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

Stem definition	Drug id	CAS RN
prostaglandins	371	155206-00-1

Description:

Molecule	Description
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

Molecule

Description

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:

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Property	Value	Reference
CL (Clearance)	25 mL/min/kg	Lombardo F, Berellini G, Obach RS
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
t_half (Half-life)	0.45 hours	Lombardo F, Berellini G, Obach RS
fu (Fraction unbound in plasma)	0.12 %	Lombardo F, Berellini G, Obach RS

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Approvals:

Date	Agency	Company	Orphan
March 16, 2001	FDA
March 8, 2002	EMA

FDA Adverse Event Reporting System (Female)

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MedDRA adverse event term	Likelihood ratio	Likelihood ratio threshold	Patients taking drug having adverse event	Patients taking drug not having adverse event	Patients not taking drug having adverse event	Patients not taking drug not having adverse event
Ocular hyperaemia	2306.72	17.83	634	15319	24510	63448559
Eye irritation	1816.36	17.83	511	15442	21460	63451609
Erythema of eyelid	1777.03	17.83	331	15622	1955	63471114
Madarosis	1714.97	17.83	337	15616	2744	63470325
Eye pruritus	1361.14	17.83	394	15559	18277	63454792
Eyelids pruritus	987.21	17.83	181	15772	961	63472108
Eyelid irritation	734.98	17.83	126	15827	417	63472652
Eye swelling	593.99	17.83	224	15729	23694	63449375
Eyelid oedema	558.77	17.83	174	15779	10305	63462764
Treatment failure	413.63	17.83	365	15588	198678	63274391

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FDA Adverse Event Reporting System (Male)

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MedDRA adverse event term	Likelihood ratio	Likelihood ratio threshold	Patients taking drug having adverse event	Patients taking drug not having adverse event	Patients not taking drug having adverse event	Patients not taking drug not having adverse event
Treatment failure	527.18	18.46	220	5598	46477	34904636
Intraocular pressure increased	331.09	18.46	91	5727	5292	34945821
Eye irritation	173.43	18.46	60	5758	7501	34943612
Ocular hyperaemia	152.63	18.46	61	5757	11391	34939722
Eye pain	104.60	18.46	49	5769	13413	34937700
Visual acuity reduced	93.23	18.46	48	5770	16101	34935012
Vision blurred	57.42	18.46	53	5765	45910	34905203
Conjunctival hyperaemia	54.79	18.46	19	5799	2383	34948730
Enophthalmos	54.70	18.46	8	5810	11	34951102
Corneal endothelial cell loss	53.91	18.46	7	5811	0	34951113

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FDA Adverse Event Reporting System (Geriatric)

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MedDRA adverse event term	Likelihood ratio	Likelihood ratio threshold	Patients taking drug having adverse event	Patients taking drug not having adverse event	Patients not taking drug having adverse event	Patients not taking drug not having adverse event
Ocular hyperaemia	1212.83	15.03	370	14529	27836	79701653
Eye irritation	1078.42	15.03	315	14584	20366	79709123
Erythema of eyelid	1032.43	15.03	204	14695	2366	79727123
Madarosis	751.23	15.03	159	14740	2643	79726846
Eye pruritus	671.77	15.03	219	14680	20351	79709138
Eyelids pruritus	623.27	15.03	114	14785	839	79728650
Eyelid irritation	446.55	15.03	77	14822	384	79729105
Intraocular pressure increased	395.88	15.03	121	14778	9084	79720405
Eyelid oedema	372.05	15.03	127	14772	13560	79715929
Eye swelling	307.03	15.03	132	14767	26336	79703153

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FDA Adverse Event Reporting System (Pediatric)

None

Pharmacologic Action:

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

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Drug Use | Suggest Off label Use Form| |View source of the data|

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Disease	Relation	SNOMED_ID	DOID
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

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🐶 Veterinary Drug Use

None

🐶 Veterinary products

None

Acid dissociation constants calculated using MoKa v3.0.0

Dissociation level	Dissociation constant	Type (acidic/basic)
pKa1	13.89	acidic

Orange Book patent data (new drug applications)

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Formulation strength	Trade name	Applicant	Application number	Approval date	Type	Dose form	Route	Patent number	Patent expiration date	Patent use
0.01%	LUMIGAN	ABBVIE	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	ABBVIE	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	ABBVIE	N022184	Aug. 31, 2010	RX	SOLUTION/DROPS	OPHTHALMIC	8309605	March 16, 2025	METHOD OF TREATING GLAUCOMA IN A PATIENT
0.01%	LUMIGAN	ABBVIE	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	ABBVIE	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	ABBVIE	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	ABBVIE	N022184	Aug. 31, 2010	RX	SOLUTION/DROPS	OPHTHALMIC	8772338	March 16, 2025	A METHOD OF LOWERING INTRAOCULAR PRESSURE
0.01%	LUMIGAN	ABBVIE	N022184	Aug. 31, 2010	RX	SOLUTION/DROPS	OPHTHALMIC	9155716	March 16, 2025	A METHOD OF LOWERING INTRAOCULAR PRESSURE
0.01%	LUMIGAN	ABBVIE	N022184	Aug. 31, 2010	RX	SOLUTION/DROPS	OPHTHALMIC	9241918	March 16, 2025	METHOD OF TREATING GLAUCOMA OR ELEVATED INTRAOCULAR PRESSURE
0.03%	LATISSE	ABBVIE	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

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Orange Book exclusivity data (new drug applications)

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Formulation strength	Trade name	Applicant	Application number	Approval date	Type	Dose form	Route	Exclusivity date	Description
10MCG	DURYSTA	ABBVIE	N211911	March 4, 2020	RX	IMPLANT	OPHTHALMIC	March 4, 2023	NEW PRODUCT

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Bioactivity Summary:

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Target	Class	Pharos	UniProt	Action	Type	Activity value (-log[M])	Mechanism action	Bioact source	MoA source
Prostaglandin F2-alpha receptor	GPCR	P43088	PF2R_HUMAN	AGONIST	Ki	5.30		WOMBAT-PK	CHEMBL
Aldo-keto reductase family 1 member C3	Enzyme	P42330	AK1C3_HUMAN		IC50	5.30		CHEMBL

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External reference:

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ID	Source
15M	PDB_CHEM_ID
009115	NDDF
129492005	SNOMEDCT_US
15937	MMSL
1958	IUPHAR_LIGAND_ID
234008	MMSL
283810	RXNORM
395300006	SNOMEDCT_US
4021262	VANDF
41256	MMSL

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Pharmaceutical products:

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Product	Category	Ingredients	NDC	Form	Quantity	Route	Marketing	Label
Bimatoprost	HUMAN PRESCRIPTION DRUG LABEL	1	0781-6206	SOLUTION/ DROPS	0.30 mg	OPHTHALMIC	ANDA	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	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	24 sections
BIMATOPROST	HUMAN PRESCRIPTION DRUG LABEL	1	42571-128	SOLUTION/ DROPS	0.30 mg	OPHTHALMIC	ANDA	24 sections
Bimatoprost	Human Prescription Drug Label	1	46708-507	SOLUTION/ DROPS	0.30 mg	OPHTHALMIC	ANDA	23 sections
bimatoprost	Human Prescription Drug Label	1	46708-511	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	50383-908	SOLUTION/ DROPS	0.30 mg	OPHTHALMIC	ANDA	23 sections
Bimatoprost	HUMAN PRESCRIPTION DRUG LABEL	1	50383-912	SOLUTION	3 ug	TOPICAL	ANDA	22 sections

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