U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

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
Structure of BRIMONIDINE

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)

HIDE SMILES / InChI

Molecular Formula C11H10BrN5
Molecular Weight 292.1345
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description
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.

Originator

Curator's Comment:: # Pfizer

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Target ID: P18089
Gene ID: 151.0
Gene Symbol: ADRA2B
Target Organism: Homo sapiens (Human)
Target ID: P18825
Gene ID: 152.0
Gene Symbol: ADRA2C
Target Organism: Homo sapiens (Human)
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
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
Primary
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
Primary
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
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
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

AUC

ValueDoseCo-administeredAnalytePopulation
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

T1/2

ValueDoseCo-administeredAnalytePopulation
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

Doses

DosePopulationAdverse 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...
Other AEs:
Bradycardia
Somnolence
Sources:
0.5 % single, ophthalmic
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%)
Erythema (0.3%)
Sources: Page: p. 66
AEs

AEs

AESignificanceDosePopulation
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
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

PubMed

TitleDatePubMed
Antiglaucomatous drugs effects on optic nerve head flow: design, baseline and preliminary report.
2001
Effect of topical brimonidine on intraocular pressure after small incision cataract surgery.
2001 Aug
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 Dec
The impact of new drugs on management of glaucoma in Scotland: observational study.
2001 Dec 15
Noradrenaline stimulates 5-hydroxytryptamine release from mouse ileal tissues via alpha(2)-adrenoceptors.
2001 Dec 7
Comparative effects of antiglaucoma drugs on voltage-dependent calcium channels.
2001 Jul
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
Brimonidine (Alphagan): a clinical profile four years after launch.
2001 Jul-Sep
Influence of topical brimonidine on visual field in glaucoma.
2001 Jul-Sep
Brimonidine's neuroprotective effects against transient ischaemia-induced retinal ganglion cell death.
2001 Jul-Sep
Alpha-2 adrenergic receptor agonists are neuroprotective in experimental models of glaucoma.
2001 Jul-Sep
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
Neuroprotection of retinal ganglion cells by brimonidine in rats with laser-induced chronic ocular hypertension.
2001 Nov
Ca2+ influx mediates enhanced alpha2-adrenergic contraction in aortas from rats treated with NOS inhibitor.
2001 Nov
Functional characterization of alpha1-adrenoceptor subtypes in human subcutaneous resistance arteries.
2001 Nov
Switching patients with glaucoma or ocular hypertension from dual therapy to monotherapy: evaluation of brimonidine as a model.
2001 Nov-Dec
[Prevention of early postoperative increase in intraocular pressure after phacoemulsification. Comparison of different antiglaucoma drugs].
2001 Oct
[Prospects for neuroprotective glaucoma therapy].
2001 Oct
[Brimonidine absorption and release from 1. Day acuvue disposable contact lenses].
2001 Oct
Safety and efficacy of brimonidine in children with glaucoma.
2001 Oct
alpha(2)-adrenoceptor antagonist properties of OPC-28326, a novel selective peripheral vasodilator.
2001 Oct
[Experience with topical brimonidine in the treatment of glaucomas].
2001 Sep
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 Sep
Effects of central imidazolinergic and alpha2-adrenergic activation on water intake.
2001 Sep
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
Failure of naloxone to reverse brimonidine-induced coma in an infant.
2002 Apr
The efficacy of brimonidine in preventing intraocular pressure elevation in the provocative test for primary angle-closure glaucoma.
2002 Apr
Twelve-month evaluation of brimonidine-purite versus brimonidine in patients with glaucoma or ocular hypertension.
2002 Apr
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
Effects of acute and subchronic administration of dexefaroxan, an alpha(2)-adrenoceptor antagonist, on memory performance in young adult and aged rodents.
2002 Apr
Neuroprotective effects of brimonidine against transient ischemia-induced retinal ganglion cell death: a dose response in vivo study.
2002 Feb
Allergic reactions to brimonidine in patients treated for glaucoma.
2002 Feb
Lysophosphatidylcholine potentiates vascular contractile responses in rat aorta via activation of tyrosine kinase.
2002 Feb
Substance P, insulinlike growth factor 1, and surface healing.
2002 Feb
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
Clinical effects of brimonidine ophthalmic drops ingestion in 52 dogs.
2002 Feb
A short term study of the additive effect of timolol and brimonidine on intraocular pressure.
2002 Jan
Minimally invasive spectroscopic system for intraocular drug detection.
2002 Jan
Presynaptic modulation of cholinergic neurotransmission in the human proximal stomach.
2002 Jan
alpha(2C)-Adrenergic receptors mediate spinal analgesia and adrenergic-opioid synergy.
2002 Jan
Tumor necrosis factor expressed by primary hippocampal neurons and SH-SY5Y cells is regulated by alpha(2)-adrenergic receptor activation.
2002 Jan 15
Modification of serotonin neuron properties in mice lacking 5-HT1A receptors.
2002 Jan 25
Pre- and postjunctional alpha(2)-adrenergic receptors in fetal and adult ovine cerebral arteries.
2002 Jun
Delayed hypersensitivity to brimonidine tartrate 0.2% associated with high intraocular pressure.
2002 Mar
Analysis of the effects of graded levels of hypoxia on noradrenaline-evoked contraction in the rat iliac artery in vitro.
2002 Mar
Release inhibitory receptors activation favours the A2A-adenosine receptor-mediated facilitation of noradrenaline release in isolated rat tail artery.
2002 May
Brimonidine 0.2% to prevent post laser IOP elevation.
2002 May
The effects of new topical treatments on management of glaucoma in Scotland: an examination of ophthalmological health care.
2002 May
ATP release in human kidney cortex and its mitogenic effects in visceral glomerular epithelial cells.
2002 May
alpha 2B-adrenergic receptor activates MAPK via a pathway involving arachidonic acid metabolism, matrix metalloproteinases, and epidermal growth factor receptor transactivation.
2002 May 31
Patents

Sample Use Guides

One drop in the affected eye(s), three times daily, approximately 8 hours apart
Route of Administration: Topical
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 Jun 25 22:08:31 UTC 2021
Edited
by admin
on Fri Jun 25 22:08:31 UTC 2021
Record UNII
E6GNX3HHTE
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
BRIMONIDINE
INN   MI   VANDF   WHO-DD  
INN  
Official Name English
AGN-190342 FREE BASE
Code English
5-BROMO-6-(2-IMIDAZOLIN-2-YLAMINO)QUINOXALINE D-TARTRATE (1:1).
Systematic Name English
BRIMONIDINE [WHO-DD]
Common Name English
BRIMONIDINE [VANDF]
Common Name English
UK-1430418 FREE BASE
Code English
BRIMONIDINE [INN]
Common Name English
6-QUINOXALINAMINE, 5-BROMO-N-(4,5-DIHYDRO-1H-IMIDAZOL-2-YL)-, (S-(R*,R*))-2,3-DIHYDROXYBUTANEDIOATE (1:1)
Systematic Name English
UK-14304
Code English
BRIMONIDINE [MI]
Common Name English
NSC-318825
Code English
Classification Tree Code System Code
WHO-VATC QS01EA05
Created by admin on Fri Jun 25 22:08:32 UTC 2021 , Edited by admin on Fri Jun 25 22:08:32 UTC 2021
WHO-ATC S01EA05
Created by admin on Fri Jun 25 22:08:32 UTC 2021 , Edited by admin on Fri Jun 25 22:08:32 UTC 2021
WHO-VATC QD11AX21
Created by admin on Fri Jun 25 22:08:32 UTC 2021 , Edited by admin on Fri Jun 25 22:08:32 UTC 2021
NCI_THESAURUS C29709
Created by admin on Fri Jun 25 22:08:32 UTC 2021 , Edited by admin on Fri Jun 25 22:08:32 UTC 2021
FDA ORPHAN DRUG 564016
Created by admin on Fri Jun 25 22:08:32 UTC 2021 , Edited by admin on Fri Jun 25 22:08:32 UTC 2021
FDA ORPHAN DRUG 125699
Created by admin on Fri Jun 25 22:08:32 UTC 2021 , Edited by admin on Fri Jun 25 22:08:32 UTC 2021
WHO-ATC D11AX21
Created by admin on Fri Jun 25 22:08:32 UTC 2021 , Edited by admin on Fri Jun 25 22:08:32 UTC 2021
NDF-RT N0000175552
Created by admin on Fri Jun 25 22:08:32 UTC 2021 , Edited by admin on Fri Jun 25 22:08:32 UTC 2021
NDF-RT N0000000209
Created by admin on Fri Jun 25 22:08:32 UTC 2021 , Edited by admin on Fri Jun 25 22:08:32 UTC 2021
NCI_THESAURUS C29705
Created by admin on Fri Jun 25 22:08:32 UTC 2021 , Edited by admin on Fri Jun 25 22:08:32 UTC 2021
Code System Code Type Description
PUBCHEM
2435
Created by admin on Fri Jun 25 22:08:32 UTC 2021 , Edited by admin on Fri Jun 25 22:08:32 UTC 2021
PRIMARY
DRUG BANK
DB00484
Created by admin on Fri Jun 25 22:08:32 UTC 2021 , Edited by admin on Fri Jun 25 22:08:32 UTC 2021
PRIMARY
IUPHAR
520
Created by admin on Fri Jun 25 22:08:32 UTC 2021 , Edited by admin on Fri Jun 25 22:08:32 UTC 2021
PRIMARY
LACTMED
Brimonidine
Created by admin on Fri Jun 25 22:08:32 UTC 2021 , Edited by admin on Fri Jun 25 22:08:32 UTC 2021
PRIMARY
MERCK INDEX
M2651
Created by admin on Fri Jun 25 22:08:32 UTC 2021 , Edited by admin on Fri Jun 25 22:08:32 UTC 2021
PRIMARY Merck Index
WIKIPEDIA
BRIMONIDINE
Created by admin on Fri Jun 25 22:08:32 UTC 2021 , Edited by admin on Fri Jun 25 22:08:32 UTC 2021
PRIMARY
EVMPD
SUB05889MIG
Created by admin on Fri Jun 25 22:08:32 UTC 2021 , Edited by admin on Fri Jun 25 22:08:32 UTC 2021
PRIMARY
FDA UNII
E6GNX3HHTE
Created by admin on Fri Jun 25 22:08:32 UTC 2021 , Edited by admin on Fri Jun 25 22:08:32 UTC 2021
PRIMARY
NCI_THESAURUS
C65269
Created by admin on Fri Jun 25 22:08:32 UTC 2021 , Edited by admin on Fri Jun 25 22:08:32 UTC 2021
PRIMARY
EPA CompTox
59803-98-4
Created by admin on Fri Jun 25 22:08:32 UTC 2021 , Edited by admin on Fri Jun 25 22:08:32 UTC 2021
PRIMARY
INN
6863
Created by admin on Fri Jun 25 22:08:32 UTC 2021 , Edited by admin on Fri Jun 25 22:08:32 UTC 2021
PRIMARY
CAS
59803-98-4
Created by admin on Fri Jun 25 22:08:32 UTC 2021 , Edited by admin on Fri Jun 25 22:08:32 UTC 2021
PRIMARY
DRUG CENTRAL
395
Created by admin on Fri Jun 25 22:08:32 UTC 2021 , Edited by admin on Fri Jun 25 22:08:32 UTC 2021
PRIMARY
ChEMBL
CHEMBL844
Created by admin on Fri Jun 25 22:08:32 UTC 2021 , Edited by admin on Fri Jun 25 22:08:32 UTC 2021
PRIMARY
MESH
C015620
Created by admin on Fri Jun 25 22:08:32 UTC 2021 , Edited by admin on Fri Jun 25 22:08:32 UTC 2021
PRIMARY
RXCUI
134615
Created by admin on Fri Jun 25 22:08:32 UTC 2021 , Edited by admin on Fri Jun 25 22:08:32 UTC 2021
PRIMARY RxNorm
Related Record Type Details
SALT/SOLVATE -> PARENT
TARGET -> AGONIST
SHORT-ACTING
Related Record Type Details
METABOLITE -> PARENT
Related Record Type Details
ACTIVE MOIETY
Name Property Type Amount Referenced Substance Defining Parameters References
Biological Half-life PHARMACOKINETIC