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

Stem definitionDrug idCAS RN
prostaglandins 371 155206-00-1

Description:

MoleculeDescription

Molfile Inchi Smiles

Synonyms:

  • lumigan
  • bimatoprost
  • prostamide
A cloprostenol-derived amide that is used as an ANTIHYPERTENSIVE AGENT in the treatment of OPEN-ANGLE GLAUCOMA and OCULAR HYPERTENSION.
  • Molecular weight: 415.57
  • Formula: C25H37NO4
  • CLOGP: 1.75
  • LIPINSKI: 0
  • HAC: 5
  • HDO: 4
  • TPSA: 89.79
  • ALOGS: -4.35
  • ROTB: 12

  • 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) 0.80 mg/mL Benet LZ, Broccatelli F, Oprea TI
Vd (Volume of distribution) 0.67 L/kg Lombardo F, Berellini G, Obach RS
CL (Clearance) 25 mL/min/kg Lombardo F, Berellini G, Obach RS
fu (Fraction unbound in plasma) 0.12 % Lombardo F, Berellini G, Obach RS
t_half (Half-life) 0.45 hours Lombardo F, Berellini G, Obach RS

Approvals:

DateAgencyCompanyOrphan
March 8, 2002 EMA
March 16, 2001 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 1915.31 17.75 539 13317 19171 46653035
Madarosis 1643.57 17.75 306 13550 1480 46670726
Eye irritation 1561.57 17.75 443 13413 16171 46656035
Erythema of eyelid 1479.85 17.75 282 13574 1579 46670627
Eye pruritus 1285.11 17.75 354 13502 11544 46660662
Eyelids pruritus 915.42 17.75 159 13697 468 46671738
Treatment failure 614.09 17.75 367 13489 92720 46579486
Eyelid irritation 539.13 17.75 94 13762 284 46671922
Eyelid oedema 536.47 17.75 175 13681 10182 46662024
Eye swelling 499.21 17.75 197 13659 19906 46652300
Eye pain 310.87 17.75 156 13700 27784 46644422
Intraocular pressure increased 309.70 17.75 101 13755 5856 46666350
Blepharal pigmentation 225.09 17.75 35 13821 35 46672171
Trichorrhexis 219.23 17.75 53 13803 1005 46671201
Skin hyperpigmentation 216.86 17.75 75 13781 5207 46666999
Dry eye 187.40 17.75 115 13741 30207 46641999
Eye discharge 179.44 17.75 64 13792 4864 46667342
Drug ineffective 178.74 17.75 520 13336 677318 45994888
Lacrimation increased 174.64 17.75 88 13768 15773 46656433
Vision blurred 172.10 17.75 161 13695 79547 46592659
Growth of eyelashes 166.36 17.75 31 13825 149 46672057
Scleral hyperaemia 152.58 17.75 31 13825 250 46671956
Eyelid pain 135.78 17.75 28 13828 245 46671961
Blepharitis 124.94 17.75 40 13816 2181 46670025
Eyelid exfoliation 118.35 17.75 22 13834 104 46672102
Hypersensitivity 117.77 17.75 181 13675 150140 46522066
Inappropriate schedule of product administration 115.33 17.75 118 13738 64895 46607311
Iris hyperpigmentation 115.24 17.75 17 13839 7 46672199
Eyelash discolouration 110.95 17.75 18 13838 29 46672177
Wrong technique in product usage process 107.99 17.75 105 13751 54317 46617889
Foreign body sensation in eyes 106.40 17.75 34 13822 1842 46670364
Eyelid thickening 84.87 17.75 15 13841 50 46672156
Visual acuity reduced 83.91 17.75 62 13794 22051 46650155
Product administered at inappropriate site 83.17 17.75 30 13826 2353 46669853
Corneal endothelial cell loss 82.03 17.75 12 13844 4 46672202
Eye colour change 74.61 17.75 17 13839 246 46671960
Erythema 71.21 17.75 141 13715 142679 46529527
Abnormal sensation in eye 68.97 17.75 24 13832 1694 46670512
Eyelid rash 64.68 17.75 12 13844 56 46672150
Hair growth abnormal 59.66 17.75 24 13832 2534 46669672
Ocular discomfort 59.01 17.75 25 13831 3010 46669196
Glaucoma 58.96 17.75 44 13812 15877 46656329
Skin discolouration 55.51 17.75 58 13798 32622 46639584
Eyelid margin crusting 54.11 17.75 16 13840 667 46671539
Iris disorder 51.37 17.75 10 13846 63 46672143
Skin irritation 51.09 17.75 30 13826 7257 46664949
Eyelid disorder 49.00 17.75 17 13839 1189 46671017
Eyelid skin dryness 47.83 17.75 9 13847 46 46672160
Hordeolum 42.36 17.75 18 13838 2183 46670023
Cataract 40.19 17.75 58 13798 45357 46626849
Eyelash changes 39.67 17.75 6 13850 4 46672202
Eye infection 37.82 17.75 27 13829 9096 46663110
Conjunctival hyperaemia 37.39 17.75 16 13840 1973 46670233
Dark circles under eyes 37.26 17.75 11 13845 456 46671750
Pyrexia 36.56 17.75 30 13826 348772 46323434
Body height decreased 36.46 17.75 27 13829 9625 46662581
Eyelid sensory disorder 36.11 17.75 7 13849 43 46672163
Lid sulcus deepened 36.11 17.75 7 13849 43 46672163
Eye inflammation 35.76 17.75 19 13837 3790 46668416
Periorbital fat atrophy 35.62 17.75 5 13851 0 46672206
Visual impairment 34.57 17.75 67 13789 66622 46605584
Toxicity to various agents 34.57 17.75 10 13846 211756 46460450
Corneal oedema 33.47 17.75 14 13842 1632 46670574
Trichiasis 33.47 17.75 7 13849 66 46672140
Conjunctivitis 32.90 17.75 31 13825 15393 46656813
Product delivery mechanism issue 32.23 17.75 9 13847 305 46671901
Incorrect dose administered 31.63 17.75 52 13804 45498 46626708
Scleral discolouration 30.89 17.75 9 13847 356 46671850
Eye disorder 30.44 17.75 32 13824 18109 46654097
Punctate keratitis 30.41 17.75 10 13846 593 46671613
Application site pain 29.35 17.75 17 13839 4006 46668200
Photophobia 28.69 17.75 28 13828 14516 46657690
Eyelash hyperpigmentation 28.49 17.75 4 13852 0 46672206
Asthenopia 27.94 17.75 13 13843 1953 46670253
Eye allergy 27.57 17.75 9 13847 522 46671684
Joint swelling 26.81 17.75 8 13848 166065 46506141
Application site pruritus 26.76 17.75 16 13840 3997 46668209
Product quality issue 26.52 17.75 42 13814 35606 46636600
Nausea 26.40 17.75 110 13746 687344 45984862
Milia 24.87 17.75 5 13851 38 46672168
Expired product administered 24.14 17.75 17 13839 5605 46666601
Application site discolouration 24.02 17.75 9 13847 785 46671421
Meibomianitis 24.02 17.75 5 13851 46 46672160
Application site erythema 23.82 17.75 16 13840 4888 46667318
Application site irritation 22.70 17.75 11 13845 1808 46670398
Exposure during pregnancy 22.04 17.75 3 13853 108209 46563997
Eyelash thickening 21.68 17.75 4 13852 18 46672188
Enophthalmos 21.68 17.75 4 13852 18 46672188
Choroidal effusion 21.10 17.75 7 13849 427 46671779
Periorbital disorder 21.01 17.75 4 13852 22 46672184
Maternal exposure during pregnancy 20.51 17.75 3 13853 102546 46569660
Swelling of eyelid 20.49 17.75 9 13847 1182 46671024
Ocular hypertension 20.44 17.75 8 13848 786 46671420
Product container issue 19.84 17.75 10 13846 1789 46670417
Pain 19.72 17.75 74 13782 476874 46195332
Vomiting 19.55 17.75 69 13787 452725 46219481
Sepsis 19.46 17.75 8 13848 136006 46536200
Intraocular pressure decreased 19.44 17.75 5 13851 123 46672083
Overdose 18.20 17.75 4 13852 101975 46570231
Intraocular pressure test abnormal 18.18 17.75 5 13851 160 46672046

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
Treatment failure 570.99 17.47 223 5523 34456 29912276
Intraocular pressure increased 382.80 17.47 104 5642 5016 29941716
Ocular hyperaemia 154.64 17.47 60 5686 8983 29937749
Eye irritation 146.31 17.47 51 5695 5645 29941087
Eye pain 89.01 17.47 44 5702 11745 29934987
Visual acuity reduced 76.77 17.47 44 5702 15802 29930930
Glaucoma 66.22 17.47 29 5717 5879 29940853
Enophthalmos 61.80 17.47 9 5737 9 29946723
Growth of eyelashes 56.44 17.47 10 5736 58 29946674
Corneal oedema 50.71 17.47 16 5730 1296 29945436
Corneal endothelial cell loss 49.76 17.47 7 5739 4 29946728
Choroidal detachment 49.71 17.47 12 5734 356 29946376
Conjunctival hyperaemia 49.48 17.47 18 5728 2249 29944483
Vision blurred 47.84 17.47 49 5697 41767 29904965
Eye pruritus 46.37 17.47 20 5726 3907 29942825
Cataract 39.38 17.47 33 5713 21802 29924930
Fat tissue decreased 39.03 17.47 7 5739 44 29946688
Visual field defect 37.81 17.47 18 5728 4418 29942314
Blepharal pigmentation 37.80 17.47 5 5741 0 29946732
Scleral hyperaemia 37.55 17.47 7 5739 56 29946676
Corneal opacity 35.12 17.47 10 5736 569 29946163
Ocular surface disease 35.06 17.47 7 5739 83 29946649
Corneal neovascularisation 31.55 17.47 6 5740 54 29946678
Foreign body sensation in eyes 31.14 17.47 9 5737 540 29946192
Punctate keratitis 30.88 17.47 8 5738 318 29946414
Eyelid irritation 30.54 17.47 6 5740 65 29946667
Lacrimation increased 30.05 17.47 18 5728 6998 29939734
Erythema of eyelid 29.92 17.47 9 5737 621 29946111
Cardioactive drug level increased 28.43 17.47 11 5735 1628 29945104
Instillation site pain 27.46 17.47 6 5740 113 29946619
Blepharitis 25.76 17.47 9 5737 1000 29945732
Visual impairment 24.99 17.47 30 5716 30408 29916324
Corneal disorder 23.65 17.47 8 5738 806 29945926
Corneal infiltrates 23.52 17.47 6 5740 224 29946508
Keratitis interstitial 23.42 17.47 4 5742 18 29946714
Uveitis 23.32 17.47 14 5732 5463 29941269
Open angle glaucoma 23.32 17.47 6 5740 232 29946500
Corneal erosion 22.74 17.47 5 5741 97 29946635
Intraocular pressure decreased 22.01 17.47 5 5741 113 29946619
Computerised tomogram head abnormal 21.57 17.47 4 5742 31 29946701
Eye swelling 21.43 17.47 16 5730 8948 29937784
Hypotony of eye 21.34 17.47 5 5741 130 29946602
Eye disorder 21.20 17.47 15 5731 7719 29939013
Dry eye 21.18 17.47 14 5732 6454 29940278
Hypersensitivity 20.51 17.47 37 5709 53991 29892741
Corneal pigmentation 20.14 17.47 3 5743 4 29946728
Visual acuity tests abnormal 19.42 17.47 4 5742 56 29946676
Aortic stenosis 18.94 17.47 11 5735 4037 29942695
Lid sulcus deepened 18.53 17.47 4 5742 71 29946661
Eyelids pruritus 18.03 17.47 4 5742 81 29946651
Blood pressure systolic increased 17.79 17.47 18 5728 15092 29931640

Pharmacologic Action:

SourceCodeDescription
ATC S01EE03 SENSORY ORGANS
OPHTHALMOLOGICALS
ANTIGLAUCOMA PREPARATIONS AND MIOTICS
Prostaglandin analogues
FDA CS M0017805 Prostaglandins
FDA EPC N0000175454 Prostaglandin Analog
MeSH PA D000959 Antihypertensive Agents
MeSH PA D002317 Cardiovascular Agents
CHEBI has role CHEBI:35674 antihypertensive
CHEBI has role CHEBI:39456 antiglaucoma agent

Drug Use (View source of the data)

DiseaseRelationSNOMED_IDDOID
Ocular hypertension indication 4210003 DOID:9282
Hypertrichosis of eyelid indication 79830009 DOID:11669
Open-angle glaucoma indication 84494001 DOID:1067
Aphakia contraindication 24010005
Macular retinal edema contraindication 37231002 DOID:4449
Iritis contraindication 65074000 DOID:1406
Pseudophakia contraindication 95217000
Uveitis contraindication 128473001 DOID:13141
Liver function tests abnormal contraindication 166603001
Cystoid macular edema contraindication 193387007 DOID:4447
Disease of liver contraindication 235856003 DOID:409

Acid dissociation constants calculated using MoKa v3.0.0

Dissociation levelDissociation constantType (acidic/basic)
pKa1 13.89 acidic

Orange Book patent data (new drug applications)

None

Orange Book exclusivity data (new drug applications)

Formulation strengthTrade nameApplicantApplication numberApproval dateTypeDose formRouteExclusivity dateDescription
10MCG DURYSTA ALLERGAN INC N211911 March 4, 2020 RX IMPLANT OPHTHALMIC March 4, 2023 NEW PRODUCT

Bioactivity Summary:

TargetClassPharosUniProtActionTypeActivity value
(-log[M])
Mechanism
action
Bioact sourceMoA source
Prostaglandin F2-alpha receptor GPCR AGONIST Ki 5.30 WOMBAT-PK CHEMBL

External reference:

IDSource
QXS94885MZ UNII
D02724 KEGG_DRUG
4021262 VANDF
C0937917 UMLSCUI
CHEBI:51230 CHEBI
15M PDB_CHEM_ID
CHEMBL1200963 ChEMBL_ID
DB00905 DRUGBANK_ID
D000069580 MESH_DESCRIPTOR_UI
8035 INN_ID
5311027 PUBCHEM_CID
1958 IUPHAR_LIGAND_ID
283810 RXNORM
15937 MMSL
234008 MMSL
41256 MMSL
009115 NDDF
129492005 SNOMEDCT_US
395300006 SNOMEDCT_US

Pharmaceutical products:

ProductCategoryIngredientsNDCFormQuantityRouteMarketingLabel
LUMIGAN HUMAN PRESCRIPTION DRUG LABEL 1 0023-3205 SOLUTION/ DROPS 0.10 mg OPHTHALMIC NDA 25 sections
LATISSE HUMAN PRESCRIPTION DRUG LABEL 1 0023-3616 SOLUTION/ DROPS 0.30 mg OPHTHALMIC NDA 25 sections
LUMIGAN HUMAN PRESCRIPTION DRUG LABEL 1 0023-9187 SOLUTION/ DROPS 0.30 mg OPHTHALMIC EXPORT ONLY 1 sections
DURYSTA HUMAN PRESCRIPTION DRUG LABEL 1 0023-9652 IMPLANT 10 ug INTRACAMERAL NDA 23 sections
Bimatoprost HUMAN PRESCRIPTION DRUG LABEL 1 0781-6206 SOLUTION/ DROPS 0.30 mg OPHTHALMIC ANDA 23 sections
BIMATOPROST HUMAN PRESCRIPTION DRUG LABEL 1 42571-128 SOLUTION/ DROPS 0.30 mg OPHTHALMIC ANDA 22 sections
Bimatoprost HUMAN PRESCRIPTION DRUG LABEL 1 50383-908 SOLUTION/ DROPS 0.30 mg OPHTHALMIC ANDA 23 sections
Bimatoprost HUMAN PRESCRIPTION DRUG LABEL 1 50383-912 SOLUTION 3 ug TOPICAL ANDA 22 sections
LUMIGAN HUMAN PRESCRIPTION DRUG LABEL 1 54868-4575 SOLUTION/ DROPS 0.30 mg OPHTHALMIC NDA 25 sections
LUMIGAN HUMAN PRESCRIPTION DRUG LABEL 1 54868-6304 SOLUTION/ DROPS 0.10 mg OPHTHALMIC NDA 25 sections
bimatoprost HUMAN PRESCRIPTION DRUG LABEL 1 57297-429 SOLUTION/ DROPS 0.30 mg OPHTHALMIC ANDA 23 sections
Bimatoprost HUMAN PRESCRIPTION DRUG LABEL 1 60505-0583 SOLUTION/ DROPS 0.30 mg OPHTHALMIC ANDA 24 sections
Bimatoprost Human Prescription Drug Label 1 62332-507 SOLUTION/ DROPS 0.30 mg OPHTHALMIC ANDA 24 sections
bimatoprost Human Prescription Drug Label 1 62332-511 SOLUTION/ DROPS 0.30 mg OPHTHALMIC ANDA 22 sections
Bimatoprost Human Prescription Drug Label 1 68083-295 SOLUTION/ DROPS 0.30 mg OPHTHALMIC ANDA 23 sections
Bimatoprost Human Prescription Drug Label 1 68083-296 SOLUTION/ DROPS 0.30 mg OPHTHALMIC ANDA 23 sections
bimatoprost HUMAN PRESCRIPTION DRUG LABEL 1 68180-429 SOLUTION/ DROPS 0.30 mg OPHTHALMIC ANDA 21 sections
Bimatoprost HUMAN PRESCRIPTION DRUG LABEL 1 70069-401 SOLUTION/ DROPS 0.30 mg OPHTHALMIC ANDA 23 sections
Bimatoprost HUMAN PRESCRIPTION DRUG LABEL 1 70069-402 SOLUTION/ DROPS 0.30 mg OPHTHALMIC ANDA 23 sections
Bimatoprost HUMAN PRESCRIPTION DRUG LABEL 1 70069-403 SOLUTION/ DROPS 0.30 mg OPHTHALMIC ANDA 23 sections
Bimatoprost HUMAN PRESCRIPTION DRUG LABEL 1 72266-139 SOLUTION/ DROPS 0.30 mg OPHTHALMIC ANDA 23 sections
Bimatoprost HUMAN PRESCRIPTION DRUG LABEL 1 72266-140 SOLUTION/ DROPS 0.30 mg OPHTHALMIC ANDA 23 sections