You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on DrugBank.
Identification
NameBimatoprost
Accession NumberDB00905  (APRD00826, DB06863)
TypeSmall Molecule
GroupsApproved, Investigational
DescriptionBimatoprost 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 Identifiers
  • AGN 192024
Approved Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Latissesolution/ drops.3 mg/mLophthalmicAllergan, Inc.2009-01-26Not applicableUs
Latissesolution0.03 %topicalAllergan Inc2010-11-01Not applicableCanada
Lumigansolution/ drops.1 mg/mLophthalmicAllergan, Inc.2010-09-10Not applicableUs
Lumigansolution0.03 %ophthalmicAllergan Inc2002-05-24Not applicableCanada
Lumigansolution/ drops.3 mg/mLophthalmicPhysicians Total Care, Inc.2001-03-22Not applicableUs
Lumigansolution/ drops.1 mg/mLophthalmicPhysicians Total Care, Inc.2011-09-14Not applicableUs
Lumigan PFsolution0.03 %ophthalmicAllergan IncNot applicableNot applicableCanada
Lumigan Rcsolution0.01 %ophthalmicAllergan Inc2009-06-16Not applicableCanada
Vistitansolution0.03 %ophthalmicSandoz Canada Incorporated2016-05-13Not applicableCanada
Approved Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Apo-bimatoprostsolution0.03 %ophthalmicApotex IncNot applicableNot applicableCanada
Apo-bimatoprostsolution0.03 %topicalApotex IncNot applicableNot applicableCanada
Bimatoprostsolution/ drops.3 mg/mLophthalmicLupin Pharmaceuticals, Inc.2015-05-13Not applicableUs
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International BrandsNot Available
Brand mixturesNot Available
SaltsNot Available
Categories
UNIIQXS94885MZ
CAS number155206-00-1
WeightAverage: 415.5656
Monoisotopic: 415.272258677
Chemical FormulaC25H37NO4
InChI KeyInChIKey=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[C@@H](O)C[C@@H](O)[C@@H]1\C=C\[C@@H](O)CCC1=CC=CC=C1
Taxonomy
DescriptionThis 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.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassEicosanoids
Direct ParentProstaglandins and related compounds
Alternative Parents
Substituents
  • Prostaglandin skeleton
  • Benzenoid
  • N-acyl-amine
  • Fatty amide
  • Cyclopentanol
  • Monocyclic benzene moiety
  • Cyclic alcohol
  • Secondary carboxylic acid amide
  • Secondary alcohol
  • Carboxamide group
  • Carboxylic acid derivative
  • Carboxylic acid amide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Alcohol
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Pharmacology
IndicationFor 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.
PharmacodynamicsBimatoprost 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 actionBimatoprost 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.
Related Articles
AbsorptionSystemically absorbed when administered to the eye.
Volume of distribution
  • 0.67 L/kg
Protein bindingApproximately 88% of bimatoprost is bound in human plasma.
Metabolism

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

Route of eliminationUp to 67% of the administered dose was excreted in the urine while 25% of the dose was recovered in the feces.
Half lifeElimination half-life is approximately 45 minutes.
Clearance
  • 1.5 L/hr/kg [Healthy subjects receiving IV administration of 3.12 ug/kg]
ToxicityIn 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
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
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 )
Pharmacoeconomics
Manufacturers
  • Allergan inc
Packagers
Dosage forms
FormRouteStrength
Solutiontopical0.03 %
Solution/ dropsophthalmic.3 mg/mL
Solutionophthalmic0.03 %
Solution/ dropsophthalmic.1 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)
CA2144967 No2003-11-112013-09-09Canada
CA2585691 No2009-05-192026-03-14Canada
US6403649 No1992-09-212012-09-21Us
US7351404 No2004-05-252024-05-25Us
US7388029 No2002-01-212022-01-21Us
US7851504 No2007-06-132027-06-13Us
US8038988 No2003-08-252023-08-25Us
US8101161 No2004-05-252024-05-25Us
US8263054 No2003-01-152023-01-15Us
US8278353 No2005-03-162025-03-16Us
US8299118 No2005-03-162025-03-16Us
US8309605 No2005-03-162025-03-16Us
US8338479 No2005-03-162025-03-16Us
US8524777 No2005-03-162025-03-16Us
US8541466 No2001-01-312021-01-31Us
US8586630 No2005-03-162025-03-16Us
US8632760 No2003-01-152023-01-15Us
US8758733 No2003-01-152023-01-15Us
US8772338 No2005-03-162025-03-16Us
US8906962 No2001-01-312021-01-31Us
US8926953 No2003-01-152023-01-15Us
US8933120 No2005-03-162025-03-16Us
US8933127 No2005-03-162025-03-16Us
US8986715 No2003-01-152023-01-15Us
US9155716 No2005-03-162025-03-16Us
US9216183 No2003-01-152023-01-15Us
US9226931 No2003-01-152023-01-15Us
US9241918 No2005-03-162025-03-16Us
Properties
StateSolid
Experimental Properties
PropertyValueSource
water solubilitySlightly solubleNot Available
logP3.2Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.0187 mg/mLALOGPS
logP3.41ALOGPS
logP2.63ChemAxon
logS-4.3ALOGPS
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 RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot 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
ATC CodesS01EE03
AHFS Codes
  • 52:92.00
PDB EntriesNot Available
FDA labelDownload (24.4 KB)
MSDSDownload (19.2 KB)
Interactions
Drug Interactions
Drug
7,8-DICHLORO-1,2,3,4-TETRAHYDROISOQUINOLINE7,8-DICHLORO-1,2,3,4-TETRAHYDROISOQUINOLINE may increase the hypotensive activities of Bimatoprost.
AcebutololBimatoprost may increase the hypotensive activities of Acebutolol.
AceclofenacThe therapeutic efficacy of Bimatoprost can be decreased when used in combination with Aceclofenac.
Acetylsalicylic acidThe therapeutic efficacy of Bimatoprost can be decreased when used in combination with Acetylsalicylic acid.
AdapaleneThe therapeutic efficacy of Bimatoprost can be decreased when used in combination with Adapalene.
AlfuzosinAlfuzosin may increase the hypotensive activities of Bimatoprost.
AliskirenBimatoprost may increase the hypotensive activities of Aliskiren.
AlprenololAlprenolol may increase the hypotensive activities of Bimatoprost.
AmbrisentanBimatoprost may increase the hypotensive activities of Ambrisentan.
AmifostineBimatoprost may increase the hypotensive activities of Amifostine.
AmlodipineAmlodipine may increase the hypotensive activities of Bimatoprost.
AntipyrineThe therapeutic efficacy of Bimatoprost can be decreased when used in combination with Antipyrine.
ApremilastThe therapeutic efficacy of Bimatoprost can be decreased when used in combination with Apremilast.
AtenololAtenolol may increase the hypotensive activities of Bimatoprost.
AzapropazoneThe therapeutic efficacy of Bimatoprost can be decreased when used in combination with Azapropazone.
AzelastineThe therapeutic efficacy of Bimatoprost can be decreased when used in combination with Azelastine.
BalsalazideThe therapeutic efficacy of Bimatoprost can be decreased when used in combination with Balsalazide.
BenazeprilBenazepril may increase the hypotensive activities of Bimatoprost.
BendroflumethiazideBendroflumethiazide may increase the hypotensive activities of Bimatoprost.
BenmoxinBenmoxin may increase the hypotensive activities of Bimatoprost.
BenoxaprofenThe therapeutic efficacy of Bimatoprost can be decreased when used in combination with Benoxaprofen.
BepridilBimatoprost may increase the hypotensive activities of Bepridil.
BetaxololBetaxolol may increase the hypotensive activities of Bimatoprost.
BethanidineBethanidine may increase the hypotensive activities of Bimatoprost.
BisoprololBisoprolol may increase the hypotensive activities of Bimatoprost.
BosentanBosentan may increase the hypotensive activities of Bimatoprost.
BretyliumBimatoprost may increase the hypotensive activities of Bretylium.
BrimonidineBimatoprost may increase the hypotensive activities of Brimonidine.
BrimonidineBrimonidine may increase the antihypertensive activities of Bimatoprost.
BromfenacThe therapeutic efficacy of Bimatoprost can be decreased when used in combination with Bromfenac.
BupranololBimatoprost may increase the hypotensive activities of Bupranolol.
CandesartanCandesartan may increase the hypotensive activities of Bimatoprost.
CandoxatrilCandoxatril may increase the hypotensive activities of Bimatoprost.
CaptoprilBimatoprost may increase the hypotensive activities of Captopril.
CaroxazoneCaroxazone may increase the hypotensive activities of Bimatoprost.
CarprofenThe therapeutic efficacy of Bimatoprost can be decreased when used in combination with Carprofen.
CarteololCarteolol may increase the hypotensive activities of Bimatoprost.
CarvedilolBimatoprost may increase the hypotensive activities of Carvedilol.
CastanospermineThe therapeutic efficacy of Bimatoprost can be decreased when used in combination with Castanospermine.
CelecoxibThe therapeutic efficacy of Bimatoprost can be decreased when used in combination with Celecoxib.
CeliprololBimatoprost may increase the hypotensive activities of Celiprolol.
ChloroquineThe therapeutic efficacy of Bimatoprost can be decreased when used in combination with Chloroquine.
ChlorothiazideChlorothiazide may increase the hypotensive activities of Bimatoprost.
ChlorthalidoneChlorthalidone may increase the hypotensive activities of Bimatoprost.
CilazaprilBimatoprost may increase the hypotensive activities of Cilazapril.
ClonidineClonidine may increase the hypotensive activities of Bimatoprost.
ClonixinThe therapeutic efficacy of Bimatoprost can be decreased when used in combination with Clonixin.
CryptenamineCryptenamine may increase the hypotensive activities of Bimatoprost.
CyclothiazideCyclothiazide may increase the hypotensive activities of Bimatoprost.
D-LimoneneThe therapeutic efficacy of Bimatoprost can be decreased when used in combination with D-Limonene.
DebrisoquinBimatoprost may increase the hypotensive activities of Debrisoquin.
DeserpidineBimatoprost may increase the hypotensive activities of Deserpidine.
DiazoxideDiazoxide may increase the hypotensive activities of Bimatoprost.
DiclofenacThe therapeutic efficacy of Bimatoprost can be decreased when used in combination with Diclofenac.
DiflunisalThe therapeutic efficacy of Bimatoprost can be decreased when used in combination with Diflunisal.
DiltiazemDiltiazem may increase the hypotensive activities of Bimatoprost.
DorzolamideDorzolamide may increase the hypotensive activities of Bimatoprost.
DoxazosinDoxazosin may increase the hypotensive activities of Bimatoprost.
DroxicamThe therapeutic efficacy of Bimatoprost can be decreased when used in combination with Droxicam.
EfonidipineBimatoprost may increase the hypotensive activities of Efonidipine.
EnalaprilEnalapril may increase the hypotensive activities of Bimatoprost.
EnalaprilatBimatoprost may increase the hypotensive activities of Enalaprilat.
EpirizoleThe therapeutic efficacy of Bimatoprost can be decreased when used in combination with Epirizole.
EpoprostenolBimatoprost may increase the hypotensive activities of Epoprostenol.
EprosartanEprosartan may increase the hypotensive activities of Bimatoprost.
EtanerceptThe therapeutic efficacy of Bimatoprost can be decreased when used in combination with Etanercept.
EtodolacThe therapeutic efficacy of Bimatoprost can be decreased when used in combination with Etodolac.
EtofenamateThe therapeutic efficacy of Bimatoprost can be decreased when used in combination with Etofenamate.
EtoricoxibThe therapeutic efficacy of Bimatoprost can be decreased when used in combination with Etoricoxib.
Evening primrose oilThe therapeutic efficacy of Bimatoprost can be decreased when used in combination with Evening primrose oil.
exisulindThe therapeutic efficacy of Bimatoprost can be decreased when used in combination with exisulind.
FelodipineBimatoprost may increase the hypotensive activities of Felodipine.
FenbufenThe therapeutic efficacy of Bimatoprost can be decreased when used in combination with Fenbufen.
FenoldopamFenoldopam may increase the hypotensive activities of Bimatoprost.
FenoprofenThe therapeutic efficacy of Bimatoprost can be decreased when used in combination with Fenoprofen.
FloctafenineThe therapeutic efficacy of Bimatoprost can be decreased when used in combination with Floctafenine.
FlunixinThe therapeutic efficacy of Bimatoprost can be decreased when used in combination with Flunixin.
FlurbiprofenThe therapeutic efficacy of Bimatoprost can be decreased when used in combination with Flurbiprofen.
FosinoprilFosinopril may increase the hypotensive activities of Bimatoprost.
FurazolidoneFurazolidone may increase the hypotensive activities of Bimatoprost.
GuanabenzGuanabenz may increase the hypotensive activities of Bimatoprost.
GuanadrelGuanadrel may increase the hypotensive activities of Bimatoprost.
GuanethidineBimatoprost may increase the hypotensive activities of Guanethidine.
GuanfacineBimatoprost may increase the hypotensive activities of Guanfacine.
HexamethoniumBimatoprost may increase the hypotensive activities of Hexamethonium.
HMPL-004The therapeutic efficacy of Bimatoprost can be decreased when used in combination with HMPL-004.
HydracarbazineHydracarbazine may increase the hypotensive activities of Bimatoprost.
HydralazineBimatoprost may increase the hypotensive activities of Hydralazine.
HydrochlorothiazideBimatoprost may increase the hypotensive activities of Hydrochlorothiazide.
HydroflumethiazideHydroflumethiazide may increase the hypotensive activities of Bimatoprost.
IbuprofenThe therapeutic efficacy of Bimatoprost can be decreased when used in combination with Ibuprofen.
IbuproxamThe therapeutic efficacy of Bimatoprost can be decreased when used in combination with Ibuproxam.
IcatibantThe therapeutic efficacy of Bimatoprost can be decreased when used in combination with Icatibant.
IloprostIloprost may increase the hypotensive activities of Bimatoprost.
IndapamideIndapamide may increase the hypotensive activities of Bimatoprost.
IndenololBimatoprost may increase the hypotensive activities of Indenolol.
IndomethacinThe therapeutic efficacy of Bimatoprost can be decreased when used in combination with Indomethacin.
IndoprofenThe therapeutic efficacy of Bimatoprost can be decreased when used in combination with Indoprofen.
IndoraminBimatoprost may increase the hypotensive activities of Indoramin.
IproclozideIproclozide may increase the hypotensive activities of Bimatoprost.
IproniazidIproniazid may increase the hypotensive activities of Bimatoprost.
IrbesartanBimatoprost may increase the hypotensive activities of Irbesartan.
IsocarboxazidIsocarboxazid may increase the hypotensive activities of Bimatoprost.
IsoxicamThe therapeutic efficacy of Bimatoprost can be decreased when used in combination with Isoxicam.
IsradipineIsradipine may increase the hypotensive activities of Bimatoprost.
KebuzoneThe therapeutic efficacy of Bimatoprost can be decreased when used in combination with Kebuzone.
KetoprofenThe therapeutic efficacy of Bimatoprost can be decreased when used in combination with Ketoprofen.
KetorolacThe therapeutic efficacy of Bimatoprost can be decreased when used in combination with Ketorolac.
LabetalolLabetalol may increase the hypotensive activities of Bimatoprost.
LacidipineBimatoprost may increase the hypotensive activities of Lacidipine.
LatanoprostLatanoprost may increase the hypotensive activities of Bimatoprost.
LeflunomideThe therapeutic efficacy of Bimatoprost can be decreased when used in combination with Leflunomide.
LercanidipineLercanidipine may increase the hypotensive activities of Bimatoprost.
LisinoprilLisinopril may increase the hypotensive activities of Bimatoprost.
LofexidineBimatoprost may increase the hypotensive activities of Lofexidine.
LornoxicamThe therapeutic efficacy of Bimatoprost can be decreased when used in combination with Lornoxicam.
LosartanLosartan may increase the hypotensive activities of Bimatoprost.
LoxoprofenThe therapeutic efficacy of Bimatoprost can be decreased when used in combination with Loxoprofen.
LumiracoxibThe therapeutic efficacy of Bimatoprost can be decreased when used in combination with Lumiracoxib.
MacitentanBimatoprost may increase the hypotensive activities of Macitentan.
Magnesium salicylateThe therapeutic efficacy of Bimatoprost can be decreased when used in combination with Magnesium salicylate.
ManidipineBimatoprost may increase the hypotensive activities of Manidipine.
MasoprocolThe therapeutic efficacy of Bimatoprost can be decreased when used in combination with Masoprocol.
MebanazineMebanazine may increase the hypotensive activities of Bimatoprost.
MecamylamineMecamylamine may increase the hypotensive activities of Bimatoprost.
Meclofenamic acidThe therapeutic efficacy of Bimatoprost can be decreased when used in combination with Meclofenamic acid.
Mefenamic acidThe therapeutic efficacy of Bimatoprost can be decreased when used in combination with Mefenamic acid.
MeloxicamThe therapeutic efficacy of Bimatoprost can be decreased when used in combination with Meloxicam.
MesalazineThe therapeutic efficacy of Bimatoprost can be decreased when used in combination with Mesalazine.
MetamizoleThe therapeutic efficacy of Bimatoprost can be decreased when used in combination with Metamizole.
MethyldopaBimatoprost may increase the hypotensive activities of Methyldopa.
Methylene blueMethylene blue may increase the hypotensive activities of Bimatoprost.
MethylphenidateMethylphenidate may decrease the antihypertensive activities of Bimatoprost.
MetipranololBimatoprost may increase the hypotensive activities of Metipranolol.
MetolazoneMetolazone may increase the hypotensive activities of Bimatoprost.
MetoprololMetoprolol may increase the hypotensive activities of Bimatoprost.
MibefradilBimatoprost may increase the hypotensive activities of Mibefradil.
MinaprineMinaprine may increase the hypotensive activities of Bimatoprost.
MinoxidilMinoxidil may increase the hypotensive activities of Bimatoprost.
MoclobemideMoclobemide may increase the hypotensive activities of Bimatoprost.
MoexiprilMoexipril may increase the hypotensive activities of Bimatoprost.
MolsidomineMolsidomine may increase the hypotensive activities of Bimatoprost.
MoxonidineBimatoprost may increase the hypotensive activities of Moxonidine.
Mycophenolate mofetilThe therapeutic efficacy of Bimatoprost can be decreased when used in combination with Mycophenolate mofetil.
Mycophenolic acidThe therapeutic efficacy of Bimatoprost can be decreased when used in combination with Mycophenolic acid.
NabumetoneThe therapeutic efficacy of Bimatoprost can be decreased when used in combination with Nabumetone.
NadololBimatoprost may increase the hypotensive activities of Nadolol.
NaftifineThe therapeutic efficacy of Bimatoprost can be decreased when used in combination with Naftifine.
NaproxenThe therapeutic efficacy of Bimatoprost can be decreased when used in combination with Naproxen.
NCX 4016The therapeutic efficacy of Bimatoprost can be decreased when used in combination with NCX 4016.
NebivololBimatoprost may increase the hypotensive activities of Nebivolol.
NepafenacThe therapeutic efficacy of Bimatoprost can be decreased when used in combination with Nepafenac.
NialamideNialamide may increase the hypotensive activities of Bimatoprost.
NicardipineNicardipine may increase the hypotensive activities of Bimatoprost.
NicorandilBimatoprost may increase the hypotensive activities of Nicorandil.
Niflumic AcidThe therapeutic efficacy of Bimatoprost can be decreased when used in combination with Niflumic Acid.
NiguldipineBimatoprost may increase the hypotensive activities of Niguldipine.
NilvadipineBimatoprost may increase the hypotensive activities of Nilvadipine.
NimesulideThe therapeutic efficacy of Bimatoprost can be decreased when used in combination with Nimesulide.
NimodipineNimodipine may increase the hypotensive activities of Bimatoprost.
NisoldipineNisoldipine may increase the hypotensive activities of Bimatoprost.
NitrendipineBimatoprost may increase the hypotensive activities of Nitrendipine.
NitroprussideNitroprusside may increase the hypotensive activities of Bimatoprost.
ObinutuzumabBimatoprost may increase the hypotensive activities of Obinutuzumab.
OctamoxinOctamoxin may increase the hypotensive activities of Bimatoprost.
OlmesartanOlmesartan may increase the hypotensive activities of Bimatoprost.
OlopatadineThe therapeutic efficacy of Bimatoprost can be decreased when used in combination with Olopatadine.
OlsalazineThe therapeutic efficacy of Bimatoprost can be decreased when used in combination with Olsalazine.
OmapatrilatOmapatrilat may increase the hypotensive activities of Bimatoprost.
OrgoteinThe therapeutic efficacy of Bimatoprost can be decreased when used in combination with Orgotein.
OxaprozinThe therapeutic efficacy of Bimatoprost can be decreased when used in combination with Oxaprozin.
OxprenololBimatoprost may increase the hypotensive activities of Oxprenolol.
OxyphenbutazoneThe therapeutic efficacy of Bimatoprost can be decreased when used in combination with Oxyphenbutazone.
ParecoxibThe therapeutic efficacy of Bimatoprost can be decreased when used in combination with Parecoxib.
PargylineBimatoprost may increase the hypotensive activities of Pargyline.
PenbutololBimatoprost may increase the hypotensive activities of Penbutolol.
PentoliniumBimatoprost may increase the hypotensive activities of Pentolinium.
PentoxifyllinePentoxifylline may increase the hypotensive activities of Bimatoprost.
PerindoprilPerindopril may increase the hypotensive activities of Bimatoprost.
PhenelzinePhenelzine may increase the hypotensive activities of Bimatoprost.
PheniprazinePheniprazine may increase the hypotensive activities of Bimatoprost.
PhenoxybenzamineBimatoprost may increase the hypotensive activities of Phenoxybenzamine.
PhenoxypropazinePhenoxypropazine may increase the hypotensive activities of Bimatoprost.
PhentolaminePhentolamine may increase the hypotensive activities of Bimatoprost.
PhenylbutazoneThe therapeutic efficacy of Bimatoprost can be decreased when used in combination with Phenylbutazone.
PimecrolimusThe therapeutic efficacy of Bimatoprost can be decreased when used in combination with Pimecrolimus.
PinacidilBimatoprost may increase the hypotensive activities of Pinacidil.
PindololBimatoprost may increase the hypotensive activities of Pindolol.
PirfenidoneThe therapeutic efficacy of Bimatoprost can be decreased when used in combination with Pirfenidone.
PirlindolePirlindole may increase the hypotensive activities of Bimatoprost.
PiroxicamThe therapeutic efficacy of Bimatoprost can be decreased when used in combination with Piroxicam.
PivhydrazinePivhydrazine may increase the hypotensive activities of Bimatoprost.
PolythiazideBimatoprost may increase the hypotensive activities of Polythiazide.
PrazosinPrazosin may increase the hypotensive activities of Bimatoprost.
PropacetamolThe therapeutic efficacy of Bimatoprost can be decreased when used in combination with Propacetamol.
PropranololPropranolol may increase the hypotensive activities of Bimatoprost.
PTC299The therapeutic efficacy of Bimatoprost can be decreased when used in combination with PTC299.
QuinaprilQuinapril may increase the hypotensive activities of Bimatoprost.
QuinineQuinine may increase the hypotensive activities of Bimatoprost.
RamiprilRamipril may increase the hypotensive activities of Bimatoprost.
RasagilineRasagiline may increase the hypotensive activities of Bimatoprost.
RemikirenRemikiren may increase the hypotensive activities of Bimatoprost.
RescinnamineBimatoprost may increase the hypotensive activities of Rescinnamine.
ReserpineReserpine may increase the hypotensive activities of Bimatoprost.
ResveratrolThe therapeutic efficacy of Bimatoprost can be decreased when used in combination with Resveratrol.
RiociguatBimatoprost may increase the hypotensive activities of Riociguat.
RituximabBimatoprost may increase the hypotensive activities of Rituximab.
RofecoxibThe therapeutic efficacy of Bimatoprost can be decreased when used in combination with Rofecoxib.
SafrazineSafrazine may increase the hypotensive activities of Bimatoprost.
SalicylamideThe therapeutic efficacy of Bimatoprost can be decreased when used in combination with Salicylamide.
Salicylic acidThe therapeutic efficacy of Bimatoprost can be decreased when used in combination with Salicylic acid.
SalsalateThe therapeutic efficacy of Bimatoprost can be decreased when used in combination with Salsalate.
SaprisartanBimatoprost may increase the hypotensive activities of Saprisartan.
SelegilineSelegiline may increase the hypotensive activities of Bimatoprost.
SelexipagBimatoprost may increase the hypotensive activities of Selexipag.
SeratrodastThe therapeutic efficacy of Bimatoprost can be decreased when used in combination with Seratrodast.
SildenafilSildenafil may increase the antihypertensive activities of Bimatoprost.
SitaxentanBimatoprost may increase the hypotensive activities of Sitaxentan.
SpiraprilBimatoprost may increase the hypotensive activities of Spirapril.
SRT501The therapeutic efficacy of Bimatoprost can be decreased when used in combination with SRT501.
SulfasalazineThe therapeutic efficacy of Bimatoprost can be decreased when used in combination with Sulfasalazine.
SulindacThe therapeutic efficacy of Bimatoprost can be decreased when used in combination with Sulindac.
SuprofenThe therapeutic efficacy of Bimatoprost can be decreased when used in combination with Suprofen.
TadalafilTadalafil may increase the antihypertensive activities of Bimatoprost.
TelmisartanBimatoprost may increase the hypotensive activities of Telmisartan.
TemocaprilBimatoprost may increase the hypotensive activities of Temocapril.
TenoxicamThe therapeutic efficacy of Bimatoprost can be decreased when used in combination with Tenoxicam.
TepoxalinThe therapeutic efficacy of Bimatoprost can be decreased when used in combination with Tepoxalin.
TeriflunomideThe therapeutic efficacy of Bimatoprost can be decreased when used in combination with Teriflunomide.
TerlipressinBimatoprost may increase the hypotensive activities of Terlipressin.
Tiaprofenic acidThe therapeutic efficacy of Bimatoprost can be decreased when used in combination with Tiaprofenic acid.
TiboloneBimatoprost may increase the hypotensive activities of Tibolone.
TicrynafenBimatoprost may increase the hypotensive activities of Ticrynafen.
TimololTimolol may increase the hypotensive activities of Bimatoprost.
TolazolineTolazoline may increase the hypotensive activities of Bimatoprost.
Tolfenamic AcidThe therapeutic efficacy of Bimatoprost can be decreased when used in combination with Tolfenamic Acid.
TolmetinThe therapeutic efficacy of Bimatoprost can be decreased when used in combination with Tolmetin.
ToloxatoneToloxatone may increase the hypotensive activities of Bimatoprost.
TorasemideTorasemide may increase the hypotensive activities of Bimatoprost.
TrandolaprilTrandolapril may increase the hypotensive activities of Bimatoprost.
TranilastThe therapeutic efficacy of Bimatoprost can be decreased when used in combination with Tranilast.
Trans-2-PhenylcyclopropylamineTrans-2-Phenylcyclopropylamine may increase the hypotensive activities of Bimatoprost.
TranylcypromineTranylcypromine may increase the hypotensive activities of Bimatoprost.
TravoprostTravoprost may increase the hypotensive activities of Bimatoprost.
TreprostinilTreprostinil may increase the hypotensive activities of Bimatoprost.
TrichlormethiazideBimatoprost may increase the hypotensive activities of Trichlormethiazide.
TrimazosinBimatoprost may increase the hypotensive activities of Trimazosin.
TrimethaphanBimatoprost may increase the hypotensive activities of Trimethaphan.
Trisalicylate-cholineThe therapeutic efficacy of Bimatoprost can be decreased when used in combination with Trisalicylate-choline.
UdenafilUdenafil may increase the antihypertensive activities of Bimatoprost.
UnoprostoneBimatoprost may increase the hypotensive activities of Unoprostone.
ValdecoxibThe therapeutic efficacy of Bimatoprost can be decreased when used in combination with Valdecoxib.
ValsartanValsartan may increase the hypotensive activities of Bimatoprost.
VardenafilVardenafil may increase the antihypertensive activities of Bimatoprost.
XylometazolineBimatoprost may increase the hypotensive activities of Xylometazoline.
YohimbineYohimbine may decrease the antihypertensive activities of Bimatoprost.
ZaltoprofenThe therapeutic efficacy of Bimatoprost can be decreased when used in combination with Zaltoprofen.
ZileutonThe therapeutic efficacy of Bimatoprost can be decreased when used in combination with Zileuton.
ZomepiracThe therapeutic efficacy of Bimatoprost can be decreased when used in combination with Zomepirac.
Food InteractionsNot Available

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 in the corpus luteum (By similarity). Isoforms 2 to 7 do not bind PGF2-alpha but are proposed to modulate signaling by participating in variant receptor complexes; heterodimers between isoform 1 and ...
Gene Name:
PTGFR
Uniprot ID:
P43088
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 important modulator of renal function. Implicated the smooth muscle contractile response to PGE2 in various tissues.
Gene Name:
PTGER1
Uniprot ID:
P34995
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 of sodium and water reabsorption in kidney tubulus and contraction in uterine smooth muscle. The activity of this receptor can couple to both the inhibition of adenylate cyclase mediated by G-I protei...
Gene Name:
PTGER3
Uniprot ID:
P43115
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. Functions as a bi-directional 3-alpha-, 17-beta- and 20-alpha HSD. Can interconvert active androgens, estrogens and progestins with their cognate inactive metabolites. Preferentially transforms andro...
Gene Name:
AKR1C3
Uniprot ID:
P42330
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 ]
Comments
comments powered by Disqus
Drug created on June 13, 2005 07:24 / Updated on September 28, 2016 02:35