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=C(NC2=NCCN2)C=CC3=C1N=CC=N3

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	C11H10BrN5
Molecular Weight	292.135
Charge	0
Count

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

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

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 2678
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 2678
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 2678

Conditions

Condition	Modality	Highest Phase	Product
Open-angle glaucoma 51 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2010/021262s020,021770s004lbl.pdf	Primary	Approved 8429	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 1.12440954E12
Ocular hypertension 50 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2010/021262s020,021770s004lbl.pdf	Primary	Approved 8429	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 1.12440954E12
Persistent (nontransient) facial erythema of rosacea 2 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2016/204708s005lbl.pdf	Primary	Approved 8429	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 1.37712959E12

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 n = 1 Health Status: unhealthy Age Group: 4 years Sex: M Population Size: 1 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 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: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2001/20-490S007_Brimonidine%20Tartrate%20Ophthalmic_medr.pdf Page: p. 19	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 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: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2013/204708Orig1s000MedR.pdf Page: p. 66	unhealthy, adult n = 330 Health Status: unhealthy Age Group: adult Sex: M+F Population Size: 330 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2013/204708Orig1s000MedR.pdf Page: p. 66	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 Page: p. 66

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 n = 1 Health Status: unhealthy Age Group: 4 years Sex: M Population Size: 1 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 n = 1 Health Status: unhealthy Age Group: 4 years Sex: M Population Size: 1 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 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: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2001/20-490S007_Brimonidine%20Tartrate%20Ophthalmic_medr.pdf 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: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2013/204708Orig1s000MedR.pdf Page: p. 66	unhealthy, adult n = 330 Health Status: unhealthy Age Group: adult Sex: M+F Population Size: 330 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2013/204708Orig1s000MedR.pdf 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: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2013/204708Orig1s000MedR.pdf Page: p. 66	unhealthy, adult n = 330 Health Status: unhealthy Age Group: adult Sex: M+F Population Size: 330 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2013/204708Orig1s000MedR.pdf Page: p. 66

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
MolPort	MolPort-003-959-841	https://www.molport.com/shop/molecule-link/MolPort-003-959-841
ZINC	ZINC000021303210	http://zinc15.docking.org/substances/ZINC000021303210
eMolecules	595250	https://www.emolecules.com/cgi-bin/more?vid=595250

PubMed

Title	Date	PubMed
Brain alpha(2)-adrenoceptors in monoamine-depleted rats: increased receptor density, G coupling proteins, receptor turnover and receptor mRNA.	2001 Apr	11264240
Alpha2-adrenoceptor-mediated inhibition of cultured sympathetic neurons: changes in alpha2A/D-adrenoceptor-deficient mice.	2001 Jan	11191829
alpha(2)-Adrenoceptor agonists inhibit vitreal glutamate and aspartate accumulation and preserve retinal function after transient ischemia.	2001 Jan	11123383
Increased alpha(1)- and alpha(2)-adrenoceptor-mediated contractile responses of human skeletal muscle resistance arteries in chronic limb ischemia.	2001 Jan	11121814
Receptor reserve analysis of the human alpha(2C)-adrenoceptor using.	2001 Jan 12	11164378
Comparative effects of antiglaucoma drugs on voltage-dependent calcium channels.	2001 Jul	11521697
Disturbance of the prejunctional modulation of cholinergic neurotransmission during chronic granulomatous inflammation of the mouse ileum.	2001 Jul	11429394
The effect of adrenergic compounds on neurogenic dural vasodilatation.	2001 Jul 13	11470260
Clinical and economic impact of new trends in glaucoma treatment.	2001 Jul 26	11549985
Brimonidine (Alphagan): a clinical profile four years after launch.	2001 Jul-Sep	11592536
Influence of topical brimonidine on visual field in glaucoma.	2001 Jul-Sep	11592534
Alpha-2 adrenergic receptor agonists are neuroprotective in experimental models of glaucoma.	2001 Jul-Sep	11592528
Apoptosis and anti-apoptosis signalling in glaucomatous retinopathy.	2001 Jul-Sep	11592526
Effectiveness and safety of brimonidine as adjunctive therapy for patients with elevated intraocular pressure in a large, open-label community trial.	2001 Jun	11442187
Differential effects of alpha-adrenoceptor agonists on human retinal microvessel diameter.	2001 Jun	11436946
Effect of brimonidine tartrate on ocular hemodynamics in healthy volunteers.	2001 Jun	11436940
Washout periods for brimonidine 0.2% and latanoprost 0.005%.	2001 Jun	11384581
Brimonidine 0.2% given two or three times daily versus timolol maleate 0.5% in primary open-angle glaucoma.	2001 Jun	11384568
Brimonidine 0.2% versus apraclonidine 0.5% for prevention of intraocular pressure elevations after anterior segment laser surgery.	2001 Jun	11382625
Quantitation of mitomycin C in human ocular tissues by high-performance liquid chromatography-photo-diode array detection.	2001 May 5	11393734
Switching patients with glaucoma or ocular hypertension from dual therapy to monotherapy: evaluation of brimonidine as a model.	2001 Nov-Dec	11841198
Circadian change of adenylate cyclase activity in rabbit ciliary processes.	2001 Oct	11852425
alpha(2)-adrenoceptor antagonist properties of OPC-28326, a novel selective peripheral vasodilator.	2001 Oct	11606316
Enhanced interaction between renovascular alpha(2)-adrenoceptors and angiotensin II receptors in genetic hypertension.	2001 Sep	11566904
Allergic reactions to brimonidine in patients treated for glaucoma.	2002 Feb	11865954
Modification of serotonin neuron properties in mice lacking 5-HT1A receptors.	2002 Jan 25	11821026
Analysis of the effects of graded levels of hypoxia on noradrenaline-evoked contraction in the rat iliac artery in vitro.	2002 Mar	11856962
Release inhibitory receptors activation favours the A2A-adenosine receptor-mediated facilitation of noradrenaline release in isolated rat tail artery.	2002 May	12010771
Brimonidine 0.2% to prevent post laser IOP elevation.	2002 May	11986075

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 `Fri Dec 15 14:58:25 UTC 2023` Edited by `admin` on `Fri Dec 15 14:58:25 UTC 2023`
Record UNII	4S9CL2DY2H
Record Status	`Validated (UNII)`
Record Version

Download

Name

Type

Language

BRIMONIDINE TARTRATE

Official 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 D-TARTRATE

Common 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 COMPONENT OF COMBIGAN

Common Name

English

BRIMONIDINE TARTRATE [VANDF]

Common Name

English

BRIMONIDINE TARTRATE [MART.]

Common Name

English

BRIMONIDINE TARTRATE COMPONENT OF SIMBRINZA

Brand 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)