brimonidine indications/contra

Stem definitionDrug idCAS RN
antihypertensives, clonidine derivatives 395 59803-98-4

Description:

MoleculeDescription

Molfile Inchi Smiles

Synonyms:

  • UK 14,304
  • mirvaso
  • brimonidine
  • brimonidine tartrate
  • bromoxidine
A quinoxaline derivative and ADRENERGIC ALHPA-2 RECEPTOR AGONIST that is used to manage INTRAOCULAR PRESSURE associated with OPEN-ANGLE GLAUCOMA and OCULAR HYPERTENSION.
  • Molecular weight: 292.14
  • Formula: C11H10BrN5
  • CLOGP: 1.49
  • LIPINSKI: 0
  • HAC: 5
  • HDO: 2
  • TPSA: 62.20
  • ALOGS: -3.28
  • ROTB: 1

Drug dosage:

None

Approvals:

DateAgencyCompanyOrphan
Sept. 6, 1996 FDA

FDA Adverse Event Reporting System

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MedDRA adverse event termLikelihood ratioLikelihood ratio thresholdPatients taking drug having adverse eventPatients taking drug not having adverse eventPatients not taking drug having adverse eventPatients not taking drug not having adverse event
Ocular hyperaemia 895.43 57.65 170 1341 4983 3379365
Eye irritation 839.41 57.65 156 1355 4043 3380305
Intraocular pressure increased 732.53 57.65 128 1383 2294 3382054
Eye pain 422.08 57.65 94 1417 5953 3378395
Inappropriate schedule of drug administration 364.20 57.65 98 1413 13655 3370693
Erythema 341.44 57.65 110 1401 28700 3355648
Vision blurred 334.29 57.65 99 1412 19490 3364858
Eye pruritus 332.19 57.65 67 1444 2604 3381744
Foreign body sensation in eyes 224.26 57.65 38 1473 545 3383803
Visual acuity reduced 213.52 57.65 59 1452 8955 3375393
Drug ineffective 212.86 57.65 117 1394 115973 3268375
Erythema of eyelid 176.02 57.65 32 1479 700 3383648
Corneal oedema 175.37 57.65 31 1480 575 3383773
Conjunctivitis 169.88 57.65 39 1472 2779 3381569
Lacrimation increased 168.16 57.65 40 1471 3328 3381020
Scleral hyperaemia 157.90 57.65 24 1487 162 3384186
Eye swelling 151.55 57.65 40 1471 5077 3379271
Iridocyclitis 146.24 57.65 27 1484 644 3383704
Dizziness 144.61 57.65 79 1432 76433 3307915
Rebound effect 138.11 57.65 25 1486 532 3383816
Dry mouth 134.10 57.65 42 1469 9780 3374568
Glaucoma 129.70 57.65 31 1480 2625 3381723
Eye discharge 128.31 57.65 26 1485 1020 3383328
Uveitis 127.38 57.65 29 1482 1984 3382364
Hypersensitivity 120.67 57.65 51 1460 27849 3356499
Conjunctivitis allergic 117.09 57.65 19 1492 204 3384144
Dry eye 112.76 57.65 30 1481 3912 3380436
Rosacea 111.02 57.65 21 1490 572 3383776
Somnolence 107.27 57.65 49 1462 32155 3352193
Condition aggravated 98.05 57.65 49 1462 39184 3345164

Pharmacologic Action:

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SourceCodeDescription
ATC D11AX21 DERMATOLOGICALS
OTHER DERMATOLOGICAL PREPARATIONS
OTHER DERMATOLOGICAL PREPARATIONS
Other dermatologicals
ATC S01EA05 SENSORY ORGANS
OPHTHALMOLOGICALS
ANTIGLAUCOMA PREPARATIONS AND MIOTICS
Sympathomimetics in glaucoma therapy1)
MeSH PA D018663 Adrenergic Agents
MeSH PA D000322 Adrenergic Agonists
MeSH PA D058647 Adrenergic alpha-2 Receptor Agonists
MeSH PA D000316 Adrenergic alpha-Agonists
CHEBI has role CHEBI:37886 adrenergic agonist
CHEBI has role CHEBI:35674 antihypertensive agent
CHEBI has role CHEBI:35569 alpha-adrenergic agonist
MeSH PA D000959 Antihypertensive Agents
MeSH PA D002317 Cardiovascular Agents
MeSH PA D018377 Neurotransmitter Agents

Drug Use (View source of the data)

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DiseaseRelationSNOMED_IDDOID
Ocular hypertension indication 4210003 DOID:9282
Open-angle glaucoma indication 84494001 DOID:1067
Rosacea indication 398909004 DOID:8881
Bronchospasm contraindication 4386001
Complete atrioventricular block contraindication 27885002
Orthostatic hypotension contraindication 28651003
Acute cerebrovascular insufficiency contraindication 29322000
Hyperthyroidism contraindication 34486009 DOID:7998
Depressive disorder contraindication 35489007 DOID:2848
Anaphylaxis contraindication 39579001
Sinus bradycardia contraindication 49710005
General anesthesia contraindication 50697003
Thromboangiitis obliterans contraindication 52403007 DOID:12918
Cerebrovascular disease contraindication 62914000 DOID:6713
Diabetes mellitus contraindication 73211009 DOID:9351
Pulmonary emphysema contraindication 87433001
Cardiogenic shock contraindication 89138009
Myasthenia gravis contraindication 91637004 DOID:437
Acute disease of cardiovascular system contraindication 128487001
Partial atrioventricular block contraindication 195039008
Decompensated cardiac failure contraindication 195111005
Hypoglycemic disorder contraindication 237630007 DOID:9993
Raynaud's phenomenon contraindication 266261006
Pregnancy, function contraindication 289908002
Severe chronic obstructive pulmonary disease contraindication 313299006

Acid dissociation constants calculated using MoKa v3.0.0

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Dissociation levelDissociation constantType (acidic/basic)
pKa1 7.64 Basic
pKa2 1.82 Basic

Orange Book patent data (new drug applications)

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Formulation strengthTrade nameApplicantApplication numberApproval dateTypeDose formRoutePatent numberPatent expiration datePatent use
0.2% SIMBRINZA NOVARTIS PHARMS CORP N204251 April 19, 2013 RX SUSPENSION/DROPS OPHTHALMIC 6316441 Dec. 7, 2019 REDUCTION OF ELEVATED INTRAOCULAR PRESSURE IN PATIENTS WITH OPEN ANGLE GLAUCOMA OR OCULAR HYPERTENSION
0.15% ALPHAGAN P ALLERGAN N021262 March 16, 2001 RX SOLUTION/DROPS OPHTHALMIC 9295641 July 10, 2021 REDUCTION OF ELEVATED INTRAOCULAR PRESSURE IN PATIENTS WITH OPEN ANGLE GLAUCOMA OR OCULAR HYPERTENSION
0.1% ALPHAGAN P ALLERGAN N021770 Aug. 19, 2005 RX SOLUTION/DROPS OPHTHALMIC 9295641 July 10, 2021 REDUCTION OF ELEVATED INTRAOCULAR PRESSURE IN PATIENTS WITH OPEN ANGLE GLAUCOMA OR OCULAR HYPERTENSION
0.2% COMBIGAN ALLERGAN N021398 Oct. 30, 2007 RX SOLUTION/DROPS OPHTHALMIC 7030149 April 19, 2022 REDUCTION OF ELEVATED INTRAOCULAR PRESSURE (IOP) IN PATIENTS WITH GLAUCOMA OR OCULAR HYPERTENSION WHO REQUIRE ADJUNCTIVE OR REPLACEMENT THERAPY DUE TO INADEQUATELY CONTROLLED IOP. DOSE IS ONE DROP OF COMBIGAN IN THE AFFECTED EYE TWICE DAILY
0.2% COMBIGAN ALLERGAN N021398 Oct. 30, 2007 RX SOLUTION/DROPS OPHTHALMIC 7320976 April 19, 2022 REDUCTION OF ELEVATED INTRAOCULAR PRESSURE (IOP) IN PATIENTS WITH GLAUCOMA OR OCULAR HYPERTENSION WHO REQUIRE ADJUNCTIVE OR REPLACEMENT THERAPY DUE TO INADEQUATELY CONTROLLED IOP. DOSE IS ONE DROP OF COMBIGAN IN THE AFFECTED EYE TWICE DAILY
0.2% COMBIGAN ALLERGAN N021398 Oct. 30, 2007 RX SOLUTION/DROPS OPHTHALMIC 7642258 April 19, 2022 REDUCTION OF ELEVATED INTRAOCULAR PRESSURE IN PATIENTS WITH GLAUCOMA OR OCULAR HYPERTENSION WHO REQUIRE ADJUNCTIVE OR REPLACEMENT THERAPY DUE TO INADEQUATELY CONTROLLED IOP
0.2% COMBIGAN ALLERGAN N021398 Oct. 30, 2007 RX SOLUTION/DROPS OPHTHALMIC 8133890 April 19, 2022 REDUCTION OF ELEVATED INTRAOCULAR PRESSURE IN PATIENTS WITH GLAUCOMA OR OCULAR HYPERTENSION
0.2% COMBIGAN ALLERGAN N021398 Oct. 30, 2007 RX SOLUTION/DROPS OPHTHALMIC 8354409 April 19, 2022 REDUCTION OF INTRAOCULAR PRESSURE IN PATIENTS WITH ELEVATED INTRAOCULAR PRESSURE OR GLAUCOMA
0.2% COMBIGAN ALLERGAN N021398 Oct. 30, 2007 RX SOLUTION/DROPS OPHTHALMIC 8748425 April 19, 2022 REDUCTION OF ELEVATED INTRAOCULAR PRESSURE
0.2% COMBIGAN ALLERGAN N021398 Oct. 30, 2007 RX SOLUTION/DROPS OPHTHALMIC 9474751 April 19, 2022 REDUCTION OF ELEVATED INTRAOCULAR PRESSURE
0.2% COMBIGAN ALLERGAN N021398 Oct. 30, 2007 RX SOLUTION/DROPS OPHTHALMIC 9770453 April 19, 2022 REDUCTION OF ELEVATED INTRAOCULAR PRESSURE (IOP) IN PATIENTS WITH GLAUCOMA OR OCULAR HYPERTENSION, WITH COMPARABLE EFFICACY, AND A REDUCTION IN SPECIFIED ADVERSE EVENTS, COMPARED TO BRIMONIDINE 0.2% TID
0.2% COMBIGAN ALLERGAN N021398 Oct. 30, 2007 RX SOLUTION/DROPS OPHTHALMIC 9907801 April 19, 2022 REDUCTION OF ELEVATED INTRAOCULAR PRESSURE (IOP) IN PATIENTS WITH GLAUCOMA OR OCULAR HYPERTENSION, WITH A REDUCTION IN SPECIFIED ADVERSE EVENTS, COMPARED TO BRIMONIDINE 0.2% TID
0.2% COMBIGAN ALLERGAN N021398 Oct. 30, 2007 RX SOLUTION/DROPS OPHTHALMIC 9907802 April 19, 2022 REDUCTION OF ELEVATED INTRAOCULAR PRESSURE (IOP) IN PATIENTS WITH GLAUCOMA OR OCULAR HYPERTENSION, WITH COMPARABLE EFFICACY TO BRIMONIDINE 0.2% TID
EQ 0.33% BASE MIRVASO GALDERMA LABS LP N204708 Aug. 23, 2013 RX GEL TOPICAL 8859551 May 25, 2024 TOPICAL TREATMENT OF FACIAL ERYTHEMA OF ROSACEA
EQ 0.33% BASE MIRVASO GALDERMA LABS LP N204708 Aug. 23, 2013 RX GEL TOPICAL 8410102 May 24, 2025 TOPICAL TREATMENT OF FACIAL ERYTHEMA OF ROSACEA
EQ 0.33% BASE MIRVASO GALDERMA LABS LP N204708 Aug. 23, 2013 RX GEL TOPICAL 8426410 May 24, 2025 TOPICAL TREATMENT OF FACIAL ERYTHEMA OF ROSACEA
EQ 0.33% BASE MIRVASO GALDERMA LABS LP N204708 Aug. 23, 2013 RX GEL TOPICAL 7439241 Aug. 25, 2025 TOPICAL TREATMENT OF FACIAL ERYTHEMA OF ROSACEA
0.025% LUMIFY BAUSCH AND LOMB INC N208144 Dec. 22, 2017 OTC SOLUTION/DROPS OPHTHALMIC 8293742 July 14, 2030 RELIEVES REDNESS OF THE EYE DUE TO MINOR EYE IRRITATIONS
EQ 0.33% BASE MIRVASO GALDERMA LABS LP N204708 Aug. 23, 2013 RX GEL TOPICAL 8513247 March 25, 2031 TOPICAL TREATMENT OF FACIAL ERYTHEMA OF ROSACEA
EQ 0.33% BASE MIRVASO GALDERMA LABS LP N204708 Aug. 23, 2013 RX GEL TOPICAL 8513249 March 25, 2031 TOPICAL TREATMENT OF FACIAL ERYTHEMA OF ROSACEA
EQ 0.33% BASE MIRVASO GALDERMA LABS LP N204708 Aug. 23, 2013 RX GEL TOPICAL 9861631 March 25, 2031 TOPICAL TREATMENT OF FACIAL ERYTHEMA OF ROSACEA
EQ 0.33% BASE MIRVASO GALDERMA LABS LP N204708 Aug. 23, 2013 RX GEL TOPICAL 9861632 March 25, 2031 TOPICAL TREATMENT OF FACIAL ERYTHEMA OF ROSACEA
EQ 0.33% BASE MIRVASO GALDERMA LABS LP N204708 Aug. 23, 2013 RX GEL TOPICAL 8053427 June 13, 2031 TOPICAL TREATMENT OF FACIAL ERYTHEMA OF ROSACEA

Orange Book exclusivity data (new drug applications)

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Formulation strengthTrade nameApplicantApplication numberApproval dateTypeDose formRouteExclusivity dateDescription
0.025% LUMIFY BAUSCH AND LOMB INC N208144 Dec. 22, 2017 OTC SOLUTION/DROPS OPHTHALMIC Dec. 22, 2020 NEW PRODUCT

Bioactivity Summary:

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TargetClassPharosUniProtActionTypeActivity value
(-log[M])
Mechanism
action
Bioact sourceMoA source
Alpha-2B adrenergic receptor GPCR AGONIST EC50 7.26 WOMBAT-PK CHEMBL
Alpha-2A adrenergic receptor GPCR AGONIST EC50 8.39 WOMBAT-PK CHEMBL
Alpha-2C adrenergic receptor GPCR AGONIST EC50 8.47 WOMBAT-PK CHEMBL
Alpha-1A adrenergic receptor GPCR Ki 5.55 CHEMBL
Alpha-1B adrenergic receptor GPCR Ki 5.27 CHEMBL
5-hydroxytryptamine receptor 1A GPCR Ki 5.84 DRUG MATRIX
Alpha-1D adrenergic receptor GPCR Ki 6.07 DRUG MATRIX
Adrenergic receptor alpha-2 GPCR Ki 7.52 CHEMBL
Alpha-2B adrenergic receptor GPCR Ki 7.28 CHEMBL
Adrenergic receptor alpha-1 GPCR Ki 6.13 CHEMBL
5-hydroxytryptamine receptor 1A GPCR IC50 5.59 CHEMBL

External reference:

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IDSource
DB00484 DRUGBANK_ID
520 IUPHAR_LIGAND_ID
C3666439 UMLSCUI
D02076 KEGG_DRUG
4S9CL2DY2H UNII
70359-46-5 SECONDARY_CAS_RN
CHEMBL844 ChEMBL_ID
2435 PUBCHEM_CID
4024043 VANDF
N0000006121 NDFRT
N0000022048 NDFRT
006196 NDDF
4297 MMSL
134615 RXNORM
108827001 SNOMEDCT_US
46686 MMSL
372547000 SNOMEDCT_US
CHEBI:3175 CHEBI
6863 INN_ID
CHEMBL2062257 ChEMBL_ID
D000068438 MESH_DESCRIPTOR_UI

Pharmaceutical products:

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ProductCategoryIngredientsNDCFormQuantityRoute MarketingLabel
ALPHAGAN P HUMAN PRESCRIPTION DRUG LABEL 1 0023-9177 SOLUTION/ DROPS 1.50 mg OPHTHALMIC NDA 16 sections
COMBIGAN HUMAN PRESCRIPTION DRUG LABEL 2 0023-9211 SOLUTION/ DROPS 2 mg OPHTHALMIC NDA 17 sections
ALPHAGAN P HUMAN PRESCRIPTION DRUG LABEL 1 0023-9321 SOLUTION/ DROPS 1 mg OPHTHALMIC NDA 16 sections
SIMBRINZA HUMAN PRESCRIPTION DRUG LABEL 2 0065-4147 SUSPENSION/ DROPS 2 mg OPHTHALMIC NDA 16 sections
Mirvaso HUMAN PRESCRIPTION DRUG LABEL 1 0299-5980 GEL 5 mg TOPICAL NDA 19 sections
BRIMONIDINE TARTRATE HUMAN PRESCRIPTION DRUG LABEL 1 16590-883 SOLUTION/ DROPS 2 mg OPHTHALMIC ANDA 11 sections
Brimonidine HUMAN PRESCRIPTION DRUG LABEL 1 17478-715 SOLUTION/ DROPS 2 mg OPHTHALMIC ANDA 16 sections
Brimonidine Tartrate HUMAN PRESCRIPTION DRUG LABEL 1 24208-411 SOLUTION/ DROPS 2 mg OPHTHALMIC ANDA 12 sections
LUMIFY Redness Reliever Eye Drops HUMAN OTC DRUG LABEL 1 24208-537 SOLUTION/ DROPS 0.25 mg OPHTHALMIC NDA 9 sections
Brimonidine Tartrate HUMAN PRESCRIPTION DRUG LABEL 1 25685-715 SOLUTION/ DROPS 2 mg OPHTHALMIC ANDA 13 sections
Brimonidine Tartrate HUMAN PRESCRIPTION DRUG LABEL 1 42843-501 SOLUTION/ DROPS 2 mg OPHTHALMIC ANDA 10 sections
Brimonidine Tartrate HUMAN PRESCRIPTION DRUG LABEL 1 50090-1800 SOLUTION/ DROPS 2 mg OPHTHALMIC ANDA 12 sections
ALPHAGAN P HUMAN PRESCRIPTION DRUG LABEL 1 54868-4276 SOLUTION/ DROPS 1 mg OPHTHALMIC NDA 16 sections
ALPHAGAN P HUMAN PRESCRIPTION DRUG LABEL 1 54868-4690 SOLUTION/ DROPS 1.50 mg OPHTHALMIC NDA 16 sections
Brimonidine Tartrate HUMAN PRESCRIPTION DRUG LABEL 1 54868-6094 SOLUTION 1.50 mg OPHTHALMIC NDA 10 sections
Brimonidine Tartrate HUMAN PRESCRIPTION DRUG LABEL 1 54868-6287 SOLUTION/ DROPS 2 mg OPHTHALMIC ANDA 12 sections
COMBIGAN HUMAN PRESCRIPTION DRUG LABEL 2 54868-6295 SOLUTION/ DROPS 2 mg OPHTHALMIC NDA 16 sections
Brimonidine Tartrate HUMAN PRESCRIPTION DRUG LABEL 1 61314-143 SOLUTION 2 mg OPHTHALMIC ANDA 11 sections
Brimonidine Tartrate HUMAN PRESCRIPTION DRUG LABEL 1 61314-144 SOLUTION 1.50 mg OPHTHALMIC NDA 16 sections
Brimonidine Tartrate Ophthalmic Solution, 0.2% HUMAN PRESCRIPTION DRUG LABEL 1 69367-109 SOLUTION/ DROPS 2 mg OPHTHALMIC ANDA 13 sections