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Identification
NameLatanoprost
Accession NumberDB00654  (APRD01065)
TypeSmall Molecule
GroupsApproved, Investigational
DescriptionLatanoprost 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 is also known by the brand name of Xalatan manufactured by Pfizer.
Structure
Thumb
Synonyms
Isopropyl (Z)-7-((1R,2R,3R,5S)-3,5-dihydroxy-2-((3R)-3-hydroxy-5-phenylpentyl)cyclopentyl)-5-heptenoate
Latanoprost
Latanoprostum
PhXA 41
Propan-2-yl (5Z)-7-{(1R,2R,3R,5S)-3,5-dihydroxy-2-[(3R)-3-hydroxy-5-phenylpentyl]cyclopentyl}hept-5-enoate
Xalatan
External Identifiers
  • PHXA 41
  • XA 41
Approved Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Act LatanoprostSolution0.05 mgOphthalmicActavis Pharma Company2011-10-13Not applicableCanada
Bl LatanoprostSolution50 mcgOphthalmicBausch & Lomb IncNot applicableNot applicableCanada
Gd-latanoprostSolution50 mcgOphthalmicGenmed A Division Of Pfizer Canada Inc2011-10-03Not applicableCanada
Jamp-latanoprostSolution50 mcgOphthalmicJamp Pharma CorporationNot applicableNot applicableCanada
LatanoprostSolution50 ug/mLOphthalmicGreenstone LLC1995-03-20Not applicableUs
LatanoprostSolution50 mcgOphthalmicLaboratoire Riva IncNot applicableNot applicableCanada
Latanoprost Ophthalmic SolutionSolution50 mcgOphthalmicSandoz Canada IncorporatedNot applicableNot applicableCanada
Med-latanoprostSolution50 mcgOphthalmicGeneric Medical Partners Inc2015-01-09Not applicableCanada
Mint-latanoprostSolution50 mcgOphthalmicMint Pharmaceuticals IncNot applicableNot applicableCanada
MonoprostSolution50 mcgOphthalmicLaboratoires TheaNot applicableNot applicableCanada
PMS-latanoprostSolution50 mcgOphthalmicPharmascience Inc2014-10-23Not applicableCanada
Riva-latanoprostSolution50 mcgOphthalmicLaboratoire Riva Inc2015-05-11Not applicableCanada
Sandoz LatanoprostSolution50 mcgOphthalmicSandoz Canada Incorporated2011-12-06Not applicableCanada
Taro-latanoprostSolution50 mcgOphthalmicTaro Pharmaceuticals IncNot applicableNot applicableCanada
Teva-latanoprostSolution50 mcgOphthalmicTeva Canada LimitedNot applicableNot applicableCanada
XalatanSolution50 ug/mLOphthalmicDispensing Solutions, Inc.1995-03-20Not applicableUs
XalatanSolution50 mcgOphthalmicPfizer Canada Inc1997-07-28Not applicableCanada
XalatanSolution50 ug/mLOphthalmicPharmacia And Upjohn Company Llc1995-03-20Not applicableUs
Approved Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Apo-latanoprostSolution50 mcgOphthalmicApotex Inc2011-10-03Not applicableCanada
LatanoprostSolution50 ug/mLOphthalmicMylan Pharmaceuticals Inc.2011-03-22Not applicableUs
LatanoprostSolution50 ug/mLOphthalmicRising Pharmaceuticals, Inc.2016-09-01Not applicableUs
LatanoprostSolution / drops50 ug/mLOphthalmicREMEDYREPACK INC.2013-06-12Not applicableUs
LatanoprostSolution50 ug/mLOphthalmicAmerican Regent, Inc.2011-08-02Not applicableUs
LatanoprostSolution / drops50 ug/mLOphthalmicMwi2015-04-08Not applicableUs
LatanoprostSolution / drops50 ug/mLOphthalmicA S Medication Solutions2011-03-22Not applicableUs
LatanoprostSolution / drops50 ug/mLOphthalmicPhysicians Total Care, Inc.2011-06-21Not applicableUs
LatanoprostSolution / drops50 ug/mLOphthalmicBausch & Lomb Incorporated2011-03-22Not applicableUs
LatanoprostSolution / drops50 ug/mLOphthalmicAkorn, Inc.2012-07-01Not applicableUs
LatanoprostSolution50 ug/mLOphthalmicSandoz Inc2011-01-07Not applicableUs
LatanoprostSolution / drops50 ug/mLOphthalmicA S Medication Solutions2012-07-01Not applicableUs
LatanoprostSolution / drops50 ug/mLOphthalmicRebel Distributors Corp2011-03-22Not applicableUs
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International Brands
NameCompany
ArulatanDr. Gerhard Mann
GaapSophia
Gaap OftenoSophia
GaaxChile
GlaucogesicAtlas
GlaumaxKevelt
GlauprostArrow
HysitePfizer
IopizeSIFI
IoprostFDC
IoptameCadila
KlonaprostKlonal
LanoprostSynpac-Kingdom
LanotanKuk Je
LaprostOftalmi
LatacrisSun-Farm
LataluxJelfa
Latan-OphtalWinzer
LataneauAlapis Pharma
Brand mixtures
NameLabellerIngredients
Act Latanoprost/timololActavis Pharma Company
Apo-latanoprost-timopApotex Inc
Gd-latanoprost/timololGenmed A Division Of Pfizer Canada Inc
Jamp-latanoprost/timololJamp Pharma Corporation
Med-latanoprost-timololGeneric Medical Partners Inc
Mint-latanoprost/timololMint Pharmaceuticals Inc
Mylan-latanoprost/timololMylan Pharmaceuticals Ulc
PMS-latanoprost-timololPharmascience Inc
Sandoz Latanoprost/timololSandoz Canada Incorporated
Teva-latanoprost/timololTeva Canada Limited
XalacomPfizer Canada Inc
SaltsNot Available
Categories
UNII6Z5B6HVF6O
CAS number130209-82-4
WeightAverage: 432.5928
Monoisotopic: 432.28757439
Chemical FormulaC26H40O5
InChI KeyGGXICVAJURFBLW-CEYXHVGTSA-N
InChI
InChI=1S/C26H40O5/c1-19(2)31-26(30)13-9-4-3-8-12-22-23(25(29)18-24(22)28)17-16-21(27)15-14-20-10-6-5-7-11-20/h3,5-8,10-11,19,21-25,27-29H,4,9,12-18H2,1-2H3/b8-3-/t21-,22+,23+,24-,25+/m0/s1
IUPAC Name
propan-2-yl (5Z)-7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-[(3R)-3-hydroxy-5-phenylpentyl]cyclopentyl]hept-5-enoate
SMILES
CC(C)OC(=O)CCC\C=C/C[[email protected]]1[C@@H](O)C[C@@H](O)[C@@H]1CC[C@@H](O)CCC1=CC=CC=C1
Pharmacology
IndicationFor the reduction of elevated intraocular pressure in patients with open-angle glaucoma or ocular hypertension.
Structured Indications
PharmacodynamicsLatanoprost is an isopropyl ester prodrug which is inactive but which becomes active after hydrolysis to the acid from. Latanoprost opthalmic 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.
Mechanism of actionLatanoprost is a prostaglandin F2a analogue. Specifically, Latanoprost is a prostanoid selective FP receptor agonist that is believed to reduce the intraocular pressure (IOP) by increasing the outflow of aqueous humor. Studies in animals and man suggest that the main mechanism of action is increased uveoscleral outflow. Elevated IOP represents 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.
TargetKindPharmacological actionActionsOrganismUniProt ID
Prostaglandin F2-alpha receptorProteinyes
agonist
HumanP43088 details
Related Articles
AbsorptionLatanoprost is well absorbed through the cornea where the isopropyl ester prodrug is hydrolyzed to the acid form. Peak concentration is reached 2 hrs after topical administration.
Volume of distributionNot Available
Protein bindingNot Available
Metabolism

Primarily hepatic (none except hydrolysis in the eye). Latanoprost is an isopropyl ester prodrug. It is hydrolyzed by esterases in the cornea to latanoprost acid, which is biologically active. The portion of the latanoprost acid that reaches the systemic circulation is metabolized primarily by the liver to 1,2-dinor and 1,2,3,4-tetranor metabolites by fatty acid beta-oxidation.

Route of eliminationNot Available
Half life17 minutes
Clearance
  • 7 mL/min/kg
ToxicitySymptoms of overdose include bloodshot eyes and eye irritation.
Affected organisms
  • Humans and other mammals
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot 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 Latanoprost.Experimental
AcebutololLatanoprost may increase the hypotensive activities of Acebutolol.Approved
AceclofenacThe therapeutic efficacy of Latanoprost can be decreased when used in combination with Aceclofenac.Approved
AcetovanilloneThe therapeutic efficacy of Latanoprost can be decreased when used in combination with Acetovanillone.Investigational
Acetylsalicylic acidThe therapeutic efficacy of Latanoprost can be decreased when used in combination with Acetylsalicylic acid.Approved, Vet Approved
AdapaleneThe therapeutic efficacy of Latanoprost can be decreased when used in combination with Adapalene.Approved
AlfuzosinAlfuzosin may increase the hypotensive activities of Latanoprost.Approved, Investigational
AliskirenLatanoprost may increase the hypotensive activities of Aliskiren.Approved, Investigational
AlprenololLatanoprost may increase the hypotensive activities of Alprenolol.Approved, Withdrawn
AmbrisentanLatanoprost may increase the hypotensive activities of Ambrisentan.Approved, Investigational
AmifostineLatanoprost may increase the hypotensive activities of Amifostine.Approved, Investigational
AmlodipineAmlodipine may increase the hypotensive activities of Latanoprost.Approved
AnisodamineThe therapeutic efficacy of Latanoprost can be decreased when used in combination with Anisodamine.Investigational
AntipyrineThe therapeutic efficacy of Latanoprost can be decreased when used in combination with Antipyrine.Approved
ApremilastThe therapeutic efficacy of Latanoprost can be decreased when used in combination with Apremilast.Approved, Investigational
AtenololAtenolol may increase the hypotensive activities of Latanoprost.Approved
AzapropazoneThe therapeutic efficacy of Latanoprost can be decreased when used in combination with Azapropazone.Withdrawn
AzelastineThe therapeutic efficacy of Latanoprost can be decreased when used in combination with Azelastine.Approved
BalsalazideThe therapeutic efficacy of Latanoprost can be decreased when used in combination with Balsalazide.Approved, Investigational
BenazeprilBenazepril may increase the hypotensive activities of Latanoprost.Approved, Investigational
BendroflumethiazideBendroflumethiazide may increase the hypotensive activities of Latanoprost.Approved
BenmoxinBenmoxin may increase the hypotensive activities of Latanoprost.Withdrawn
BenoxaprofenThe therapeutic efficacy of Latanoprost can be decreased when used in combination with Benoxaprofen.Withdrawn
BepridilLatanoprost may increase the hypotensive activities of Bepridil.Approved, Withdrawn
BetaxololBetaxolol may increase the hypotensive activities of Latanoprost.Approved
BethanidineBethanidine may increase the hypotensive activities of Latanoprost.Approved
Betulinic AcidThe therapeutic efficacy of Latanoprost can be decreased when used in combination with Betulinic Acid.Investigational
BimatoprostThe risk or severity of intraocular pressure can be increased when Latanoprost is combined with Bimatoprost.Approved, Investigational
BisoprololBisoprolol may increase the hypotensive activities of Latanoprost.Approved
BosentanBosentan may increase the hypotensive activities of Latanoprost.Approved, Investigational
BretyliumLatanoprost may increase the hypotensive activities of Bretylium.Approved
BrimonidineBrimonidine may increase the hypotensive activities of Latanoprost.Approved
BrimonidineBrimonidine may increase the antihypertensive activities of Latanoprost.Approved
BromfenacThe therapeutic efficacy of Latanoprost can be decreased when used in combination with Bromfenac.Approved
BucillamineThe therapeutic efficacy of Latanoprost can be decreased when used in combination with Bucillamine.Investigational
BupranololLatanoprost may increase the hypotensive activities of Bupranolol.Approved
CandesartanLatanoprost may increase the hypotensive activities of Candesartan.Approved
CandoxatrilCandoxatril may increase the hypotensive activities of Latanoprost.Experimental
CaptoprilLatanoprost may increase the hypotensive activities of Captopril.Approved
CaroxazoneCaroxazone may increase the hypotensive activities of Latanoprost.Withdrawn
CarprofenThe therapeutic efficacy of Latanoprost can be decreased when used in combination with Carprofen.Approved, Vet Approved, Withdrawn
CarteololCarteolol may increase the hypotensive activities of Latanoprost.Approved
CarvedilolLatanoprost may increase the hypotensive activities of Carvedilol.Approved, Investigational
CastanospermineThe therapeutic efficacy of Latanoprost can be decreased when used in combination with Castanospermine.Experimental
CelecoxibThe therapeutic efficacy of Latanoprost can be decreased when used in combination with Celecoxib.Approved, Investigational
CeliprololLatanoprost may increase the hypotensive activities of Celiprolol.Approved, Investigational
ChloroquineThe therapeutic efficacy of Latanoprost can be decreased when used in combination with Chloroquine.Approved, Vet Approved
ChlorothiazideLatanoprost may increase the hypotensive activities of Chlorothiazide.Approved, Vet Approved
ChlorthalidoneChlorthalidone may increase the hypotensive activities of Latanoprost.Approved
CilazaprilLatanoprost may increase the hypotensive activities of Cilazapril.Approved
ClonidineClonidine may increase the hypotensive activities of Latanoprost.Approved
ClonixinThe therapeutic efficacy of Latanoprost can be decreased when used in combination with Clonixin.Approved
CryptenamineLatanoprost may increase the hypotensive activities of Cryptenamine.Approved
CurcuminThe therapeutic efficacy of Latanoprost can be decreased when used in combination with Curcumin.Investigational
CyclothiazideCyclothiazide may increase the hypotensive activities of Latanoprost.Approved
D-LimoneneThe therapeutic efficacy of Latanoprost can be decreased when used in combination with D-Limonene.Investigational
DebrisoquinLatanoprost may increase the hypotensive activities of Debrisoquin.Approved
DeserpidineLatanoprost may increase the hypotensive activities of Deserpidine.Approved
DiazoxideDiazoxide may increase the hypotensive activities of Latanoprost.Approved
DiclofenacThe therapeutic efficacy of Latanoprost can be decreased when used in combination with Diclofenac.Approved, Vet Approved
DiflunisalThe therapeutic efficacy of Latanoprost can be decreased when used in combination with Diflunisal.Approved
DihydralazineLatanoprost may increase the hypotensive activities of Dihydralazine.Investigational
DiltiazemDiltiazem may increase the hypotensive activities of Latanoprost.Approved
DorzolamideLatanoprost may increase the hypotensive activities of Dorzolamide.Approved
DoxazosinDoxazosin may increase the hypotensive activities of Latanoprost.Approved
DroxicamThe therapeutic efficacy of Latanoprost can be decreased when used in combination with Droxicam.Approved
DuvelisibThe therapeutic efficacy of Latanoprost can be decreased when used in combination with Duvelisib.Investigational
E6201The therapeutic efficacy of Latanoprost can be decreased when used in combination with E6201.Investigational
EbselenThe therapeutic efficacy of Latanoprost can be decreased when used in combination with Ebselen.Investigational
EfonidipineLatanoprost may increase the hypotensive activities of Efonidipine.Approved
EnalaprilEnalapril may increase the hypotensive activities of Latanoprost.Approved, Vet Approved
EnalaprilatLatanoprost may increase the hypotensive activities of Enalaprilat.Approved
EpirizoleThe therapeutic efficacy of Latanoprost can be decreased when used in combination with Epirizole.Approved
EpoprostenolLatanoprost may increase the hypotensive activities of Epoprostenol.Approved
EprosartanLatanoprost may increase the hypotensive activities of Eprosartan.Approved
EtanerceptThe therapeutic efficacy of Latanoprost can be decreased when used in combination with Etanercept.Approved, Investigational
EtodolacThe therapeutic efficacy of Latanoprost can be decreased when used in combination with Etodolac.Approved, Investigational, Vet Approved
EtofenamateThe therapeutic efficacy of Latanoprost can be decreased when used in combination with Etofenamate.Approved
EtoricoxibThe therapeutic efficacy of Latanoprost can be decreased when used in combination with Etoricoxib.Approved, Investigational
Evening primrose oilThe therapeutic efficacy of Latanoprost can be decreased when used in combination with Evening primrose oil.Approved
exisulindThe therapeutic efficacy of Latanoprost can be decreased when used in combination with exisulind.Investigational
FelodipineLatanoprost may increase the hypotensive activities of Felodipine.Approved, Investigational
FenbufenThe therapeutic efficacy of Latanoprost can be decreased when used in combination with Fenbufen.Approved
FenoldopamLatanoprost may increase the hypotensive activities of Fenoldopam.Approved
FenoprofenThe therapeutic efficacy of Latanoprost can be decreased when used in combination with Fenoprofen.Approved
FloctafenineThe therapeutic efficacy of Latanoprost can be decreased when used in combination with Floctafenine.Approved, Withdrawn
FlunixinThe therapeutic efficacy of Latanoprost can be decreased when used in combination with Flunixin.Vet Approved
FlurbiprofenThe therapeutic efficacy of Latanoprost can be decreased when used in combination with Flurbiprofen.Approved, Investigational
FosinoprilFosinopril may increase the hypotensive activities of Latanoprost.Approved
FurazolidoneFurazolidone may increase the hypotensive activities of Latanoprost.Approved, Vet Approved
GuanabenzGuanabenz may increase the hypotensive activities of Latanoprost.Approved
GuanadrelGuanadrel may increase the hypotensive activities of Latanoprost.Approved
GuanethidineLatanoprost may increase the hypotensive activities of Guanethidine.Approved
GuanfacineLatanoprost may increase the hypotensive activities of Guanfacine.Approved, Investigational
HexamethoniumLatanoprost may increase the hypotensive activities of Hexamethonium.Experimental
HigenamineThe therapeutic efficacy of Latanoprost can be decreased when used in combination with Higenamine.Investigational
HMPL-004The therapeutic efficacy of Latanoprost can be decreased when used in combination with HMPL-004.Investigational
HydracarbazineHydracarbazine may increase the hypotensive activities of Latanoprost.Approved
HydralazineLatanoprost may increase the hypotensive activities of Hydralazine.Approved
HydrochlorothiazideLatanoprost may increase the hypotensive activities of Hydrochlorothiazide.Approved, Vet Approved
HydroflumethiazideLatanoprost may increase the hypotensive activities of Hydroflumethiazide.Approved
IbuprofenThe therapeutic efficacy of Latanoprost can be decreased when used in combination with Ibuprofen.Approved
IbuproxamThe therapeutic efficacy of Latanoprost can be decreased when used in combination with Ibuproxam.Withdrawn
IcatibantThe therapeutic efficacy of Latanoprost can be decreased when used in combination with Icatibant.Approved
IloprostIloprost may increase the hypotensive activities of Latanoprost.Approved, Investigational
ImidaprilLatanoprost may increase the hypotensive activities of Imidapril.Investigational
IndapamideLatanoprost may increase the hypotensive activities of Indapamide.Approved
IndenololLatanoprost may increase the hypotensive activities of Indenolol.Withdrawn
IndomethacinThe therapeutic efficacy of Latanoprost can be decreased when used in combination with Indomethacin.Approved, Investigational
IndoprofenThe therapeutic efficacy of Latanoprost can be decreased when used in combination with Indoprofen.Withdrawn
IndoraminLatanoprost may increase the hypotensive activities of Indoramin.Withdrawn
IproclozideIproclozide may increase the hypotensive activities of Latanoprost.Withdrawn
IproniazidIproniazid may increase the hypotensive activities of Latanoprost.Withdrawn
IrbesartanLatanoprost may increase the hypotensive activities of Irbesartan.Approved, Investigational
IsocarboxazidIsocarboxazid may increase the hypotensive activities of Latanoprost.Approved
IsoxicamThe therapeutic efficacy of Latanoprost can be decreased when used in combination with Isoxicam.Withdrawn
IsradipineIsradipine may increase the hypotensive activities of Latanoprost.Approved
KebuzoneThe therapeutic efficacy of Latanoprost can be decreased when used in combination with Kebuzone.Experimental
KetanserinLatanoprost may increase the hypotensive activities of Ketanserin.Investigational
KetoprofenThe therapeutic efficacy of Latanoprost can be decreased when used in combination with Ketoprofen.Approved, Vet Approved
KetorolacThe therapeutic efficacy of Latanoprost can be decreased when used in combination with Ketorolac.Approved
LabetalolLabetalol may increase the hypotensive activities of Latanoprost.Approved
LacidipineLatanoprost may increase the hypotensive activities of Lacidipine.Approved
LeflunomideThe therapeutic efficacy of Latanoprost can be decreased when used in combination with Leflunomide.Approved, Investigational
LercanidipineLercanidipine may increase the hypotensive activities of Latanoprost.Approved, Investigational
LisinoprilLatanoprost may increase the hypotensive activities of Lisinopril.Approved, Investigational
LisofyllineThe therapeutic efficacy of Latanoprost can be decreased when used in combination with Lisofylline.Investigational
LofexidineLatanoprost may increase the hypotensive activities of Lofexidine.Approved, Investigational
LornoxicamThe therapeutic efficacy of Latanoprost can be decreased when used in combination with Lornoxicam.Approved
LosartanLatanoprost may increase the hypotensive activities of Losartan.Approved
LoxoprofenThe therapeutic efficacy of Latanoprost can be decreased when used in combination with Loxoprofen.Approved
LumiracoxibThe therapeutic efficacy of Latanoprost can be decreased when used in combination with Lumiracoxib.Approved, Investigational
MacitentanLatanoprost may increase the hypotensive activities of Macitentan.Approved
Magnesium salicylateThe therapeutic efficacy of Latanoprost can be decreased when used in combination with Magnesium salicylate.Approved
ManidipineLatanoprost may increase the hypotensive activities of Manidipine.Approved
MasoprocolThe therapeutic efficacy of Latanoprost can be decreased when used in combination with Masoprocol.Approved
MebanazineMebanazine may increase the hypotensive activities of Latanoprost.Withdrawn
MecamylamineLatanoprost may increase the hypotensive activities of Mecamylamine.Approved
Meclofenamic acidThe therapeutic efficacy of Latanoprost can be decreased when used in combination with Meclofenamic acid.Approved, Vet Approved
Mefenamic acidThe therapeutic efficacy of Latanoprost can be decreased when used in combination with Mefenamic acid.Approved
MeloxicamThe therapeutic efficacy of Latanoprost can be decreased when used in combination with Meloxicam.Approved, Vet Approved
MesalazineThe therapeutic efficacy of Latanoprost can be decreased when used in combination with Mesalazine.Approved
MetamizoleThe therapeutic efficacy of Latanoprost can be decreased when used in combination with Metamizole.Withdrawn
MethyldopaLatanoprost may increase the hypotensive activities of Methyldopa.Approved
Methylene blueMethylene blue may increase the hypotensive activities of Latanoprost.Investigational
MethylphenidateMethylphenidate may decrease the antihypertensive activities of Latanoprost.Approved, Investigational
MetipranololLatanoprost may increase the hypotensive activities of Metipranolol.Approved
MetolazoneMetolazone may increase the hypotensive activities of Latanoprost.Approved
MetoprololMetoprolol may increase the hypotensive activities of Latanoprost.Approved, Investigational
MetyrosineLatanoprost may increase the hypotensive activities of Metyrosine.Approved
MibefradilLatanoprost may increase the hypotensive activities of Mibefradil.Withdrawn
MinaprineMinaprine may increase the hypotensive activities of Latanoprost.Approved
MinoxidilMinoxidil may increase the hypotensive activities of Latanoprost.Approved
MizoribineThe therapeutic efficacy of Latanoprost can be decreased when used in combination with Mizoribine.Investigational
MoclobemideMoclobemide may increase the hypotensive activities of Latanoprost.Approved
MoexiprilLatanoprost may increase the hypotensive activities of Moexipril.Approved
MolsidomineMolsidomine may increase the hypotensive activities of Latanoprost.Approved
MoxonidineLatanoprost may increase the hypotensive activities of Moxonidine.Approved
Mycophenolate mofetilThe therapeutic efficacy of Latanoprost can be decreased when used in combination with Mycophenolate mofetil.Approved, Investigational
Mycophenolic acidThe therapeutic efficacy of Latanoprost can be decreased when used in combination with Mycophenolic acid.Approved
NabumetoneThe therapeutic efficacy of Latanoprost can be decreased when used in combination with Nabumetone.Approved
NadololLatanoprost may increase the hypotensive activities of Nadolol.Approved
NafamostatThe therapeutic efficacy of Latanoprost can be decreased when used in combination with Nafamostat.Investigational
NaftifineThe therapeutic efficacy of Latanoprost can be decreased when used in combination with Naftifine.Approved
NaftopidilLatanoprost may increase the hypotensive activities of Naftopidil.Investigational
NaproxenThe therapeutic efficacy of Latanoprost can be decreased when used in combination with Naproxen.Approved, Vet Approved
NCX 4016The therapeutic efficacy of Latanoprost can be decreased when used in combination with NCX 4016.Investigational
NebivololLatanoprost may increase the hypotensive activities of Nebivolol.Approved, Investigational
NepafenacThe therapeutic efficacy of Latanoprost can be decreased when used in combination with Nepafenac.Approved
NialamideNialamide may increase the hypotensive activities of Latanoprost.Withdrawn
NicardipineNicardipine may increase the hypotensive activities of Latanoprost.Approved
NicorandilLatanoprost may increase the hypotensive activities of Nicorandil.Approved
Niflumic AcidThe therapeutic efficacy of Latanoprost can be decreased when used in combination with Niflumic Acid.Approved
NiguldipineLatanoprost may increase the hypotensive activities of Niguldipine.Experimental
NilvadipineLatanoprost may increase the hypotensive activities of Nilvadipine.Approved
NimesulideThe therapeutic efficacy of Latanoprost can be decreased when used in combination with Nimesulide.Approved, Withdrawn
NimodipineNimodipine may increase the hypotensive activities of Latanoprost.Approved
NisoldipineNisoldipine may increase the hypotensive activities of Latanoprost.Approved
NitrendipineLatanoprost may increase the hypotensive activities of Nitrendipine.Approved
NitroaspirinThe therapeutic efficacy of Latanoprost can be decreased when used in combination with Nitroaspirin.Investigational
NitroprussideNitroprusside may increase the hypotensive activities of Latanoprost.Approved
ObinutuzumabLatanoprost may increase the hypotensive activities of Obinutuzumab.Approved
OctamoxinOctamoxin may increase the hypotensive activities of Latanoprost.Withdrawn
OlmesartanOlmesartan may increase the hypotensive activities of Latanoprost.Approved, Investigational
OlopatadineThe therapeutic efficacy of Latanoprost can be decreased when used in combination with Olopatadine.Approved
OlsalazineThe therapeutic efficacy of Latanoprost can be decreased when used in combination with Olsalazine.Approved
OmapatrilatLatanoprost may increase the hypotensive activities of Omapatrilat.Investigational
OrgoteinThe therapeutic efficacy of Latanoprost can be decreased when used in combination with Orgotein.Vet Approved
OxaprozinThe therapeutic efficacy of Latanoprost can be decreased when used in combination with Oxaprozin.Approved
OxprenololLatanoprost may increase the hypotensive activities of Oxprenolol.Approved
OxyphenbutazoneThe therapeutic efficacy of Latanoprost can be decreased when used in combination with Oxyphenbutazone.Withdrawn
ParecoxibThe therapeutic efficacy of Latanoprost can be decreased when used in combination with Parecoxib.Approved
PargylinePargyline may increase the hypotensive activities of Latanoprost.Approved
PenbutololLatanoprost may increase the hypotensive activities of Penbutolol.Approved, Investigational
PentoliniumLatanoprost may increase the hypotensive activities of Pentolinium.Approved
PentoxifyllinePentoxifylline may increase the hypotensive activities of Latanoprost.Approved, Investigational
PerindoprilLatanoprost may increase the hypotensive activities of Perindopril.Approved
PhenelzinePhenelzine may increase the hypotensive activities of Latanoprost.Approved
PheniprazinePheniprazine may increase the hypotensive activities of Latanoprost.Withdrawn
PhenoxybenzamineLatanoprost may increase the hypotensive activities of Phenoxybenzamine.Approved
PhenoxypropazinePhenoxypropazine may increase the hypotensive activities of Latanoprost.Withdrawn
PhentolamineLatanoprost may increase the hypotensive activities of Phentolamine.Approved
PhenylbutazoneThe therapeutic efficacy of Latanoprost can be decreased when used in combination with Phenylbutazone.Approved, Vet Approved
PimecrolimusThe therapeutic efficacy of Latanoprost can be decreased when used in combination with Pimecrolimus.Approved, Investigational
PinacidilLatanoprost may increase the hypotensive activities of Pinacidil.Withdrawn
PindololLatanoprost may increase the hypotensive activities of Pindolol.Approved
PirfenidoneThe therapeutic efficacy of Latanoprost can be decreased when used in combination with Pirfenidone.Investigational
PirlindolePirlindole may increase the hypotensive activities of Latanoprost.Approved
PiroxicamThe therapeutic efficacy of Latanoprost can be decreased when used in combination with Piroxicam.Approved, Investigational
PivhydrazinePivhydrazine may increase the hypotensive activities of Latanoprost.Withdrawn
PolythiazideLatanoprost may increase the hypotensive activities of Polythiazide.Approved
PrazosinPrazosin may increase the hypotensive activities of Latanoprost.Approved
PropacetamolThe therapeutic efficacy of Latanoprost can be decreased when used in combination with Propacetamol.Approved
PropranololPropranolol may increase the hypotensive activities of Latanoprost.Approved, Investigational
PTC299The therapeutic efficacy of Latanoprost can be decreased when used in combination with PTC299.Investigational
QuinaprilLatanoprost may increase the hypotensive activities of Quinapril.Approved, Investigational
QuinineQuinine may increase the hypotensive activities of Latanoprost.Approved
RamiprilRamipril may increase the hypotensive activities of Latanoprost.Approved
RasagilineRasagiline may increase the hypotensive activities of Latanoprost.Approved
RemikirenRemikiren may increase the hypotensive activities of Latanoprost.Approved
RescinnamineLatanoprost may increase the hypotensive activities of Rescinnamine.Approved
ReserpineReserpine may increase the hypotensive activities of Latanoprost.Approved
ResveratrolThe therapeutic efficacy of Latanoprost can be decreased when used in combination with Resveratrol.Experimental, Investigational
RilmenidineLatanoprost may increase the hypotensive activities of Rilmenidine.Investigational
RiociguatLatanoprost may increase the hypotensive activities of Riociguat.Approved
RituximabLatanoprost may increase the hypotensive activities of Rituximab.Approved
RofecoxibThe therapeutic efficacy of Latanoprost can be decreased when used in combination with Rofecoxib.Investigational, Withdrawn
SafrazineSafrazine may increase the hypotensive activities of Latanoprost.Withdrawn
SalicylamideThe therapeutic efficacy of Latanoprost can be decreased when used in combination with Salicylamide.Approved
Salicylic acidThe therapeutic efficacy of Latanoprost can be decreased when used in combination with Salicylic acid.Approved, Vet Approved
SalsalateThe therapeutic efficacy of Latanoprost can be decreased when used in combination with Salsalate.Approved
SaprisartanLatanoprost may increase the hypotensive activities of Saprisartan.Experimental
SelegilineSelegiline may increase the hypotensive activities of Latanoprost.Approved, Investigational, Vet Approved
SelexipagLatanoprost may increase the hypotensive activities of Selexipag.Approved
SeratrodastThe therapeutic efficacy of Latanoprost can be decreased when used in combination with Seratrodast.Approved, Investigational
SildenafilSildenafil may increase the antihypertensive activities of Latanoprost.Approved, Investigational
SitaxentanLatanoprost may increase the hypotensive activities of Sitaxentan.Approved, Investigational, Withdrawn
SpiraprilLatanoprost may increase the hypotensive activities of Spirapril.Approved
SRT501The therapeutic efficacy of Latanoprost can be decreased when used in combination with SRT501.Investigational
SulfasalazineThe therapeutic efficacy of Latanoprost can be decreased when used in combination with Sulfasalazine.Approved
SulindacThe therapeutic efficacy of Latanoprost can be decreased when used in combination with Sulindac.Approved
SuprofenThe therapeutic efficacy of Latanoprost can be decreased when used in combination with Suprofen.Approved, Withdrawn
TadalafilTadalafil may increase the antihypertensive activities of Latanoprost.Approved, Investigational
TelmisartanLatanoprost may increase the hypotensive activities of Telmisartan.Approved, Investigational
TemocaprilLatanoprost may increase the hypotensive activities of Temocapril.Experimental, Investigational
TenoxicamThe therapeutic efficacy of Latanoprost can be decreased when used in combination with Tenoxicam.Approved
TepoxalinThe therapeutic efficacy of Latanoprost can be decreased when used in combination with Tepoxalin.Vet Approved
TeriflunomideThe therapeutic efficacy of Latanoprost can be decreased when used in combination with Teriflunomide.Approved
TerlipressinLatanoprost may increase the hypotensive activities of Terlipressin.Approved, Investigational
Tiaprofenic acidThe therapeutic efficacy of Latanoprost can be decreased when used in combination with Tiaprofenic acid.Approved
TiboloneLatanoprost may increase the hypotensive activities of Tibolone.Approved
TicrynafenLatanoprost may increase the hypotensive activities of Ticrynafen.Withdrawn
TimololTimolol may increase the hypotensive activities of Latanoprost.Approved
TinoridineThe therapeutic efficacy of Latanoprost can be decreased when used in combination with Tinoridine.Investigational
TolazolineLatanoprost may increase the hypotensive activities of Tolazoline.Approved, Vet Approved
Tolfenamic AcidThe therapeutic efficacy of Latanoprost can be decreased when used in combination with Tolfenamic Acid.Approved
TolmetinThe therapeutic efficacy of Latanoprost can be decreased when used in combination with Tolmetin.Approved
ToloxatoneToloxatone may increase the hypotensive activities of Latanoprost.Approved
TorasemideTorasemide may increase the hypotensive activities of Latanoprost.Approved
TrandolaprilTrandolapril may increase the hypotensive activities of Latanoprost.Approved
TranilastThe therapeutic efficacy of Latanoprost can be decreased when used in combination with Tranilast.Approved, Investigational
Trans-2-PhenylcyclopropylamineTrans-2-Phenylcyclopropylamine may increase the hypotensive activities of Latanoprost.Experimental
TranylcypromineTranylcypromine may increase the hypotensive activities of Latanoprost.Approved
TravoprostTravoprost may increase the hypotensive activities of Latanoprost.Approved
TreprostinilTreprostinil may increase the hypotensive activities of Latanoprost.Approved, Investigational
TrichlormethiazideLatanoprost may increase the hypotensive activities of Trichlormethiazide.Approved, Vet Approved
TrimazosinLatanoprost may increase the hypotensive activities of Trimazosin.Experimental
TrimethaphanLatanoprost may increase the hypotensive activities of Trimethaphan.Approved
Trisalicylate-cholineThe therapeutic efficacy of Latanoprost can be decreased when used in combination with Trisalicylate-choline.Approved
UdenafilUdenafil may increase the antihypertensive activities of Latanoprost.Approved, Investigational
UnoprostoneLatanoprost may increase the hypotensive activities of Unoprostone.Approved
ValdecoxibThe therapeutic efficacy of Latanoprost can be decreased when used in combination with Valdecoxib.Investigational, Withdrawn
ValsartanValsartan may increase the hypotensive activities of Latanoprost.Approved, Investigational
VardenafilVardenafil may increase the antihypertensive activities of Latanoprost.Approved
VinpocetineLatanoprost may increase the hypotensive activities of Vinpocetine.Investigational
XylometazolineLatanoprost may increase the hypotensive activities of Xylometazoline.Approved
YohimbineYohimbine may decrease the antihypertensive activities of Latanoprost.Approved, Vet Approved
ZaltoprofenThe therapeutic efficacy of Latanoprost can be decreased when used in combination with Zaltoprofen.Approved
ZileutonThe therapeutic efficacy of Latanoprost can be decreased when used in combination with Zileuton.Approved, Investigational, Withdrawn
ZomepiracThe therapeutic efficacy of Latanoprost can be decreased when used in combination with Zomepirac.Withdrawn
Food InteractionsNot Available
References
Synthesis Reference

Arie Gutman, “Process for the preparation of latanoprost.” U.S. Patent US20030149294, issued August 07, 2003.

US20030149294
General References
  1. Hara T: [Increased iris pigmentation after use of latanoprost in Japanese brown eyes]. Nippon Ganka Gakkai Zasshi. 2001 May;105(5):314-21. [PubMed:11406947 ]
External Links
ATC CodesS01EE01
AHFS Codes
  • 52:92.00
PDB EntriesNot Available
FDA labelDownload (502 KB)
MSDSDownload (21.1 KB)
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9474
Blood Brain Barrier+0.6512
Caco-2 permeable+0.5337
P-glycoprotein substrateSubstrate0.5728
P-glycoprotein inhibitor INon-inhibitor0.8684
P-glycoprotein inhibitor IINon-inhibitor0.7124
Renal organic cation transporterNon-inhibitor0.8805
CYP450 2C9 substrateNon-substrate0.7819
CYP450 2D6 substrateNon-substrate0.8835
CYP450 3A4 substrateSubstrate0.5947
CYP450 1A2 substrateNon-inhibitor0.8845
CYP450 2C9 inhibitorNon-inhibitor0.7724
CYP450 2D6 inhibitorNon-inhibitor0.8985
CYP450 2C19 inhibitorNon-inhibitor0.7236
CYP450 3A4 inhibitorNon-inhibitor0.7393
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.7405
Ames testNon AMES toxic0.8324
CarcinogenicityNon-carcinogens0.9379
BiodegradationNot ready biodegradable0.6353
Rat acute toxicity4.3748 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9071
hERG inhibition (predictor II)Non-inhibitor0.8763
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Pharmacoeconomics
Manufacturers
  • Pharmacia and upjohn co
Packagers
Dosage forms
FormRouteStrength
SolutionOphthalmic0.05 mg
SolutionOphthalmic50 ug/mL
Solution / dropsOphthalmic50 ug/mL
SolutionOphthalmic
SolutionOphthalmic50 mcg
Prices
Unit descriptionCostUnit
Xalatan 0.005% Solution 2.5ml Bottle93.59USD bottle
Xalatan 0.005% eye drops45.06USD ml
Xalatan 0.005 % Solution12.18USD ml
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)
CA1339132 No1997-07-292014-07-29Canada
US5296504 No1994-03-222011-03-22Us
US6429226 No1992-09-062009-09-06Us
Properties
StateLiquid
Experimental Properties
PropertyValueSource
water solubility8 mg/mLNot Available
logP4.4Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.0129 mg/mLALOGPS
logP4.16ALOGPS
logP3.98ChemAxon
logS-4.5ALOGPS
pKa (Strongest Acidic)14.47ChemAxon
pKa (Strongest Basic)-2.7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area86.99 Å2ChemAxon
Rotatable Bond Count14ChemAxon
Refractivity124.34 m3·mol-1ChemAxon
Polarizability50.71 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
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
  • Fatty acid ester
  • Benzenoid
  • Cyclopentanol
  • Monocyclic benzene moiety
  • Cyclic alcohol
  • Secondary alcohol
  • Carboxylic acid ester
  • Monocarboxylic acid or derivatives
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Alcohol
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors

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. Ota T, Aihara M, Narumiya S, Araie M: The effects of prostaglandin analogues on IOP in prostanoid FP-receptor-deficient mice. Invest Ophthalmol Vis Sci. 2005 Nov;46(11):4159-63. [PubMed:16249494 ]
  2. Nakajima T, Matsugi T, Goto W, Kageyama M, Mori N, Matsumura Y, Hara H: New fluoroprostaglandin F(2alpha) derivatives with prostanoid FP-receptor agonistic activity as potent ocular-hypotensive agents. Biol Pharm Bull. 2003 Dec;26(12):1691-5. [PubMed:14646172 ]
  3. Takagi Y, Nakajima T, Shimazaki A, Kageyama M, Matsugi T, Matsumura Y, Gabelt BT, Kaufman PL, Hara H: Pharmacological characteristics of AFP-168 (tafluprost), a new prostanoid FP receptor agonist, as an ocular hypotensive drug. Exp Eye Res. 2004 Apr;78(4):767-76. [PubMed:15037111 ]
  4. Ocklind A: Effect of latanoprost on the extracellular matrix of the ciliary muscle. A study on cultured cells and tissue sections. Exp Eye Res. 1998 Aug;67(2):179-91. [PubMed:9733584 ]
  5. Maxey KM, Johnson JL, LaBrecque J: The hydrolysis of bimatoprost in corneal tissue generates a potent prostanoid FP receptor agonist. Surv Ophthalmol. 2002 Aug;47 Suppl 1:S34-40. [PubMed:12204699 ]
  6. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]

Transporters

Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrate
General Function:
Sodium-independent organic anion transmembrane transporter activity
Specific Function:
Mediates the Na(+)-independent transport of organic anions such as taurocholate, the prostaglandins PGD2, PGE1, PGE2, leukotriene C4, thromboxane B2 and iloprost.
Gene Name:
SLCO2B1
Uniprot ID:
O94956
Molecular Weight:
76709.98 Da
References
  1. Kraft ME, Glaeser H, Mandery K, Konig J, Auge D, Fromm MF, Schlotzer-Schrehardt U, Welge-Lussen U, Kruse FE, Zolk O: The prostaglandin transporter OATP2A1 is expressed in human ocular tissues and transports the antiglaucoma prostanoid latanoprost. Invest Ophthalmol Vis Sci. 2010 May;51(5):2504-11. doi: 10.1167/iovs.09-4290. Epub 2009 Dec 17. [PubMed:20019365 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
General Function:
Secondary active organic cation transmembrane transporter activity
Specific Function:
Translocates a broad array of organic cations with various structures and molecular weights including the model compounds 1-methyl-4-phenylpyridinium (MPP), tetraethylammonium (TEA), N-1-methylnicotinamide (NMN), 4-(4-(dimethylamino)styryl)-N-methylpyridinium (ASP), the endogenous compounds choline, guanidine, histamine, epinephrine, adrenaline, noradrenaline and dopamine, and the drugs quinine...
Gene Name:
SLC22A1
Uniprot ID:
O15245
Molecular Weight:
61153.345 Da
References
  1. Kimura H, Takeda M, Narikawa S, Enomoto A, Ichida K, Endou H: Human organic anion transporters and human organic cation transporters mediate renal transport of prostaglandins. J Pharmacol Exp Ther. 2002 Apr;301(1):293-8. [PubMed:11907186 ]
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Drug created on June 13, 2005 07:24 / Updated on August 17, 2016 12:23