Identification

Name
Brimonidine
Accession Number
DB00484  (APRD00034)
Type
Small Molecule
Groups
Approved
Description

Brimonidine is a drug used to treat glaucoma. It acts via decreasing aqueous humor synthesis. A topical gel formulation, marketed under the name Mirvaso, was FDA approved on August 2013 for the treatment of rosacea.

Structure
Thumb
Synonyms
  • 5-Bromo-6-(2-imidazolin-2-ylamino)quinoxaline
  • Brimonidina
  • Brimonidine
  • Brimonidinum
  • Bromoxidine
External IDs
AGN-190342 / UK-14304
Product Ingredients
IngredientUNIICASInChI Key
Brimonidine tartrate4S9CL2DY2H70359-46-5QZHBYNSSDLTCRG-LREBCSMRSA-N
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
AlphaganLiquid0.2 %OphthalmicAllergan1997-12-02Not applicableCanada
Alphagan PSolution / drops1.5 mg/1mLOphthalmicAllergan, Inc.2001-07-10Not applicableUs
Alphagan PSolution / drops1 mg/1mLOphthalmicPhysicians Total Care, Inc.2013-03-08Not applicableUs
Alphagan PSolution / drops1 mg/1mLOphthalmicAllergan, Inc.2006-01-25Not applicableUs
Alphagan PSolution0.15 %OphthalmicAllergan2003-11-05Not applicableCanada
Alphagan PSolution / drops1.5 mg/1mLOphthalmicPhysicians Total Care, Inc.2002-10-16Not applicableUs
BrimonidineSolution0.2 %OphthalmicPharmascience IncNot applicableNot applicableCanada
Brimonidine OphthalmicSolution0.2 %OphthalmicPharmel IncNot applicableNot applicableCanada
Brimonidine PSolution0.15 %OphthalmicAa Pharma Inc2008-07-15Not applicableCanada
Brimonidine TartrateSolution1.5 mg/1mLOphthalmicPhysicians Total Care, Inc.2009-12-22Not applicableUs
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Apo-brimonidineSolution0.2 %OphthalmicApotex Corporation2005-06-02Not applicableCanada
BrimonidineSolution / drops2 mg/1mLOphthalmicAkorn2006-09-07Not applicableUs
BrimonidineSolution / drops2 mg/1mLOphthalmicA-S Medication Solutions2006-09-072017-11-17Us
Brimonidine TartrateSolution2 mg/1mLOphthalmicIVAX Pharmaceuticals, Inc.2005-06-012007-05-31Us
Brimonidine TartrateSolution / drops2 mg/1mgOphthalmicOsmotica Pharmaceutical Corp.2015-01-01Not applicableUs
Brimonidine TartrateSolution / drops2 mg/1mLOphthalmicRemedy Repack2014-11-242015-12-22Us
Brimonidine TartrateSolution / drops2.0 mg/1mLOphthalmicRegimed Medical2016-03-03Not applicableUs
Brimonidine TartrateSolution2 mg/1mLOphthalmicSandoz2003-09-17Not applicableUs
Brimonidine TartrateSolution / drops2 mg/1mLOphthalmicPhysicians Total Care, Inc.2011-07-25Not applicableUs
Brimonidine TartrateSolution / drops2 mg/1mLOphthalmicPacific Pharma2003-04-102017-12-29Us
Over the Counter Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
LUMIFY Redness Reliever Eye DropsSolution / drops0.25 mg/1mLOphthalmicBauch & Lomb Incorporated2017-12-22Not applicableUs
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
CombiganBrimonidine tartrate (0.2 %) + Timolol (0.5 %)SolutionOphthalmicAllergan2003-12-11Not applicableCanada
CombiganBrimonidine tartrate (2 mg/1mL) + Timolol maleate (5 mg/1mL)Solution / dropsOphthalmicPhysicians Total Care, Inc.2011-08-29Not applicableUs
CombiganBrimonidine tartrate (2 mg/1mL) + Timolol maleate (5 mg/1mL)Solution / dropsOphthalmicAllergan2007-11-14Not applicableUs
SimbrinzaBrimonidine tartrate (2 mg/1mL) + Brinzolamide (10 mg/1mL)Suspension / dropsOphthalmicALCON LABORATORIES, INC.2013-05-01Not applicableUs
SimbrinzaBrimonidine tartrate (2 mg/ml) + Brinzolamide (10 mg/ml)Suspension / dropsOphthalmicNovartis Europharm Limited2014-07-18Not applicableEu
SimbrinzaBrimonidine tartrate (2 mg/ml) + Brinzolamide (10 mg/ml)Suspension / dropsOphthalmicNovartis Europharm Limited2014-07-18Not applicableEu
SimbrinzaBrimonidine tartrate (0.2 %) + Brinzolamide (1 %)SuspensionOphthalmicNovartis2015-02-17Not applicableCanada
Unapproved/Other Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
Brim-Dor PFBrimonidine tartrate (1.5 mg/1mL) + Dorzolamide Hydrochloride (20 mg/1mL)Solution / dropsOphthalmicImprimisRx NJ2018-01-01Not applicableUs
Tim-Brim-Dor PFBrimonidine tartrate (1.5 mg/1mL) + Dorzolamide Hydrochloride (20 mg/1mL) + Timolol maleate (5 mg/1mL)Solution / dropsOphthalmicImprimisRx NJ2018-01-01Not applicableUs
Tim-Brim-Dor-LatBrimonidine tartrate (1.5 mg/1mL) + Dorzolamide Hydrochloride (20 mg/1mL) + Latanoprost (0.05 mg/1mL) + Timolol maleate (5 mg/1mL)Solution / dropsOphthalmicImprimisRx NJ2018-01-01Not applicableUs
Categories
UNII
E6GNX3HHTE
CAS number
59803-98-4
Weight
Average: 292.135
Monoisotopic: 291.011957992
Chemical Formula
C11H10BrN5
InChI Key
XYLJNLCSTIOKRM-UHFFFAOYSA-N
InChI
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)
IUPAC Name
5-bromo-N-(4,5-dihydro-1H-imidazol-2-yl)quinoxalin-6-amine
SMILES
BrC1=C(NC2=NCCN2)C=CC2=NC=CN=C12

Pharmacology

Indication

The ophthalmic solution is indicated for patients with open-angle glaucoma or ocular hypertension to lower intraocular pressure. The topical gel is indicated for the treatment of persistent (nontransient) facial erythema of rosacea in adults 18 years or older.

Associated Conditions
Pharmacodynamics

Brimonidine significantly lowers intraocular pressure with minimal effects on cardiovascular and pulmonary parameters. It lowers intraocular pressure by reducing aqueous humor production and increasing uveoscleral outflow.

Mechanism of action

Brimonidine is an alpha adrenergic receptor agonist (primarily alpha-2). It has a peak ocular hypotensive effect occurring at two hours post-dosing. Fluorophotometric studies in animals and humans suggest that Brimonidine has a dual mechanism of action by reducing aqueous humor production and increasing uveoscleral outflow. The topical gel reduces erythema through direct vasocontriction.

TargetActionsOrganism
AAlpha-2A adrenergic receptor
agonist
Human
AAlpha-2B adrenergic receptor
agonist
Human
AAlpha-2C adrenergic receptor
agonist
Human
Absorption

Minimal systemic absorption occurs after ocular insertion. When the topical gel was applied to adult patients with facial erythema associated with rosacea, the plasma maximum concentration (Cmax) and area under the concentration-time curve (AUC) were 46 ± 62 pg/mL and 417 ± 264 pg.hr/mL, respectively. These values were reached on Day 15 of treatment.

Volume of distribution
Not Available
Protein binding
Not Available
Metabolism

Metabolized primarily by the liver.

Route of elimination

Urinary excretion is the major route of elimination of the drug and its metabolites.

Half life

2 hours [ophthalmic solution]

Clearance
Not Available
Toxicity

Oral LD50 is 50 mg/kg in mice and 100 mg/kg in rats. Common adverse reactions of the topical gel formulation include erythema, flushing, skin burning sensation, and contact dermatitis.

Affected organisms
  • Humans and other mammals
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteraction
1-(3-Mercapto-2-Methyl-Propionyl)-Pyrrolidine-2-Carboxylic AcidBrimonidine may increase the antihypertensive activities of 1-(3-Mercapto-2-Methyl-Propionyl)-Pyrrolidine-2-Carboxylic Acid.
2,5-Dimethoxy-4-ethylthioamphetamineBrimonidine may increase the central nervous system depressant (CNS depressant) activities of 2,5-Dimethoxy-4-ethylthioamphetamine.
3,4-MethylenedioxyamphetamineBrimonidine may increase the central nervous system depressant (CNS depressant) activities of 3,4-Methylenedioxyamphetamine.
4-Bromo-2,5-dimethoxyamphetamineBrimonidine may increase the central nervous system depressant (CNS depressant) activities of 4-Bromo-2,5-dimethoxyamphetamine.
4-MethoxyamphetamineBrimonidine may increase the central nervous system depressant (CNS depressant) activities of 4-Methoxyamphetamine.
5-methoxy-N,N-dimethyltryptamineBrimonidine may increase the central nervous system depressant (CNS depressant) activities of 5-methoxy-N,N-dimethyltryptamine.
7-NitroindazoleBrimonidine may increase the central nervous system depressant (CNS depressant) activities of 7-Nitroindazole.
AcebutololBrimonidine may increase the antihypertensive activities of Acebutolol.
AcepromazineBrimonidine may increase the central nervous system depressant (CNS depressant) activities of Acepromazine.
AceprometazineBrimonidine may increase the central nervous system depressant (CNS depressant) activities of Aceprometazine.
Food Interactions
Not Available

References

General References
Not Available
External Links
Human Metabolome Database
HMDB0014627
KEGG Drug
D07540
KEGG Compound
C07886
PubChem Compound
2435
PubChem Substance
46507305
ChemSpider
2341
BindingDB
34572
ChEBI
3175
ChEMBL
CHEMBL844
Therapeutic Targets Database
DAP000280
PharmGKB
PA448665
IUPHAR
520
Guide to Pharmacology
GtP Drug Page
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
Wikipedia
Brimonidine
ATC Codes
S01EA05 — BrimonidineD11AX21 — Brimonidine
AHFS Codes
  • 52:40.04 — Alpha-adrenergic Agonists
  • 84:92.00 — Misc. Skin and Mucous Membrane Agents
FDA label
Download (517 KB)
MSDS
Download (20.9 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
0RecruitingTreatmentAlcohol-Related Disorders / Aldehyde Dehydrogenase Deficiency / Facial Flushing1
1CompletedPreventionIntraocular Pressure1
1CompletedScreeningHyperemia1
1CompletedTreatmentEye Diseases / Glaucoma / Ocular Hypertension1
1CompletedTreatmentGlaucoma and Ocular Hypertension1
1, 2TerminatedTreatmentEye Dryness / Graft versus host disease in eye / Meibomian Gland Dysfunction (MGD)1
2CompletedNot AvailableMacular Degeneration / Macular Edema (ME) / Retinopathy, Diabetic1
2CompletedPreventionConjunctivitis, Seasonal Allergic1
2CompletedTreatmentAge Related Macular Degeneration (ARMD) / Retinopathy, Diabetic1
2CompletedTreatmentErythematous (Type One) Rosacea1
2CompletedTreatmentGlaucoma, Primary Open Angle (POAG)1
2CompletedTreatmentGlaucoma / Ocular Hypertension1
2CompletedTreatmentOcular Hypertension / Open-angle Glaucoma (OAG)1
2CompletedTreatmentOcular Redness1
2CompletedTreatmentOpen Angle Glaucoma (OAG)1
2Not Yet RecruitingNot AvailableHealthy Volunteers1
2Not Yet RecruitingTreatmentHand-foot Syndrome1
2RecruitingTreatmentEye Dryness1
2TerminatedTreatmentOcular Hypertension / Open-angle Glaucoma (OAG)1
2Unknown StatusTreatmentGlaucoma1
2, 3CompletedPreventionRetinopathy, Diabetic1
3CompletedNot AvailableHyperemia1
3CompletedTreatmentErythemas / Rosaceas2
3CompletedTreatmentGlaucoma, Primary Open Angle (POAG) / Ocular Hypertension1
3CompletedTreatmentGlaucoma / Ocular Hypertension4
3CompletedTreatmentHyperemia1
3CompletedTreatmentOcular Hypertension / Open-angle Glaucoma (OAG)7
3CompletedTreatmentRosaceas1
3Not Yet RecruitingTreatmentGlaucoma, Primary Open Angle (POAG) / Ocular Hypertension1
3RecruitingTreatmentCapillary Malformations1
3RecruitingTreatmentGlaucoma, Primary Open Angle (POAG)1
3RecruitingTreatmentGraft Versus Host Disease (GVHD) / Ocular Surface Disease1
3RecruitingTreatmentOcular Hypertension / Open Angle Glaucoma (OAG)1
3Unknown StatusTreatmentCorneal Edema / Visual Acuity1
3Unknown StatusTreatmentGlaucoma1
4Active Not RecruitingDiagnosticGlaucoma, Primary Open Angle (POAG) / Glaucoma; Drugs / Normal Tension Glaucoma1
4CompletedOtherRosaceas1
4CompletedPreventionOcular Hypertension / Posterior Capsule Opacification1
4CompletedTreatmentAcne Rosacea1
4CompletedTreatmentChronic Persistent Vascular Facial Erythema1
4CompletedTreatmentGlaucoma6
4CompletedTreatmentGlaucoma, Primary Open Angle (POAG) / Ocular Hypertension1
4CompletedTreatmentGlaucoma / Ocular Hypertension5
4CompletedTreatmentOcular Hypertension / Open Angle Glaucoma (OAG)2
4CompletedTreatmentOcular Hypertension / Open-angle Glaucoma (OAG)6
4CompletedTreatmentPhysiology, Ocular / Regional Blood Flow1
4CompletedTreatmentProstate Cancer1
4CompletedTreatmentRosaceas2
4CompletedTreatmentTelangiectasias1
4RecruitingTreatmentRosaceas1
4TerminatedTreatmentGlaucoma1
4TerminatedTreatmentGlaucoma, Angle-Closure1
4TerminatedTreatmentOcular Hypertension / Open-angle Glaucoma (OAG)1
4Unknown StatusTreatmentNormal Tension Glaucoma1
4WithdrawnSupportive CareRelapsing Remitting Multiple Sclerosis (RRMS)1
Not AvailableCompletedNot AvailableHealthy Volunteers1
Not AvailableCompletedNot AvailableOcular Hypertension / Open-angle Glaucoma (OAG)1
Not AvailableCompletedNot AvailableRosaceas1
Not AvailableCompletedBasic ScienceGlaucoma1
Not AvailableCompletedPreventionIntraocular Pressure Change in Intravitreal Injection1
Not AvailableCompletedPreventionPost-Injection Intraocular Pressure Spikes1
Not AvailableCompletedTreatmentGlaucoma1
Not AvailableCompletedTreatmentGlaucoma / Ocular Hypertension2
Not AvailableCompletedTreatmentIntraocular Pressure1
Not AvailableCompletedTreatmentOcular Hypertension / Open Angle Glaucoma (OAG) / Pseudoexfoliation Syndrome1
Not AvailableCompletedTreatmentPhysiology, Ocular / Retina1
Not AvailableCompletedTreatmentPrimary Vascular Dysregulation1
Not AvailableNot Yet RecruitingPreventionOcular Hypertension1
Not AvailableRecruitingTreatmentComplications of Diabetes Mellitus1
Not AvailableTerminatedTreatmentErythema and Flushing Associated With Rosacea1
Not AvailableUnknown StatusNot AvailableImpact of Brimonidine on the Cornea1
Not AvailableUnknown StatusTreatmentGlaucoma / Ocular Hypertension1
Not AvailableWithdrawnBasic ScienceGlaucoma1
Not AvailableWithdrawnDiagnosticIntraocular Pressure / Physiology, Ocular1

Pharmacoeconomics

Manufacturers
  • Allergan inc
  • Allergan
  • Akorn inc
  • Alcon inc
  • Alcon research ltd
  • Bausch and lomb pharmaceuticals inc
  • Sandoz canada inc
  • Teva parenteral medicines inc
  • Allergan, Inc
Packagers
  • Akorn Inc.
  • Alcon Laboratories
  • Allergan Inc.
  • Bausch & Lomb Inc.
  • Falcon Pharmaceuticals Ltd.
  • Ivax Pharmaceuticals
  • Pacific Pharma Lp
  • Physicians Total Care Inc.
  • Stat Rx Usa
Dosage forms
FormRouteStrength
LiquidOphthalmic0.2 %
SolutionOphthalmic0.15 %
Solution / dropsOphthalmic1 mg/1mL
Solution / dropsOphthalmic1.5 mg/1mL
SolutionOphthalmic1.5 mg/1mL
SolutionOphthalmic2 mg/1mL
Solution / dropsOphthalmic2 mg/1mg
Solution / dropsOphthalmic2 mg/1mL
Solution / dropsOphthalmic2.0 mg/1mL
SolutionOphthalmic
Solution / dropsOphthalmic
Solution / dropsOphthalmic0.25 mg/1mL
GelCutaneous3 mg/g
GelTopical5 mg/1g
GelTopical0.33 %
SolutionOphthalmic0.2 %
SuspensionOphthalmic
Suspension / dropsOphthalmic
Prices
Unit descriptionCostUnit
Alphagan P 15ml Bottle .15% 15ml Bottle228.5USD bottle
Brimonidine Tartrate 0.15% Solution 15ml Bottle218.5USD bottle
Alphagan P 0.1% Solution 15ml Bottle208.94USD bottle
Alphagan P 10ml Bottle .15% 10ml Bottle152.32USD bottle
Brimonidine Tartrate 0.15% Solution 10ml Bottle145.65USD bottle
Alphagan P 0.1% Solution 10ml Bottle143.97USD bottle
Alphagan P 5ml Bottle .15% 5ml Bottle79.52USD bottle
Brimonidine Tartrate 0.15% Solution 5ml Bottle72.85USD bottle
Brimonidine Tartrate 0.2% Solution 10ml Bottle67.85USD bottle
Brimonidine Tartrate 0.2% Solution 15ml Bottle56.88USD bottle
Brimonidine Tartrate 0.2% Solution 5ml Bottle33.96USD bottle
Brimonidine tartrate 0.15% drp29.82USD ml
Alphagan p 0.15% eye drops14.65USD ml
Alphagan p 0.1% drops13.85USD ml
Brimonidine 0.2% eye drop6.53USD ml
Alphagan 0.2 % Solution3.72USD ml
Apo-Brimonidine 0.2 % Solution2.08USD ml
Pms-Brimonidine 0.2 % Solution2.08USD ml
Ratio-Brimonidine 0.2 % Solution2.08USD ml
Sandoz Brimonidine 0.2 % Solution2.08USD ml
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)
US5424078No1995-06-132012-06-13Us
CA2173974No2006-05-022014-09-19Canada
CA2225626No2002-09-032016-06-17Canada
US9295641Yes2016-03-292022-01-10Us
US6627210Yes2003-09-302022-01-18Us
US6673337Yes2004-01-062022-01-26Us
US6562873Yes2003-05-132022-01-10Us
US6641834Yes2003-11-042022-01-28Us
US7030149No2006-04-182022-04-19Us
US7320976No2008-01-222022-04-19Us
US7642258No2010-01-052022-04-19Us
US8133890No2012-03-132022-04-19Us
US8354409No2013-01-152022-04-19Us
US8748425No2014-06-102022-04-19Us
US7323463No2008-01-292023-01-19Us
US7265117No2007-09-042025-08-19Us
US8858961Yes2014-10-142024-03-02Us
US6316441No2001-11-132019-12-07Us
US9044484No2015-06-022030-10-30Us
US8410102No2013-04-022025-05-24Us
US8053427No2011-11-082031-06-13Us
US7439241No2008-10-212025-08-25Us
US8513247No2013-08-202031-03-25Us
US8426410No2013-04-232025-05-24Us
US8513249No2013-08-202031-03-25Us
US8859551No2014-10-142024-05-25Us
US8231885No2012-07-312025-05-24Us
US8163725No2012-04-242031-06-13Us
US9474751No2016-10-252022-04-19Us
US9687443Yes2017-06-272022-01-10Us
US9421265No2016-08-232030-06-17Us
US9770453No2017-09-262022-04-19Us
US9861631No2018-01-092031-03-25Us
US8293742No2012-10-232030-07-14Us
US9861632No2018-01-092031-03-25Us
US9907801No2018-03-062022-04-19Us
US9907802No2018-03-062022-04-19Us

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)207.5 °CNot Available
water solubilitySoluble (1.5 mg/mL)Not Available
logP1.7Not Available
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 Count1ChemAxon
Refractivity68.49 m3·mol-1ChemAxon
Polarizability25.74 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.978
Blood Brain Barrier+0.717
Caco-2 permeable+0.5435
P-glycoprotein substrateSubstrate0.7017
P-glycoprotein inhibitor INon-inhibitor0.5688
P-glycoprotein inhibitor IIInhibitor0.5951
Renal organic cation transporterInhibitor0.8266
CYP450 2C9 substrateNon-substrate0.8403
CYP450 2D6 substrateNon-substrate0.7533
CYP450 3A4 substrateNon-substrate0.5617
CYP450 1A2 substrateNon-inhibitor0.9046
CYP450 2C9 inhibitorNon-inhibitor0.9071
CYP450 2D6 inhibitorNon-inhibitor0.9231
CYP450 2C19 inhibitorNon-inhibitor0.9025
CYP450 3A4 inhibitorInhibitor0.6898
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.7044
Ames testNon AMES toxic0.8222
CarcinogenicityNon-carcinogens0.9446
BiodegradationNot ready biodegradable1.0
Rat acute toxicity3.0196 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.8093
hERG inhibition (predictor II)Non-inhibitor0.6711
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
MS/MS Spectrum - , positiveLC-MS/MSsplash10-0006-0190000000-49c10e93a1977cbe01da

Taxonomy

Description
This compound belongs to the class of organic compounds known as quinoxalines. These are compounds containing a quinoxaline moiety, a bicyclic heterocycle made up of a benzene ring fused to a pyrazine ring.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Diazanaphthalenes
Sub Class
Benzodiazines
Direct Parent
Quinoxalines
Alternative Parents
Pyrazines / Benzenoids / Aryl bromides / Imidazolines / Heteroaromatic compounds / Guanidines / Propargyl-type 1,3-dipolar organic compounds / Carboximidamides / Azacyclic compounds / Organopnictogen compounds
show 2 more
Substituents
Quinoxaline / Aryl bromide / Aryl halide / Pyrazine / Benzenoid / 2-imidazoline / Heteroaromatic compound / Guanidine / Azacycle / Carboximidamide
show 9 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
imidazoles, quinoxaline derivative, secondary amine (CHEBI:3175)

Targets

Kind
Protein
Organism
Human
Pharmacological action
Yes
Actions
Agonist
General Function
Thioesterase binding
Specific Function
Alpha-2 adrenergic receptors mediate the catecholamine-induced inhibition of adenylate cyclase through the action of G proteins. The rank order of potency for agonists of this receptor is oxymetazo...
Gene Name
ADRA2A
Uniprot ID
P08913
Uniprot Name
Alpha-2A adrenergic receptor
Molecular Weight
48956.275 Da
References
  1. Rauly I, Ailhaud M, Wurch T, Pauwels PJ: alpha(2A)-adrenoceptor: G(alphai1) protein-mediated pertussis toxin-resistant attenuation of G(s) coupling to the cyclic AMP pathway. Biochem Pharmacol. 2000 Jun 15;59(12):1531-8. [PubMed:10799649]
  2. Wikberg-Matsson A, Simonsen U: Potent alpha(2A)-adrenoceptor-mediated vasoconstriction by brimonidine in porcine ciliary arteries. Invest Ophthalmol Vis Sci. 2001 Aug;42(9):2049-55. [PubMed:11481271]
  3. Meana JJ, Barturen F, Garro MA, Garcia-Sevilla JA, Fontan A, Zarranz JJ: Decreased density of presynaptic alpha 2-adrenoceptors in postmortem brains of patients with Alzheimer's disease. J Neurochem. 1992 May;58(5):1896-904. [PubMed:1373179]
  4. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352]
Kind
Protein
Organism
Human
Pharmacological action
Yes
Actions
Agonist
General Function
Epinephrine binding
Specific Function
Alpha-2 adrenergic receptors mediate the catecholamine-induced inhibition of adenylate cyclase through the action of G proteins. The rank order of potency for agonists of this receptor is clonidine...
Gene Name
ADRA2B
Uniprot ID
P18089
Uniprot Name
Alpha-2B adrenergic receptor
Molecular Weight
49565.8 Da
References
  1. Trendelenburg AU, Philipp M, Meyer A, Klebroff W, Hein L, Starke K: All three alpha2-adrenoceptor types serve as autoreceptors in postganglionic sympathetic neurons. Naunyn Schmiedebergs Arch Pharmacol. 2003 Dec;368(6):504-12. Epub 2003 Nov 11. [PubMed:14610637]
  2. Bohmann C, Schollmeyer P, Rump LC: Methoxamine inhibits noradrenaline release through activation of alpha 1- and alpha 2-adrenoceptors in rat isolated kidney: involvement of purines and prostaglandins. Naunyn Schmiedebergs Arch Pharmacol. 1993 Mar;347(3):273-9. [PubMed:8097565]
Kind
Protein
Organism
Human
Pharmacological action
Yes
Actions
Agonist
General Function
Protein homodimerization activity
Specific Function
Alpha-2 adrenergic receptors mediate the catecholamine-induced inhibition of adenylate cyclase through the action of G proteins.
Gene Name
ADRA2C
Uniprot ID
P18825
Uniprot Name
Alpha-2C adrenergic receptor
Molecular Weight
49521.585 Da
References
  1. Trendelenburg AU, Philipp M, Meyer A, Klebroff W, Hein L, Starke K: All three alpha2-adrenoceptor types serve as autoreceptors in postganglionic sympathetic neurons. Naunyn Schmiedebergs Arch Pharmacol. 2003 Dec;368(6):504-12. Epub 2003 Nov 11. [PubMed:14610637]
  2. Orito K, Kishi M, Imaizumi T, Nakazawa T, Hashimoto A, Mori T, Kambe T: alpha(2)-adrenoceptor antagonist properties of OPC-28326, a novel selective peripheral vasodilator. Br J Pharmacol. 2001 Oct;134(4):763-70. [PubMed:11606316]
  3. Zhang W, Ordway GA: The alpha2C-adrenoceptor modulates GABA release in mouse striatum. Brain Res Mol Brain Res. 2003 Apr 10;112(1-2):24-32. [PubMed:12670699]
  4. Prinster SC, Holmqvist TG, Hall RA: Alpha2C-adrenergic receptors exhibit enhanced surface expression and signaling upon association with beta2-adrenergic receptors. J Pharmacol Exp Ther. 2006 Sep;318(3):974-81. Epub 2006 Jun 6. [PubMed:16757535]

Enzymes

Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
General Function
Xanthine dehydrogenase activity
Specific Function
Oxidase with broad substrate specificity, oxidizing aromatic azaheterocycles, such as N1-methylnicotinamide and N-methylphthalazinium, as well as aldehydes, such as benzaldehyde, retinal, pyridoxal...
Gene Name
AOX1
Uniprot ID
Q06278
Uniprot Name
Aldehyde oxidase
Molecular Weight
147916.735 Da
References
  1. Acheampong AA, Chien DS, Lam S, Vekich S, Breau A, Usansky J, Harcourt D, Munk SA, Nguyen H, Garst M, Tang-Liu D: Characterization of brimonidine metabolism with rat, rabbit, dog, monkey and human liver fractions and rabbit liver aldehyde oxidase. Xenobiotica. 1996 Oct;26(10):1035-55. [PubMed:8905918]

Drug created on June 13, 2005 07:24 / Updated on December 10, 2018 13:39