Brimonidine

Chemical compound From Wikipedia, the free encyclopedia

Brimonidine is an α2 agonist medication used to treat open-angle glaucoma, ocular hypertension, and rosacea.[5][6] In rosacea it improves the redness.[6] It is used as eye drops or applied to the skin.[5][6] It is also available in the fixed-dose combination medication brimonidine/timolol along with timolol maleate.[7]

Pronunciation/brɪˈmoʊnɪdiːn/ bri-MOH-nid-een
Trade namesAlphagan, Mirvaso, Lumify, others
AHFS/Drugs.comMonograph
MedlinePlusa601232
Quick facts Clinical data, Pronunciation ...
Brimonidine
Clinical data
Pronunciation/brɪˈmoʊnɪdiːn/ bri-MOH-nid-een
Trade namesAlphagan, Mirvaso, Lumify, others
AHFS/Drugs.comMonograph
MedlinePlusa601232
License data
Pregnancy
category
  • AU: B3
Routes of
administration		Topical
ATC code
Legal status
Legal status
Pharmacokinetic data
MetabolismPrimarily liver
Elimination half-life3 hours (ocular), 12 hours (topical)
Identifiers
  • 5-Bromo-N-(4,5-dihydro-1H-imidazol-2-yl) quinoxalin-6-amine
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.149.042 Edit this at Wikidata
Chemical and physical data
FormulaC11H10BrN5
Molar mass292.140 g·mol−1
3D model (JSmol)
Melting point252 °C (486 °F)
  • Brc2c1nccnc1ccc2N/C3=N/CCN3
  • InChI=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) checkY
  • Key:XYLJNLCSTIOKRM-UHFFFAOYSA-N checkY
  (verify)
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Common side effects when used in the eyes include itchiness, redness, and a dry mouth.[5] Common side effects when used on the skin include redness, burning, and headaches.[6] More significant side effects may include allergic reactions and low blood pressure.[6][5] Use in pregnancy appears to be safe.[6][5] When applied to the eye it works by decreasing the amount of aqueous humor made while increasing the amount that drains from the eye.[5] When applied to the skin it works by causing blood vessels to contract.[6]

Brimonidine was patented in 1972 and came into medical use in 1996.[8] It is available as a generic medication.[9][10] In 2023, it was the 213th most commonly prescribed medication in the United States, with more than 2 million prescriptions.[11][12]

Medical uses

Brimonidine is indicated for the lowering of intraocular pressure in people with open-angle glaucoma or ocular hypertension.[2] It is also used to reduce redness of the eye.[4] The gel is indicated for the topical treatment of persistent (nontransient) facial erythema of rosacea in adults 18 years of age or older.[3]

A 2017 Cochrane review found insufficient evidence to determine if brimonidine slows optic nerve damage.[13]

Mechanism of action

Brimonidine is an α2 adrenergic agonist.[5]

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.[14]

Society and culture

Names

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

References

Further reading

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