Brimonidine tartrateProduct ingredient for Brimonidine

Name
Brimonidine tartrate
Drug Entry
Brimonidine

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

Accession Number
DBSALT000195
Structure
Thumb
Synonyms
Brominide tartrate
External IDs
AGN 190342-LF / AGN 190342LF / UK-14304-18
UNII
4S9CL2DY2H
CAS Number
70359-46-5
Weight
Average: 442.221
Monoisotopic: 441.028395916
Chemical Formula
C15H16BrN5O6
InChI Key
QZHBYNSSDLTCRG-LREBCSMRSA-N
InChI
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
IUPAC Name
(2R,3R)-2,3-dihydroxybutanedioic acid; 5-bromo-N-(4,5-dihydro-1H-imidazol-2-yl)quinoxalin-6-amine
SMILES
[H][C@](O)(C(O)=O)[C@@]([H])(O)C(O)=O.BrC1=C(NC2=NCCN2)C=CC2=C1N=CC=N2
External Links
KEGG Drug
D02076
PubChem Compound
54405
ChemSpider
49142
ChEBI
774340
Wikipedia
Brimonidine
Predicted Properties
PropertyValueSource
Water Solubility0.154 mg/mLALOGPS
logP1.27ALOGPS
logP1.37ChemAxon
logS-3.3ALOGPS
pKa (Strongest Basic)8.32ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area62.2 Å2ChemAxon
Rotatable Bond Count4ChemAxon
Refractivity68.49 m3·mol-1ChemAxon
Polarizability25.79 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon