Identification

Name
Bimatoprost
Accession Number
DB00905  (APRD00826, DB06863)
Type
Small Molecule
Groups
Approved, Investigational
Description

Bimatoprost ophthalmic solution is a topical medication used for controlling the progression of glaucoma or ocular hypertension, by reducing intraocular pressure. It is a prostaglandin analogue that works by increasing the outflow of aqueous fluid from the eyes. It binds to the prostanoid FP receptor.

Structure
Thumb
Synonyms
  • (Z)-7-((1R,2R,3R,5S)-3,5-Dihydroxy-2-((1e,3S)-3-hydroxy-5-phenyl-1-pentenyl)cyclopentyl)-N-ethyl-5-heptenamide
  • Bimatoprostum
External IDs
AGN 192024 / AGN-192024
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
LatisseSolution / drops.3 mg/mLOphthalmicAllergan2009-01-26Not applicableUs
LatisseSolution0.03 %TopicalAllergan2010-11-01Not applicableCanada
LumiganSolution / drops.3 mg/mLOphthalmicPhysicians Total Care, Inc.2001-03-22Not applicableUs
LumiganSolution / drops.1 mg/mLOphthalmicAllergan2010-09-10Not applicableUs
LumiganSolution / drops.1 mg/mLOphthalmicPhysicians Total Care, Inc.2011-09-14Not applicableUs
LumiganSolution0.03 %OphthalmicAllergan2002-05-24Not applicableCanada
Lumigan PFSolution0.03 %OphthalmicAllerganNot applicableNot applicableCanada
Lumigan RcSolution0.01 %OphthalmicAllergan2009-06-16Not applicableCanada
VistitanSolution0.03 %OphthalmicSandoz Canada Incorporated2016-05-13Not applicableCanada
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Apo-bimatoprostSolution0.03 %OphthalmicApotex CorporationNot applicableNot applicableCanada
Apo-bimatoprostSolution0.03 %TopicalApotex CorporationNot applicableNot applicableCanada
BimatoprostSolution / drops.3 mg/mLOphthalmicLupin Pharmaceuticals2015-05-13Not applicableUs
BimatoprostSolution / drops.3 mg/mLOphthalmicSandoz2016-12-06Not applicableUs
BimatoprostSolution / drops.3 mg/mLOphthalmicLupin Pharmaceuticals2015-05-13Not applicableUs
Categories
UNII
QXS94885MZ
CAS number
155206-00-1
Weight
Average: 415.5656
Monoisotopic: 415.272258677
Chemical Formula
C25H37NO4
InChI Key
AQOKCDNYWBIDND-FTOWTWDKSA-N
InChI
InChI=1S/C25H37NO4/c1-2-26-25(30)13-9-4-3-8-12-21-22(24(29)18-23(21)28)17-16-20(27)15-14-19-10-6-5-7-11-19/h3,5-8,10-11,16-17,20-24,27-29H,2,4,9,12-15,18H2,1H3,(H,26,30)/b8-3-,17-16+/t20-,21+,22+,23-,24+/m0/s1
IUPAC Name
(5Z)-7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-[(1E,3S)-3-hydroxy-5-phenylpent-1-en-1-yl]cyclopentyl]-N-ethylhept-5-enamide
SMILES
CCNC(=O)CCC\C=C/C[[email protected]]1[[email protected]@H](O)C[[email protected]@H](O)[[email protected]@H]1\C=C\[[email protected]@H](O)CCC1=CC=CC=C1

Pharmacology

Indication

For the reduction of elevated intraocular pressure in patients with open angle glaucoma or ocular hypertension who are intolerant of other intraocular pressure lowering medications or insufficiently responsive (failed to achieve target IOP determined after multiple measurements over time) to another intraocular pressure lowering medication.

Structured Indications
Pharmacodynamics

Bimatoprost is a prostamide, a synthetic structural analog of prostaglandin with ocular hypotensive activity, that is chemically related to prostamide F. It selectively mimics the effects of naturally occurring substances, prostamides. Bimatoprost lowers intraocular pressure (IOP) in humans. Elevated IOP presents a major risk factor for glaucomatous field loss. The higher the level of IOP, the greater the likelihood of optic nerve damage and visual field loss.

Mechanism of action

Bimatoprost is believed to lower intraocular pressure (IOP) in humans by increasing outflow of aqueous humor through both the trabecular meshwork and uveoscleral routes. Bimatoprost reduces the pressure in the eye by mimicking the action of a naturally-occuring prostaglandin. Prostaglandins are a group of chemicals found in many places in the body. In the eye, they increase the drainage of the aqueous humour out of the eyeball. Bimatoprost is a synthetic compound related to one of the natural prostaglandins, and works by increasing the drainage of aqueous humour out of the eyeball. Bimatoprost may also lower the rate of aqueous formation in the eye. Both these effects decrease the pressure within the eye.

TargetActionsOrganism
AProstaglandin F2-alpha receptor
agonist
Human
AProstaglandin E2 receptor EP1 subtype
agonist
Human
AProstaglandin E2 receptor EP3 subtype
agonist
Human
UAldo-keto reductase family 1 member C3Not AvailableHuman
Absorption

Systemically absorbed when administered to the eye.

Volume of distribution
  • 0.67 L/kg
Protein binding

Approximately 88% of bimatoprost is bound in human plasma.

Metabolism

Bimatoprost undergoes oxidation, N-deethylation and glucuronidation to form a variety of metabolites.

Route of elimination

Up to 67% of the administered dose was excreted in the urine while 25% of the dose was recovered in the feces.

Half life

Elimination half-life is approximately 45 minutes.

Clearance
  • 1.5 L/hr/kg [Healthy subjects receiving IV administration of 3.12 ug/kg]
Toxicity

In oral (by gavage) mouse and rat studies, doses up to 100 mg/kg/day did not produce any toxicity. This dose expressed as mg/m2 is at least 70 times higher than the accidental dose of one bottle of bimatoprost for a 10 kg child.

Affected organisms
  • Humans and other mammals
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteractionDrug group
7,8-Dichloro-1,2,3,4-tetrahydroisoquinoline7,8-Dichloro-1,2,3,4-tetrahydroisoquinoline may increase the hypotensive activities of Bimatoprost.Experimental
AcebutololBimatoprost may increase the hypotensive activities of Acebutolol.Approved
AceclofenacThe therapeutic efficacy of Bimatoprost can be decreased when used in combination with Aceclofenac.Approved, Investigational
AcemetacinThe therapeutic efficacy of Bimatoprost can be decreased when used in combination with Acemetacin.Approved, Experimental, Investigational
Acetylsalicylic acidThe therapeutic efficacy of Bimatoprost can be decreased when used in combination with Acetylsalicylic acid.Approved, Vet Approved
AdapaleneThe therapeutic efficacy of Bimatoprost can be decreased when used in combination with Adapalene.Approved
AlclofenacThe therapeutic efficacy of Bimatoprost can be decreased when used in combination with Alclofenac.Approved, Withdrawn
AlfuzosinAlfuzosin may increase the hypotensive activities of Bimatoprost.Approved, Investigational
AliskirenBimatoprost may increase the hypotensive activities of Aliskiren.Approved, Investigational
AlminoprofenThe therapeutic efficacy of Bimatoprost can be decreased when used in combination with Alminoprofen.Experimental
AlprenololAlprenolol may increase the hypotensive activities of Bimatoprost.Approved, Withdrawn
AmbrisentanBimatoprost may increase the hypotensive activities of Ambrisentan.Approved, Investigational
AmifostineBimatoprost may increase the hypotensive activities of Amifostine.Approved, Investigational
AmlodipineAmlodipine may increase the hypotensive activities of Bimatoprost.Approved
AmphetamineAmphetamine may increase the hypotensive activities of Bimatoprost.Approved, Illicit
AndrographolideThe therapeutic efficacy of Bimatoprost can be decreased when used in combination with Andrographolide.Investigational
AnisodamineThe therapeutic efficacy of Bimatoprost can be decreased when used in combination with Anisodamine.Investigational
AntipyrineThe therapeutic efficacy of Bimatoprost can be decreased when used in combination with Antipyrine.Approved
ApocyninThe therapeutic efficacy of Bimatoprost can be decreased when used in combination with Apocynin.Investigational
ApremilastThe therapeutic efficacy of Bimatoprost can be decreased when used in combination with Apremilast.Approved, Investigational
AtenololAtenolol may increase the hypotensive activities of Bimatoprost.Approved
AvanafilAvanafil may increase the antihypertensive activities of Bimatoprost.Approved
AzapropazoneThe therapeutic efficacy of Bimatoprost can be decreased when used in combination with Azapropazone.Withdrawn
AzelastineThe therapeutic efficacy of Bimatoprost can be decreased when used in combination with Azelastine.Approved
BalsalazideThe therapeutic efficacy of Bimatoprost can be decreased when used in combination with Balsalazide.Approved, Investigational
BenazeprilBenazepril may increase the hypotensive activities of Bimatoprost.Approved, Investigational
BendazacThe therapeutic efficacy of Bimatoprost can be decreased when used in combination with Bendazac.Experimental
BendroflumethiazideBendroflumethiazide may increase the hypotensive activities of Bimatoprost.Approved
BenmoxinBenmoxin may increase the hypotensive activities of Bimatoprost.Withdrawn
BenorilateThe therapeutic efficacy of Bimatoprost can be decreased when used in combination with Benorilate.Experimental
BenoxaprofenThe therapeutic efficacy of Bimatoprost can be decreased when used in combination with Benoxaprofen.Withdrawn
BenzydamineThe therapeutic efficacy of Bimatoprost can be decreased when used in combination with Benzydamine.Approved
BepridilBimatoprost may increase the hypotensive activities of Bepridil.Approved, Withdrawn
BetaxololBetaxolol may increase the hypotensive activities of Bimatoprost.Approved
BethanidineBethanidine may increase the hypotensive activities of Bimatoprost.Approved
BevoniumThe therapeutic efficacy of Bimatoprost can be decreased when used in combination with Bevonium.Experimental
BietaserpineBietaserpine may increase the hypotensive activities of Bimatoprost.Experimental
BisoprololBisoprolol may increase the hypotensive activities of Bimatoprost.Approved
BosentanBosentan may increase the hypotensive activities of Bimatoprost.Approved, Investigational
BQ-123Bimatoprost may increase the hypotensive activities of BQ-123.Investigational
BretyliumBimatoprost may increase the hypotensive activities of Bretylium.Approved
BrimonidineBrimonidine may increase the antihypertensive activities of Bimatoprost.Approved
BrofaromineBrofaromine may increase the hypotensive activities of Bimatoprost.Experimental
BromfenacThe therapeutic efficacy of Bimatoprost can be decreased when used in combination with Bromfenac.Approved
BucillamineThe therapeutic efficacy of Bimatoprost can be decreased when used in combination with Bucillamine.Investigational
BufexamacThe therapeutic efficacy of Bimatoprost can be decreased when used in combination with Bufexamac.Experimental
BumadizoneThe therapeutic efficacy of Bimatoprost can be decreased when used in combination with Bumadizone.Experimental
BupranololBimatoprost may increase the hypotensive activities of Bupranolol.Approved
CadralazineCadralazine may increase the hypotensive activities of Bimatoprost.Experimental
CafedrineBimatoprost may increase the hypotensive activities of Cafedrine.Investigational
CandesartanBimatoprost may increase the hypotensive activities of Candesartan.Experimental
Candesartan cilexetilCandesartan cilexetil may increase the hypotensive activities of Bimatoprost.Approved
CandoxatrilCandoxatril may increase the hypotensive activities of Bimatoprost.Experimental
CaptoprilBimatoprost may increase the hypotensive activities of Captopril.Approved
CaroxazoneCaroxazone may increase the hypotensive activities of Bimatoprost.Withdrawn
CarprofenThe therapeutic efficacy of Bimatoprost can be decreased when used in combination with Carprofen.Approved, Vet Approved, Withdrawn
CarteololCarteolol may increase the hypotensive activities of Bimatoprost.Approved
CarvedilolBimatoprost may increase the hypotensive activities of Carvedilol.Approved, Investigational
CastanospermineThe therapeutic efficacy of Bimatoprost can be decreased when used in combination with Castanospermine.Experimental
CelecoxibThe therapeutic efficacy of Bimatoprost can be decreased when used in combination with Celecoxib.Approved, Investigational
CeliprololBimatoprost may increase the hypotensive activities of Celiprolol.Approved, Investigational
ChloroquineThe therapeutic efficacy of Bimatoprost can be decreased when used in combination with Chloroquine.Approved, Vet Approved
ChlorothiazideChlorothiazide may increase the hypotensive activities of Bimatoprost.Approved, Vet Approved
ChlorthalidoneChlorthalidone may increase the hypotensive activities of Bimatoprost.Approved
Choline magnesium trisalicylateThe therapeutic efficacy of Bimatoprost can be decreased when used in combination with Choline magnesium trisalicylate.Approved
CicletanineBimatoprost may increase the hypotensive activities of Cicletanine.Investigational
CilazaprilBimatoprost may increase the hypotensive activities of Cilazapril.Approved
ClonidineClonidine may increase the hypotensive activities of Bimatoprost.Approved
ClonixinThe therapeutic efficacy of Bimatoprost can be decreased when used in combination with Clonixin.Approved
CloranololBimatoprost may increase the hypotensive activities of Cloranolol.Experimental
CryptenamineCryptenamine may increase the hypotensive activities of Bimatoprost.Approved
CurcuminThe therapeutic efficacy of Bimatoprost can be decreased when used in combination with Curcumin.Investigational
CyclopenthiazideBimatoprost may increase the hypotensive activities of Cyclopenthiazide.Experimental
CyclothiazideCyclothiazide may increase the hypotensive activities of Bimatoprost.Approved
D-LimoneneThe therapeutic efficacy of Bimatoprost can be decreased when used in combination with D-Limonene.Investigational
DebrisoquinDebrisoquin may increase the hypotensive activities of Bimatoprost.Approved, Investigational
DelaprilBimatoprost may increase the hypotensive activities of Delapril.Experimental
DeserpidineBimatoprost may increase the hypotensive activities of Deserpidine.Approved
DiazoxideDiazoxide may increase the hypotensive activities of Bimatoprost.Approved
DiclofenacThe therapeutic efficacy of Bimatoprost can be decreased when used in combination with Diclofenac.Approved, Vet Approved
diethylnorspermineBimatoprost may increase the hypotensive activities of diethylnorspermine.Investigational
DifenpiramideThe therapeutic efficacy of Bimatoprost can be decreased when used in combination with Difenpiramide.Experimental
DiflunisalThe therapeutic efficacy of Bimatoprost can be decreased when used in combination with Diflunisal.Approved
DihydralazineDihydralazine may increase the hypotensive activities of Bimatoprost.Investigational
DiltiazemDiltiazem may increase the hypotensive activities of Bimatoprost.Approved
DorzolamideDorzolamide may increase the hypotensive activities of Bimatoprost.Approved
DoxazosinDoxazosin may increase the hypotensive activities of Bimatoprost.Approved
DroxicamThe therapeutic efficacy of Bimatoprost can be decreased when used in combination with Droxicam.Approved
DuvelisibThe therapeutic efficacy of Bimatoprost can be decreased when used in combination with Duvelisib.Investigational
E-6201The therapeutic efficacy of Bimatoprost can be decreased when used in combination with E-6201.Investigational
EfonidipineBimatoprost may increase the hypotensive activities of Efonidipine.Approved, Investigational
EnalaprilEnalapril may increase the hypotensive activities of Bimatoprost.Approved, Vet Approved
EnalaprilatBimatoprost may increase the hypotensive activities of Enalaprilat.Approved
EndralazineEndralazine may increase the hypotensive activities of Bimatoprost.Experimental
EpanololBimatoprost may increase the hypotensive activities of Epanolol.Experimental
EpirizoleThe therapeutic efficacy of Bimatoprost can be decreased when used in combination with Epirizole.Approved
EpoprostenolBimatoprost may increase the hypotensive activities of Epoprostenol.Approved
EprosartanEprosartan may increase the hypotensive activities of Bimatoprost.Approved
EtanerceptThe therapeutic efficacy of Bimatoprost can be decreased when used in combination with Etanercept.Approved, Investigational
EthenzamideThe therapeutic efficacy of Bimatoprost can be decreased when used in combination with Ethenzamide.Experimental
EtodolacThe therapeutic efficacy of Bimatoprost can be decreased when used in combination with Etodolac.Approved, Investigational, Vet Approved
EtofenamateThe therapeutic efficacy of Bimatoprost can be decreased when used in combination with Etofenamate.Approved, Investigational
EtoricoxibThe therapeutic efficacy of Bimatoprost can be decreased when used in combination with Etoricoxib.Approved, Investigational
Evening primrose oilThe therapeutic efficacy of Bimatoprost can be decreased when used in combination with Evening primrose oil.Approved, Investigational
exisulindThe therapeutic efficacy of Bimatoprost can be decreased when used in combination with exisulind.Investigational
FelbinacThe therapeutic efficacy of Bimatoprost can be decreased when used in combination with Felbinac.Experimental
FelodipineBimatoprost may increase the hypotensive activities of Felodipine.Approved, Investigational
FenbufenThe therapeutic efficacy of Bimatoprost can be decreased when used in combination with Fenbufen.Approved
FenoldopamFenoldopam may increase the hypotensive activities of Bimatoprost.Approved
FenoprofenThe therapeutic efficacy of Bimatoprost can be decreased when used in combination with Fenoprofen.Approved
FentiazacThe therapeutic efficacy of Bimatoprost can be decreased when used in combination with Fentiazac.Experimental
FeprazoneThe therapeutic efficacy of Bimatoprost can be decreased when used in combination with Feprazone.Experimental
Ferulic acidThe therapeutic efficacy of Bimatoprost can be decreased when used in combination with Ferulic acid.Experimental
FloctafenineThe therapeutic efficacy of Bimatoprost can be decreased when used in combination with Floctafenine.Approved, Withdrawn
FlunixinThe therapeutic efficacy of Bimatoprost can be decreased when used in combination with Flunixin.Vet Approved
FlunoxaprofenThe therapeutic efficacy of Bimatoprost can be decreased when used in combination with Flunoxaprofen.Experimental
FlurbiprofenThe therapeutic efficacy of Bimatoprost can be decreased when used in combination with Flurbiprofen.Approved, Investigational
FosinoprilFosinopril may increase the hypotensive activities of Bimatoprost.Approved
FurazolidoneFurazolidone may increase the hypotensive activities of Bimatoprost.Approved, Investigational, Vet Approved
GuacetisalThe therapeutic efficacy of Bimatoprost can be decreased when used in combination with Guacetisal.Experimental
GuanabenzGuanabenz may increase the hypotensive activities of Bimatoprost.Approved, Investigational
GuanadrelGuanadrel may increase the hypotensive activities of Bimatoprost.Approved
GuanazodineBimatoprost may increase the hypotensive activities of Guanazodine.Experimental
GuanethidineBimatoprost may increase the hypotensive activities of Guanethidine.Approved
GuanfacineGuanfacine may increase the hypotensive activities of Bimatoprost.Approved, Investigational
GuanoclorBimatoprost may increase the hypotensive activities of Guanoclor.Experimental
GuanoxabenzBimatoprost may increase the hypotensive activities of Guanoxabenz.Experimental
GuanoxanBimatoprost may increase the hypotensive activities of Guanoxan.Experimental
HarmalineHarmaline may increase the hypotensive activities of Bimatoprost.Experimental
HexamethoniumBimatoprost may increase the hypotensive activities of Hexamethonium.Experimental
HigenamineThe therapeutic efficacy of Bimatoprost can be decreased when used in combination with Higenamine.Investigational
HydracarbazineHydracarbazine may increase the hypotensive activities of Bimatoprost.Experimental
HydralazineHydralazine may increase the hypotensive activities of Bimatoprost.Approved
HydrochlorothiazideBimatoprost may increase the hypotensive activities of Hydrochlorothiazide.Approved, Vet Approved
HydroflumethiazideHydroflumethiazide may increase the hypotensive activities of Bimatoprost.Approved, Investigational
IbuprofenThe therapeutic efficacy of Bimatoprost can be decreased when used in combination with Ibuprofen.Approved
IbuproxamThe therapeutic efficacy of Bimatoprost can be decreased when used in combination with Ibuproxam.Withdrawn
IcatibantThe therapeutic efficacy of Bimatoprost can be decreased when used in combination with Icatibant.Approved
IloprostIloprost may increase the hypotensive activities of Bimatoprost.Approved, Investigational
ImidaprilBimatoprost may increase the hypotensive activities of Imidapril.Investigational
Imidazole salicylateThe therapeutic efficacy of Bimatoprost can be decreased when used in combination with Imidazole salicylate.Experimental
IndapamideIndapamide may increase the hypotensive activities of Bimatoprost.Approved
IndenololBimatoprost may increase the hypotensive activities of Indenolol.Withdrawn
IndobufenThe therapeutic efficacy of Bimatoprost can be decreased when used in combination with Indobufen.Investigational
IndomethacinThe therapeutic efficacy of Bimatoprost can be decreased when used in combination with Indomethacin.Approved, Investigational
IndoprofenThe therapeutic efficacy of Bimatoprost can be decreased when used in combination with Indoprofen.Withdrawn
IndoraminIndoramin may increase the hypotensive activities of Bimatoprost.Withdrawn
IproclozideIproclozide may increase the hypotensive activities of Bimatoprost.Withdrawn
IproniazidIproniazid may increase the hypotensive activities of Bimatoprost.Withdrawn
IrbesartanBimatoprost may increase the hypotensive activities of Irbesartan.Approved, Investigational
IsocarboxazidIsocarboxazid may increase the hypotensive activities of Bimatoprost.Approved
IsoxicamThe therapeutic efficacy of Bimatoprost can be decreased when used in combination with Isoxicam.Withdrawn
IsradipineIsradipine may increase the hypotensive activities of Bimatoprost.Approved
KebuzoneThe therapeutic efficacy of Bimatoprost can be decreased when used in combination with Kebuzone.Experimental
KetanserinKetanserin may increase the hypotensive activities of Bimatoprost.Investigational
KetoprofenThe therapeutic efficacy of Bimatoprost can be decreased when used in combination with Ketoprofen.Approved, Vet Approved
KetorolacThe therapeutic efficacy of Bimatoprost can be decreased when used in combination with Ketorolac.Approved
LabetalolLabetalol may increase the hypotensive activities of Bimatoprost.Approved
LacidipineBimatoprost may increase the hypotensive activities of Lacidipine.Approved, Investigational
LatanoprostThe risk or severity of intraocular pressure can be increased when Latanoprost is combined with Bimatoprost.Approved, Investigational
LeflunomideThe therapeutic efficacy of Bimatoprost can be decreased when used in combination with Leflunomide.Approved, Investigational
LercanidipineLercanidipine may increase the hypotensive activities of Bimatoprost.Approved, Investigational
LinsidomineBimatoprost may increase the hypotensive activities of Linsidomine.Experimental
LisinoprilLisinopril may increase the hypotensive activities of Bimatoprost.Approved, Investigational
LisofyllineThe therapeutic efficacy of Bimatoprost can be decreased when used in combination with Lisofylline.Investigational
LofexidineBimatoprost may increase the hypotensive activities of Lofexidine.Approved, Investigational
LonazolacThe therapeutic efficacy of Bimatoprost can be decreased when used in combination with Lonazolac.Experimental
LornoxicamThe therapeutic efficacy of Bimatoprost can be decreased when used in combination with Lornoxicam.Approved, Investigational
LosartanLosartan may increase the hypotensive activities of Bimatoprost.Approved
LoxoprofenThe therapeutic efficacy of Bimatoprost can be decreased when used in combination with Loxoprofen.Approved, Investigational
LumiracoxibThe therapeutic efficacy of Bimatoprost can be decreased when used in combination with Lumiracoxib.Approved, Investigational
MacitentanBimatoprost may increase the hypotensive activities of Macitentan.Approved
Magnesium salicylateThe therapeutic efficacy of Bimatoprost can be decreased when used in combination with Magnesium salicylate.Approved
ManidipineBimatoprost may increase the hypotensive activities of Manidipine.Approved, Investigational
MasoprocolThe therapeutic efficacy of Bimatoprost can be decreased when used in combination with Masoprocol.Approved, Investigational
MebanazineMebanazine may increase the hypotensive activities of Bimatoprost.Withdrawn
MecamylamineMecamylamine may increase the hypotensive activities of Bimatoprost.Approved
Meclofenamic acidThe therapeutic efficacy of Bimatoprost can be decreased when used in combination with Meclofenamic acid.Approved, Vet Approved
Mefenamic acidThe therapeutic efficacy of Bimatoprost can be decreased when used in combination with Mefenamic acid.Approved
MeloxicamThe therapeutic efficacy of Bimatoprost can be decreased when used in combination with Meloxicam.Approved, Vet Approved
MesalazineThe therapeutic efficacy of Bimatoprost can be decreased when used in combination with Mesalazine.Approved
MetamizoleThe therapeutic efficacy of Bimatoprost can be decreased when used in combination with Metamizole.Investigational, Withdrawn
MethoserpidineBimatoprost may increase the hypotensive activities of Methoserpidine.Experimental
MethyldopaBimatoprost may increase the hypotensive activities of Methyldopa.Approved
Methylene blueMethylene blue may increase the hypotensive activities of Bimatoprost.Approved, Investigational
MethylphenidateMethylphenidate may decrease the antihypertensive activities of Bimatoprost.Approved, Investigational
MetipranololBimatoprost may increase the hypotensive activities of Metipranolol.Approved
MetolazoneMetolazone may increase the hypotensive activities of Bimatoprost.Approved
MetoprololMetoprolol may increase the hypotensive activities of Bimatoprost.Approved, Investigational
MetyrosineBimatoprost may increase the hypotensive activities of Metyrosine.Approved
MibefradilBimatoprost may increase the hypotensive activities of Mibefradil.Investigational, Withdrawn
MinaprineMinaprine may increase the hypotensive activities of Bimatoprost.Approved
MinoxidilMinoxidil may increase the hypotensive activities of Bimatoprost.Approved
MirodenafilMirodenafil may increase the antihypertensive activities of Bimatoprost.Investigational
MizoribineThe therapeutic efficacy of Bimatoprost can be decreased when used in combination with Mizoribine.Investigational
MoclobemideMoclobemide may increase the hypotensive activities of Bimatoprost.Approved
MoexiprilMoexipril may increase the hypotensive activities of Bimatoprost.Approved
MofebutazoneThe therapeutic efficacy of Bimatoprost can be decreased when used in combination with Mofebutazone.Experimental
MolsidomineMolsidomine may increase the hypotensive activities of Bimatoprost.Approved, Investigational
MoxonidineMoxonidine may increase the hypotensive activities of Bimatoprost.Approved, Investigational
MuzolimineBimatoprost may increase the hypotensive activities of Muzolimine.Experimental
Mycophenolate mofetilThe therapeutic efficacy of Bimatoprost can be decreased when used in combination with Mycophenolate mofetil.Approved, Investigational
Mycophenolic acidThe therapeutic efficacy of Bimatoprost can be decreased when used in combination with Mycophenolic acid.Approved
NabumetoneThe therapeutic efficacy of Bimatoprost can be decreased when used in combination with Nabumetone.Approved
NadololBimatoprost may increase the hypotensive activities of Nadolol.Approved
NafamostatThe therapeutic efficacy of Bimatoprost can be decreased when used in combination with Nafamostat.Approved, Investigational
NaftifineThe therapeutic efficacy of Bimatoprost can be decreased when used in combination with Naftifine.Approved
NaftopidilBimatoprost may increase the hypotensive activities of Naftopidil.Investigational
NaproxenThe therapeutic efficacy of Bimatoprost can be decreased when used in combination with Naproxen.Approved, Vet Approved
NebivololBimatoprost may increase the hypotensive activities of Nebivolol.Approved, Investigational
NepafenacThe therapeutic efficacy of Bimatoprost can be decreased when used in combination with Nepafenac.Approved
NialamideNialamide may increase the hypotensive activities of Bimatoprost.Withdrawn
NicardipineNicardipine may increase the hypotensive activities of Bimatoprost.Approved
NicorandilBimatoprost may increase the hypotensive activities of Nicorandil.Approved, Investigational
NifenazoneThe therapeutic efficacy of Bimatoprost can be decreased when used in combination with Nifenazone.Experimental
Niflumic AcidThe therapeutic efficacy of Bimatoprost can be decreased when used in combination with Niflumic Acid.Approved
NiguldipineBimatoprost may increase the hypotensive activities of Niguldipine.Experimental
NilvadipineBimatoprost may increase the hypotensive activities of Nilvadipine.Approved, Investigational
NimesulideThe therapeutic efficacy of Bimatoprost can be decreased when used in combination with Nimesulide.Approved, Investigational, Withdrawn
NimodipineNimodipine may increase the hypotensive activities of Bimatoprost.Approved
NisoldipineNisoldipine may increase the hypotensive activities of Bimatoprost.Approved
NitrendipineBimatoprost may increase the hypotensive activities of Nitrendipine.Approved, Investigational
NitroaspirinThe therapeutic efficacy of Bimatoprost can be decreased when used in combination with Nitroaspirin.Investigational
NitroprussideNitroprusside may increase the hypotensive activities of Bimatoprost.Approved
ObinutuzumabBimatoprost may increase the hypotensive activities of Obinutuzumab.Approved
OctamoxinOctamoxin may increase the hypotensive activities of Bimatoprost.Withdrawn
OlmesartanOlmesartan may increase the hypotensive activities of Bimatoprost.Approved, Investigational
OlopatadineThe therapeutic efficacy of Bimatoprost can be decreased when used in combination with Olopatadine.Approved
OlsalazineThe therapeutic efficacy of Bimatoprost can be decreased when used in combination with Olsalazine.Approved
OmapatrilatOmapatrilat may increase the hypotensive activities of Bimatoprost.Investigational
OrgoteinThe therapeutic efficacy of Bimatoprost can be decreased when used in combination with Orgotein.Vet Approved
OxaprozinThe therapeutic efficacy of Bimatoprost can be decreased when used in combination with Oxaprozin.Approved
OxprenololBimatoprost may increase the hypotensive activities of Oxprenolol.Approved
OxyphenbutazoneThe therapeutic efficacy of Bimatoprost can be decreased when used in combination with Oxyphenbutazone.Approved, Withdrawn
ParecoxibThe therapeutic efficacy of Bimatoprost can be decreased when used in combination with Parecoxib.Approved
PargylinePargyline may increase the hypotensive activities of Bimatoprost.Approved
ParthenolideThe therapeutic efficacy of Bimatoprost can be decreased when used in combination with Parthenolide.Investigational
PenbutololBimatoprost may increase the hypotensive activities of Penbutolol.Approved, Investigational
PentoliniumBimatoprost may increase the hypotensive activities of Pentolinium.Approved
PentoxifyllinePentoxifylline may increase the hypotensive activities of Bimatoprost.Approved, Investigational
PerindoprilPerindopril may increase the hypotensive activities of Bimatoprost.Approved
PhenelzinePhenelzine may increase the hypotensive activities of Bimatoprost.Approved
PheniprazinePheniprazine may increase the hypotensive activities of Bimatoprost.Withdrawn
PhenoxybenzamineBimatoprost may increase the hypotensive activities of Phenoxybenzamine.Approved
PhenoxypropazinePhenoxypropazine may increase the hypotensive activities of Bimatoprost.Withdrawn
PhentolaminePhentolamine may increase the hypotensive activities of Bimatoprost.Approved
PhenylbutazoneThe therapeutic efficacy of Bimatoprost can be decreased when used in combination with Phenylbutazone.Approved, Vet Approved
PimecrolimusThe therapeutic efficacy of Bimatoprost can be decreased when used in combination with Pimecrolimus.Approved, Investigational
PinacidilPinacidil may increase the hypotensive activities of Bimatoprost.Withdrawn
PindololBimatoprost may increase the hypotensive activities of Pindolol.Approved
PirfenidoneThe therapeutic efficacy of Bimatoprost can be decreased when used in combination with Pirfenidone.Approved, Investigational
PirlindolePirlindole may increase the hypotensive activities of Bimatoprost.Approved
PiroxicamThe therapeutic efficacy of Bimatoprost can be decreased when used in combination with Piroxicam.Approved, Investigational
PirprofenThe therapeutic efficacy of Bimatoprost can be decreased when used in combination with Pirprofen.Experimental
PivhydrazinePivhydrazine may increase the hypotensive activities of Bimatoprost.Withdrawn
Platelet Activating FactorBimatoprost may increase the hypotensive activities of Platelet Activating Factor.Experimental
PolythiazideBimatoprost may increase the hypotensive activities of Polythiazide.Approved
PranoprofenThe therapeutic efficacy of Bimatoprost can be decreased when used in combination with Pranoprofen.Experimental, Investigational
PrazosinPrazosin may increase the hypotensive activities of Bimatoprost.Approved
ProcarbazineProcarbazine may increase the hypotensive activities of Bimatoprost.Approved
ProglumetacinThe therapeutic efficacy of Bimatoprost can be decreased when used in combination with Proglumetacin.Experimental
PropacetamolThe therapeutic efficacy of Bimatoprost can be decreased when used in combination with Propacetamol.Approved, Investigational
PropranololPropranolol may increase the hypotensive activities of Bimatoprost.Approved, Investigational
PropyphenazoneThe therapeutic efficacy of Bimatoprost can be decreased when used in combination with Propyphenazone.Experimental
ProquazoneThe therapeutic efficacy of Bimatoprost can be decreased when used in combination with Proquazone.Experimental
PTC299The therapeutic efficacy of Bimatoprost can be decreased when used in combination with PTC299.Investigational
QuinaprilQuinapril may increase the hypotensive activities of Bimatoprost.Approved, Investigational
QuinineQuinine may increase the hypotensive activities of Bimatoprost.Approved
RamiprilRamipril may increase the hypotensive activities of Bimatoprost.Approved
RasagilineRasagiline may increase the hypotensive activities of Bimatoprost.Approved
RemikirenRemikiren may increase the hypotensive activities of Bimatoprost.Approved
RescinnamineBimatoprost may increase the hypotensive activities of Rescinnamine.Approved
ReserpineReserpine may increase the hypotensive activities of Bimatoprost.Approved, Investigational
ResveratrolThe therapeutic efficacy of Bimatoprost can be decreased when used in combination with Resveratrol.Approved, Experimental, Investigational
RilmenidineRilmenidine may increase the hypotensive activities of Bimatoprost.Investigational
RiociguatBimatoprost may increase the hypotensive activities of Riociguat.Approved
RituximabBimatoprost may increase the hypotensive activities of Rituximab.Approved
RofecoxibThe therapeutic efficacy of Bimatoprost can be decreased when used in combination with Rofecoxib.Investigational, Withdrawn
SafrazineSafrazine may increase the hypotensive activities of Bimatoprost.Withdrawn
SalicylamideThe therapeutic efficacy of Bimatoprost can be decreased when used in combination with Salicylamide.Approved
Salicylic acidThe therapeutic efficacy of Bimatoprost can be decreased when used in combination with Salicylic acid.Approved, Vet Approved
SalsalateThe therapeutic efficacy of Bimatoprost can be decreased when used in combination with Salsalate.Approved
SaprisartanBimatoprost may increase the hypotensive activities of Saprisartan.Experimental
SelegilineSelegiline may increase the hypotensive activities of Bimatoprost.Approved, Investigational, Vet Approved
SelexipagBimatoprost may increase the hypotensive activities of Selexipag.Approved
SemapimodThe therapeutic efficacy of Bimatoprost can be decreased when used in combination with Semapimod.Investigational
SeratrodastThe therapeutic efficacy of Bimatoprost can be decreased when used in combination with Seratrodast.Approved
SerrapeptaseThe therapeutic efficacy of Bimatoprost can be decreased when used in combination with Serrapeptase.Investigational
SildenafilSildenafil may increase the antihypertensive activities of Bimatoprost.Approved, Investigational
SitaxentanBimatoprost may increase the hypotensive activities of Sitaxentan.Approved, Investigational, Withdrawn
SpiraprilBimatoprost may increase the hypotensive activities of Spirapril.Approved
SRT501The therapeutic efficacy of Bimatoprost can be decreased when used in combination with SRT501.Investigational
SulfasalazineThe therapeutic efficacy of Bimatoprost can be decreased when used in combination with Sulfasalazine.Approved
SulindacThe therapeutic efficacy of Bimatoprost can be decreased when used in combination with Sulindac.Approved
SuprofenThe therapeutic efficacy of Bimatoprost can be decreased when used in combination with Suprofen.Approved, Withdrawn
SuxibuzoneThe therapeutic efficacy of Bimatoprost can be decreased when used in combination with Suxibuzone.Experimental
TadalafilTadalafil may increase the antihypertensive activities of Bimatoprost.Approved, Investigational
TalinololBimatoprost may increase the hypotensive activities of Talinolol.Investigational
TarenflurbilThe therapeutic efficacy of Bimatoprost can be decreased when used in combination with Tarenflurbil.Investigational
TelmisartanBimatoprost may increase the hypotensive activities of Telmisartan.Approved, Investigational
TemocaprilBimatoprost may increase the hypotensive activities of Temocapril.Experimental, Investigational
TenidapThe therapeutic efficacy of Bimatoprost can be decreased when used in combination with Tenidap.Experimental
TenoxicamThe therapeutic efficacy of Bimatoprost can be decreased when used in combination with Tenoxicam.Approved
TepoxalinThe therapeutic efficacy of Bimatoprost can be decreased when used in combination with Tepoxalin.Vet Approved
TeriflunomideThe therapeutic efficacy of Bimatoprost can be decreased when used in combination with Teriflunomide.Approved
TerlipressinBimatoprost may increase the hypotensive activities of Terlipressin.Approved, Investigational
TetrahydropalmatineBimatoprost may increase the hypotensive activities of Tetrahydropalmatine.Investigational
TheodrenalineBimatoprost may increase the hypotensive activities of Theodrenaline.Investigational
Tiaprofenic acidThe therapeutic efficacy of Bimatoprost can be decreased when used in combination with Tiaprofenic acid.Approved
TiboloneBimatoprost may increase the hypotensive activities of Tibolone.Approved, Investigational
TicrynafenBimatoprost may increase the hypotensive activities of Ticrynafen.Withdrawn
TimololTimolol may increase the hypotensive activities of Bimatoprost.Approved
TinoridineThe therapeutic efficacy of Bimatoprost can be decreased when used in combination with Tinoridine.Investigational
TolazolineTolazoline may increase the hypotensive activities of Bimatoprost.Approved, Vet Approved
Tolfenamic AcidThe therapeutic efficacy of Bimatoprost can be decreased when used in combination with Tolfenamic Acid.Approved
TolmetinThe therapeutic efficacy of Bimatoprost can be decreased when used in combination with Tolmetin.Approved
TolonidineBimatoprost may increase the hypotensive activities of Tolonidine.Experimental
ToloxatoneToloxatone may increase the hypotensive activities of Bimatoprost.Approved
TorasemideTorasemide may increase the hypotensive activities of Bimatoprost.Approved
TrandolaprilTrandolapril may increase the hypotensive activities of Bimatoprost.Approved
TranilastThe therapeutic efficacy of Bimatoprost can be decreased when used in combination with Tranilast.Approved, Investigational
Trans-2-PhenylcyclopropylamineTrans-2-Phenylcyclopropylamine may increase the hypotensive activities of Bimatoprost.Experimental
TranylcypromineTranylcypromine may increase the hypotensive activities of Bimatoprost.Approved
TravoprostTravoprost may increase the hypotensive activities of Bimatoprost.Approved
TreprostinilTreprostinil may increase the hypotensive activities of Bimatoprost.Approved, Investigational
TribenosideThe therapeutic efficacy of Bimatoprost can be decreased when used in combination with Tribenoside.Experimental
TrichlormethiazideBimatoprost may increase the hypotensive activities of Trichlormethiazide.Approved, Vet Approved
TrimazosinTrimazosin may increase the hypotensive activities of Bimatoprost.Experimental
TrimethaphanTrimethaphan may increase the hypotensive activities of Bimatoprost.Approved, Investigational
TriptolideThe therapeutic efficacy of Bimatoprost can be decreased when used in combination with Triptolide.Investigational
UdenafilUdenafil may increase the antihypertensive activities of Bimatoprost.Approved, Investigational
UnoprostoneBimatoprost may increase the hypotensive activities of Unoprostone.Approved
UrapidilUrapidil may increase the hypotensive activities of Bimatoprost.Investigational
ValdecoxibThe therapeutic efficacy of Bimatoprost can be decreased when used in combination with Valdecoxib.Investigational, Withdrawn
ValsartanValsartan may increase the hypotensive activities of Bimatoprost.Approved, Investigational
VardenafilVardenafil may increase the antihypertensive activities of Bimatoprost.Approved
VincamineBimatoprost may increase the hypotensive activities of Vincamine.Experimental
VinpocetineBimatoprost may increase the hypotensive activities of Vinpocetine.Investigational
XipamideBimatoprost may increase the hypotensive activities of Xipamide.Experimental
XylometazolineBimatoprost may increase the hypotensive activities of Xylometazoline.Approved
YohimbineYohimbine may decrease the antihypertensive activities of Bimatoprost.Approved, Vet Approved
ZaltoprofenThe therapeutic efficacy of Bimatoprost can be decreased when used in combination with Zaltoprofen.Approved, Investigational
ZileutonThe therapeutic efficacy of Bimatoprost can be decreased when used in combination with Zileuton.Approved, Investigational, Withdrawn
ZofenoprilBimatoprost may increase the hypotensive activities of Zofenopril.Experimental
ZomepiracThe therapeutic efficacy of Bimatoprost can be decreased when used in combination with Zomepirac.Withdrawn
Food Interactions
Not Available

References

Synthesis Reference

Jiang Xing Chen, "Process for the production of intermediates for making prostaglandin derivatives such as latanaprost, travaprost, and bimatoprost." U.S. Patent US20090287003, issued November 19, 2009.

US20090287003
General References
  1. Chen MJ, Cheng CY, Chen YC, Chou CK, Hsu WM: Effects of bimatoprost 0.03% on ocular hemodynamics in normal tension glaucoma. J Ocul Pharmacol Ther. 2006 Jun;22(3):188-93. [PubMed:16808680]
  2. Kruse P, Rieck P, Sherif Z, Liekfeld A: [Cystoid macular edema in a pseudophakic patient after several glaucoma procedures. Is local therapy with bimatoprost the reason?]. Klin Monbl Augenheilkd. 2006 Jun;223(6):534-7. [PubMed:16804825]
  3. Steinhauser SL: Decreased high-density lipoprotein serum levels associated with topical bimatoprost therapy. Optometry. 2006 Apr;77(4):177-9. [PubMed:16567279]
  4. Woodward DF, Krauss AH, Chen J, Lai RK, Spada CS, Burk RM, Andrews SW, Shi L, Liang Y, Kedzie KM, Chen R, Gil DW, Kharlamb A, Archeampong A, Ling J, Madhu C, Ni J, Rix P, Usansky J, Usansky H, Weber A, Welty D, Yang W, Tang-Liu DD, Garst ME, Brar B, Wheeler LA, Kaplan LJ: The pharmacology of bimatoprost (Lumigan). Surv Ophthalmol. 2001 May;45 Suppl 4:S337-45. [PubMed:11434936]
  5. Lim KS, Nau CB, O'Byrne MM, Hodge DO, Toris CB, McLaren JW, Johnson DH: Mechanism of action of bimatoprost, latanoprost, and travoprost in healthy subjects. A crossover study. Ophthalmology. 2008 May;115(5):790-795.e4. doi: 10.1016/j.ophtha.2007.07.002. [PubMed:18452763]
  6. Brubaker RF: Mechanism of action of bimatoprost (Lumigan). Surv Ophthalmol. 2001 May;45 Suppl 4:S347-51. [PubMed:11434937]
  7. Christiansen GA, Nau CB, McLaren JW, Johnson DH: Mechanism of ocular hypotensive action of bimatoprost (Lumigan) in patients with ocular hypertension or glaucoma. Ophthalmology. 2004 Sep;111(9):1658-62. [PubMed:15350319]
  8. Easthope SE, Perry CM: Topical bimatoprost: a review of its use in open-angle glaucoma and ocular hypertension. Drugs Aging. 2002;19(3):231-48. [PubMed:12027782]
  9. Patil AJ, Vajaranant TS, Edward DP: Bimatoprost - a review. Expert Opin Pharmacother. 2009 Nov;10(16):2759-68. doi: 10.1517/14656560903292649. [PubMed:19874254]
External Links
Human Metabolome Database
HMDB15041
PubChem Compound
5311027
PubChem Substance
46505334
ChemSpider
4470565
BindingDB
220120
ChEBI
51230
ChEMBL
CHEMBL1200963
Therapeutic Targets Database
DAP001217
PharmGKB
PA164748867
IUPHAR
1958
Guide to Pharmacology
GtP Drug Page
HET
15M
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
PDRhealth
PDRhealth Drug Page
Wikipedia
Bimatoprost
ATC Codes
S01EE03 — Bimatoprost
AHFS Codes
  • 52:40.28 — Prostaglandin Analogs
PDB Entries
2f38
FDA label
Download (24.4 KB)
MSDS
Download (19.2 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
0Active Not RecruitingTreatmentDermatochalasis1
1TerminatedTreatmentAndrogenetic Alopecia / Hair Thinning1
1, 2CompletedTreatmentGlaucoma / Ocular Hypertension1
1, 2CompletedTreatmentOcular Hypertension / Open-angle Glaucoma (OAG)2
2CompletedTreatmentAndrogenetic Alopecia / Male Pattern Hair Loss1
2CompletedTreatmentEyelash Hypotrichosis1
2CompletedTreatmentGlaucoma, Primary Open Angle (POAG) / Ocular Hypertension2
2CompletedTreatmentGlaucoma / Ocular Hypertension3
2CompletedTreatmentOcular Hypertension / Open-angle Glaucoma (OAG)3
2, 3CompletedTreatmentOcular Hypertension1
3CompletedTreatmentEyebrow Hypotrichosis1
3CompletedTreatmentEyelash Hypotrichosis2
3CompletedTreatmentEyelashes1
3CompletedTreatmentGlaucoma1
3CompletedTreatmentGlaucoma / Ocular Hypertension2
3CompletedTreatmentHypotrichosis1
3CompletedTreatmentHypotrichosis / Madarosis1
3CompletedTreatmentIdiopathic Eyelash Hypotrichosis1
3RecruitingPreventionGlaucoma1
3RecruitingTreatmentThyroid Associated Ophthalmopathy1
4Active Not RecruitingTreatmentNormal Tension Glaucoma / Open-angle Glaucoma (OAG)1
4CompletedNot AvailableGlaucoma1
4CompletedNot AvailableGlaucoma, Primary Open Angle (POAG) / Ocular Hypertension2
4CompletedTreatmentAlopecia Areata (AA) / Eyelash Hypotrichosis1
4CompletedTreatmentAnterior Uveitis (AU) / Cystoid Macular Edema1
4CompletedTreatmentApplication Site Pigmentation Changes / Glaucoma1
4CompletedTreatmentCataracts1
4CompletedTreatmentCrow's Feet Lines / Facial Rhytides / Glabellar Lines / Nasolabial Folds1
4CompletedTreatmentEndocrine ophthalmopathy1
4CompletedTreatmentEyelash Hypotrichosis1
4CompletedTreatmentGlaucoma, Primary Open Angle (POAG) / Ocular Hypertension1
4CompletedTreatmentGlaucoma / Intraocular Pressure / Ocular Hypertension1
4CompletedTreatmentGlaucoma / Ocular Hypertension10
4CompletedTreatmentGlaucoma / Ocular Hypertension / Open-angle Glaucoma (OAG)1
4CompletedTreatmentHypotrichosis4
4CompletedTreatmentOcular Hypertension1
4CompletedTreatmentOcular Hypertension / Open Angle Glaucoma (OAG)2
4CompletedTreatmentOcular Hypertension / Open-angle Glaucoma (OAG)5
4CompletedTreatmentOpen-angle Glaucoma (OAG)1
4RecruitingTreatmentGlaucoma1
4RecruitingTreatmentGlaucoma, Primary Open Angle (POAG) / Ocular Hypertension1
4RecruitingTreatmentGlaucoma / Ocular Hypertension1
4RecruitingTreatmentOcular Hypertension / Open-angle Glaucoma (OAG)1
4Unknown StatusPreventionGlaucoma / Ocular Hypertension / Thyroid Eye Disease1
4WithdrawnTreatmentRepigmentation / Vitiligo1
Not AvailableActive Not RecruitingNot AvailableEyelash Hypotrichosis1
Not AvailableActive Not RecruitingTreatmentIntraocular Pressure / Nail Growth Cessation1
Not AvailableCompletedNot AvailableEyelash Hypotrichosis1
Not AvailableCompletedNot AvailableOcular Hypertension / Open-angle Glaucoma (OAG)8
Not AvailableCompletedTreatmentAlopecia Areata (AA)1
Not AvailableCompletedTreatmentHypertrichosis1
Not AvailableCompletedTreatmentOcular Hypertension / Open-angle Glaucoma (OAG)1
Not AvailableRecruitingTreatmentGlaucoma1
Not AvailableUnknown StatusTreatmentGlaucoma, Angle-Closure1
Not AvailableUnknown StatusTreatmentOcular Hypertension / Primary Glaucoma1
Not AvailableWithdrawnSupportive CareCancer, Breast / Hair Thinning1

Pharmacoeconomics

Manufacturers
  • Allergan inc
Packagers
Dosage forms
FormRouteStrength
SolutionOphthalmic0.03 %
SolutionTopical0.03 %
Solution / dropsOphthalmic.1 mg/mL
Solution / dropsOphthalmic.3 mg/mL
SolutionOphthalmic0.01 %
Prices
Unit descriptionCostUnit
Lumigan .03% 7.5ml Bottle279.56USD bottle
Lumigan .03% 5ml Bottle171.4USD bottle
Lumigan .03% 2.5ml Bottle91.16USD bottle
Lumigan 0.03% eye drops44.82USD ml
Latisse 0.03% eyelash solution36.0USD ml
Lumigan 0.03 % Solution12.18USD ml
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)
US6403649No1992-09-212012-09-21Us
CA2585691No2009-05-192026-03-14Canada
CA2144967No2003-11-112013-09-09Canada
US8299118No2005-03-162025-03-16Us
US8309605No2005-03-162025-03-16Us
US8338479No2005-03-162025-03-16Us
US8586630No2005-03-162025-03-16Us
US8524777No2005-03-162025-03-16Us
US8772338No2005-03-162025-03-16Us
US9155716No2005-03-162025-03-16Us
US9241918No2005-03-162025-03-16Us
US7851504No2007-06-132027-06-13Us
US8933120No2005-03-162025-03-16Us
US8933127No2005-03-162025-03-16Us
US8278353No2005-03-162025-03-16Us
US8906962No2001-01-312021-01-31Us
US8038988No2003-08-252023-08-25Us
US8101161No2004-05-252024-05-25Us
US8263054No2003-01-152023-01-15Us
US8632760No2003-01-152023-01-15Us
US8758733No2003-01-152023-01-15Us
US8926953No2003-01-152023-01-15Us
US8541466No2001-01-312021-01-31Us
US7388029No2002-01-212022-01-21Us
US7351404No2004-05-252024-05-25Us
US9216183No2003-01-152023-01-15Us
US9226931No2003-01-152023-01-15Us
US8986715No2003-01-152023-01-15Us
US9579270No2001-01-312021-01-31Us

Properties

State
Solid
Experimental Properties
PropertyValueSource
water solubilitySlightly solubleNot Available
logP3.2Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.0187 mg/mLALOGPS
logP3.41ALOGPS
logP2.63ChemAxon
logS-4.4ALOGPS
pKa (Strongest Acidic)14.35ChemAxon
pKa (Strongest Basic)-0.23ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area89.79 Å2ChemAxon
Rotatable Bond Count12ChemAxon
Refractivity122.83 m3·mol-1ChemAxon
Polarizability48.99 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9975
Blood Brain Barrier+0.825
Caco-2 permeable-0.5699
P-glycoprotein substrateSubstrate0.5541
P-glycoprotein inhibitor INon-inhibitor0.8671
P-glycoprotein inhibitor IINon-inhibitor0.8616
Renal organic cation transporterNon-inhibitor0.8078
CYP450 2C9 substrateNon-substrate0.7703
CYP450 2D6 substrateNon-substrate0.7406
CYP450 3A4 substrateSubstrate0.552
CYP450 1A2 substrateNon-inhibitor0.6764
CYP450 2C9 inhibitorNon-inhibitor0.7695
CYP450 2D6 inhibitorNon-inhibitor0.6384
CYP450 2C19 inhibitorNon-inhibitor0.7632
CYP450 3A4 inhibitorNon-inhibitor0.757
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.7049
Ames testNon AMES toxic0.7646
CarcinogenicityNon-carcinogens0.9257
BiodegradationNot ready biodegradable0.6415
Rat acute toxicity2.1085 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9251
hERG inhibition (predictor II)Non-inhibitor0.7822
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Taxonomy

Description
This compound belongs to the class of organic compounds known as prostaglandins and related compounds. These are unsaturated carboxylic acids consisting of a 20 carbon skeleton that also contains a five member ring, and are based upon the fatty acid arachidonic acid.
Kingdom
Organic compounds
Super Class
Lipids and lipid-like molecules
Class
Fatty Acyls
Sub Class
Eicosanoids
Direct Parent
Prostaglandins and related compounds
Alternative Parents
N-acyl amines / Cyclopentanols / Benzene and substituted derivatives / Secondary carboxylic acid amides / Cyclic alcohols and derivatives / Organopnictogen compounds / Organonitrogen compounds / Organic oxides / Hydrocarbon derivatives / Carbonyl compounds
Substituents
Prostaglandin skeleton / Monocyclic benzene moiety / Cyclopentanol / Fatty amide / Benzenoid / N-acyl-amine / Cyclic alcohol / Carboxamide group / Secondary carboxylic acid amide / Secondary alcohol
Molecular Framework
Aromatic homomonocyclic compounds
External Descriptors
monocarboxylic acid amide (CHEBI:51230)

Targets

Kind
Protein
Organism
Human
Pharmacological action
Yes
Actions
Agonist
General Function
Prostaglandin f receptor activity
Specific Function
Receptor for prostaglandin F2-alpha (PGF2-alpha). The activity of this receptor is mediated by G proteins which activate a phosphatidylinositol-calcium second messenger system. Initiates luteolysis...
Gene Name
PTGFR
Uniprot ID
P43088
Uniprot Name
Prostaglandin F2-alpha receptor
Molecular Weight
40054.1 Da
References
  1. Sharif NA, Williams GW, Kelly CR: Bimatoprost and its free acid are prostaglandin FP receptor agonists. Eur J Pharmacol. 2001 Dec 7;432(2-3):211-3. [PubMed:11740958]
  2. Sharif NA, Kelly CR, Crider JY: Agonist activity of bimatoprost, travoprost, latanoprost, unoprostone isopropyl ester and other prostaglandin analogs at the cloned human ciliary body FP prostaglandin receptor. J Ocul Pharmacol Ther. 2002 Aug;18(4):313-24. [PubMed:12222762]
  3. Sharif NA, Kelly CR, Crider JY, Williams GW, Xu SX: Ocular hypotensive FP prostaglandin (PG) analogs: PG receptor subtype binding affinities and selectivities, and agonist potencies at FP and other PG receptors in cultured cells. J Ocul Pharmacol Ther. 2003 Dec;19(6):501-15. [PubMed:14733708]
  4. Lim KS, Nau CB, O'Byrne MM, Hodge DO, Toris CB, McLaren JW, Johnson DH: Mechanism of action of bimatoprost, latanoprost, and travoprost in healthy subjects. A crossover study. Ophthalmology. 2008 May;115(5):790-795.e4. doi: 10.1016/j.ophtha.2007.07.002. [PubMed:18452763]
  5. Mintz EE: Group supervision: an experiential approach. Int J Group Psychother. 1978 Oct;28(4):467-9. [PubMed:689791]
  6. Neacsu AM: [Receptors involved in the mechanism of action of topical prostaglandines]. Oftalmologia. 2009;53(2):3-7. [PubMed:19697832]
  7. Wan Z, Woodward DF, Cornell CL, Fliri HG, Martos JL, Pettit SN, Wang JW, Kharlamb AB, Wheeler LA, Garst ME, Landsverk KJ, Struble CS, Stamer WD: Bimatoprost, prostamide activity, and conventional drainage. Invest Ophthalmol Vis Sci. 2007 Sep;48(9):4107-15. [PubMed:17724194]
  8. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352]
Kind
Protein
Organism
Human
Pharmacological action
Yes
Actions
Agonist
General Function
Prostaglandin e receptor activity
Specific Function
Receptor for prostaglandin E2 (PGE2). The activity of this receptor is mediated by G(q) proteins which activate a phosphatidylinositol-calcium second messenger system. May play a role as an importa...
Gene Name
PTGER1
Uniprot ID
P34995
Uniprot Name
Prostaglandin E2 receptor EP1 subtype
Molecular Weight
41800.655 Da
References
  1. Sharif NA, Kelly CR, Crider JY, Williams GW, Xu SX: Ocular hypotensive FP prostaglandin (PG) analogs: PG receptor subtype binding affinities and selectivities, and agonist potencies at FP and other PG receptors in cultured cells. J Ocul Pharmacol Ther. 2003 Dec;19(6):501-15. [PubMed:14733708]
  2. Ota T, Aihara M, Saeki T, Narumiya S, Araie M: The effects of prostaglandin analogues on prostanoid EP1, EP2, and EP3 receptor-deficient mice. Invest Ophthalmol Vis Sci. 2006 Aug;47(8):3395-9. [PubMed:16877408]
Kind
Protein
Organism
Human
Pharmacological action
Yes
Actions
Agonist
General Function
Rna polymerase ii transcription factor activity, ligand-activated sequence-specific dna binding
Specific Function
Receptor for prostaglandin E2 (PGE2); the EP3 receptor may be involved in inhibition of gastric acid secretion, modulation of neurotransmitter release in central and peripheral neurons, inhibition ...
Gene Name
PTGER3
Uniprot ID
P43115
Uniprot Name
Prostaglandin E2 receptor EP3 subtype
Molecular Weight
43309.335 Da
References
  1. Sharif NA, Kelly CR, Crider JY, Williams GW, Xu SX: Ocular hypotensive FP prostaglandin (PG) analogs: PG receptor subtype binding affinities and selectivities, and agonist potencies at FP and other PG receptors in cultured cells. J Ocul Pharmacol Ther. 2003 Dec;19(6):501-15. [PubMed:14733708]
  2. Gabelt BT, Hennes EA, Bendel MA, Constant CE, Okka M, Kaufman PL: Prostaglandin subtype-selective and non-selective IOP-lowering comparison in monkeys. J Ocul Pharmacol Ther. 2009 Feb;25(1):1-8. doi: 10.1089/jop.2008.0089. [PubMed:19232013]
  3. Ota T, Aihara M, Saeki T, Narumiya S, Araie M: The effects of prostaglandin analogues on prostanoid EP1, EP2, and EP3 receptor-deficient mice. Invest Ophthalmol Vis Sci. 2006 Aug;47(8):3395-9. [PubMed:16877408]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase activity
Specific Function
Catalyzes the conversion of aldehydes and ketones to alcohols. Catalyzes the reduction of prostaglandin (PG) D2, PGH2 and phenanthrenequinone (PQ) and the oxidation of 9-alpha,11-beta-PGF2 to PGD2....
Gene Name
AKR1C3
Uniprot ID
P42330
Uniprot Name
Aldo-keto reductase family 1 member C3
Molecular Weight
36852.89 Da
References
  1. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [PubMed:10592235]

Drug created on June 13, 2005 07:24 / Updated on December 10, 2017 17:18