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Brimonidine information


Brimonidine
Clinical data
Pronunciation/brɪˈmnɪdn/ bri-MOH-nid-een
Trade namesAlphagan, Mirvaso, Lumify, others
AHFS/Drugs.comMonograph
MedlinePlusa601232
License data
  • US DailyMed: Brimonidine
Pregnancy
category
  • AU: B3
Routes of
administration
Topical
ATC code
  • D11AX21 (WHO) S01EA05 (WHO), S01GA07 (WHO)
Legal status
Legal status
  • US: ℞-only / OTC
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
  • 59803-98-4 checkY
PubChem CID
  • 2435
IUPHAR/BPS
  • 520
DrugBank
  • DB00484 checkY
ChemSpider
  • 2341 checkY
UNII
  • E6GNX3HHTE
KEGG
  • D07540 checkY
ChEBI
  • CHEBI:3175 checkY
ChEMBL
  • ChEMBL844 checkY
CompTox Dashboard (EPA)
  • DTXSID3045221 Edit this at Wikidata
ECHA InfoCard100.149.042 Edit this at Wikidata
Chemical and physical data
FormulaC11H10BrN5
Molar mass292.140 g·mol−1
3D model (JSmol)
  • Interactive image
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) checkY
  • Key:XYLJNLCSTIOKRM-UHFFFAOYSA-N checkY
  (verify)

Brimonidine is an α2 agonist 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]

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][5] In 2021, it was the 160th most commonly prescribed medication in the United States, with more than 3 million prescriptions.[6][7]

  1. ^ a b c d e f "Brimonidine Tartrate eent Monograph for Professionals". Drugs.com. American Society of Health-System Pharmacists. Retrieved 17 March 2019.
  2. ^ a b c d e f g "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. ^ "Competitive Generic Therapy Approvals". U.S. Food and Drug Administration (FDA). 29 June 2023. Archived from the original on 29 June 2023. Retrieved 29 June 2023.
  5. ^ British national formulary : BNF 76 (76 ed.). Pharmaceutical Press. 2018. p. 1153. ISBN 9780857113382.
  6. ^ "The Top 300 of 2021". ClinCalc. Archived from the original on 15 January 2024. Retrieved 14 January 2024.
  7. ^ "Brimonidine - Drug Usage Statistics". ClinCalc. Retrieved 14 January 2024.

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