brimonidine

{{Drugbox

| Watchedfields = changed

| verifiedrevid = 459982442

| image = Brimonidine.svg

| width = 195

| alt =

| pronounce = {{IPAc-en|b|r|ɪ|ˈ|m|oʊ|n|ᵻ|d|iː|n}} {{respell|bri|MOH|nid-een}}

| tradename = Alphagan, Mirvaso, Lumify, others

| Drugs.com = {{drugs.com|monograph|brimonidine-tartrate-eent}}

| MedlinePlus = a601232

| DailyMedID = Brimonidine

| pregnancy_AU = B3

| pregnancy_AU_comment =

| pregnancy_category=

| routes_of_administration = Topical

| class =

| ATC_prefix = D11

| ATC_suffix = AX21

| ATC_supplemental = {{ATC|S01|EA05}}, {{ATC|S01|EA55}}, {{ATC|S01|GA07}}

| legal_US = Rx-only

| legal_US_comment = / OTC{{cite web | title=Alphagan P- brimonidine tartrate solution/ drops | website=DailyMed | date=27 June 2024 | url=https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=264c4494-c225-486f-888a-caaf36be46b3 | access-date=11 November 2024}}{{cite web | title=Mirvaso- brimonidine tartrate gel | website=DailyMed | date=24 October 2024 | url=https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=f6a4353f-ae69-4214-901f-e5d42a6fbde7 | access-date=11 November 2024}}{{cite web | title=Lumify Redness Reliever Eye Drops- brimonidine tartrate solution/ drops | website=DailyMed | date=6 November 2023 | url=https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=022de945-0b26-40ae-8e88-d3fe2464d106 | access-date=11 November 2024}}

| bioavailability =

| protein_bound =

| metabolism = Primarily liver

| elimination_half-life = 3 hours (ocular), 12 hours (topical)

| CAS_number_Ref = {{cascite|correct|??}}

| CAS_number = 59803-98-4

| PubChem = 2435

| IUPHAR_ligand = 520

| DrugBank_Ref = {{drugbankcite|correct|drugbank}}

| DrugBank = DB00484

| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

| ChemSpiderID = 2341

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = E6GNX3HHTE

| KEGG_Ref = {{keggcite|correct|kegg}}

| KEGG = D07540

| ChEBI_Ref = {{ebicite|correct|EBI}}

| ChEBI = 3175

| ChEMBL_Ref = {{ebicite|correct|EBI}}

| ChEMBL = 844

| IUPAC_name = 5-Bromo-N-(4,5-dihydro-1H-imidazol-2-yl) quinoxalin-6-amine

| C=11 | H=10 | Br=1 | N=5

| smiles = Brc2c1nccnc1ccc2N/C3=N/CCN3

| StdInChI_Ref = {{stdinchicite|correct|chemspider}}

| StdInChI = 1S/C11H10BrN5/c12-9-7(17-11-15-5-6-16-11)1-2-8-10(9)14-4-3-13-8/h1-4H,5-6H2,(H2,15,16,17)

| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}

| StdInChIKey = XYLJNLCSTIOKRM-UHFFFAOYSA-N

| melting_point = 252

}}

Brimonidine is an α₂ agonist medication used to treat open-angle glaucoma, ocular hypertension, and rosacea.{{cite web |title=Brimonidine Tartrate eent Monograph for Professionals |url=https://www.drugs.com/monograph/brimonidine-tartrate-eent.html |website=Drugs.com |publisher=American Society of Health-System Pharmacists |access-date=17 March 2019 }}{{cite web |title=Brimonidine Tartrate topical Monograph for Professionals |url=https://www.drugs.com/monograph/brimonidine-tartrate-topical.html |website=Drugs.com |publisher=American Society of Health-System Pharmacists |access-date=17 March 2019 }} In rosacea it improves the redness. It is used as eye drops or applied to the skin. It is also available in the fixed-dose combination medication brimonidine/timolol along with timolol maleate.{{cite web | title=COMBIGAN- brimonidine tartrate, timolol maleate solution/ drops | website=DailyMed | date=26 July 2024 | url=https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=feaf1480-a4b8-4486-992a-96be3a596243 | access-date=11 November 2024}}

Common side effects when used in the eyes include itchiness, redness, and a dry mouth. Common side effects when used on the skin include redness, burning, and headaches. More significant side effects may include allergic reactions and low blood pressure. Use in pregnancy appears to be safe. When applied to the eye it works by decreasing the amount of aqueous humor made while increasing the amount that drains from the eye. When applied to the skin it works by causing blood vessels to contract.

Brimonidine was patented in 1972 and came into medical use in 1996.{{cite book | vauthors = Fischer J, Ganellin CR |title=Analogue-based Drug Discovery |date=2006 |publisher=John Wiley & Sons |isbn=9783527607495 |page=550 |url=https://books.google.com/books?id=FjKfqkaKkAAC&pg=PA550 |language=en}} It is available as a generic medication.{{cite web | title=Competitive Generic Therapy Approvals | website=U.S. Food and Drug Administration (FDA) | date=29 June 2023 | url=https://www.fda.gov/drugs/generic-drugs/competitive-generic-therapy-approvals | access-date=29 June 2023 | archive-date=29 June 2023 | archive-url=https://web.archive.org/web/20230629233651/https://www.fda.gov/drugs/generic-drugs/competitive-generic-therapy-approvals | url-status=dead }}{{cite book|title=British national formulary : BNF 76|date=2018|publisher=Pharmaceutical Press|isbn=9780857113382|pages=1153|edition=76}} In 2022, it was the 199th most commonly prescribed medication in the United States, with more than 2{{nbsp}}million prescriptions.{{cite web | title=The Top 300 of 2022 | url=https://clincalc.com/DrugStats/Top300Drugs.aspx | website=ClinCalc | access-date=30 August 2024 | archive-date=30 August 2024 | archive-url=https://web.archive.org/web/20240830202410/https://clincalc.com/DrugStats/Top300Drugs.aspx | url-status=live }}{{cite web | title = Brimonidine Drug Usage Statistics, United States, 2013 - 2022 | website = ClinCalc | url = https://clincalc.com/DrugStats/Drugs/Brimonidine | access-date = 30 August 2024 }}

Medical uses

Brimonidine is indicated for the lowering of intraocular pressure in people with open-angle glaucoma or ocular hypertension. It is also used to reduce redness of the eye. The gel is indicated for the topical treatment of persistent (nontransient) facial erythema of rosacea in adults 18 years of age or older.

A 2017 Cochrane review found insufficient evidence to determine if brimonidine slows optic nerve damage.{{cite journal | vauthors = Sena DF, Lindsley K | title = Neuroprotection for treatment of glaucoma in adults | journal = The Cochrane Database of Systematic Reviews | volume = 1 | pages = CD006539 | date = January 2017 | issue = 1 | pmid = 28122126 | pmc = 5370094 | doi = 10.1002/14651858.CD006539.pub4 }}

Mechanism of action

Brimonidine is an α₂ adrenergic agonist.

Peripheral α₂ agonist activity results in vasoconstriction of blood vessels (as opposed to central α₂ agonist activity that decreases sympathetic tone, as can be seen by the medication clonidine). This vasoconstriction may explain the acute reduction in aqueous humor flow. The increased uveoscleral outflow from prolonged use may be explained by increased prostaglandin release due to α adrenergic stimulation. This may lead to relaxed ciliary muscle and increased uveoscleral outflow.{{cite journal | vauthors = Toris CB, Camras CB, Yablonski ME | title = Acute versus chronic effects of brimonidine on aqueous humor dynamics in ocular hypertensive patients | journal = American Journal of Ophthalmology | volume = 128 | issue = 1 | pages = 8–14 | date = July 1999 | pmid = 10482088 | doi = 10.1016/s0002-9394(99)00076-8 }}

Society and culture

=Names=

It is sold under the brand names Alphagan, Alphagan-P, Mirvaso, Lumify, Brymont, and others.

brimonidine

Medical uses

Mechanism of action

Society and culture

=Names=

References

Further reading