Brimonidine

Identification

Summary

Brimonidine is an alpha-2 adrenergic agonist used to treat glaucoma and ocular hypertension, as well as facial erythema in rosacea.

Brand Names

Alphagan, Combigan, Lumify, Mirvaso, Onreltea, Qoliana, Simbrinza

Generic Name

Brimonidine

DrugBank Accession Number

DB00484

Background

Brimonidine is an alpha-adrenergic agonist and 2-imidazoline derivative that was first introduced in 1996.³ It is considered to be a third generation alpha-2 aadrenergic receptor agonist, since it displays preferential binding at alpha-2 adrenoceptors over alpha-1 receptors.¹¹ Brimonidine displays a higher selectivity toward the alpha-2 adrenergic receptors than clonidine or apraclonidine, which are also alpha-2 adrenergic agonists.⁶ Alpha-2 adrenergic agonists are members of the ocular hypotensive agent drug class that are used in the chronic treatment of glaucoma. Early treatment and management of glaucoma, which predominantly involves the lowering of intraocular pressure, is critical since glaucoma is considered to be a common cause of blindness worldwide.^2,6

Ophthalmically, brimonidine is used to lower intraocular pressure by reducing aqueous humor production and increasing uveoscleral outflow. Because it is oxidately stable, brimonidine is associated with fewer reports of ocular allergic reactions compared to other alpha-2 adrenergic agonists.⁶ The ophthalmic solution of brimonidine was first approved by the FDA in 1996 as Alphagan ^Label and brimonidine is the only selective alpha-adrenergic receptor agonist approved for chronic treatment in glaucoma.⁷ Brimonidine is also found in ophthalmic solutions in combination with brinzolamide under the market name Simbrinza for the reduction in intraocular pressure. Unlike nonselective beta-blockers used in ocular hypertension, brimonidine is not associated with significantly adverse cardiopulmonary side effects.¹ Thus brimonidine is an effective and safe alternative to beta-blockers, in patients with, or at high risk for, cardiopulmonary disease.² The topical form of brimonidine was approved by the FDA in August 2013 for the symptomatic treatment of persistent facial erythema of rosacea in adults. It is marketed under the brand name Mirvaso.¹³ Brimonidine is the first topical treatment approved for facial erythema of rosacea.⁸

Type

Small Molecule

Groups

Approved

Structure

3D

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MOLSDF3D-SDFPDBSMILESInChI

Similar Structures

Structure for Brimonidine (DB00484)

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Weight

Average: 292.135
Monoisotopic: 291.011957992

Chemical Formula

C₁₁H₁₀BrN₅

Synonyms

• 5-Bromo-6-(2-imidazolin-2-ylamino)quinoxaline
• Brimonidina
• Brimonidine
• Brimonidinum
• Bromoxidine

External IDs

• AGN-190342
• UK-14304

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Pharmacology

Indication

Opthalmic

Indicated for lowering intraocular pressure (IOP) in patients with open-angle glaucoma or ocular hypertension ^Label as monotherapy or combination product with brinzolamide.

Topical

Indicated for the treatment of persistent (non-transient) facial erythema of rosacea in adults 18 years of age or older.¹³

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Associated Conditions

Indication Type	Indication	Combined Product Details	Approval Level	Age Group	Patient Characteristics	Dose Form
Used in combination to manage	Elevated intraocular pressure	Combination Product in combination with: Brinzolamide (DB01194)	••••••••••••			••••••••••
Used in combination to manage	Elevated intraocular pressure	Combination Product in combination with: Brinzolamide (DB01194)	••••••••••••			••••••••••
Used in combination to manage	Elevated intraocular pressure	Combination Product in combination with: Timolol (DB00373)	••••••••••••		•••••••••••• •••••••••• ••••••••••• ••••••••	••••••••••
Used in combination to manage	Elevated intraocular pressure	Combination Product in combination with: Timolol (DB00373)	••••••••••••		•••••••••••• •••••••••• ••••••••••• ••••••••	••••••••••
Management of	Elevated intraocular pressure		••••••••••••

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Pharmacodynamics

Brimonidine is a highly selective alpha-2 adrenergic receptor agonist that is 1000-fold more selective for the alpha2-adrenergic receptor than the alpha1-adrenergic receptor.¹⁵ This characteristic gives the drug some therapeutic advantages, since it reduces the risk of systemic side effects, such as systemic hypotension, bradycardia, and sedation. In addition, there is a reduction in the risk for developing alpha-1 mediated ocular unwanted effects, such as conjunctival blanching, mydriasis, and eyelid retraction.¹¹ However, despite high alpha-2 receptor specificity, brimonidine may still produce alpha-1 adrenoceptor-mediated ocular effects, such as conjunctival vasoconstriction.⁶ Brimonidine has a peak ocular hypotensive effect occurring at two hours post-dosing.^Label In a randomized, double-blind clinical study, ocular administration of 0.2% brimonidine in healthy volunteers resulted in a 23% reduction of mean intraocular pressure from baseline at 3 hours following administration.³ In comparative studies consisting of patients with open-angle glaucoma or ocular hypertension, the ocular hypotensive effect of brimonidine was maintained during treatment periods of up to 1 year.¹

Brimonidine mediates vasoconstrictive effects and it was shown to exhibit anti-inflammatory properties in ex vivo human skin model and in vivo inflammation models.¹² In a clinial trials consisting of adults with moderate to severe facial erythema of rosacea, brimonidine was shown to improve the extent of redness at 3 hours after application, compared to placebo.¹⁵ It was shown to be a potent vasoconstrictor of human subcutaneous vessels with a diameter of less than 200 µm. In in vivo mouse inflammation models, brimonidine displayed anti-inflammatory properties by inhibiting edema.⁸ In a randomized, double-blind study, brimonidine reduced erythema for the 12 hours of the study in a dose-dependent manner.⁸

When adminsitered systemically, brimonidine was shown to cause cardiovascular effects by decreasing blood pressure, decreasing heart and respiratory rate, and prolonging the PR interval in the electrocardiogram. This is due to the targeting of adrenoceptors by the drug.^4,5 Although the clinical significance has not been established, there is evidence that brimonidine exhibits neuroprotective activity in experimental models of cerebral ischemia and optic nerve injury.⁶ In vitro studies show that brimonidine mediated protective effects on neuronal cells from kainate acid insult and on cultured retinal ganglion cells from glutamate-induced cytotoxicity, which is a possible mediator of secondary neuronal degeneration in human glaucoma. Neuroprotective actions of brimonidine were also demonstrated in rat models of acute retinal ischemia and chronic IOP elevation. It has been proposed that brimonidine may exert neuroprotective effects on the retina and optic nerve by enhancing intrinsic retinal ganglion cell survival mechanisms and/or induction of neuronal survival factors, such as bFGF.³ However, further investigations are needed to conclude on these possible therapeutic benefits of the drug.

Mechanism of action

In the eye, alpha-1 adrenoceptors play a role in vasoconstriction, mydriasis, eyelid retraction, and elevation of intraocular pressure (IOP) whereas alpha-2 adrenoceptors are responsible for IOP reduction via a complex Gi-coupled signaling cascade pathway. Activation of alpha-2 receptors leads to inhibition of adenylyl cyclase and reduction of cyclic AMP levels. As a result, there is a decrease in norpinephrine (NE) release at the synaptic junction, NE-induced stimulation of beta-2 adrenoceptors, and production of aqueous humor by the ciliary epithelium.⁶ An elevated IOP is the most significant risk factor for developing glaucomatous optic neuropathy, which is associated with progressive visual field loss and functional disability if left untreated.¹¹ Regardless of the etiology of the disease, the aim of current therapies for glaucoma is to reduce IOP, as reduction of IOP significantly reduces the risk of progression of vision loss even when IOP is already within the normal range.⁷ When administered ophthalmically, brimonidine is rapidly absorbed into the eye, acts as an agonist at ocular alpha-2 adrenoceptors and lowers IOP via a dual mechanism of action.⁹ It is proposed that initial dosing of the drug causes a reduction in aqueous humour production and chronic dosing leads to an increase in uveoscleral outflow.¹¹ Brimonidine does not affect episcleral venous pressure.⁶ By reducing IOP, brimonidine aims to reduce the likelihood of glaucomatous visual field loss in ocular hypertension, and slow the progression of visual field defect in established open-angle glaucoma.³ When applied topically on skin, brimonidine reduces erythema through direct vasocontriction of small arteries and veins.⁸ As brimonidine mediates a potent peripheral vasoconstrictive activity by selectively working on the alpha-2 adrenoceptors, the use of brimonidine is thought to be efficacious for the treatment of facial erythema of rosacea, which is thought to arise from vasomotor instability and abnormal vasodilation of the superficial cutaneous vasculature of the face.¹⁰

Target	Actions	Organism
AAlpha-2A adrenergic receptor	agonist	Humans
AAlpha-2B adrenergic receptor	agonist	Humans
AAlpha-2C adrenergic receptor	agonist	Humans

Absorption

Brimonidine readily penetrates the cornea following ocular administration ³ to reach pharmacologically active concentrations in the aqueous humor and ciliary body, the putative sites of its IOP-lowering activity.⁷ Following ocular administration of 0.2% brimonidine solution, the peak plasma concentrations were achieved within 1 to 4 hours.^Label

In a clinical study of adult subjects with facial erythema of rosacea, brimonidine was cutaneously applied on facial skin in a repeated manner. While there was no drug accumulation in plasma, the highest peak plasma concentrations (Cmax) and AUC were 46 ± 62 pg/mL and 417 ± 264 pgxhr/mL, respectively.¹⁵

Volume of distribution

The volume of distribution of brimonidine has not been established. In animal studies, brimonidine was shown to cross the placenta and enter into the fetal circulation to a limited extent.^Label As its lipophilicity is relatively low, brimonidine is not reported to easily cross the blood-brain barrier.³

Protein binding

The protein binding of brimonidine has not been studied.

Metabolism

Brimonidine is reported to be metabolized in the cornea. Brominidine that reaches the systemic circulation upon topical administration undergoes extensive hepatic metabolism mediated by hepatic aldehyde oxidases.^Label

Hover over products below to view reaction partners

• Brimonidine
  • 2-oxobrimonidine
  • 3-oxobrimonidine

Route of elimination

Brimonidine and its metabolites are predominantly eliminated via urinary excretion, with 74% of the total dose being found in the urine.^Label

Half-life

Following ocular administration of 0.2% brimonidine solution, the systemic half-life was approximately 3 hours.^Label

Clearance

The apparent clearance has not been studied. However, the systemic clearance of brimonidine is reported to be rapid.⁷ Approximately 87% of the total radioactive dose of brimonidine was shown to be eliminated within 120 hours following oral administration.^Label

Adverse Effects

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Toxicity

LD₅₀ and Overdose

Oral LD₅₀ is 50 mg/kg in mice and 100 mg/kg in rats.^MSDS While there is limited clinial data on brimonidine overdose in adults, some common symptoms from oral overdoses of alpha-2 adrenergic agonists include hypotension, asthenia, vomiting, lethargy, sedation, bradycardia, arrhythmias, miosis, apnoea, hypotonia, hypothermia, respiratory depression and seizure. ¹⁵ Treatment of an oral overdose includes supportive and symptomatic therapy. Cases of brimonidine overdose have been reported in neonates, infants, and pediatric patients receiving brimonidine tartrate as part of medical treatment of congenital glaucoma or by accidental oral ingestion. In these cases, children experienced symptoms consistent with previously reported oral overdoses of alpha-2 adrenergic agonists in young children.¹⁵

Nonclinical Toxicology

At oral doses of up to 2.5 and 5 mg/kg/day in pregnant rats and rabbits, brimonidine was not shown to be teratogenic during gestation days 6 through 18. Findings from various in vitro and in vivo studies, including the Ames bacterial assay, CHO cell chromosomal aberration assay, and CD-1 mice studies, did not demonstrate any mutagenic or clastogenic potential of brimonidine.^Label There were no observable adverse effects on male or female fertility when tested at oral doses of up to 1 mg/kg, which is approximately 200 times the systemic exposure following the maximum recommended ophthalmic dose of 0.5% brimonidine.^Label

Use in special populations

Due to limited clinical data on the use of brimonidine pregnant or breastfeeding female patients, the use of brimonidine in these patients is generally not recommended and the use should be only considered after taking into account the benefit-to-risk ratio of continuing the drug therapy in these patients. In nursing mothers, the decision should be made whether to discontinue the drug or discontinue breastfeeding.^Label As the systemic absorption and elimination of brimonidine are not significantly affected by age, the use of brimonidine is considered safe in geriatric patients. In contrast, the use of brimonidine in infants under the age of 2 and pediatric patients under the age of 18 is strongly not recommended due to the reports of serious adverse events following ophthalmic administration of brimonidine in infants between the age of 28 days and 3 months.¹⁵

Pathways

Not Available

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Interactions

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This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.

• Approved
• Vet approved
• Nutraceutical
• Illicit
• Withdrawn
• Investigational
• Experimental
• All Drugs

Drug	Interaction
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1,2-Benzodiazepine	Brimonidine may increase the central nervous system depressant (CNS depressant) activities of 1,2-Benzodiazepine.
Acebutolol	Brimonidine may increase the antihypertensive activities of Acebutolol.
Acetazolamide	Brimonidine may increase the central nervous system depressant (CNS depressant) activities of Acetazolamide.
Acetophenazine	Brimonidine may increase the central nervous system depressant (CNS depressant) activities of Acetophenazine.
Acetyldigitoxin	Brimonidine may increase the bradycardic activities of Acetyldigitoxin.

Food Interactions

• Avoid alcohol. Alcohol intake may potentially lead to additive CNS depressant effects.

Products

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Product Ingredients

Ingredient	UNII	CAS	InChI Key
Brimonidine tartrate	4S9CL2DY2H	70359-46-5	QZHBYNSSDLTCRG-LREBCSMRSA-N

Brand Name Prescription Products

Name	Dosage	Strength	Route	Labeller	Marketing Start	Marketing End	Region	Image
Alphagan	Solution	0.2 %	Ophthalmic	Abbvie	1997-12-02	Not applicable
Alphagan P	Solution / drops	1.5 mg/1mL	Ophthalmic	Allergan, Inc.	2001-07-10	Not applicable
Alphagan P	Solution / drops	1 mg/1mL	Ophthalmic	Physicians Total Care, Inc.	2013-03-08	Not applicable
Alphagan P	Solution / drops	1 mg/1mL	Ophthalmic	Allergan, Inc.	2006-01-25	Not applicable
Alphagan P	Solution / drops	1.5 mg/1mL	Ophthalmic	Physicians Total Care, Inc.	2002-10-16	Not applicable

Generic Prescription Products

Name	Dosage	Strength	Route	Labeller	Marketing Start	Marketing End	Region	Image
Apo-brimonidine	Solution	0.2 %	Ophthalmic	Apotex Corporation	2005-06-02	Not applicable
Brimonidine	Gel	5 mg/1g	Topical	bryant ranch prepack	2023-01-01	Not applicable
Brimonidine	Solution / drops	2 mg/1mL	Ophthalmic	Akorn	2006-09-07	Not applicable
Brimonidine	Gel	5 mg/1g	Topical	Padagis Israel Pharmaceuticals Ltd	2023-01-01	Not applicable
Brimonidine	Solution / drops	2 mg/1mL	Ophthalmic	A-S Medication Solutions	2006-09-07	Not applicable

Over the Counter Products

Name	Dosage	Strength	Route	Labeller	Marketing Start	Marketing End	Region	Image
Lumify	Solution	0.025 % w/v	Ophthalmic	Bausch & Lomb Inc	2022-07-05	Not applicable
LUMIFY Redness Reliever Eye Drops	Solution / drops	0.25 mg/1mL	Ophthalmic	Bausch & Lomb Incorporated	2017-12-22	Not applicable

Mixture Products

Name	Ingredients	Dosage	Route	Labeller	Marketing Start	Marketing End	Region	Image
Apo-brimonidine-timop	Brimonidine tartrate (0.2 %) + Timolol maleate (0.5 %)	Solution	Ophthalmic	Apotex Corporation	2022-11-09	Not applicable
BRIDINE®	Brimonidine (2 mg) + Brinzolamide (10 mg)	Suspension	Ophthalmic	LABORATORIOS SYNTHESIS S.A.S.	2015-11-20	2019-06-11
BRİMO-TİM 2 MG+5 MG/ML STERİL GÖZ DAMLASI, ÇÖZELTİ, 5 ML	Brimonidine tartrate (2 mg/mL) + Timolol (5 mg/ml)	Solution / drops	Ophthalmic	VEM İLAÇ SAN. VE TİC. A.Ş.	2018-10-23	Not applicable
BRIMOCHEK -T EYE DROPS SOLUTION	Brimonidine (2.0 mg/ml) + Timolol maleate (5 mg/ml)	Solution	Ophthalmic	GOLDPLUS UNIVERSAL PTE LTD	2017-09-03	Not applicable
BRIMOCOMB	Brimonidine tartrate (2 MG/ML) + Timolol (5 MG/ML)	Solution / drops	Ophthalmic	Doc Generici Srl	2017-06-07	Not applicable

Unapproved/Other Products

Name	Ingredients	Dosage	Route	Labeller	Marketing Start	Marketing End	Region	Image
Brim-Dor PF	Brimonidine tartrate (1.5 mg/1mL) + Dorzolamide hydrochloride (20 mg/1mL)	Solution / drops	Ophthalmic	ImprimisRx NJ	2018-01-01	Not applicable
Brimonidine Tartrate 0.25% / Ivermectin 1% / Metronidazole 1% / Niacinamide 4%	Brimonidine tartrate (0.25 g/100g) + Ivermectin (1 g/100g) + Metronidazole (1 g/100g) + Nicotinamide (4 g/100g)	Gel	Topical	Sincerus Florida, LLC	2019-05-16	Not applicable
Brimonidine Tartrate 0.25% / Potassium Azeloyl Diglycinate 8%	Brimonidine tartrate (0.25 g/100g)	Gel	Topical	Sincerus Florida, LLC	2019-05-16	Not applicable
Tim-Brim-Dor PF	Brimonidine tartrate (1.5 mg/1mL) + Dorzolamide hydrochloride (20 mg/1mL) + Timolol maleate (5 mg/1mL)	Solution / drops	Ophthalmic	ImprimisRx NJ	2018-01-01	Not applicable
Tim-Brim-Dor-Lat	Brimonidine tartrate (1.5 mg/1mL) + Dorzolamide hydrochloride (20 mg/1mL) + Latanoprost (0.05 mg/1mL) + Timolol maleate (5 mg/1mL)	Solution / drops	Ophthalmic	ImprimisRx NJ	2018-01-01	Not applicable

Categories

ATC Codes

D11AX21 — Brimonidine

• D11AX — Other dermatologicals
• D11A — OTHER DERMATOLOGICAL PREPARATIONS
• D11 — OTHER DERMATOLOGICAL PREPARATIONS
• D — DERMATOLOGICALS

S01GA07 — Brimonidine

• S01GA — Sympathomimetics used as decongestants
• S01G — DECONGESTANTS AND ANTIALLERGICS
• S01 — OPHTHALMOLOGICALS
• S — SENSORY ORGANS

S01EA05 — Brimonidine

• S01EA — Sympathomimetics in glaucoma therapy
• S01E — ANTIGLAUCOMA PREPARATIONS AND MIOTICS
• S01 — OPHTHALMOLOGICALS
• S — SENSORY ORGANS

Drug Categories

• Adrenergic Agents
• Adrenergic Agonists
• Adrenergic alpha-2 Receptor Agonists
• Adrenergic alpha-Agonists
• Antiglaucoma Preparations and Miotics
• Cardiovascular Agents
• Central Nervous System Depressants
• Decongestants and Antiallergics
• Dermatologicals
• Heterocyclic Compounds, Fused-Ring
• Hypotensive Agents
• Misc. Skin and Mucous Membrane Agents
• Ophthalmologicals
• Quinoxalines
• Sensory Organs
• Sympathomimetics in Glaucoma Therapy
• Sympathomimetics Used as Decongestants

Chemical TaxonomyProvided by Classyfire

Description

This compound belongs to the class of organic compounds known as quinoxalines. These 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

Pyrazines / Benzenoids / Aryl bromides / Imidazolines / Heteroaromatic compounds / Guanidines / Propargyl-type 1,3-dipolar organic compounds / Carboximidamides / Azacyclic compounds / Organopnictogen compounds / Organobromides / Hydrocarbon derivatives

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Substituents

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

show 9 more

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

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

Affected organisms

• Humans and other mammals

Chemical Identifiers

UNII

E6GNX3HHTE

CAS number

59803-98-4

InChI Key

XYLJNLCSTIOKRM-UHFFFAOYSA-N

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)

IUPAC Name

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

SMILES

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

References

General References

1. Adkins JC, Balfour JA: Brimonidine. A review of its pharmacological properties and clinical potential in the management of open-angle glaucoma and ocular hypertension. Drugs Aging. 1998 Mar;12(3):225-41. doi: 10.2165/00002512-199812030-00005. [Article]
2. Cantor LB, Burke J: Brimonidine. Expert Opin Investig Drugs. 1997 Aug;6(8):1063-83. doi: 10.1517/13543784.6.8.1063 . [Article]
3. Cantor LB: The evolving pharmacotherapeutic profile of brimonidine, an alpha 2-adrenergic agonist, after four years of continuous use. Expert Opin Pharmacother. 2000 May;1(4):815-34. doi: 10.1517/14656566.1.4.815 . [Article]
4. Stewart WC, Stewart JA, Jackson AL: Cardiovascular effects of timolol maleate, brimonidine or brimonidine/timolol maleate in concomitant therapy. Acta Ophthalmol Scand. 2002 Jun;80(3):277-81. [Article]
5. Suwanwipat S, Buranakarl C, Chaiyabutr N: Effects of brimonidine ingestion on cardiovascular responses and renal function in conscious dogs. Vet Res Commun. 2007 Apr;31(3):323-34. doi: 10.1007/s11259-006-3414-1. Epub 2006 Dec 28. [Article]
6. Greenfield DS, Liebmann JM, Ritch R: Brimonidine: a new alpha2-adrenoreceptor agonist for glaucoma treatment. J Glaucoma. 1997 Aug;6(4):250-8. [Article]
7. Cantor LB: Brimonidine in the treatment of glaucoma and ocular hypertension. Ther Clin Risk Manag. 2006 Dec;2(4):337-46. [Article]
8. Jackson JM, Knuckles M, Minni JP, Johnson SM, Belasco KT: The role of brimonidine tartrate gel in the treatment of rosacea. Clin Cosmet Investig Dermatol. 2015 Oct 23;8:529-38. doi: 10.2147/CCID.S58920. eCollection 2015. [Article]
9. Toris CB, Gleason ML, Camras CB, Yablonski ME: Effects of brimonidine on aqueous humor dynamics in human eyes. Arch Ophthalmol. 1995 Dec;113(12):1514-7. [Article]
10. Benkali K, Leoni M, Rony F, Bouer R, Fernando A, Graeber M, Wagner N: Comparative pharmacokinetics and bioavailability of brimonidine following ocular and dermal administration of brimonidine tartrate ophthalmic solution and gel in patients with moderate-to-severe facial erythema associated with rosacea. Br J Dermatol. 2014 Jul;171(1):162-9. doi: 10.1111/bjd.12881. Epub 2014 Jul 16. [Article]
11. Galanopoulos A, Goldberg I: Clinical efficacy and neuroprotective effects of brimonidine in the management of glaucoma and ocular hypertension. Clin Ophthalmol. 2009;3:117-22. Epub 2009 Jun 2. [Article]
12. Piwnica D, Pathak A, Schafer G, Docherty JR: In Vitro Safety Pharmacology Profiling of Topical alpha-Adrenergic Agonist Treatments for Erythema of Rosacea. Drugs R D. 2018 Mar;18(1):87-90. doi: 10.1007/s40268-018-0227-y. [Article]
13. MIRVASO (brimonidine) topical gel - FDA Label [Link]
14. Brimonidine (brimonidine tartrate) ophthalmic solution - Product Monograph [Link]
15. Mirvaso (brimonidine) topical gel - EU Summary of Product Characteristics [Link]
16. ALPHAGAN® (brimonidine tartrate ophthalmic solution) 0.2% - FDA Label [Link]
17. FDA Approved Drug Products: COMBIGAN (brimonidine tartrate/timolol maleate) ophthalmic solution [Link]
18. FDA Approved Drug Products: SIMBRINZA (brinzolamide and brimonidine tartrate) suspension [Link]

External Links

Human Metabolome Database

HMDB0014627

KEGG Drug

D07540

KEGG Compound

C07886

PubChem Compound

2435

PubChem Substance

46507305

ChemSpider

2341

BindingDB

34572

RxNav

134615

ChEBI

3175

ChEMBL

CHEMBL844

ZINC

ZINC000021303210

Therapeutic Targets Database

DAP000280

PharmGKB

PA448665

Guide to Pharmacology

GtP Drug Page

PDBe Ligand

J59

RxList

RxList Drug Page

Drugs.com

Drugs.com Drug Page

Wikipedia

Brimonidine

PDB Entries

7ej8

FDA label

Download (174 KB)

MSDS

Download (285 KB)

Clinical Trials

Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">

Phase	Status	Purpose	Conditions	Count
4	Completed	Not Available	Glaucoma	1
4	Completed	Diagnostic	Glaucoma; Drugs / Normal Tension Glaucoma / Ocular Hypertension, Primary Open-angle Glaucoma (POAG)	1
4	Completed	Other	Rosacea	1
4	Completed	Prevention	Intraocular Pressure (IOP)	1
4	Completed	Prevention	Ocular Hypertension / Posterior Capsule Opacification	1

Pharmacoeconomics

Manufacturers

• Allergan inc
• Allergan
• Akorn inc
• Alcon inc
• Alcon research ltd
• Bausch and lomb pharmaceuticals inc
• Sandoz canada inc
• Teva parenteral medicines inc
• Allergan, Inc

Packagers

• Akorn Inc.
• Alcon Laboratories
• Allergan Inc.
• Bausch & Lomb Inc.
• Falcon Pharmaceuticals Ltd.
• Ivax Pharmaceuticals
• Pacific Pharma Lp
• Physicians Total Care Inc.
• Stat Rx Usa

Dosage Forms

Form	Route	Strength
Liquid	Ophthalmic	2 mg/1ml
Solution	Ophthalmic	0.2 %
Solution / drops	Ophthalmic	0.2 %
Liquid	Ophthalmic	1.5 mg/1ml
Solution	Ophthalmic	0.15 %
Solution / drops	Ophthalmic	1 mg/1mL
Solution / drops	Ophthalmic	1.5 mg/1mL
Solution / drops	Ophthalmic	0.1 %
Solution / drops	Ophthalmic	0.15 %
Solution	Ophthalmic	0.15 % w/v
Solution	Ophthalmic	2 mg
Solution	Conjunctival; Ophthalmic	1 mg/mL
Solution	Ophthalmic	2.0 mg/ml
Gel		0.33 %
Solution / drops	Ophthalmic	2 MG/ML
Solution	Conjunctival; Ophthalmic	1.5 mg
Solution	Conjunctival; Ophthalmic	1 mg
Solution / drops	Ophthalmic	1.5 mg/ml
Solution	Ophthalmic	2 mg
Solution / drops	Ophthalmic
Solution	Ophthalmic	1.5 mg/1mL
Solution	Ophthalmic	2 mg/1mL
Solution / drops	Ophthalmic	2 mg/1mg
Solution / drops	Ophthalmic	2 mg/1mL
Solution / drops	Ophthalmic	2.0 mg/1mL
Gel	Topical
Gel	Topical	0.25 g/100g
Solution / drops	Topical
Solution	Ophthalmic
Solution / drops	Ophthalmic
Liquid	Ophthalmic
Solution	Ophthalmic	2.0 MG/ML
Solution	Ophthalmic	2.0000 mg
Gel	Cutaneous	0.5000 g
Solution / drops	Ophthalmic	0.15 % w/v
Solution	Ophthalmic	0.2 % w/v
Solution	Ophthalmic; Topical
Solution	Ophthalmic	0.025 % w/v
Solution / drops	Ophthalmic	0.25 mg/1mL
Gel	Cutaneous	3 MG/G
Gel	Topical	0.5 g
Gel	Topical	5 mg/1g
Gel	Cutaneous	3.3 MG/G
Solution	Ophthalmic	2.000 mg
Gel	Topical	0.33 % w/w
Solution	Ophthalmic	200000 mg
Suspension	Ophthalmic
Suspension / drops	Ophthalmic
Solution	Conjunctival; Ophthalmic	2 mg
Solution	Conjunctival; Ophthalmic

Prices

Unit description	Cost	Unit
Alphagan P 15ml Bottle .15% 15ml Bottle	228.5USD	bottle
Brimonidine Tartrate 0.15% Solution 15ml Bottle	218.5USD	bottle
Alphagan P 0.1% Solution 15ml Bottle	208.94USD	bottle
Alphagan P 10ml Bottle .15% 10ml Bottle	152.32USD	bottle
Brimonidine Tartrate 0.15% Solution 10ml Bottle	145.65USD	bottle
Alphagan P 0.1% Solution 10ml Bottle	143.97USD	bottle
Alphagan P 5ml Bottle .15% 5ml Bottle	79.52USD	bottle
Brimonidine Tartrate 0.15% Solution 5ml Bottle	72.85USD	bottle
Brimonidine Tartrate 0.2% Solution 10ml Bottle	67.85USD	bottle
Brimonidine Tartrate 0.2% Solution 15ml Bottle	56.88USD	bottle
Brimonidine Tartrate 0.2% Solution 5ml Bottle	33.96USD	bottle
Brimonidine tartrate 0.15% drp	29.82USD	ml
Alphagan p 0.15% eye drops	14.65USD	ml
Alphagan p 0.1% drops	13.85USD	ml
Brimonidine 0.2% eye drop	6.53USD	ml
Alphagan 0.2 % Solution	3.72USD	ml
Apo-Brimonidine 0.2 % Solution	2.08USD	ml
Pms-Brimonidine 0.2 % Solution	2.08USD	ml
Ratio-Brimonidine 0.2 % Solution	2.08USD	ml
Sandoz Brimonidine 0.2 % Solution	2.08USD	ml

DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.

Patents

Patent Number	Pediatric Extension	Approved	Expires (estimated)	Region
US5424078	No	1995-06-13	2012-06-13
CA2173974	No	2006-05-02	2014-09-19
CA2225626	No	2002-09-03	2016-06-17
US9295641	Yes	2016-03-29	2022-01-10
US6627210	Yes	2003-09-30	2022-01-18
US6673337	Yes	2004-01-06	2022-01-26
US6562873	Yes	2003-05-13	2022-01-10
US6641834	Yes	2003-11-04	2022-01-28
US7030149	No	2006-04-18	2022-04-19
US7320976	No	2008-01-22	2022-04-19
US7642258	No	2010-01-05	2022-04-19
US8133890	No	2012-03-13	2022-04-19
US8354409	No	2013-01-15	2022-04-19
US8748425	No	2014-06-10	2022-04-19
US7323463	No	2008-01-29	2023-01-19
US7265117	No	2007-09-04	2025-08-19
US8858961	Yes	2014-10-14	2024-03-02
US6316441	No	2001-11-13	2019-12-07
US9044484	No	2015-06-02	2030-10-30
US8410102	No	2013-04-02	2025-05-24
US8053427	No	2011-11-08	2031-06-13
US7439241	No	2008-10-21	2025-08-25
US8513247	No	2013-08-20	2031-03-25
US8426410	No	2013-04-23	2025-05-24
US8513249	No	2013-08-20	2031-03-25
US8859551	No	2014-10-14	2024-05-25
US8231885	No	2012-07-31	2025-05-24
US8163725	No	2012-04-24	2031-06-13
US9474751	No	2016-10-25	2022-04-19
US9687443	Yes	2017-06-27	2022-01-10
US9421265	No	2016-08-23	2030-06-17
US9770453	No	2017-09-26	2022-04-19
US9861631	No	2018-01-09	2031-03-25
US8293742	No	2012-10-23	2030-07-14
US9861632	No	2018-01-09	2031-03-25
US9907801	No	2018-03-06	2022-04-19
US9907802	No	2018-03-06	2022-04-19
US10201517	No	2019-02-12	2031-06-13
US10307368	No	2019-06-04	2021-07-10
US9259425	No	2016-02-16	2030-07-14
US11596600	No	2009-07-27	2029-07-27
US11833245	No	2009-07-27	2029-07-27

Properties

State

Solid

Experimental Properties

Property	Value	Source
melting point (°C)	207.5 °C	Sandoz Canada Product Monograph
water solubility	34 mg/mL	Sandoz Canada Product Monograph
pKa	7.78	Sandoz Canada Product Monograph

Predicted Properties

Property	Value	Source
Water Solubility	0.154 mg/mL	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	1	Chemaxon
Rule of Five	Yes	Chemaxon
Ghose Filter	Yes	Chemaxon
Veber's Rule	No	Chemaxon
MDDR-like Rule	No	Chemaxon

Predicted ADMET Features

Property	Value	Probability
Human Intestinal Absorption	+	0.978
Blood Brain Barrier	+	0.717
Caco-2 permeable	+	0.5435
P-glycoprotein substrate	Substrate	0.7017
P-glycoprotein inhibitor I	Non-inhibitor	0.5688
P-glycoprotein inhibitor II	Inhibitor	0.5951
Renal organic cation transporter	Inhibitor	0.8266
CYP450 2C9 substrate	Non-substrate	0.8403
CYP450 2D6 substrate	Non-substrate	0.7533
CYP450 3A4 substrate	Non-substrate	0.5617
CYP450 1A2 substrate	Non-inhibitor	0.9046
CYP450 2C9 inhibitor	Non-inhibitor	0.9071
CYP450 2D6 inhibitor	Non-inhibitor	0.9231
CYP450 2C19 inhibitor	Non-inhibitor	0.9025
CYP450 3A4 inhibitor	Inhibitor	0.6898
CYP450 inhibitory promiscuity	Low CYP Inhibitory Promiscuity	0.7044
Ames test	Non AMES toxic	0.8222
Carcinogenicity	Non-carcinogens	0.9446
Biodegradation	Not ready biodegradable	1.0
Rat acute toxicity	3.0196 LD50, mol/kg	Not applicable
hERG inhibition (predictor I)	Weak inhibitor	0.8093
hERG inhibition (predictor II)	Non-inhibitor	0.6711

ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)

Not Available

Spectra

Spectrum	Spectrum Type	Splash Key
Predicted GC-MS Spectrum - GC-MS	Predicted GC-MS	splash10-03xr-0190000000-cd1ec9d5bf9d24fab607
MS/MS Spectrum - , positive	LC-MS/MS	splash10-0006-0190000000-49c10e93a1977cbe01da
Predicted MS/MS Spectrum - 10V, Positive (Annotated)	Predicted LC-MS/MS	splash10-0006-0090000000-aebee4f7497a9f34939c
Predicted MS/MS Spectrum - 10V, Negative (Annotated)	Predicted LC-MS/MS	splash10-0006-0090000000-37c8fb2b1025ff877ec1
Predicted MS/MS Spectrum - 20V, Positive (Annotated)	Predicted LC-MS/MS	splash10-0006-0090000000-24be834e62b351a3967e
Predicted MS/MS Spectrum - 20V, Negative (Annotated)	Predicted LC-MS/MS	splash10-0006-1090000000-a488f19ed6154f56f192
Predicted MS/MS Spectrum - 40V, Positive (Annotated)	Predicted LC-MS/MS	splash10-0giv-1190000000-ce122d00fb1e823a8b13
Predicted MS/MS Spectrum - 40V, Negative (Annotated)	Predicted LC-MS/MS	splash10-004j-9380000000-73fd99896e1ff3d10479
Predicted 1H NMR Spectrum	1D NMR	Not Applicable
Predicted 13C NMR Spectrum	1D NMR	Not Applicable

Chromatographic Properties

Collision Cross Sections (CCS)

Adduct	CCS Value (Å2)	Source type	Source
[M-H]-	158.1313811	predicted	DarkChem Lite v0.1.0
[M-H]-	146.95404	predicted	DeepCCS 1.0 (2019)
[M+H]+	159.0894811	predicted	DarkChem Lite v0.1.0
[M+H]+	149.31204	predicted	DeepCCS 1.0 (2019)
[M+Na]+	158.4472811	predicted	DarkChem Lite v0.1.0
[M+Na]+	155.66415	predicted	DeepCCS 1.0 (2019)

Targets

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Binding Properties

×

Property	Measurement	pH	Temperature (°C)	References
EC 50 (nM)	4.1	N/A	N/A	A28433
Ki (nM)	2.7	N/A	N/A	A28433
Ki (nM)	213.8	N/A	N/A	A28266

Details

Binding Properties1. Alpha-2A adrenergic receptor

Kind

Protein

Organism

Humans

Pharmacological action

Yes

Actions

Agonist

General Function

Thioesterase binding

Specific Function

Alpha-2 adrenergic receptors mediate the catecholamine-induced inhibition of adenylate cyclase through the action of G proteins. The rank order of potency for agonists of this receptor is oxymetazo...

Gene Name

ADRA2A

Uniprot ID

P08913

Uniprot Name

Alpha-2A adrenergic receptor

Molecular Weight

48956.275 Da

References

1. Rauly I, Ailhaud M, Wurch T, Pauwels PJ: alpha(2A)-adrenoceptor: G(alphai1) protein-mediated pertussis toxin-resistant attenuation of G(s) coupling to the cyclic AMP pathway. Biochem Pharmacol. 2000 Jun 15;59(12):1531-8. [Article]
2. Wikberg-Matsson A, Simonsen U: Potent alpha(2A)-adrenoceptor-mediated vasoconstriction by brimonidine in porcine ciliary arteries. Invest Ophthalmol Vis Sci. 2001 Aug;42(9):2049-55. [Article]
3. Meana JJ, Barturen F, Garro MA, Garcia-Sevilla JA, Fontan A, Zarranz JJ: Decreased density of presynaptic alpha 2-adrenoceptors in postmortem brains of patients with Alzheimer's disease. J Neurochem. 1992 May;58(5):1896-904. [Article]
4. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [Article]

Binding Properties

×

Property	Measurement	pH	Temperature (°C)	References
Ki (nM)	954.99	N/A	N/A	A28266

Details

Binding Properties2. Alpha-2B adrenergic receptor

Kind

Protein

Organism

Humans

Pharmacological action

Yes

Actions

Agonist

General Function

Epinephrine binding

Specific Function

Alpha-2 adrenergic receptors mediate the catecholamine-induced inhibition of adenylate cyclase through the action of G proteins. The rank order of potency for agonists of this receptor is clonidine...

Gene Name

ADRA2B

Uniprot ID

P18089

Uniprot Name

Alpha-2B adrenergic receptor

Molecular Weight

49565.8 Da

References

1. Trendelenburg AU, Philipp M, Meyer A, Klebroff W, Hein L, Starke K: All three alpha2-adrenoceptor types serve as autoreceptors in postganglionic sympathetic neurons. Naunyn Schmiedebergs Arch Pharmacol. 2003 Dec;368(6):504-12. Epub 2003 Nov 11. [Article]
2. Bohmann C, Schollmeyer P, Rump LC: Methoxamine inhibits noradrenaline release through activation of alpha 1- and alpha 2-adrenoceptors in rat isolated kidney: involvement of purines and prostaglandins. Naunyn Schmiedebergs Arch Pharmacol. 1993 Mar;347(3):273-9. [Article]

Binding Properties

×

Property	Measurement	pH	Temperature (°C)	References
EC 50 (nM)	3.4	N/A	N/A	A28433
Ki (nM)	44	N/A	N/A	A28433
Ki (nM)	1949.84	N/A	N/A	A28266

Details

Binding Properties3. Alpha-2C adrenergic receptor

Kind

Protein

Organism

Humans

Pharmacological action

Yes

Actions

Agonist

General Function

Protein homodimerization activity

Specific Function

Alpha-2 adrenergic receptors mediate the catecholamine-induced inhibition of adenylate cyclase through the action of G proteins.

Gene Name

ADRA2C

Uniprot ID

P18825

Uniprot Name

Alpha-2C adrenergic receptor

Molecular Weight

49521.585 Da

References

1. Trendelenburg AU, Philipp M, Meyer A, Klebroff W, Hein L, Starke K: All three alpha2-adrenoceptor types serve as autoreceptors in postganglionic sympathetic neurons. Naunyn Schmiedebergs Arch Pharmacol. 2003 Dec;368(6):504-12. Epub 2003 Nov 11. [Article]
2. Orito K, Kishi M, Imaizumi T, Nakazawa T, Hashimoto A, Mori T, Kambe T: alpha(2)-adrenoceptor antagonist properties of OPC-28326, a novel selective peripheral vasodilator. Br J Pharmacol. 2001 Oct;134(4):763-70. [Article]
3. Zhang W, Ordway GA: The alpha2C-adrenoceptor modulates GABA release in mouse striatum. Brain Res Mol Brain Res. 2003 Apr 10;112(1-2):24-32. [Article]
4. Prinster SC, Holmqvist TG, Hall RA: Alpha2C-adrenergic receptors exhibit enhanced surface expression and signaling upon association with beta2-adrenergic receptors. J Pharmacol Exp Ther. 2006 Sep;318(3):974-81. Epub 2006 Jun 6. [Article]

×

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Drug created at June 13, 2005 13:24 / Updated at February 20, 2024 23:55