bimatoprost indications/contra

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

Drug dosage:

None

Approvals:

DateAgencyCompanyOrphan
March 8, 2002 EMA
March 16, 2001 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 2431.63 98.13 428 2159 4725 3378547
Eye irritation 1943.48 98.13 344 2243 3855 3379417
Madarosis 1800.64 98.13 249 2338 363 3382909
Erythema of eyelid 1643.06 98.13 235 2352 497 3382775
Eye pruritus 1633.22 98.13 278 2309 2393 3380879
Eyelids pruritus 945.62 98.13 132 2455 207 3383065
Eyelid oedema 832.53 98.13 164 2423 3261 3380011
Drug ineffective 715.57 98.13 315 2272 115775 3267497
Eye swelling 665.26 98.13 146 2441 4971 3378301
Eyelid irritation 497.47 98.13 70 2517 118 3383154
Intraocular pressure increased 432.79 98.13 90 2497 2332 3380940
Skin hyperpigmentation 411.15 98.13 77 2510 1137 3382135
Eye pain 375.52 98.13 95 2492 5952 3377320
Dry eye 341.57 98.13 81 2506 3861 3379411
Trichorrhexis 311.10 98.13 48 2539 192 3383080
Lacrimation increased 295.83 98.13 70 2517 3298 3379974
Eye discharge 264.76 98.13 52 2535 994 3382278
Inappropriate schedule of drug administration 233.51 98.13 79 2508 13674 3369598
Vision blurred 231.71 98.13 86 2501 19503 3363769
Growth of eyelashes 226.27 98.13 33 2554 80 3383192
Erythema 219.55 98.13 92 2495 28718 3354554
Wrong technique in product usage process 195.98 98.13 73 2514 16678 3366594
Blepharal pigmentation 182.43 98.13 25 2562 30 3383242
Scleral hyperaemia 180.63 98.13 29 2558 157 3383115
Hypersensitivity 169.52 98.13 76 2511 27824 3355448
Blepharitis 149.28 98.13 29 2558 520 3382752
Eyelid pain 139.32 98.13 22 2565 105 3383167
Skin discolouration 131.89 98.13 43 2544 6593 3376679
Foreign body sensation in eyes 129.43 98.13 26 2561 557 3382715
Hair growth abnormal 119.93 98.13 25 2562 647 3382625

Pharmacologic Action:

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SourceCodeDescription
ATC S01EE03 SENSORY ORGANS
OPHTHALMOLOGICALS
ANTIGLAUCOMA PREPARATIONS AND MIOTICS
Prostaglandin analogues1)
FDA EPC N0000175454 Prostaglandin Analog
FDA Chemical/Ingredient N0000007706 Prostaglandins
MeSH PA D000959 Antihypertensive Agents
MeSH PA D002317 Cardiovascular Agents
CHEBI has role CHEBI:35674 antihypertensive agent
CHEBI has role CHEBI:39456 antiglaucoma drug

Drug Use (View source of the data)

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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

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Dissociation levelDissociation constantType (acidic/basic)
pKa1 13.89 acidic

Orange Book patent data (new drug applications)

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Formulation strengthTrade nameApplicantApplication numberApproval dateTypeDose formRoutePatent numberPatent expiration datePatent use
0.03% LATISSE ALLERGAN N022369 Dec. 24, 2008 RX SOLUTION/DROPS TOPICAL 8541466 Jan. 31, 2021 METHOD OF INCREASING HAIR GROWTH
0.03% LATISSE ALLERGAN N022369 Dec. 24, 2008 RX SOLUTION/DROPS TOPICAL 8906962 Jan. 31, 2021 METHOD OF INCREASING HAIR GROWTH
0.03% LATISSE ALLERGAN N022369 Dec. 24, 2008 RX SOLUTION/DROPS TOPICAL 9579270 Jan. 31, 2021 METHOD OF INCREASING EYELASH GROWTH WITH BIMATOPROST
0.03% LATISSE ALLERGAN N022369 Dec. 24, 2008 RX SOLUTION/DROPS TOPICAL 8263054 Jan. 15, 2023 METHOD OF INCREASING EYELASH GROWTH INCLUDING LENGTH, THICKNESS, DARKNESS AND/OR NUMBER OF EYELASHES BY ADMINISTERING BIMATOPROST TO AN EYELID MARGIN
0.03% LATISSE ALLERGAN N022369 Dec. 24, 2008 RX SOLUTION/DROPS TOPICAL 8632760 Jan. 15, 2023 METHOD OF INCREASING EYELASH GROWTH
0.03% LATISSE ALLERGAN N022369 Dec. 24, 2008 RX SOLUTION/DROPS TOPICAL 8758733 Jan. 15, 2023 METHOD OF INCREASING EYELASH GROWTH
0.03% LATISSE ALLERGAN N022369 Dec. 24, 2008 RX SOLUTION/DROPS TOPICAL 8986715 Jan. 15, 2023 METHOD OF INCREASING HAIR GROWTH
0.03% LATISSE ALLERGAN N022369 Dec. 24, 2008 RX SOLUTION/DROPS TOPICAL 9216183 Jan. 15, 2023 METHOD OF INCREASING EYELASH GROWTH
0.03% LATISSE ALLERGAN N022369 Dec. 24, 2008 RX SOLUTION/DROPS TOPICAL 9226931 Jan. 15, 2023 METHOD OF INCREASING GROWTH OF HAIR INCLUDING EYELASHES
0.03% LATISSE ALLERGAN N022369 Dec. 24, 2008 RX SOLUTION/DROPS TOPICAL 8038988 Aug. 25, 2023 TREATMENT OF HYPOTRICHOSIS OF THE EYELASHES BY INCREASING THEIR GROWTH INCLUDING LENGTH, THICKNESS AND DARKNESS
0.03% LATISSE ALLERGAN N022369 Dec. 24, 2008 RX SOLUTION/DROPS TOPICAL 8101161 May 25, 2024 METHOD OF INCREASING HAIR GROWTH
0.03% LATISSE ALLERGAN N022369 Dec. 24, 2008 RX SOLUTION/DROPS TOPICAL 8101161 May 25, 2024 METHOD OF STIMULATING HAIR GROWTH
0.01% LUMIGAN ALLERGAN N022184 Aug. 31, 2010 RX SOLUTION/DROPS OPHTHALMIC 8299118 March 16, 2025 A METHOD OF TREATING A PATIENT WITH GLAUCOMA OR OCULAR HYPERTENSION
0.01% LUMIGAN ALLERGAN N022184 Aug. 31, 2010 RX SOLUTION/DROPS OPHTHALMIC 8309605 March 16, 2025 A METHOD OF LOWERING INTRAOCULAR PRESSURE IN A PATIENT WITH OPEN ANGLE GLAUCOMA OR OCULAR HYPERTENSION
0.01% LUMIGAN ALLERGAN N022184 Aug. 31, 2010 RX SOLUTION/DROPS OPHTHALMIC 8309605 March 16, 2025 METHOD OF TREATING GLAUCOMA IN A PATIENT
0.01% LUMIGAN ALLERGAN N022184 Aug. 31, 2010 RX SOLUTION/DROPS OPHTHALMIC 8338479 March 16, 2025 A METHOD OF TREATING A PATIENT WITH GLAUCOMA OR OCULAR HYPERTENSION
0.01% LUMIGAN ALLERGAN N022184 Aug. 31, 2010 RX SOLUTION/DROPS OPHTHALMIC 8524777 March 16, 2025 REDUCTION OF ELEVATED INTRAOCULAR PRESSURE IN PATIENTS WITH GLAUCOMA OR OCULAR HYPERTENSION
0.01% LUMIGAN ALLERGAN N022184 Aug. 31, 2010 RX SOLUTION/DROPS OPHTHALMIC 8586630 March 16, 2025 A METHOD OF REDUCING INTRAOCULAR PRESSURE IN PATIENTS WITH OPEN ANGLE GLAUCOMA OR OCULAR HYPERTENSION
0.01% LUMIGAN ALLERGAN N022184 Aug. 31, 2010 RX SOLUTION/DROPS OPHTHALMIC 8772338 March 16, 2025 A METHOD OF LOWERING INTRAOCULAR PRESSURE
0.01% LUMIGAN ALLERGAN N022184 Aug. 31, 2010 RX SOLUTION/DROPS OPHTHALMIC 9155716 March 16, 2025 A METHOD OF LOWERING INTRAOCULAR PRESSURE
0.01% LUMIGAN ALLERGAN N022184 Aug. 31, 2010 RX SOLUTION/DROPS OPHTHALMIC 9241918 March 16, 2025 METHOD OF TREATING GLAUCOMA OR ELEVATED INTRAOCULAR PRESSURE

Orange Book exclusivity data (new drug applications)

None

Bioactivity Summary:

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

External reference:

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IDSource
1958 IUPHAR_LIGAND_ID
C0939372 UMLSCUI
D02724 KEGG_DRUG
DB00905 DRUGBANK_ID
15937 MMSL
283810 RXNORM
4021262 VANDF
129492005 SNOMEDCT_US
395300006 SNOMEDCT_US
N0000010075 NDFRT
N0000148703 NDFRT
009115 NDDF
234008 MMSL
5311027 PUBCHEM_CID
CHEMBL1200963 ChEMBL_ID
QXS94885MZ UNII
8035 INN_ID
D000069580 MESH_DESCRIPTOR_UI
CHEBI:51230 CHEBI
15M PDB_CHEM_ID

Pharmaceutical products:

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ProductCategoryIngredientsNDCFormQuantityRoute MarketingLabel
LUMIGAN HUMAN PRESCRIPTION DRUG LABEL 1 0023-3205 SOLUTION/ DROPS 0.10 mg OPHTHALMIC NDA 16 sections
LATISSE HUMAN PRESCRIPTION DRUG LABEL 1 0023-3616 SOLUTION/ DROPS 0.30 mg OPHTHALMIC NDA 15 sections
LUMIGAN HUMAN PRESCRIPTION DRUG LABEL 1 0023-9187 SOLUTION/ DROPS 0.30 mg OPHTHALMIC Export only 1 sections
Bimatoprost HUMAN PRESCRIPTION DRUG LABEL 1 0781-6206 SOLUTION/ DROPS 0.30 mg OPHTHALMIC ANDA 15 sections
LUMIGAN HUMAN PRESCRIPTION DRUG LABEL 1 54868-4575 SOLUTION/ DROPS 0.30 mg OPHTHALMIC NDA 15 sections
LUMIGAN HUMAN PRESCRIPTION DRUG LABEL 1 54868-6304 SOLUTION/ DROPS 0.10 mg OPHTHALMIC NDA 15 sections
bimatoprost HUMAN PRESCRIPTION DRUG LABEL 1 57297-429 SOLUTION/ DROPS 0.30 mg OPHTHALMIC ANDA 16 sections
bimatoprost HUMAN PRESCRIPTION DRUG LABEL 1 68180-429 SOLUTION/ DROPS 0.30 mg OPHTHALMIC ANDA 16 sections