Details
Stereochemistry | ACHIRAL |
Molecular Formula | C11H10BrN5 |
Molecular Weight | 292.1345 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
c1cc2c(c(c1NC3=NCCN3)Br)nccn2
InChI
InChIKey=XYLJNLCSTIOKRM-UHFFFAOYSA-N
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)
DescriptionCurator'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
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 |
---|---|---|---|
Target ID: P08913 Gene ID: 150.0 Gene Symbol: ADRA2A Target Organism: Homo sapiens (Human) |
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Target ID: P18089 Gene ID: 151.0 Gene Symbol: ADRA2B Target Organism: Homo sapiens (Human) |
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Target ID: P18825 Gene ID: 152.0 Gene Symbol: ADRA2C Target Organism: Homo sapiens (Human) |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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Primary | ALPHAGAN P Approved UseBrimonidine 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 Date1.12440954E12 |
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Primary | ALPHAGAN P Approved UseBrimonidine 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 Date1.12440954E12 |
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Primary | MIRVASO Approved UseBrimonidine 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 Date1.37712959E12 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
73 pg/mL |
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 |
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 |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
2.1 h |
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: |
unhealthy, 4 years n = 1 Health Status: unhealthy Age Group: 4 years Sex: M Population Size: 1 Sources: |
Other AEs: Bradycardia, Somnolence... |
0.5 % single, ophthalmic Dose: 0.5 % Route: ophthalmic Route: single Dose: 0.5 % Sources: Page: p. 19 |
unhealthy, 4.8 years (range: 2-7 years) n = 38 Health Status: unhealthy Age Group: 4.8 years (range: 2-7 years) Sex: M+F Population Size: 38 Sources: Page: p. 19 |
Disc. AE: Somnolence... AEs leading to discontinuation/dose reduction: Somnolence Sources: Page: p. 19 |
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: Page: p. 66 |
unhealthy, adult n = 330 Health Status: unhealthy Age Group: adult Sex: M+F Population Size: 330 Sources: Page: p. 66 |
Disc. AE: Contact dermatitis, Erythema... AEs leading to discontinuation/dose reduction: Contact dermatitis (0.6%) Sources: Page: p. 66Erythema (0.3%) |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
Bradycardia | 0.33 % single, oromucosal Dose: 0.33 % Route: oromucosal Route: single Dose: 0.33 % Sources: |
unhealthy, 4 years n = 1 Health Status: unhealthy Age Group: 4 years Sex: M Population Size: 1 Sources: |
|
Somnolence | 0.33 % single, oromucosal Dose: 0.33 % Route: oromucosal Route: single Dose: 0.33 % Sources: |
unhealthy, 4 years n = 1 Health Status: unhealthy Age Group: 4 years Sex: M Population Size: 1 Sources: |
|
Somnolence | Disc. AE | 0.5 % single, ophthalmic Dose: 0.5 % Route: ophthalmic Route: single Dose: 0.5 % Sources: Page: p. 19 |
unhealthy, 4.8 years (range: 2-7 years) n = 38 Health Status: unhealthy Age Group: 4.8 years (range: 2-7 years) Sex: M+F Population Size: 38 Sources: Page: p. 19 |
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: Page: p. 66 |
unhealthy, adult n = 330 Health Status: unhealthy Age Group: adult Sex: M+F Population Size: 330 Sources: Page: p. 66 |
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: Page: p. 66 |
unhealthy, adult n = 330 Health Status: unhealthy Age Group: adult Sex: M+F Population Size: 330 Sources: Page: p. 66 |
PubMed
Title | Date | PubMed |
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Neuroprotective effects of alpha(2)-selective adrenergic agonists against ischemia-induced retinal ganglion cell death. | 2001 Aug |
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Potent alpha(2A)-adrenoceptor-mediated vasoconstriction by brimonidine in porcine ciliary arteries. | 2001 Aug |
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The adverse effect of perioperative brimonidine tartrate 0.2% on flap adherence and enhancement rates in laser in situ keratomileusis patients. | 2001 Aug |
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The impact of new drugs on management of glaucoma in Scotland: observational study. | 2001 Dec 15 |
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Noradrenaline stimulates 5-hydroxytryptamine release from mouse ileal tissues via alpha(2)-adrenoceptors. | 2001 Dec 7 |
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Comparison of the clinical success and quality-of-life impact of brimonidine 0.2% and betaxolol 0.25 % suspension in patients with elevated intraocular pressure. | 2001 Jul |
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Role of the extracellular signal-regulated kinase (Erk) signal transduction cascade in alpha(2) adrenoceptor-mediated vasoconstriction in porcine palmar lateral vein. | 2001 Jul |
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Disturbance of the prejunctional modulation of cholinergic neurotransmission during chronic granulomatous inflammation of the mouse ileum. | 2001 Jul |
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The effect of adrenergic compounds on neurogenic dural vasodilatation. | 2001 Jul 13 |
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Role of alpha(2)-adrenoceptors in the sympathetic inhibition of motility reflexes of guinea-pig ileum. | 2001 Jul 15 |
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Clinical and economic impact of new trends in glaucoma treatment. | 2001 Jul 26 |
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Brimonidine (Alphagan): a clinical profile four years after launch. | 2001 Jul-Sep |
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Influence of topical brimonidine on visual field in glaucoma. | 2001 Jul-Sep |
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Brimonidine's neuroprotective effects against transient ischaemia-induced retinal ganglion cell death. | 2001 Jul-Sep |
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Apoptosis and anti-apoptosis signalling in glaucomatous retinopathy. | 2001 Jul-Sep |
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Effectiveness and safety of brimonidine as adjunctive therapy for patients with elevated intraocular pressure in a large, open-label community trial. | 2001 Jun |
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Effect of brimonidine tartrate on ocular hemodynamics in healthy volunteers. | 2001 Jun |
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Brimonidine 0.2% given two or three times daily versus timolol maleate 0.5% in primary open-angle glaucoma. | 2001 Jun |
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Topically applied clonidine protects the rat retina from ischaemia/reperfusion by stimulating alpha(2)-adrenoceptors and not by an action on imidazoline receptors. | 2001 Jun 15 |
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The alpha(1A)-adrenoceptor subtype mediates contraction in rat femoral resistance arteries. | 2001 Jun 22 |
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Brimonidine and inhibition of nitrite production in isolated porcine ciliary processes. | 2001 May |
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Ca2+ influx mediates enhanced alpha2-adrenergic contraction in aortas from rats treated with NOS inhibitor. | 2001 Nov |
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Functional characterization of alpha1-adrenoceptor subtypes in human subcutaneous resistance arteries. | 2001 Nov |
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Circadian change of adenylate cyclase activity in rabbit ciliary processes. | 2001 Oct |
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[Prevention of early postoperative increase in intraocular pressure after phacoemulsification. Comparison of different antiglaucoma drugs]. | 2001 Oct |
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[Prospects for neuroprotective glaucoma therapy]. | 2001 Oct |
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[Brimonidine absorption and release from 1. Day acuvue disposable contact lenses]. | 2001 Oct |
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alpha(2)-adrenoceptor antagonist properties of OPC-28326, a novel selective peripheral vasodilator. | 2001 Oct |
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[Experience with topical brimonidine in the treatment of glaucomas]. | 2001 Sep |
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Effects of central imidazolinergic and alpha2-adrenergic activation on water intake. | 2001 Sep |
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Effects of acute and chronic ethanol administration on the response of mouse adipose tissue hormone-sensitive lipase to alpha(2)-adrenoceptor activation bu UK 14304. | 2001 Sep-Oct |
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Failure of naloxone to reverse brimonidine-induced coma in an infant. | 2002 Apr |
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The efficacy of brimonidine in preventing intraocular pressure elevation in the provocative test for primary angle-closure glaucoma. | 2002 Apr |
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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 Apr |
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Effects of acute and subchronic administration of dexefaroxan, an alpha(2)-adrenoceptor antagonist, on memory performance in young adult and aged rodents. | 2002 Apr |
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Distribution of brimonidine into anterior and posterior tissues of monkey, rabbit, and rat eyes. | 2002 Apr |
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Lysophosphatidylcholine potentiates vascular contractile responses in rat aorta via activation of tyrosine kinase. | 2002 Feb |
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Substance P, insulinlike growth factor 1, and surface healing. | 2002 Feb |
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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 Feb |
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Clinical effects of brimonidine ophthalmic drops ingestion in 52 dogs. | 2002 Feb |
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A short term study of the additive effect of timolol and brimonidine on intraocular pressure. | 2002 Jan |
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Presynaptic modulation of cholinergic neurotransmission in the human proximal stomach. | 2002 Jan |
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alpha(2C)-Adrenergic receptors mediate spinal analgesia and adrenergic-opioid synergy. | 2002 Jan |
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A comparison of the short-term hypotensive effects and side effects of unilateral brimonidine and apraclonidine in patients with elevated intraocular pressure. | 2002 Jan-Feb |
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Pre- and postjunctional alpha(2)-adrenergic receptors in fetal and adult ovine cerebral arteries. | 2002 Jun |
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Delayed hypersensitivity to brimonidine tartrate 0.2% associated with high intraocular pressure. | 2002 Mar |
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Analysis of the effects of graded levels of hypoxia on noradrenaline-evoked contraction in the rat iliac artery in vitro. | 2002 Mar |
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Release inhibitory receptors activation favours the A2A-adenosine receptor-mediated facilitation of noradrenaline release in isolated rat tail artery. | 2002 May |
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The effects of new topical treatments on management of glaucoma in Scotland: an examination of ophthalmological health care. | 2002 May |
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alpha 2B-adrenergic receptor activates MAPK via a pathway involving arachidonic acid metabolism, matrix metalloproteinases, and epidermal growth factor receptor transactivation. | 2002 May 31 |
Sample Use Guides
One drop in the affected eye(s), three times daily, approximately 8 hours apart
Route of Administration:
Topical
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/26624556
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.
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WHO-VATC |
QS01EA05
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WHO-ATC |
S01EA05
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WHO-VATC |
QD11AX21
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NCI_THESAURUS |
C29709
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FDA ORPHAN DRUG |
564016
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FDA ORPHAN DRUG |
125699
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WHO-ATC |
D11AX21
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NDF-RT |
N0000175552
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NDF-RT |
N0000000209
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NCI_THESAURUS |
C29705
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2435
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DB00484
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520
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Brimonidine
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M2651
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BRIMONIDINE
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SUB05889MIG
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E6GNX3HHTE
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C65269
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59803-98-4
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6863
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59803-98-4
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395
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CHEMBL844
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C015620
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134615
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PRIMARY | RxNorm |
ACTIVE MOIETY
METABOLITE (PARENT)
SALT/SOLVATE (PARENT)