS_number_Ref = {{cascite|correct|??}}
⚫
| CAS_number = 87233-61-2
| ATC_prefix = S01
| ATC_suffix = GX06
| PubChem = 3219
| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
| DrugBank = DB01084
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 3106
⚫
| UNII_Ref = {{fdacite|correct|FDA}}
⚫
| UNII = 9J1H7Y9OJV
| KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG = D07890
| ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEBI = 4779
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 594


== Contraindications ==
<!--Chemical data-->
⚫
Emedastine should not be used in patients who are hypersensitive to emedastine or any other excipients of the preparation. [[Benzalkonium chloride]] contained in the bottle of emedastine solution can discolor soft [[contact lens]]es, so people who wear contact lenses should be careful using it.
| C=17 | H=26 | N=4 | O=1
| molecular_weight = 302.415 [[Gram|g]]/[[Mole (unit)|mol]]
| smiles = O(CC)CCn1c(nc2ccccc12)N3CCCN(C)CC3
| InChI = 1/C17H26N4O/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/h4-5,7-8H,3,6,9-14H2,1-2H3
| InChIKey = KBUZBQVCBVDWKX-UHFFFAOYAT
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C17H26N4O/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/h4-5,7-8H,3,6,9-14H2,1-2H3
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = KBUZBQVCBVDWKX-UHFFFAOYSA-N
⚫
}}


== Adverse events ==
'''Emedastine''' (trade name '''Emadine''') is a second generation{{fact|date=December 2013}} [[antihistamine]] used in [[eye drop]]s to treat [[allergic conjunctivitis]]. It acts as a [[H1 receptor antagonist|H<sub>1</sub> receptor antagonist]]. It works by blocking certain natural substances, histamines that cause allergic symptoms. It is used in form of the di[[fumarate]].<ref>{{pmid|15631542}}</ref> The formation of emedastine difumarate is a white, crystalline, water-soluble fine powder. Emedasine is applied as an eye drop with 2 times a day. When the patients with allergic conjunctivitis were treated with 0.05% emedastin difumarate ophthalmic solution for six weeks, the signs and symptoms such as redness, itching and swelling of the eyes were relieved. Emedastine appears to be devoid of effects on adrenergic, dopaminergic and serotonin receptors.
⚫
The most common adverse effect was headache (11%). The other minor adverse effects encountered in less than 5% of patients were [[Weakness|asthenia]], burning or stinging sensation, unpleasant taste, blurred vision, eye dryness and tearing.

⚫
Emedastine is significantly selective to H1 histamine receptors (Ki=1.3 nM), whereas its affinities for other histamine receptor are low (H2: Ki=49067 nM and H3: Ki=12430 nM ) in vitro study. Tropical ocular administration of emedastine inhibits histamine-stimulated vascular permeability in the conjunctiva as a concentration dependent manner in vitro study.

⚫
The human oral bioavailability is approximately 50% and maximum plasma concentration were achieved within 1-2 hours after dosing. Emedastine is mainly metabolized by the liver. There are two primary metabolites: 5-hydroxyemedastine and 6-hydroxyemedastine. They are excreted in the urine as both free and conjugated forms. The 5'-oxoanalogs of 5-hydroxyemedastine and 6-hydroxy-emedastine and the N-oxide are also formed as minor metabolites. The elimination half-life of oral emedastine in plasma is 3-4 hours, whereas that of topical emedastine is 10 hours. Approximately 44% of the oral dose is recovered in the urine over 24 hours with only 3.6% of the dose excreted as parent drug.

⚫
Emedastine should not be used in patients who are hypersensitive to any other ingredients or emedastin. Benzalkonium chloride contained in the bottle of emedastines can discolor soft contact lenses, so people who wear the lenses should be careful with using it.
⚫
The most common adverse effect was headache (11%). The other minor adverse effect less than 5% of patients: asthenia, burning or stinging, bad taste, blurred vision, dry eye and tearing.


== References ==
== References ==
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[[Category:Ethers]]
[[Category:Ethers]]
[[Category:Diazepanes]]
[[Category:Diazepanes]]
[[Category:Ethanolamines]]

[[Category:Ethoxy compounds]]


{{respiratory-system-drug-stub}}
{{respiratory-system-drug-stub}}

Latest revision as of 13:06, 6 March 2024

Emedastine
Identifiers
  • 1-(2-Ethoxyethyl)-2-(hexahydro-4-methyl-1H-1,4-diazepin-1-yl)-1H-benzimidazole
CAS Number
UNII
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC17 H26 N4 O
Eye drop of emedastine

Emedastine (trade name Emadine) is a second generation antihistamine used in eye drops to alleviate the symptoms of allergic conjunctivitis.[1] It acts as a H1 receptor antagonist. It works by blocking the action of histamine that causes allergic symptoms. It is used in form of the difumarate.[2] The emedastine difumarate is a white, crystalline, water-soluble fine powder. Emedastine eye drops is usually applied twice a day to the affected eye. When the patients with allergic conjunctivitis were treated with 0.05% emedastine difumarate ophthalmic solution for six weeks, the signs and symptoms such as redness, itching and swelling of the eyes were relieved. Emedastine appears to be devoid of effects on adrenergic, dopaminergic and serotonin receptors. This drug was developed by Alcon, which is global medical company specializing in eye care products.

Pharmacodynamics

[edit]

Emedastine is significantly selective to H1 histamine receptors (Ki = 1.3 nM), whereas its affinities for other histamine receptors were low (H2: Ki = 49067 nM and H3: Ki = 12430 nM) ub in vitro study. Topical ocular administration of emedastine inhibits histamine-stimulated vascular permeability in the conjunctiva as a concentration-dependent manner in in vitro study.

Pharmacokinetics

[edit]

The human oral bioavailability is approximately 50% and maximum plasma concentration was achieved within 1–2 hours after dosing. Emedastine is mainly metabolized by the liver. There are two primary metabolites: 5-hydroxyemedastine and 6-hydroxyemedastine. They are excreted in the urine as both free and conjugated forms. The 5'-oxoanalogs of 5-hydroxyemedastine, 6-hydroxyemedastine and the N-oxide are also formed as minor metabolites. The elimination half-life of oral emedastine in plasma is 3–4 hours, whereas that of topical emedastine is 10 hours. Approximately 44% of the oral dose is recovered in the urine over 24 hours with only 3.6% of the dose excreted as parent drug.[3]

Contraindications

[edit]

Emedastine should not be used in patients who are hypersensitive to emedastine or any other excipients of the preparation. Benzalkonium chloride contained in the bottle of emedastine solution can discolor soft contact lenses, so people who wear contact lenses should be careful using it.

Adverse events

[edit]

The most common adverse effect was headache (11%). The other minor adverse effects encountered in less than 5% of patients were asthenia, burning or stinging sensation, unpleasant taste, blurred vision, eye dryness and tearing.

References

[edit]
  1. ^ "Emedastine (Ophthalmic)". The American Society of Health-System Pharmacists. Archived from the original on 6 August 2019. Retrieved 11 February 2020.
  2. ^ Bielory L, Lien KW, Bigelsen S (2005). "Efficacy and tolerability of newer antihistamines in the treatment of allergic conjunctivitis". Drugs. 65 (2): 215–28. doi:10.2165/00003495-200565020-00004. PMID 15631542. S2CID 46791611.
  3. ^ "Emadine (emedastine difumarate ophthalmic solution) 0.05%. Full Prescribing Information" (PDF). Alcon Laboratories, Inc. 6201 South Freeway Fort Worth, Texas 76134, USA. Retrieved 5 January 2016.
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