BRIMONIDINE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C11H10BrN5
Molecular Weight	292.135
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

SMILES

BrC1=C(NC2=NCCN2)C=CC3=C1N=CC=N3

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	292.135
Charge	0
Count	MOL RATIO 1 MOL RATIO (average)

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

Description

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	Agonist 2,678
Alpha-2B adrenergic receptor 13	Agonist 2,678
Alpha-2C adrenergic receptor 11	Agonist 2,678

Conditions

Condition	Modality	Highest Phase	Product
Open-angle glaucoma 51	Primary	Approved 8,429	ALPHAGAN P
Ocular hypertension 50	Primary	Approved 8,429	ALPHAGAN P
Persistent (nontransient) facial erythema of rosacea 2	Primary	Approved 8,429	MIRVASO

C_max

Value	Dose	Co-administered	Analyte	Population
73 pg/mL	1 drop single, ocular		BRIMONIDINE TARTRATE plasma	Homo sapiens

AUC

Value	Dose	Co-administered	Analyte	Population
375 pg × h/mL	1 drop single, ocular		BRIMONIDINE TARTRATE plasma	Homo sapiens

T_1/2

Value	Dose	Co-administered	Analyte	Population
2.1 h	1 drop single, ocular		BRIMONIDINE TARTRATE plasma	Homo sapiens

Doses

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Dose	Population	Adverse events
0.33 % single, oromucosal	unhealthy, 4 years	Other AEs: Bradycardia, Somnolence...
0.5 % single, ophthalmic	unhealthy, 4.8 years (range: 2-7 years)	Disc. AE: Somnolence...
0.33 % 1 times / day steady, topical Recommended	unhealthy, adult	Disc. AE: Contact dermatitis, Erythema...

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AEs

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AE	Significance	Dose	Population
Bradycardia		0.33 % single, oromucosal	unhealthy, 4 years
Somnolence		0.33 % single, oromucosal	unhealthy, 4 years
Somnolence	Disc. AE	0.5 % single, ophthalmic	unhealthy, 4.8 years (range: 2-7 years)
Erythema	0.3% Disc. AE	0.33 % 1 times / day steady, topical Recommended	unhealthy, adult
Contact dermatitis	0.6% Disc. AE	0.33 % 1 times / day steady, topical Recommended	unhealthy, adult

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Sourcing

Sourcing

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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

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PubMed

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Title	Date	PubMed
Antiglaucomatous drugs effects on optic nerve head flow: design, baseline and preliminary report.	2001	11944863
Influence of nitric oxide donors and of the alpha(2)-agonist UK-14,304 on acetylcholine release in the pig gastric fundus.	2001	11114406
Efficacy of brimonidine 0.2% and dorzolamide 2% as adjunctive therapy to beta-blockers in adult patients with glaucoma or ocular hypertension.	2001 Apr	11354394
Systemic beta-blocker therapy and brimonidine and timolol.	2001 Aug	11470677
[New medical treatments of glaucoma. New strategies?].	2001 Dec	11913242

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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.