Brimonidine

Brimonidine is a medication used to treat open-angle glaucoma, ocular hypertension, and rosacea.[1][2] In rosacea it improves the redness.[2] It is used as eye drops or applied to the skin.[1][2]

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 (eye drop, gel)
ATC code
Legal status
Legal status
  • US: OTC for 0.025% Rx-only for other doses
Pharmacokinetic data
MetabolismPrimarily liver
Elimination half-life3 hours (ocular), 12 hours (topical)
Identifiers
IUPAC name
  • 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
Chemical and physical data
FormulaC11H10BrN5
Molar mass292.135 g·mol−1
3D model (JSmol)
Melting point252 °C (486 °F)
SMILES
  • Brc2c1nccnc1ccc2N/C3=N/CCN3
InChI
  • 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) Y
  • Key:XYLJNLCSTIOKRM-UHFFFAOYSA-N Y
  (verify)

Common side effects when used in the eyes include itchiness, redness, and a dry mouth.[1] Common side effects when used on the skin include redness, burning, and headaches.[2] More significant side effects may include allergic reactions and low blood pressure.[2][1] Use in pregnancy appears to be safe.[2][1] When applied to the eye it works by decreasing the amount of aqueous humor made while increasing the amount that drains from the eye.[1] When applied to the skin it works by causing blood vessels to contract.[2]

Brimonidine was patented in 1972 and came into medical use in 1996.[3] It is available as a generic medication.[4] In 2019, it was the 217th most commonly prescribed medication in the United States, with more than 2 million prescriptions.[5][6]

Medical uses

Brimonidine is indicated for the lowering of intraocular pressure in patients with open-angle glaucoma or ocular hypertension. It is also the active ingredient of brimonidine/timolol along with timolol maleate.

A 2017 Cochrane review found insufficient evidence to determine if brimonidine slows optic nerve damage.[7]

In 2013, the FDA approved topical application of brimonidine 0.33% gel for persistent facial redness of rosacea.

Mechanism of action

Brimonidine is an α2 adrenergic agonist.[1]

α2 agonists, through the activation of a G protein-coupled receptor, inhibit the activity of adenylate cyclase. This reduces cAMP and hence aqueous humour production by the ciliary body.

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.[8]

Society and culture

Names

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

Over the counter

In July 2018, Bausch and Lomb began to market over the counter (OTC) eye drops, using brimonidine's tartrate formulation in a concentration of 0.025%, as an ophthalmic vasoconstrictor under the brand name Lumify. Intended to relieve redness in the sclerae of the eyes for periods of up to eight hours at a time through its vasoconstrictive effects, Lumify was marketed as an alternative to Visine, the brand of tetrahydrozoline hydrochloride solution most commonly used for that purpose.

References
  1. "Brimonidine Tartrate eent Monograph for Professionals". Drugs.com. American Society of Health-System Pharmacists. Retrieved 17 March 2019.
  2. "Brimonidine Tartrate topical Monograph for Professionals". Drugs.com. American Society of Health-System Pharmacists. Retrieved 17 March 2019.
  3. Fischer J, Ganellin CR (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 550. ISBN 9783527607495.
  4. British national formulary : BNF 76 (76 ed.). Pharmaceutical Press. 2018. p. 1153. ISBN 9780857113382.
  5. "The Top 300 of 2019". ClinCalc. Retrieved 16 October 2021.
  6. "Brimonidine - Drug Usage Statistics". ClinCalc. Retrieved 16 October 2021.
  7. Sena DF, Lindsley K (January 2017). "Neuroprotection for treatment of glaucoma in adults". The Cochrane Database of Systematic Reviews. 1: CD006539. doi:10.1002/14651858.CD006539.pub4. PMC 5370094. PMID 28122126.
  8. Toris CB, Camras CB, Yablonski ME (July 1999). "Acute versus chronic effects of brimonidine on aqueous humor dynamics in ocular hypertensive patients". American Journal of Ophthalmology. 128 (1): 8–14. doi:10.1016/s0002-9394(99)00076-8. PMID 10482088.

Further reading
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