Brimonidine (CED0004342)

Record Information

Version

1.0

Creation Date

2009-07-30 17:58:43 UTC

Update Date

2026-05-14 16:40:08 UTC

SynCED ID

CED0004342

Secondary Accession Numbers

CHEM002507
T3D3487

Identification

Common Name

Brimonidine

Class

Small Molecule

Description

Brimonidine is an exogenous compound with the formula C11H10BrN5 and an average molecular weight of 292.13 g/mol. It exists as a solid at room temperature. Brimonidine belongs to the benzodiazines, a subclass of diazanaphthalenes within the organic compounds. Functioning as an alpha-adrenergic agonist, this compound targets the Alpha-2A (ADRA2A), Alpha-2B (ADRA2B), and Alpha-2C (ADRA2C) adrenergic receptors. It is utilized as an antihypertensive agent and an adrenergic agonist. In clinical applications, it is used to treat glaucoma by decreasing aqueous humor synthesis. Fluorophotometric studies in humans and animals suggest a dual mechanism of action characterized by the reduction of aqueous humor production and the increase of uveoscleral outflow, with a peak ocular hypotensive effect occurring two hours after dosing. Additionally, a topical gel formulation marketed as Mirvaso received FDA approval in August 2013 for the treatment of rosacea. Brimonidine is found in various recorded sources, including healthcare, pharmaceuticals, and veterinary products such as miotics, antiglaucoma preparations, antiallergics, and decongestants, as well as dermatological preparations. It is also identified in food preservation, electrical and electronic equipment like electrically stimulated smoking devices, and household consumer products including tobacco smoke filters, cigar cigarettes, non-electric simulated smoking devices, and other smoking requisites. Exposure to the compound occurs via topical and ophthalmic routes.

Contaminant Type

Adrenergic alpha-2 Receptor Agonist
Adrenergic alpha-Agonist
Amide
Amine
Antihypertensive Agent
Bromide Compound
Drug
EENT Preparation
Metabolite
Organic Compound
Organobromide
Synthetic Compound

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
5-Bromo-6-(2-imidazolin-2-ylamino)quinoxaline	ChEBI
Brimonidina	ChEBI
Brimonidinum	ChEBI
Bromoxidine	ChEBI
Brimonidine tartrate	HMDB
Alphagan	HMDB
Purite, brimonidine	HMDB
RatioBrimonidine	HMDB
Sanrosa	HMDB
Brimonidine tartrate (1:1)	HMDB
Brimonidine tartrate (1:1), (S-(r,r))-isomer	HMDB
5-Bromo-6-(2-imidazolin-2-ylamino)quinoxaline D-tartrate	HMDB
Ratio brimonidine	HMDB
Tartrate, brimonidine	HMDB
Mirvaso	HMDB
5-Bromo-6-(imidazolidinylideneamino)quinoxaline	HMDB
5-Bromo-6-(imidazolin-2-ylamino)quinoxaline	HMDB
Alphagan p	HMDB
Ratio-brimonidine	HMDB
Brimonidine purite	HMDB
Brimonidine tartrate, (R-(r,r))-isomer	HMDB

Chemical Formula

C₁₁H₁₀BrN₅

Average Molecular Mass

292.135 g/mol

Monoisotopic Mass

291.012 g/mol

CAS Registry Number

59803-98-4

IUPAC Name

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

Traditional Name

brimonidine

SMILES

BrC1=C(NC2=NCCN2)C=CC2=NC=CN=C12

InChI Identifier

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

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as quinoxalines. Quinoxalines are compounds containing a quinoxaline moiety, a bicyclic heterocycle made up of a benzene ring fused to a pyrazine ring.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Diazanaphthalenes

Sub Class

Benzodiazines

Direct Parent

Quinoxalines

Alternative Parents

Substituents

Quinoxaline
Aryl bromide
Aryl halide
Pyrazine
Benzenoid
2-imidazoline
Heteroaromatic compound
Guanidine
Azacycle
Carboximidamide
Propargyl-type 1,3-dipolar organic compound
Organic 1,3-dipolar compound
Organic nitrogen compound
Hydrocarbon derivative
Organonitrogen compound
Organobromide
Organohalogen compound
Organopnictogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

imidazoles (CHEBI:3175 )
quinoxaline derivative (CHEBI:3175 )
secondary amine (CHEBI:3175 )

Biological Properties

Status

Detected and Not Quantified

Origin

Exogenous

Cellular Locations

Cytoplasm
Extracellular
Membrane

Biofluid Locations

Not Available

Tissue Locations

Not Available

Applications

Biological Roles

Chemical Roles

Not Available

Organoleptic Effects

Not Available

Physical Properties

State

Solid

Appearance

White powder.

Experimental Properties

Property	Value
Melting Point	207.5°C
Boiling Point	Not Available
Solubility	Soluble (1.5 mg/mL)

Predicted Properties

Property	Value	Source
Water Solubility	0.15 g/L	ALOGPS
logP	1.27	ALOGPS
logP	1.37	ChemAxon
logS	-3.3	ALOGPS
pKa (Strongest Basic)	8.32	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	62.2 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	68.49 m³·mol⁻¹	ChemAxon
Polarizability	25.74 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum	splash10-03xr-0190000000-cd1ec9d5bf9d24fab607	Not Available	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum	Not Available	Not Available	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum	Not Available	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0006-0190000000-49c10e93a1977cbe01da	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0006-0090000000-2f188927245c7fb3c618	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0006-1090000000-fdfdc04ca6c5f2b62c3e	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-014i-9030000000-2d727aeec5962a767e61	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0006-0090000000-91069ec802c3a06026d7	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0006-0090000000-7bd1085ed4367b683e29	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0002-2290000000-6351edb1d68a299dfd2d	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0006-0090000000-5f6f82bdb9f8c51818c9	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0006-0090000000-5f6f82bdb9f8c51818c9	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-000f-0490000000-2720653740ec8305f05d	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0006-0090000000-ffef408a4fb5db76cb85	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0006-1090000000-0b1325c866472eaa216a	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0f9j-3690000000-b5ba2dea82c37975ad75	Not Available	View Spectrum

Toxicity Profile

Toxicity Values

Toxicity Value	Organism	Dose Descriptor	Route of Exposure	Predicted or Experimental	Toxicity Rating	Reference
50.0 mg/kg	mice	LD50	oral	experimental	Not Available	Not Available
100.0 mg/kg	rat	LD50	oral	experimental	Not Available	Not Available
219.0 Log mg/kg [120:390]	Rat	LD50	oral	predicted	Not Available	Not Available

Toxicity / Toxin Class

Not Available

Mechanism of Toxicity

Brimonidine is an alpha adrenergic receptor agonist (primarily alpha-2). It has a peak ocular hypotensive effect occurring at two hours post-dosing. Fluorophotometric studies in animals and humans suggest that Brimonidine has a dual mechanism of action by reducing aqueous humor production and increasing uveoscleral outflow. The topical gel reduces erythema through direct vasocontriction.

Carcinogenicity (IARC Classification)

No indication of carcinogenicity to humans (not listed by IARC).

Minimum Risk Level

Not Available

Symptoms

Oral LD₅₀ is 50 mg/kg in mice and 100 mg/kg in rats.

Treatment

Not Available

Health Effects

Health Effect	Relationship	Direction	Description	Reference
glaucoma	Not Available	Not Available	A disorder characterized by an increase in pressure in the eyeball due to obstruction of the aqueous humor outflow. (NCI CTCAE)	PMC6687460 , PMC7248996
rosacea	Not Available	Not Available	Not Available	PMC7201191
ocular hypertension	Not Available	Not Available	An eye disease that is characterized by elevated intraocular pressure in the absence of optic nerve damage or visual field loss. (DO)	PMC7201191 , PMC7248996
open-angle glaucoma	Not Available	Not Available	Not Available	PMC7201191
Macular geographic atrophy	Not Available	Not Available	Not Available	PMC10892262

Exposure Sources

Source ID	Source	Sector	Reference
CEDs000010	Insecticides?Insecticides are synthetic chemicals designed to control or eliminate insect pests that threaten crops and other agricultural products.	Agriculture & land management	PubChem
CEDs000315	Dermatological preparations?Dermatological preparations encompass a wide range of topical products, including creams, ointments, gels, and lotions, designed for the treatment of skin conditions.	Healthcare, pharmaceuticals & veterinary products	Not Available
CEDs000398	Antiglaucoma preparations and miotics?Antiglaucoma preparations and miotics are pharmacological agents utilized to manage intraocular pressure in patients with glaucoma.	Healthcare, pharmaceuticals & veterinary products	Not Available
CEDs000400	Decongestants and antiallergics?Decongestants and antiallergics are synthetic chemicals commonly used in the treatment of nasal congestion and allergic reactions, respectively.	Healthcare, pharmaceuticals & veterinary products	Not Available
CEDs000518	Electrically Stimulated Smoking Devices?Electrically stimulated smoking devices, commonly known as e-cigarettes or vape pens, utilize electrical components to heat a liquid solution, often containing nicotine, flavorings, and other additives, to produce an aerosol for inhalation.	Electrical & Electronic Equipment	PubChem
CEDs000545	Food Preservation?Food preservation often involves the use of synthetic chemicals, such as preservatives, flavor enhancers, and color additives, to extend shelf life and enhance the sensory qualities of food products.	Food, food processing & cookware	PubChem
CEDs000556	Cigar Cigarettes?Cigar cigarettes are a source of synthetic chemical contamination due to the combustion of various tobacco blends and additives.	Household cleaning & consumer products	PubChem
CEDs000559	Non Electric Simulated Smoking Devices?Non-electric simulated smoking devices, often designed to mimic the experience of smoking without combustion, can be sources of synthetic chemical contamination due to the materials and chemicals used in their construction and operation.	Household cleaning & consumer products	PubChem
CEDs000560	Other Smoking Requisites?Other smoking requisites, including items such as lighters, matches, and rolling papers, can introduce synthetic chemical contamination through various components and additives.	Household cleaning & consumer products	PubChem
CEDs000569	Tobacco Smoke Filters?Tobacco smoke filters are designed to reduce the inhalation of harmful substances in cigarette smoke, including tar and other particulate matter.	Household cleaning & consumer products	PubChem
CEDs000580	Manufacture Preparation Of Tobacco Products?The manufacture and preparation of tobacco products involve various processes that can result in the introduction of synthetic chemicals into the environment.	Industrial manufacturing & chemical processing	PubChem
CEDs000596	Acaricides?Acaricides are synthetic chemicals specifically designed to target and control mite populations that can damage crops and plants.	Agriculture & land management	PubChem
CEDs000606	Plant Growth Regulators?Plant Growth Regulators (PGRs) are synthetic chemicals designed to influence the growth and development of plants.	Agriculture & land management	PubChem
CEDs000610	Aftersun Products?Aftersun products are designed to soothe and hydrate the skin after sun exposure, often containing various synthetic chemicals such as emollients, preservatives, and fragrances.	Personal care & cosmetics	PubChem
CEDs000611	Anti Perspirants Or Body Deoderants?Antiperspirants and body deodorants commonly contain synthetic chemicals such as aluminum compounds, parabens, and synthetic fragrances.	Personal care & cosmetics	PubChem
CEDs000615	Eye Makeup Products?Eye makeup products, including mascaras, eyeliners, and eyeshadows, often contain a variety of synthetic chemicals such as pigments, preservatives, and film-forming agents.	Personal care & cosmetics	PubChem
CEDs000632	Apparel?Apparel production often involves the use of various synthetic chemicals, including dyes, finishing agents, and preservatives.	Textiles, leather & furnishings	PubChem
CEDs000650	Purses Luggage Hand Bags?Purses, luggage, and handbags are often manufactured using synthetic materials such as polyvinyl chloride (PVC), polyurethane, and various types of nylon.	Textiles, leather & furnishings	PubChem
CEDs000662	Yarns Or Threads?Yarns or threads used in textiles can be a source of synthetic chemical contamination due to the production processes and treatments they undergo.	Textiles, leather & furnishings	PubChem
CEDs000685	Ceramics?Ceramics can be a source of synthetic chemical contamination through various additives and processing agents used in their production.	Building & Construction	PubChem
CEDs000688	Glass Coatings?Glass coatings are synthetic chemical formulations applied to glass surfaces to enhance properties such as durability, UV resistance, and aesthetic appeal.	Building & Construction	PubChem
CEDs000696	Nanotechnology?Nanotechnology involves the manipulation of materials at the molecular or atomic level, typically within the range of 1 to 100 nanometers.	Industrial manufacturing & chemical processing	PubChem
CEDs000730	Contact Lens Cases?Contact lens cases are small containers designed to store contact lenses in a sterile environment, typically made from various synthetic materials including plastics such as polypropylene or polycarbonate.	Healthcare, pharmaceuticals & veterinary products	PubChem
CEDs000744	Water, Wastewater, & Sewage Treatment?Water, wastewater, and sewage treatment processes are critical for managing and mitigating pollutants in water systems.	Wastewater, sanitation & biosolids	PubChem

Pathways

1 pathwayPathway Source: PathBank

Brimonidine Drug Metabolism Action Pathway

Targets

Structure	Protein	UniProt ID	Organism	Relationship	Details
Click to view 3D structure	Alpha-2B adrenergic receptor	P18089	Humans	Predicted (SEA)	Prediction Confidence Score 0.76 Applicability Domain 1.0 Statistical Significance 6.00e-05 Supporting Reference Compounds 340 E-value 0.467095
Click to view 3D structure	Alpha-2A adrenergic receptor	P08913	Humans	Predicted (SEA)	Prediction Confidence Score 0.76 Applicability Domain 1.0 Statistical Significance 6.00e-05 Supporting Reference Compounds 487 E-value 0.467095
Click to view 3D structure	Alpha-2C adrenergic receptor	P18825	Humans	Predicted (SEA)	Prediction Confidence Score 0.76 Applicability Domain 1.0 Statistical Significance 6.00e-05 Supporting Reference Compounds 386 E-value 0.467095
Click to view 3D structure	Alpha-1D adrenergic receptor	P25100	Humans	Predicted (SEA)	Prediction Confidence Score 0.76 Applicability Domain 1.0 Statistical Significance 4.00e-05 Supporting Reference Compounds 258 E-value 0.311397
Click to view 3D structure	Alpha-1B adrenergic receptor	P35368	Humans	Predicted (SEA)	Prediction Confidence Score 0.655 Applicability Domain 1.0 Statistical Significance 2.10e-04 Supporting Reference Compounds 298 E-value 1.63483
Click to view 3D structure	Alpha-1A adrenergic receptor	P35348	Humans	Predicted (SEA)	Prediction Confidence Score 0.641 Applicability Domain 1.0 Statistical Significance 3.40e-04 Supporting Reference Compounds 376 E-value 2.64687
Click to view 3D structure	Alpha-2B adrenergic receptor	P19328	Rattus norvegicus	Predicted (SEA)	Prediction Confidence Score 0.553 Applicability Domain 1.0 Statistical Significance 2.00e-05 Supporting Reference Compounds 30 E-value 0.155698
Click to view 3D structure	Alpha-1A adrenergic receptor	P18130	Bos taurus	Predicted (SEA)	Prediction Confidence Score 0.447 Applicability Domain 1.0 Statistical Significance 8.10e-04 Supporting Reference Compounds 85 E-value 6.30579
Click to view 3D structure	5-hydroxytryptamine receptor 1A	P19327	Rattus norvegicus	Predicted (SEA)	Prediction Confidence Score 0.403 Applicability Domain 1.0 Statistical Significance 0.0122 Supporting Reference Compounds 541 E-value 94.9761
Click to view 3D structure	Alpha-1B adrenergic receptor	G3HDX1	Cricetulus griseus	Predicted (SEA)	Prediction Confidence Score 0.4 Applicability Domain 1.0 Statistical Significance 2.00e-05 Supporting Reference Compounds 5 E-value 0.155698
Click to view 3D structure	Alpha-1A adrenergic receptor	P43140	Rattus norvegicus	Predicted (SEA)	Prediction Confidence Score 0.393 Applicability Domain 1.0 Statistical Significance 0.0051 Supporting Reference Compounds 208 E-value 39.4696
Click to view 3D structure	5-hydroxytryptamine receptor 7	P34969	Humans	Predicted (SEA)	Prediction Confidence Score 0.382 Applicability Domain 0.778 Statistical Significance 0.0135 Supporting Reference Compounds 565 E-value 104.785
Click to view 3D structure	Nischarin	Q9Y2I1	Humans	Predicted (SEA)	Prediction Confidence Score 0.333 Applicability Domain 0.412 Statistical Significance 5.60e-04 Supporting Reference Compounds 37 E-value 4.35956
Click to view 3D structure	Sigma intracellular receptor 2	Q5BJF2	Humans	Predicted (SEA)	Prediction Confidence Score 0.326 Applicability Domain 0.778 Statistical Significance 0.0191 Supporting Reference Compounds 308 E-value 149.081
Click to view 3D structure	Nischarin	Q4G017	Rattus norvegicus	Predicted (SEA)	Prediction Confidence Score 0.291 Applicability Domain 0.4 Statistical Significance 6.40e-04 Supporting Reference Compounds 18 E-value 4.98235
Click to view 3D structure	Sodium-dependent serotonin transporter	P31645	Humans	Predicted (SEA)	Prediction Confidence Score 0.283 Applicability Domain 0.778 Statistical Significance 0.076 Supporting Reference Compounds 593 E-value 592.043
Click to view 3D structure	Alpha-2A adrenergic receptor	Q28838	Bos taurus	Predicted (SEA)	Prediction Confidence Score 0.26 Applicability Domain 0.4 Statistical Significance 0.0051 Supporting Reference Compounds 32 E-value 39.7031
Click to view 3D structure	5-hydroxytryptamine receptor 1A	P08908	Humans	Predicted (SEA)	Prediction Confidence Score 0.257 Applicability Domain 0.4 Statistical Significance 0.2213 Supporting Reference Compounds 953 E-value 1723.04
Click to view 3D structure	5-hydroxytryptamine receptor 2C	P28335	Humans	Predicted (SEA)	Prediction Confidence Score 0.244 Applicability Domain 0.391 Statistical Significance 0.3238 Supporting Reference Compounds 823 E-value 2520.99
Click to view 3D structure	Voltage-gated inwardly rectifying potassium channel KCNH2	Q12809	Humans	Predicted (SEA)	Prediction Confidence Score 0.24 Applicability Domain 0.385 Statistical Significance 0.6641 Supporting Reference Compounds 1498 E-value 5170.36
Click to view 3D structure	Alpha-1B adrenergic receptor	P15823	Rattus norvegicus	Predicted (SEA)	Prediction Confidence Score 0.229 Applicability Domain 0.4 Statistical Significance 0.1007 Supporting Reference Compounds 130 E-value 783.708
Click to view 3D structure	5-hydroxytryptamine receptor 2A	P28223	Humans	Predicted (SEA)	Prediction Confidence Score 0.222 Applicability Domain 0.391 Statistical Significance 0.5944 Supporting Reference Compounds 955 E-value 4627.67
Click to view 3D structure	5-hydroxytryptamine receptor 1D	P28221	Humans	Predicted (SEA)	Prediction Confidence Score 0.216 Applicability Domain 0.265 Low confidence Statistical Significance 0.4162 Supporting Reference Compounds 365 E-value 3240.4
Click to view 3D structure	Mitogen-activated protein kinase kinase kinase kinase 4	O95819	Humans	Predicted (SEA)	Prediction Confidence Score 0.206 Applicability Domain 0.235 Low confidence Statistical Significance 0.7654 Supporting Reference Compounds 714 E-value 5958.97
Click to view 3D structure	Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit alpha isoform	P42336	Humans	Predicted (SEA)	Prediction Confidence Score 0.204 Applicability Domain 0.235 Low confidence Statistical Significance 0.6611 Supporting Reference Compounds 536 E-value 5146.69
Click to view 3D structure	Alpha-2A adrenergic receptor	P08913	Humans	Known	Brimonidine is an alpha adrenergic receptor agonist. It has a peak ocular hypotensive effect occurring at two hours post-dosing. Fluorophotometric studies in animals and humans suggest that Brimonidine has a dual mechanism of action by reducing aqueous humor production and increasing uveoscleral outflow.
Click to view 3D structure	Alpha-2C adrenergic receptor	P18825	Humans	Known	Brimonidine is an alpha adrenergic receptor agonist. It has a peak ocular hypotensive effect occurring at two hours post-dosing. Fluorophotometric studies in animals and humans suggest that Brimonidine has a dual mechanism of action by reducing aqueous humor production and increasing uveoscleral outflow.
Click to view 3D structure	Alpha-2B adrenergic receptor	P18089	Humans	Known	Brimonidine is an alpha adrenergic receptor agonist. It has a peak ocular hypotensive effect occurring at two hours post-dosing. Fluorophotometric studies in animals and humans suggest that Brimonidine has a dual mechanism of action by reducing aqueous humor production and increasing uveoscleral outflow.