brimonidine Indications/Contra | FAERs-F | FAERs-M | Orange Bk | BioActivity |

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

  • Status: OFP

  • Legend:
    OFP - off patent
    OFM - off market
    ONP - on patent

Drug dosage:

None

ADMET properties:

PropertyValueReference
BDDCS (Biopharmaceutical Drug Disposition Classification System) 1 Benet LZ, Broccatelli F, Oprea TI
S (Water solubility) 1.50 mg/mL Benet LZ, Broccatelli F, Oprea TI
EoM (Fraction excreted unchanged in urine) 10 % Benet LZ, Broccatelli F, Oprea TI
MRTD (Maximum Recommended Therapeutic Daily Dose) 0.01 ┬ÁM/kg/day Contrera JF, Matthews EJ, Kruhlak NL, Benz RD

Approvals:

DateAgencyCompanyOrphan
Sept. 6, 1996 FDA

FDA Adverse Event Reporting System (Female)

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 622.15 55.45 119 933 3937 2353096
Eye irritation 575.43 55.45 109 943 3403 2353630
Intraocular pressure increased 574.98 55.45 96 956 1413 2355620
Eye pain 341.91 55.45 75 977 4816 2352217
Inappropriate schedule of product administration 273.76 55.45 75 977 12129 2344904
Erythema 240.18 55.45 80 972 25079 2331954
Vision blurred 220.27 55.45 66 986 14602 2342431
Eye pruritus 205.42 55.45 44 1008 2487 2354546
Drug ineffective 205.22 55.45 106 946 101518 2255515
Glaucoma 156.24 55.45 34 1018 2061 2354972
Rebound effect 135.95 55.45 25 1027 634 2356399
Dry mouth 118.53 55.45 36 1016 8217 2348816
Erythema of eyelid 110.38 55.45 21 1031 642 2356391
Conjunctivitis 108.99 55.45 26 1026 2367 2354666
Scleral hyperaemia 106.77 55.45 16 1036 106 2356927
Hypersensitivity 101.58 55.45 42 1010 23551 2333482
Foreign body sensation in eyes 99.18 55.45 18 1034 422 2356611
Skin burning sensation 98.19 55.45 23 1029 1933 2355100
Uveitis 91.87 55.45 21 1031 1584 2355449
Dizziness 91.47 55.45 52 1000 58613 2298420
Dry eye 91.34 55.45 25 1027 3931 2353102
Eye allergy 90.65 55.45 14 1038 116 2356917
Visual impairment 86.67 55.45 31 1021 11724 2345309
Product dropper issue 84.25 55.45 13 1039 107 2356926
Eye swelling 84.23 55.45 24 1028 4366 2352667
Visual acuity reduced 79.78 55.45 24 1028 5274 2351759
Corneal oedema 76.72 55.45 14 1038 338 2356695
Ocular surface disease 72.07 55.45 9 1043 9 2357024
Drug hypersensitivity 71.61 55.45 41 1011 46602 2310431
Flushing 71.54 55.45 27 1025 11844 2345189
Condition aggravated 71.18 55.45 36 1016 31943 2325090
Rosacea 71.11 55.45 14 1038 512 2356521
Somnolence 69.03 55.45 32 1020 23453 2333580
Lacrimation increased 65.82 55.45 18 1034 2812 2354221
Iris adhesions 64.50 55.45 10 1042 85 2356948
Eye discharge 63.26 55.45 14 1038 909 2356124
Product quality issue 62.95 55.45 24 1028 10805 2346228
Cataract 60.71 55.45 20 1032 5888 2351145
Conjunctival hyperaemia 57.46 55.45 12 1040 591 2356442
Pain of skin 56.98 55.45 14 1038 1434 2355599
Eyelid irritation 56.53 55.45 10 1042 201 2356832

FDA Adverse Event Reporting System (Male)

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
Intraocular pressure increased 508.09 75.02 84 598 1097 1745002
Ocular hyperaemia 359.98 75.02 68 614 1942 1744157
Eye irritation 311.68 75.02 57 625 1346 1744753
Vision blurred 177.40 75.02 50 632 8373 1737726
Eye pruritus 159.21 75.02 30 652 820 1745279
Eye pain 156.04 75.02 35 647 2296 1743803
Corneal oedema 137.36 75.02 23 659 310 1745789
Ocular surface disease 128.71 75.02 16 666 13 1746086
Visual acuity reduced 123.47 75.02 32 650 3856 1742243
Foreign body sensation in eyes 121.15 75.02 19 663 164 1745935
Drug ineffective 114.34 75.02 63 619 63738 1682361
Uveitis 105.15 75.02 22 660 1029 1745070
Conjunctivitis 90.22 75.02 21 661 1608 1744491
Blepharitis 88.50 75.02 15 667 217 1745882
Open angle glaucoma 80.57 75.02 12 670 70 1746029
Hypotony of eye 76.70 75.02 11 671 47 1746052
Erythema 75.60 75.02 30 652 14158 1731941

Pharmacologic Action:

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)

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
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
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

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

Orange Book patent data (new drug applications)

Formulation strengthTrade nameApplicantApplication numberApproval dateTypeDose formRoutePatent numberPatent expiration datePatent use
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)

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:

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:

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

Pharmaceutical products:

ProductCategoryIngredientsNDCFormQuantityRouteMarketingLabel
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 18 sections
Brimonidine Tartrate HUMAN PRESCRIPTION DRUG LABEL 1 14445-400 SOLUTION/ DROPS 2 mg OPHTHALMIC ANDA 16 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 16 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 50090-4224 SOLUTION 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 HUMAN PRESCRIPTION DRUG LABEL 1 70069-231 SOLUTION/ DROPS 2 mg OPHTHALMIC ANDA 16 sections
BRIMONIDINE TARTRATE HUMAN PRESCRIPTION DRUG LABEL 1 70069-232 SOLUTION/ DROPS 2 mg OPHTHALMIC ANDA 16 sections
BRIMONIDINE TARTRATE HUMAN PRESCRIPTION DRUG LABEL 1 70069-233 SOLUTION/ DROPS 2 mg OPHTHALMIC ANDA 16 sections
Brim-Dor PF HUMAN PRESCRIPTION DRUG LABEL 2 70261-518 SOLUTION/ DROPS 1.50 mg OPHTHALMIC unapproved drug other 2 sections
Tim-Brim-Dor PF HUMAN PRESCRIPTION DRUG LABEL 3 70261-520 SOLUTION/ DROPS 1.50 mg OPHTHALMIC unapproved drug other 2 sections
Tim-Brim-Dor-Lat HUMAN PRESCRIPTION DRUG LABEL 4 70261-522 SOLUTION/ DROPS 1.50 mg OPHTHALMIC unapproved drug other 2 sections
BRIMONIDINE TARTRATE 0.25% / POTASSIUM AZELOYL DIGLYCINATE 8% HUMAN PRESCRIPTION DRUG LABEL 1 72934-1027 GEL 0.25 g TOPICAL unapproved drug other 4 sections
BRIMONIDINE TARTRATE 0.25% / IVERMECTIN 1% / METRONIDAZOLE 1% / NIACINAMIDE 4% HUMAN PRESCRIPTION DRUG LABEL 4 72934-1028 GEL 0.25 g TOPICAL unapproved drug other 4 sections