Brimonidine

Summary

Brimonidine (CHEMBL844) is an approved small-molecule adrenergic agonist (ATC S01GA07) targeting ADRA2A, ADRA2B, and ADRA2C; indicated across 8 conditions including eye allergy and glaucoma.

At a glance

• Status: Approved (max clinical phase 4)
• Modality: Small molecule
• ATC class: S01GA07 (+2 more)
• Targets: 3 (ADRA2A, ADRA2B, ADRA2C)
• Indications: 8 conditions
• Clinical trials: 56
• Chemistry: 292.13 Da · C11H10BrN5

Identifiers

Drug identity and classification

Field	Value
ChEMBL ID	CHEMBL844
Name	Brimonidine
Type	Small molecule
Max phase	4
FDA approved	yes
PubChem CID	2435
ChEBI	CHEBI:3175
ATC	S01GA07, S01EA05, D11AX21
Molecular formula	C11H10BrN5
Molecular weight	292.13
InChIKey	XYLJNLCSTIOKRM-UHFFFAOYSA-N

SMILES: C1CN=C(N1)NC2=C(C3=NC=CN=C3C=C2)Br

IUPAC name: 5-bromo-N-(4,5-dihydro-1H-imidazol-2-yl)quinoxalin-6-amine

Pharmacological roles (ChEBI): adrenergic agonist, antihypertensive agent, α-adrenergic agonist.

Also known as: AGN-190342 FREE BASE, Brimonidina, Brimonidine, NSC-318825, UK-14304, UK-1430418 FREE BASE, SID11111939, SID11113354, SID26751556, SID50104157, SID85231282, SID855898

Parent form; salt/anhydrous children: CHEMBL1200389, CHEMBL2062257

Patent coverage: 2,976 distinct patent families (11,912 SureChEMBL compound mentions), from 3 matched compound structure(s). One matched structure accounts for 11,518 (97%) of the total. Mentions count patents naming the compound (not distinct inventions), so promiscuous / reference molecules inflate the mention figure — families are the dedup metric.

Targets

Targets

Primary targets (GtoPdb curated mechanism): the Cancer dependency column is the DepMap CRISPR fitness signal (% of screened cell lines dependent on the target).

Gene	Target	Action	pAffinity	Cancer dependency	UniProt
ADRA2A	α2A-adrenoceptor	Agonist	8.9	0.1%	P08913
ADRA2B	α2B-adrenoceptor	Agonist	7.2	0.2%	P18089
ADRA2C	α2C-adrenoceptor	Agonist	6.88	0%	P18825

Broader ChEMBL bioactivity targets: 33 (assay-derived). Sample: Microtubule-associated protein tau, Lysine-specific demethylase 4E, Fructose-bisphosphate aldolase, Prelamin-A/C, RecQ-like DNA helicase BLM, 4’-phosphopantetheinyl transferase ffp, Ferritin light chain, 15-hydroxyprostaglandin dehydrogenase [NAD(+)], Endonuclease 4, Alpha-2A adrenergic receptor.

Bioactivity

ChEMBL activities: 52 potent at pChembl ≥ 5 of 77 total. Top 30 by potency (10 = 0.1 nM, 6 = 1 µM):

Target	pChembl	Type	Value	Unit	Activity ID
ADRA2A	9.21	EC50	0.62	nM	CHEMBL_ACT_1233171
ADRA2A	9.07	EC50	0.86	nM	CHEMBL_ACT_16896925
ADRA2A	8.85	Ki	1.41	nM	CHEMBL_ACT_2500590
ADRA2A	8.62	AC50	2.4	nM	CHEMBL_ACT_25221639
ADRA2A	8.62	Ki	2.4	nM	CHEMBL_ACT_372491
ADRA2A	8.62	Ki	2.4	nM	CHEMBL_ACT_825359
ADRA2A	8.57	Ki	2.7	nM	CHEMBL_ACT_958214
ADRA2A	8.52	IC50	3	nM	CHEMBL_ACT_253179
ADRA2C	8.47	EC50	3.4	nM	CHEMBL_ACT_958219
P19328	8.44	IC50	3.6	nM	CHEMBL_ACT_166569
ADRA2A	8.39	EC50	4.1	nM	CHEMBL_ACT_958217
BLM	8.25	Potency	5.6	nM	CHEMBL_ACT_4745854
BLM	8.25	Potency	5.6	nM	CHEMBL_ACT_4917957
ADRA2A	8.17	Ki	6.76	nM	CHEMBL_ACT_1233170
ADRA2C	8.1	EC50	8	nM	CHEMBL_ACT_16896935
ADRA2C	8.02	EC50	9.55	nM	CHEMBL_ACT_1233177
P19328	7.52	Ki	30	nM	CHEMBL_ACT_878961
ADRA2B	7.46	Ki	34.67	nM	CHEMBL_ACT_1233173
ADRA2C	7.36	Ki	44	nM	CHEMBL_ACT_958216
P19328	7.28	Ki	52	nM	CHEMBL_ACT_958215
P19328	7.26	EC50	55	nM	CHEMBL_ACT_958218
ADRA2C	7.08	Ki	83.18	nM	CHEMBL_ACT_1233176
ADRA2A	6.95	Ki	112	nM	CHEMBL_ACT_7621257
ADRA2B	6.55	EC50	281.8	nM	CHEMBL_ACT_1233174
ADRA2A	6.53	IC50	298	nM	CHEMBL_ACT_7621256
CYP3A4	6.4	Potency	398.1	nM	CHEMBL_ACT_4973353
CYP3A4	6.4	Potency	398.1	nM	CHEMBL_ACT_5038578
CYP3A4	6.4	AC50	398.1	nM	CHEMBL_ACT_6027211
ADRA2B	6.32	Ki	478	nM	CHEMBL_ACT_7621259
ADRA1A	6.19	AC50	644.8	nM	CHEMBL_ACT_25230261

Target pathways

Aggregated over 3 target gene(s): ADRA2A, ADRA2B, ADRA2C.

Top Reactome pathways

19 total, by targets touching each:

Pathway	Targets	Genes
Hemostasis	3	ADRA2A, ADRA2B, ADRA2C
Signal Transduction	3	ADRA2A, ADRA2B, ADRA2C
Signaling by GPCR	3	ADRA2A, ADRA2B, ADRA2C
Class A/1 (Rhodopsin-like receptors)	3	ADRA2A, ADRA2B, ADRA2C
Amine ligand-binding receptors	3	ADRA2A, ADRA2B, ADRA2C
GPCR downstream signalling	3	ADRA2A, ADRA2B, ADRA2C
Adrenoceptors	3	ADRA2A, ADRA2B, ADRA2C
Adrenaline signalling through Alpha-2 adrenergic receptor	3	ADRA2A, ADRA2B, ADRA2C
G alpha (i) signalling events	3	ADRA2A, ADRA2B, ADRA2C
G alpha (z) signalling events	3	ADRA2A, ADRA2B, ADRA2C
GPCR ligand binding	3	ADRA2A, ADRA2B, ADRA2C
Platelet activation, signaling and aggregation	3	ADRA2A, ADRA2B, ADRA2C
Platelet Aggregation (Plug Formation)	3	ADRA2A, ADRA2B, ADRA2C
Metabolism	2	ADRA2A, ADRA2C
Integration of energy metabolism	2	ADRA2A, ADRA2C
Metabolism of proteins	2	ADRA2A, ADRA2C
Adrenaline,noradrenaline inhibits insulin secretion	2	ADRA2A, ADRA2C
Regulation of insulin secretion	2	ADRA2A, ADRA2C
Surfactant metabolism	2	ADRA2A, ADRA2C

Dominant GO biological processes

GO term	Targets
epidermal growth factor receptor signaling pathway	3
G protein-coupled receptor signaling pathway	3
negative regulation of norepinephrine secretion	3
regulation of vasoconstriction	3
platelet activation	3
negative regulation of epinephrine secretion	3
positive regulation of MAPK cascade	3
positive regulation of phosphatidylinositol 3-kinase/protein kinase B signal transduction	3
adrenergic receptor signaling pathway	3
adenylate cyclase-inhibiting adrenergic receptor signaling pathway	3
regulation of smooth muscle contraction	3
signal transduction	3
adenylate cyclase-inhibiting G protein-coupled receptor signaling pathway	2
female pregnancy	2
negative regulation of insulin secretion	2

Indications & clinical

Indications

8 indications (2 at ChEMBL trial phase 4). Phase below is the highest clinical-trial phase recorded for this drug against each disease — not the molecule’s overall approval status (that is in the Summary).

Indication	Trial phase	MONDO	EFO
eye allergy	4	MONDO:0005551	EFO:0005751
glaucoma	4	MONDO:0005041	MONDO:0005041
rosacea	3	MONDO:0006604	EFO:1000760
ocular hypertension	3	MONDO:0006875	EFO:1001069
diabetic retinopathy	2	MONDO:0005266	EFO:0003770
open-angle glaucoma	2	MONDO:0005338	EFO:0004190
dry eye syndrome	2	MONDO:0006733	EFO:1000906
presbyopia	1	MONDO:0001330	MONDO:0001330

Clinical trials

Total trials: 56.

Phase distribution

Phase	Trials
PHASE4	20
Not specified	11
PHASE3	10
PHASE2	7
EARLY_PHASE1	3
PHASE1	3
PHASE2/PHASE3	1
PHASE1/PHASE2	1

Top trials by phase / activity

NCT	Phase	Status	Title
NCT07390578	PHASE4	NOT_YET_RECRUITING	Upneeq vs. Lumify Ptosis
NCT00312416	PHASE4	COMPLETED	Effects of Topical Clonidine vs. Brimonidine on Choroidal Blood Flow and Intraocular Pressure During Isometric Exercise
NCT00347035	PHASE4	TERMINATED	INFLUENCE OF TOPICAL INDOMETHACIN ON HYPOTHENSIVE EFFECT OF BRIMONIDINE
NCT00457795	PHASE4	COMPLETED	24-hour IOP-lowering Effect of Brimonidine 0.1%
NCT00466479	PHASE4	COMPLETED	Brimonidine vs ALTP in Progressing Human Glaucoma
NCT00800540	PHASE4	COMPLETED	Circadian Ocular Perfusion Pressure and Ocular Blood Flow
NCT00869141	PHASE4	COMPLETED	Earlier Intraocular Pressure Control After Ahmed Glaucoma Valve Implantation for Glaucoma
NCT00972257	PHASE4	COMPLETED	24-hr Intraocular Pressure Control With Dorzolamide/Timolol vs the Brimonidine/Timolol Fixed Combination
NCT00981786	PHASE4	COMPLETED	24-Hour Intraocular Pressure With Brinzolamide/Timolol Versus Brimonidine/Timolol
NCT01151904	PHASE4	TERMINATED	Study of Brimonidine and Timolol Ophthalmic Solution With Latanoprost Compared With Latanoprost in Glaucoma Patients
NCT01446497	PHASE4	UNKNOWN	Efficacy and Safety Study of Combigan and 0.5% Timoptic in Normal Tension Glaucoma
NCT02147691	PHASE4	COMPLETED	Finacea 15% and Brimonidine 0.33% Gel in the Treatment of Rosacea - A Pilot Study
NCT02249065	PHASE4	COMPLETED	Mirvaso in Use Study
NCT02616250	PHASE4	COMPLETED	MirvasO Soolantra Association In the Treatment of Moderate to Severe rosaCea.
NCT02761174	PHASE4	COMPLETED	Topical Brimonidine to Reduce Inflammation After IPL-treatment in Patients With Facial Telangiectasias
NCT03192826	PHASE4	COMPLETED	Brinzolamide/Brimonidine Combination vs Brimonidine 0.2% in the Prevention of IOP Rise After Nd-YAG Laser Capsulotomy
NCT03959176	PHASE4	COMPLETED	The Effect of Brimonidine
NCT05480098	PHASE4	WITHDRAWN	Brimonidine for Intraoperative Hemostasis
NCT06449352	PHASE4	COMPLETED	Effect of Netarsudil vs Brimonidine in NTG Patients on Latanoprost
NCT07431476	PHASE4	COMPLETED	Brimonidine 0.33% for Rosacea-Related Facial Erythema
NCT00168363	PHASE3	COMPLETED	Safety and Efficacy of Brimonidine in Patients With Glaucoma or Ocular Hypertension
NCT00332384	PHASE3	COMPLETED	Safety and Efficacy Study of Brimonidine/Timolol Fixed Combination in Patients With Glaucoma or Ocular Hypertension
NCT00332436	PHASE3	COMPLETED	Safety and Efficacy Study of Brimonidine/Timolol Fixed Combination in Patients With Glaucoma or Ocular Hypertension
NCT00651612	PHASE3	COMPLETED	Study to Evaluate Safety of Brimonidine/Timolol Fixed Combination in Glaucoma or Ocular Hypertension Patients
NCT00652106	PHASE3	COMPLETED	Safety and Efficacy Study of Brimonidine/Timolol Fixed Combination in Patients With Glaucoma or Ocular Hypertension
NCT01004900	PHASE3	UNKNOWN	Intraocular Pressure (IOP) Lowering Effect of Selective Laser Trabeculoplasty Versus Prostaglandin Analogues in Angle Closure Glaucoma
NCT01726075	PHASE2/PHASE3	COMPLETED	Trial to Assess the Efficacy of Neuroprotective Drugs Administered Topically to Prevent or Arrest Diabetic Retinopathy
NCT02289352	PHASE3	COMPLETED	Randomized, Double-blind, Multiple-site, Placebo-controlled, Parallel-design Study in Patients With Moderate to Severe Facial Erythema Associated With Rosacea
NCT02339584	PHASE3	COMPLETED	Efficacy and Safety of Brinzolamide/Brimonidine Fixed Combination BID Compared to Brinzolamide BID Plus Brimonidine BID in Subjects With Open-Angle Glaucoma (OAG) or Ocular Hypertension (OHT)
NCT02764411	PHASE3	TERMINATED	Onreltea (Brimonidine) Gel In Pediatric Patients With Capillary Malformations
NCT05656027	PHASE3	COMPLETED	Phase 3 Evaluation of the Safety and Efficacy of LNZ100 & LNZ101 for the Treatment of Presbyopia
NCT00317577	PHASE2	COMPLETED	Study of Medical Treatment of Low-Pressure (Normal Tension) Glaucoma
NCT00332345	PHASE2	COMPLETED	Safety and Efficacy Study of Brimonidine/Timolol Fixed Combination in Patients With Glaucoma or Ocular Hypertension
NCT00804921	PHASE2	COMPLETED	Effectiveness of Oral Acetazolamide, Brimonidine Tartarate, and Anterior Chamber Paracentesis in Intraocular Pressure (IOP) After Bevacizumab
NCT00864838	PHASE2	COMPLETED	Oral Acetazolamide, Brimonidine Tartarate, and Anterior Chamber Paracentesis for Ocular Hypertension Control After Intravitreal Bevacizumab
NCT01345448	PHASE2	UNKNOWN	Intraocular Pressure (IOP) Lowering Efficacy of Transdermal Brimonidine Therapy
NCT01863953	PHASE2	COMPLETED	A Safety and Efficacy Study of Fixed-Combination Bimatoprost and Brimonidine in Chronic Glaucoma or Ocular Hypertension
NCT02975557	PHASE1/PHASE2	TERMINATED	Brimonidine Eye Drops for Treatment of Ocular Graft-vs-Host Disease (oGVHD)
NCT03418727	PHASE2	COMPLETED	Dry Eye Disease Study With Brimonidine
NCT05001243	PHASE1	UNKNOWN	Comparison of a Compound With Pilocarpine and Brimonidine to Improve Near Vision in Healthy Presbyopic Patients

Clinical evidence (CIViC)

No CIViC predictive evidence (expected for non-precision-medicine drugs).

Pharmacology

Pharmacogenomics

No CPIC/DPWG dosing guideline or drug-level clinical/variant annotations in PharmGKB for this molecule.

Related molecules

Related molecules

Molecules sharing ≥1 of this drug’s curated primary targets, merged from two biobtree sources and ranked by shared-target count, then clinical phase: ChEMBL clinical-stage candidates (development phase ≥2) and PubChem drug-class bioactivity (approved / known drugs acting on the target). Deduplicated by drug name; the drug’s own salt forms are excluded. Note: for a drug with few primary targets a shared-target match can reflect off-target / promiscuous binding rather than the same therapeutic mechanism — the phase ordering surfaces bona-fide therapeutics first.

607 molecules share ≥1 primary target. Top 60 by shared-target count:

Molecule	Source	Status	Shared targets
ACLIDINIUM BROMIDE	ChEMBL + PubChem	Phase 4 (approved)	ADRA2A, ADRA2B, ADRA2C
Afatinib	ChEMBL + PubChem	Phase 4 (approved)	ADRA2A, ADRA2B, ADRA2C
Almotriptan	ChEMBL + PubChem	Phase 4 (approved)	ADRA2A, ADRA2B, ADRA2C
CHENODIOL	ChEMBL + PubChem	Phase 4 (approved)	ADRA2A, ADRA2B, ADRA2C
CLOZAPINE	ChEMBL + PubChem	Phase 4 (approved)	ADRA2A, ADRA2B, ADRA2C
CRIZOTINIB	ChEMBL + PubChem	Phase 4 (approved)	ADRA2A, ADRA2B, ADRA2C
DESLORATADINE	ChEMBL + PubChem	Phase 4 (approved)	ADRA2A, ADRA2B, ADRA2C
DIHYDROERGOTAMINE	ChEMBL + PubChem	Phase 4 (approved)	ADRA2A, ADRA2B, ADRA2C
GENTIAN VIOLET	ChEMBL + PubChem	Phase 4 (approved)	ADRA2A, ADRA2B, ADRA2C
NAPHAZOLINE	ChEMBL + PubChem	Phase 4 (approved)	ADRA2A, ADRA2B, ADRA2C
OLANZAPINE	ChEMBL + PubChem	Phase 4 (approved)	ADRA2A, ADRA2B, ADRA2C
OLODATEROL	ChEMBL + PubChem	Phase 4 (approved)	ADRA2A, ADRA2B, ADRA2C
PALIPERIDONE	ChEMBL + PubChem	Phase 4 (approved)	ADRA2A, ADRA2B, ADRA2C
PRAMIPEXOLE	ChEMBL + PubChem	Phase 4 (approved)	ADRA2A, ADRA2B, ADRA2C
TAMSULOSIN	ChEMBL + PubChem	Phase 4 (approved)	ADRA2A, ADRA2B, ADRA2C
TEGASEROD	ChEMBL + PubChem	Phase 4 (approved)	ADRA2A, ADRA2B, ADRA2C
ACETOPHENAZINE	ChEMBL	Phase 4 (approved)	ADRA2A, ADRA2B, ADRA2C
ALFUZOSIN	ChEMBL	Phase 4 (approved)	ADRA2A, ADRA2B, ADRA2C
AMISULPRIDE	ChEMBL	Phase 4 (approved)	ADRA2A, ADRA2B, ADRA2C
AMITRIPTYLINE	ChEMBL	Phase 4 (approved)	ADRA2A, ADRA2B, ADRA2C
AMOXAPINE	ChEMBL	Phase 4 (approved)	ADRA2A, ADRA2B, ADRA2C
APOMORPHINE	ChEMBL	Phase 4 (approved)	ADRA2A, ADRA2B, ADRA2C
APRACLONIDINE	ChEMBL	Phase 4 (approved)	ADRA2A, ADRA2B, ADRA2C
ARIPIPRAZOLE	ChEMBL	Phase 4 (approved)	ADRA2A, ADRA2B, ADRA2C
ASENAPINE	ChEMBL	Phase 4 (approved)	ADRA2A, ADRA2B, ADRA2C
ASTEMIZOLE	ChEMBL	Phase 4 (approved)	ADRA2A, ADRA2B, ADRA2C
AZELASTINE	ChEMBL	Phase 4 (approved)	ADRA2A, ADRA2B, ADRA2C
BAZEDOXIFENE	ChEMBL	Phase 4 (approved)	ADRA2A, ADRA2B, ADRA2C
BENFLUOREX	ChEMBL	Phase 4 (approved)	ADRA2A, ADRA2B, ADRA2C
BENPERIDOL	ChEMBL	Phase 4 (approved)	ADRA2A, ADRA2B, ADRA2C
BENZBROMARONE	ChEMBL	Phase 4 (approved)	ADRA2A, ADRA2B, ADRA2C
BENZQUINAMIDE	ChEMBL	Phase 4 (approved)	ADRA2A, ADRA2B, ADRA2C
BENZTHIAZIDE	ChEMBL	Phase 4 (approved)	ADRA2A, ADRA2B, ADRA2C
BENZTROPINE	ChEMBL	Phase 4 (approved)	ADRA2A, ADRA2B, ADRA2C
BITHIONOL	ChEMBL	Phase 4 (approved)	ADRA2A, ADRA2B, ADRA2C
BREXPIPRAZOLE	ChEMBL	Phase 4 (approved)	ADRA2A, ADRA2B, ADRA2C
BROMOCRIPTINE	ChEMBL	Phase 4 (approved)	ADRA2A, ADRA2B, ADRA2C
BROMPERIDOL	ChEMBL	Phase 4 (approved)	ADRA2A, ADRA2B, ADRA2C
CABERGOLINE	ChEMBL	Phase 4 (approved)	ADRA2A, ADRA2B, ADRA2C
CANDESARTAN CILEXETIL	ChEMBL	Phase 4 (approved)	ADRA2A, ADRA2B, ADRA2C
CARIPRAZINE	ChEMBL	Phase 4 (approved)	ADRA2A, ADRA2B, ADRA2C
CARVEDILOL	ChEMBL	Phase 4 (approved)	ADRA2A, ADRA2B, ADRA2C
CHLORHEXIDINE	ChEMBL	Phase 4 (approved)	ADRA2A, ADRA2B, ADRA2C
CHLOROQUINE	ChEMBL	Phase 4 (approved)	ADRA2A, ADRA2B, ADRA2C
CHLORPROMAZINE	ChEMBL	Phase 4 (approved)	ADRA2A, ADRA2B, ADRA2C
CINNARIZINE	ChEMBL	Phase 4 (approved)	ADRA2A, ADRA2B, ADRA2C
CISAPRIDE	ChEMBL	Phase 4 (approved)	ADRA2A, ADRA2B, ADRA2C
CLEMASTINE	ChEMBL	Phase 4 (approved)	ADRA2A, ADRA2B, ADRA2C
CLOMIPRAMINE	ChEMBL	Phase 4 (approved)	ADRA2A, ADRA2B, ADRA2C
CLONIDINE	ChEMBL	Phase 4 (approved)	ADRA2A, ADRA2B, ADRA2C
CLOTRIMAZOLE	ChEMBL	Phase 4 (approved)	ADRA2A, ADRA2B, ADRA2C
CYPROHEPTADINE	ChEMBL	Phase 4 (approved)	ADRA2A, ADRA2B, ADRA2C
DANAZOL	ChEMBL	Phase 4 (approved)	ADRA2A, ADRA2B, ADRA2C
DARIFENACIN	ChEMBL	Phase 4 (approved)	ADRA2A, ADRA2B, ADRA2C
DEXMEDETOMIDINE	ChEMBL	Phase 4 (approved)	ADRA2A, ADRA2B, ADRA2C
DIETHYLSTILBESTROL	ChEMBL	Phase 4 (approved)	ADRA2A, ADRA2B, ADRA2C
DOBUTAMINE	ChEMBL	Phase 4 (approved)	ADRA2A, ADRA2B, ADRA2C
DOMPERIDONE	ChEMBL	Phase 4 (approved)	ADRA2A, ADRA2B, ADRA2C
DOTHIEPIN	ChEMBL	Phase 4 (approved)	ADRA2A, ADRA2B, ADRA2C
DOXAZOSIN	ChEMBL	Phase 4 (approved)	ADRA2A, ADRA2B, ADRA2C