BRIMONIDINE TARTRATE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C11H10BrN5.C4H6O6
Molecular Weight	442.221
Optical Activity	UNSPECIFIED
Defined Stereocenters	2 / 2
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

O[C@H]([C@@H](O)C(O)=O)C(O)=O.BrC1=C2N=CC=NC2=CC=C1NC3=NCCN3

InChI

InChIKey=QZHBYNSSDLTCRG-LREBCSMRSA-N

InChI=1S/C11H10BrN5.C4H6O6/c12-9-7(17-11-15-5-6-16-11)1-2-8-10(9)14-4-3-13-8;5-1(3(7)8)2(6)4(9)10/h1-4H,5-6H2,(H2,15,16,17);1-2,5-6H,(H,7,8)(H,9,10)/t;1-,2-/m.1/s1

HIDE SMILES / InChI

Molecular Formula	C4H6O6
Molecular Weight	150.0868
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	2 / 2
E/Z Centers	0
Optical Activity	UNSPECIFIED

Molecular Formula	C11H10BrN5
Molecular Weight	292.135
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description
Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2010/021262s020,021770s004lbl.pdf
Curator's Comment: description was created based on several sources, including: https://www.drugs.com/mtm/brimonidine-ophthalmic.html http://www.drugbank.ca/drugs/DB00484 DOI: 10.1002/9781118541203.xen125

Brimonidine reduces the amount of fluid in the eye, which decreases pressure inside the eye. Brimonidine ophthalmic (for the eyes) is used to treat open-angle glaucoma or ocular hypertension (high pressure inside the eye). Brimonidine is an alpha adrenergic receptor agonist (primarily alpha-2). Fluorophotometric studies in animals and humans suggest that Brimonidine has a dual mechanism of action by reducing aqueous humor production and increasing uveoscleral outflow. Adverse reactions occurring in approximately 1020% of the subjects receiving brimonidine ophthalmic solution (0.1-0.2%) included: allergic conjunctivitis, conjunctival hyperemia, and eye pruritus. Because Brimonidine may reduce blood pressure, caution in using drugs such as antihypertensives and/or cardiac glycosides with Brimonidine is advised.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Alpha-2A adrenergic receptor 26 Target ID: P08913 Gene ID: 150.0 Gene Symbol: ADRA2A Target Organism: Homo sapiens (Human) Sources: http://www.drugbank.ca/drugs/DB00484 \| https://www.ncbi.nlm.nih.gov/pubmed/14610637 \| https://www.ncbi.nlm.nih.gov/pubmed/11606316	Agonist 2752
Alpha-2B adrenergic receptor 13 Target ID: P18089 Gene ID: 151.0 Gene Symbol: ADRA2B Target Organism: Homo sapiens (Human) Sources: http://www.drugbank.ca/drugs/DB00484 \| https://www.ncbi.nlm.nih.gov/pubmed/8097565	Agonist 2752
Alpha-2C adrenergic receptor 11 Target ID: P18825 Gene ID: 152.0 Gene Symbol: ADRA2C Target Organism: Homo sapiens (Human) Sources: http://www.drugbank.ca/drugs/DB00484 \| https://www.ncbi.nlm.nih.gov/pubmed/11481271	Agonist 2752

Conditions

Condition	Modality	Highest Phase	Product
Open-angle glaucoma 53 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2010/021262s020,021770s004lbl.pdf	Primary	Approved 8583	ALPHAGAN P Approved Use Brimonidine Tartrate Ophthalmic Solution is indicated for lowering intraocular pressure in patients with open-angle glaucoma or ocular hypertension. The IOP lowering efficacy of Brimonidine Tartrate Ophthalmic Solution diminishes over time in some patients. This loss of effect appears with a variable time of onset in each patient and should be closely monitored. Launch Date 2005
Ocular hypertension 52 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2010/021262s020,021770s004lbl.pdf	Primary	Approved 8583	ALPHAGAN P Approved Use Brimonidine Tartrate Ophthalmic Solution is indicated for lowering intraocular pressure in patients with open-angle glaucoma or ocular hypertension. The IOP lowering efficacy of Brimonidine Tartrate Ophthalmic Solution diminishes over time in some patients. This loss of effect appears with a variable time of onset in each patient and should be closely monitored. Launch Date 2005
Persistent (nontransient) facial erythema of rosacea 2 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2016/204708s005lbl.pdf	Primary	Approved 8583	MIRVASO Approved Use Brimonidine topical gel, 0.33% is an alpha adrenergic agonist indicated for the topical treatment of persistent (nontransient) erythema of rosacea in adults 18 years of age or older. Launch Date 2013

C_max

Value	Dose	Co-administered	Analyte	Population
73 pg/mL DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2012/021764s005lbl.pdf	1 drop single, ocular dose: 1 drop route of administration: Ocular experiment type: SINGLE co-administered:		BRIMONIDINE TARTRATE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN

AUC

Value	Dose	Co-administered	Analyte	Population
375 pg × h/mL DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2012/021764s005lbl.pdf	1 drop single, ocular dose: 1 drop route of administration: Ocular experiment type: SINGLE co-administered:		BRIMONIDINE TARTRATE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN

T_1/2

Value	Dose	Co-administered	Analyte	Population
2.1 h DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2012/021764s005lbl.pdf	1 drop single, ocular dose: 1 drop route of administration: Ocular experiment type: SINGLE co-administered:		BRIMONIDINE TARTRATE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN

Doses

Dose	Population	Adverse events
0.33 % single, oromucosal Dose: 0.33 % Route: oromucosal Route: single Dose: 0.33 % Sources: https://pubmed.ncbi.nlm.nih.gov/28297016	unhealthy, 4 years Health Status: unhealthy Age Group: 4 years Sex: M Sources: https://pubmed.ncbi.nlm.nih.gov/28297016	Other AEs: Bradycardia, Somnolence... Other AEs: Bradycardia Somnolence Sources: https://pubmed.ncbi.nlm.nih.gov/28297016
0.5 % single, ophthalmic Dose: 0.5 % Route: ophthalmic Route: single Dose: 0.5 % Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2001/20-490S007_Brimonidine%20Tartrate%20Ophthalmic_medr.pdf	unhealthy, 4.8 years (range: 2-7 years) Health Status: unhealthy Age Group: 4.8 years (range: 2-7 years) Sex: M+F Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2001/20-490S007_Brimonidine%20Tartrate%20Ophthalmic_medr.pdf	Disc. AE: Somnolence... AEs leading to discontinuation/dose reduction: Somnolence Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2001/20-490S007_Brimonidine%20Tartrate%20Ophthalmic_medr.pdf
0.33 % 1 times / day steady, topical Recommended Dose: 0.33 %, 1 times / day Route: topical Route: steady Dose: 0.33 %, 1 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2013/204708Orig1s000MedR.pdf	unhealthy, adult Health Status: unhealthy Age Group: adult Sex: M+F Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2013/204708Orig1s000MedR.pdf	Disc. AE: Contact dermatitis, Erythema... AEs leading to discontinuation/dose reduction: Contact dermatitis (0.6%) Erythema (0.3%) Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2013/204708Orig1s000MedR.pdf

AEs

AE	Significance	Dose	Population
Bradycardia		0.33 % single, oromucosal Dose: 0.33 % Route: oromucosal Route: single Dose: 0.33 % Sources: https://pubmed.ncbi.nlm.nih.gov/28297016	unhealthy, 4 years Health Status: unhealthy Age Group: 4 years Sex: M Sources: https://pubmed.ncbi.nlm.nih.gov/28297016
Somnolence		0.33 % single, oromucosal Dose: 0.33 % Route: oromucosal Route: single Dose: 0.33 % Sources: https://pubmed.ncbi.nlm.nih.gov/28297016	unhealthy, 4 years Health Status: unhealthy Age Group: 4 years Sex: M Sources: https://pubmed.ncbi.nlm.nih.gov/28297016
Somnolence	Disc. AE	0.5 % single, ophthalmic Dose: 0.5 % Route: ophthalmic Route: single Dose: 0.5 % Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2001/20-490S007_Brimonidine%20Tartrate%20Ophthalmic_medr.pdf	unhealthy, 4.8 years (range: 2-7 years) Health Status: unhealthy Age Group: 4.8 years (range: 2-7 years) Sex: M+F Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2001/20-490S007_Brimonidine%20Tartrate%20Ophthalmic_medr.pdf
Erythema	0.3% Disc. AE	0.33 % 1 times / day steady, topical Recommended Dose: 0.33 %, 1 times / day Route: topical Route: steady Dose: 0.33 %, 1 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2013/204708Orig1s000MedR.pdf	unhealthy, adult Health Status: unhealthy Age Group: adult Sex: M+F Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2013/204708Orig1s000MedR.pdf
Contact dermatitis	0.6% Disc. AE	0.33 % 1 times / day steady, topical Recommended Dose: 0.33 %, 1 times / day Route: topical Route: steady Dose: 0.33 %, 1 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2013/204708Orig1s000MedR.pdf	unhealthy, adult Health Status: unhealthy Age Group: adult Sex: M+F Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2013/204708Orig1s000MedR.pdf

Sourcing

Vendor/Aggregator	ID	URL
ChEBI	CHEBI:3175	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:3175
ChemicalBook	CB9111370	https://www.chemicalbook.com/ChemicalProductProperty_EN_CB9111370
eMolecules	595250	https://www.emolecules.com/cgi-bin/more?vid=595250
MolPort	MolPort-003-959-841	https://www.molport.com/shop/molecule-link/MolPort-003-959-841
ZINC	ZINC000021303210	http://zinc15.docking.org/substances/ZINC000021303210

PubMed

Title	Date	PubMed
Pre- and postjunctional alpha(2)-adrenergic receptors in fetal and adult ovine cerebral arteries.	2002-06	12010747
alpha 2B-adrenergic receptor activates MAPK via a pathway involving arachidonic acid metabolism, matrix metalloproteinases, and epidermal growth factor receptor transactivation.	2002-05-31	11891218
Release inhibitory receptors activation favours the A2A-adenosine receptor-mediated facilitation of noradrenaline release in isolated rat tail artery.	2002-05	12010771
Brimonidine 0.2% to prevent post laser IOP elevation.	2002-05	11986075
The effects of new topical treatments on management of glaucoma in Scotland: an examination of ophthalmological health care.	2002-05	11973253
ATP release in human kidney cortex and its mitogenic effects in visceral glomerular epithelial cells.	2002-05	11967011
Failure of naloxone to reverse brimonidine-induced coma in an infant.	2002-04	12006970
The efficacy of brimonidine in preventing intraocular pressure elevation in the provocative test for primary angle-closure glaucoma.	2002-04	12002673
Twelve-month evaluation of brimonidine-purite versus brimonidine in patients with glaucoma or ocular hypertension.	2002-04	11912359
Intraocular pressure-lowering effects of latanoprost and brimonidine therapy in patients with open-angle glaucoma or ocular hypertension: a randomized observer-masked multicenter study.	2002-04	11912355
Effects of acute and subchronic administration of dexefaroxan, an alpha(2)-adrenoceptor antagonist, on memory performance in young adult and aged rodents.	2002-04	11907173
Distribution of brimonidine into anterior and posterior tissues of monkey, rabbit, and rat eyes.	2002-04	11901096
A comparison of the short-term hypotensive effects and side effects of unilateral brimonidine and apraclonidine in patients with elevated intraocular pressure.	2002-03-20	11901288
Delayed hypersensitivity to brimonidine tartrate 0.2% associated with high intraocular pressure.	2002-03	11988811
Analysis of the effects of graded levels of hypoxia on noradrenaline-evoked contraction in the rat iliac artery in vitro.	2002-03	11856962
Switching patients with glaucoma or ocular hypertension from dual therapy to monotherapy: evaluation of brimonidine as a model.	2002-02-14	11841198
Neuroprotective effects of brimonidine against transient ischemia-induced retinal ganglion cell death: a dose response in vivo study.	2002-02	11950228
Allergic reactions to brimonidine in patients treated for glaucoma.	2002-02	11865954
Lysophosphatidylcholine potentiates vascular contractile responses in rat aorta via activation of tyrosine kinase.	2002-02	11834627
Substance P, insulinlike growth factor 1, and surface healing.	2002-02	11831929
Three-month comparison of brimonidine and latanoprost as adjunctive therapy in glaucoma and ocular hypertension patients uncontrolled on beta-blockers: tolerance and peak intraocular pressure lowering.	2002-02	11825814
Clinical effects of brimonidine ophthalmic drops ingestion in 52 dogs.	2002-02	11824775
Modification of serotonin neuron properties in mice lacking 5-HT1A receptors.	2002-01-25	11821026
Tumor necrosis factor expressed by primary hippocampal neurons and SH-SY5Y cells is regulated by alpha(2)-adrenergic receptor activation.	2002-01-15	11782970
A short term study of the additive effect of timolol and brimonidine on intraocular pressure.	2002-01	11913886
Minimally invasive spectroscopic system for intraocular drug detection.	2002-01	11818009
Presynaptic modulation of cholinergic neurotransmission in the human proximal stomach.	2002-01	11786489
Latanoprost and brimonidine: therapeutic and physiologic assessment before and after oral nonsteroidal anti-inflammatory therapy.	2002-01	11755835
alpha(2C)-Adrenergic receptors mediate spinal analgesia and adrenergic-opioid synergy.	2002-01	11752127
The impact of new drugs on management of glaucoma in Scotland: observational study.	2001-12-15	11744564
Noradrenaline stimulates 5-hydroxytryptamine release from mouse ileal tissues via alpha(2)-adrenoceptors.	2001-12-07	11740950
[New medical treatments of glaucoma. New strategies?].	2001-12	11913242
A comparison of the efficacy and tolerability of brimonidine and latanoprost in adults with open-angle glaucoma or ocular hypertension: a three-month, multicenter, randomized, double-masked, parallel-group trial.	2001-12	11813932
Neuroprotection of retinal ganglion cells by brimonidine in rats with laser-induced chronic ocular hypertension.	2001-11	11687528
Ca2+ influx mediates enhanced alpha2-adrenergic contraction in aortas from rats treated with NOS inhibitor.	2001-11	11668088
Functional characterization of alpha1-adrenoceptor subtypes in human subcutaneous resistance arteries.	2001-11	11602687
Brimonidine (Alphagan): a clinical profile four years after launch.	2001-10-11	11592536
Influence of topical brimonidine on visual field in glaucoma.	2001-10-11	11592534
Brimonidine's neuroprotective effects against transient ischaemia-induced retinal ganglion cell death.	2001-10-11	11592529
Alpha-2 adrenergic receptor agonists are neuroprotective in experimental models of glaucoma.	2001-10-11	11592528
Apoptosis and anti-apoptosis signalling in glaucomatous retinopathy.	2001-10-11	11592526
Circadian change of adenylate cyclase activity in rabbit ciliary processes.	2001-10	11852425
[Prevention of early postoperative increase in intraocular pressure after phacoemulsification. Comparison of different antiglaucoma drugs].	2001-10	11699314
[Prospects for neuroprotective glaucoma therapy].	2001-10	11699312
[Brimonidine absorption and release from 1. Day acuvue disposable contact lenses].	2001-10	11685677
Safety and efficacy of brimonidine in children with glaucoma.	2001-10	11641636
alpha(2)-adrenoceptor antagonist properties of OPC-28326, a novel selective peripheral vasodilator.	2001-10	11606316
[Experience with topical brimonidine in the treatment of glaucomas].	2001-09	11680422
Acute and chronic effects of brimonidine 0.2% on intraocular pressure and pulsatile ocular blood flow in patients with primary open-angle glaucoma: an open-label, uncontrolled, prospective study.	2001-09	11589264
Antiglaucomatous drugs effects on optic nerve head flow: design, baseline and preliminary report.	2001	11944863

Patents

Sample Use Guides

In Vivo Use Guide

One drop in the affected eye(s), three times daily, approximately 8 hours apart

Route of Administration: Topical

In Vitro Use Guide

Cells were pretreated for 6 h with different doses of Brimonidine tartrate 0.1% (1/2×, 1×, 5×, 10×), followed by a 24-h exposure to 100 μM of Hydroquinone. The ROS levels decreased at 1×, 5×, and 10× doses of Brimonidine in ARPE-19 but only at 10× on MIO-M1 cells.

Substance Class	Chemical Created by `admin` on `Mon Mar 31 17:33:31 GMT 2025` Edited by `admin` on `Mon Mar 31 17:33:31 GMT 2025`
Record UNII	4S9CL2DY2H
Record Status	`Validated (UNII)`
Record Version

Download

Name

Type

Language

BRIMONIDINE TARTRATE

Official Name

English

BRIMONIDINE D-TARTRATE

Preferred Name

English

CD07805/47

Code

English

UK-14304-18

Code

English

Brimonidine tartrate [WHO-DD]

Common Name

English

AGN 190342-LF

Code

English

AGN-190342LF

Code

English

BRIMONIDINE TARTRATE [USAN]

Common Name

English

SIMBRINZA COMPONENT BRIMONIDINE TARTRATE

Brand Name

English

6-QUINOXALINAMINE, 5-BROMO-N-(4,5-DIHYDRO-1H-IMIDAZOL-2-YL)-, (R-(R*,R*))-2,3-DIHYDROXYBUTANEDIOATE (1:1)

Systematic Name

English

LUMIFY

Brand Name

English

BRIMONIDINE TARTRATE [USP-RS]

Common Name

English

ALPHAGAN

Brand Name

English

5-BROMO-6-(2-IMIDAZOLIN-2-YLAMINO)QUINOXALINE D-TARTRATE (1:1)

Systematic Name

English

BRIMONIDINE TARTRATE [EP MONOGRAPH]

Common Name

English

6-QUINOXALINAMINE, 5-BROMO-N-(4,5-DIHYDRO-1H-IMIDAZOL-2-YL)-, (2R,3R)-2,3-DIHYDROXYBUTANEDIOATE (1:1)

Systematic Name

English

BROMOXIDINE TARTRATE

Common Name

English

OCU-300

Code

English

BRIMONIDINE TARTRATE [ORANGE BOOK]

Common Name

English

CD-07805/47

Code

English

OCU300

Code

English

BRIMONIDINE TARTRATE [VANDF]

Common Name

English

BRIMONIDINE TARTRATE [MART.]

Common Name

English

BRIMONIDINE TARTRATE [USP MONOGRAPH]

Common Name

English

AGN-190342-LF

Code

English

COMBIGAN COMPONENT BRIMONIDINE TARTRATE

Common Name

English

CD-07805

Code

English

BRIMONIDINE TARTRATE [JAN]

Common Name

English

MIRVASO

Brand Name

English

UK-1430418

Code

English

BRIMONIDINE D-TARTRATE [MI]

Common Name

English

Classification Tree Code System Code

EMA ASSESSMENT REPORTS

SIMBRINZA (AUTHORIZED: OCULAR HYPERTENSION)