brimonidine (UK14304)   Click here for help

GtoPdb Ligand ID: 520

Synonyms: Alphagan® | Lumify® | Mirvaso® | UK14,304 | UK14304
Approved drug PDB Ligand Immunopharmacology Ligand
brimonidine (UK14304) is an approved drug (FDA (1996), EMA (2014))
Compound class: Synthetic organic
Comment: Brimonidine is an α-adrenoceptor agonist (primarily α2).
Click here for help
IUPHAR Pharmacology Education Project (PEP) logo

View more information in the IUPHAR Pharmacology Education Project: brimonidine

2D Structure
Click here for help
Click here for structure editor
Physico-chemical Properties
Click here for help
Hydrogen bond acceptors 5
Hydrogen bond donors 2
Rotatable bonds 2
Topological polar surface area 62.2
Molecular weight 291.01
XLogP 1.18
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
Click here for help
Canonical SMILES Brc1c(ccc2c1nccn2)NC1=NCCN1
Isomeric SMILES Brc1c(ccc2c1nccn2)NC1=NCCN1
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)
InChI Key XYLJNLCSTIOKRM-UHFFFAOYSA-N
Selectivity at GPCRs
Key to terms and symbols Click column headers to sort
Target Sp. Type Action Value Parameter Concentration range (M) Reference
α2A-adrenoceptor Primary target of this compound Hs Agonist Full agonist 6.4 – 8.7 pKi - 1,3-6
pKi 6.4 – 8.7 [1,3-6]
α2B-adrenoceptor Primary target of this compound Hs Agonist Partial agonist 5.5 – 8.3 pKi - 1,4-6
pKi 5.5 – 8.3 [1,4-6]
α2C-adrenoceptor Primary target of this compound Hs Agonist Agonist 5.7 – 7.6 pKi - 1,3-6
pKi 5.7 – 7.6 [1,3-6]
α2A-adrenoceptor Hs Agonist Agonist 9.1 pEC50 - 6
pEC50 9.1 [6]
Description: increased ERK1/2 phosphorylation
α2B-adrenoceptor Hs Agonist Agonist 7.2 – 7.8 pEC50 - 6
pEC50 7.8 [6]
Description: ERK1/2 phosphorylation
pEC50 7.2 [6]
Description: cAMP generation
α2C-adrenoceptor Hs Agonist Agonist 5.9 – 8.2 pEC50 - 2,6
pEC50 8.2 [6]
Description: ERK1/2 phosphorylation
pEC50 5.9 – 6.9 [2]
Description: 5.88 = value for β-arrestin recruitment and internalization
α2A-adrenoceptor Hs Agonist Agonist 8.9 pIC50 - 6
pIC50 8.9 [6]
Description: inhibition of forskolin stimulated cAMP generation
α2B-adrenoceptor Hs Agonist Agonist 8.4 pIC50 - 6
pIC50 8.4 [6]
Description: inhibition of forskolin stimulated cAMP generation
α2C-adrenoceptor Hs Agonist Agonist 8.0 – 8.5 pIC50 - 2,6
pIC50 8.0 – 8.5 [2,6]
Description: inhibition of cAMP production
Ligand mentioned in the following text fields