Identification

Name
Latanoprost
Accession Number
DB00654  (APRD01065)
Type
Small Molecule
Groups
Approved, Investigational
Description

Latanoprost 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
External IDs
PHXA 41 / PHXA-41 / PHXA41 / T-2345 / T2345 / XA 41 / XA-41 / XA41
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Act LatanoprostSolution50 mcgOphthalmicActavis Pharma Company2011-10-13Not applicableCanada
Bl LatanoprostSolution50 mcgOphthalmicBausch & Lomb IncNot applicableNot applicableCanada
LatanoprostSolution50 mcgOphthalmicLaboratoire Riva IncNot applicableNot applicableCanada
Latanoprost Ophthalmic SolutionSolution50 mcgOphthalmicSandoz Canada IncorporatedNot applicableNot applicableCanada
MonoprostSolution50 mcgOphthalmicLaboratoires Thea2018-01-03Not applicableCanada
Sandoz LatanoprostSolution50 mcgOphthalmicSandoz Canada Incorporated2011-12-06Not applicableCanada
XalatanSolution50 mcgOphthalmicPfizer1997-07-28Not applicableCanada
XalatanSolution50 ug/1mLOphthalmicPharmacia & Upjohn Inc1995-03-20Not applicableUs
XalatanSolution50 ug/1mLOphthalmicDispensing Solutions, Inc.1995-03-20Not applicableUs
XalatanSolution50 ug/1mLOphthalmicPharmacia and Upjohn Company1995-03-202010-06-25Us
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Apo-latanoprostSolution50 mcgOphthalmicApotex Corporation2011-10-03Not applicableCanada
Gd-latanoprostSolution50 mcgOphthalmicGenmed A Division Of Pfizer Canada Inc2011-10-03Not applicableCanada
Jamp-latanoprostSolution50 mcgOphthalmicJamp Pharma CorporationNot applicableNot applicableCanada
LatanoprostSolution50 ug/1mLOphthalmicRising Pharmaceuticals2016-09-01Not applicableUs
LatanoprostSolution50 ug/1mLOphthalmicApotex Corporation2011-03-222011-07-12Us
LatanoprostSolution / drops50 ug/1mLOphthalmicRemedy Repack2013-01-312016-09-16Us
LatanoprostSolution / drops50 ug/1mLOphthalmicA-S Medication Solutions2011-03-222017-10-31Us
LatanoprostSolution50 ug/1mLOphthalmicPaddock Laboratories, Inc.2011-10-172012-10-01Us
LatanoprostSolution / drops50 ug/1mLOphthalmicA-S Medication Solutions2012-07-01Not applicableUs
LatanoprostSolution50 ug/1mLOphthalmicGreenstone, Llc1995-03-20Not applicableUs
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
Act Latanoprost/timololLatanoprost (50 mcg) + Timolol (5 mg)SolutionOphthalmicActavis Pharma Company2015-09-29Not applicableCanada
Apo-latanoprost-timopLatanoprost (50 mcg) + Timolol (5 mg)SolutionOphthalmicApotex Corporation2014-07-02Not applicableCanada
Gd-latanoprost/timololLatanoprost (50 mcg) + Timolol (5 mg)SolutionOphthalmicGenmed A Division Of Pfizer Canada Inc2013-05-01Not applicableCanada
Jamp-latanoprost/timololLatanoprost (50 mcg) + Timolol (5 mg)SolutionOphthalmicJamp Pharma CorporationNot applicableNot applicableCanada
Med-latanoprost-timololLatanoprost (50 mcg) + Timolol (5 mg)SolutionOphthalmicGeneric Medical Partners IncNot applicableNot applicableCanada
Mint-latanoprost/timololLatanoprost (50 mcg) + Timolol (5 mg)SolutionOphthalmicMint Pharmaceuticals IncNot applicableNot applicableCanada
Mylan-latanoprost/timololLatanoprost (50 mcg) + Timolol (5.0 mg)SolutionOphthalmicMylan PharmaceuticalsNot applicableNot applicableCanada
PMS-latanoprost-timololLatanoprost (50 mcg) + Timolol (5 mg)SolutionOphthalmicPharmascience IncNot applicableNot applicableCanada
Riva-latanoprost/timololLatanoprost (50 mcg) + Timolol (5 mg)SolutionOphthalmicLaboratoire Riva Inc2017-01-03Not applicableCanada
Sandoz Latanoprost/timololLatanoprost (50 mcg) + Timolol (5 mg)SolutionOphthalmicSandoz Canada Incorporated2013-03-04Not applicableCanada
Unapproved/Other Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
Latanoprost PFLatanoprost (0.05 mg/1mL)Solution / dropsOphthalmicImprimisRx NJ2018-01-01Not applicableUs
Tim-Brim-Dor-LatLatanoprost (0.05 mg/1mL) + Brimonidine tartrate (1.5 mg/1mL) + Dorzolamide Hydrochloride (20 mg/1mL) + Timolol maleate (5 mg/1mL)Solution / dropsOphthalmicImprimisRx NJ2018-01-01Not applicableUs
Tim-Dor-LatLatanoprost (0.05 mg/1mL) + Dorzolamide Hydrochloride (20 mg/1mL) + Timolol maleate (5 mg/1mL)Solution / dropsOphthalmicImprimisRx NJ2018-01-01Not applicableUs
Tim-Lat -PFLatanoprost (0.05 mg/1mL) + Timolol maleate (5 mg/1mL)Solution / dropsOphthalmicImprimisRx NJ2018-01-01Not applicableUs
International/Other Brands
Arulatan (Dr. Gerhard Mann) / Gaap (Sophia) / Gaap Ofteno (Sophia) / Gaax (Chile) / Glaucogesic (Atlas) / Glaumax (Kevelt) / Glauprost (Arrow) / Hysite (Pfizer) / Iopize (SIFI) / Ioprost (FDC) / Ioptame (Cadila) / Klonaprost (Klonal) / Lanoprost (Synpac-Kingdom) / Lanotan (Kuk Je) / Laprost (Oftalmi) / Latacris (Sun-Farm) / Latalux (Jelfa) / Latan-Ophtal (Winzer) / Lataneau (Alapis Pharma) / Xalatan
Categories
UNII
6Z5B6HVF6O
CAS number
130209-82-4
Weight
Average: 432.5928
Monoisotopic: 432.28757439
Chemical Formula
C26H40O5
InChI Key
GGXICVAJURFBLW-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[C@H]1[C@@H](O)C[C@@H](O)[C@@H]1CC[C@@H](O)CCC1=CC=CC=C1

Pharmacology

Indication

For the reduction of elevated intraocular pressure in patients with open-angle glaucoma or ocular hypertension.

Associated Conditions
Pharmacodynamics

Latanoprost 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 action

Latanoprost 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.

TargetActionsOrganism
AProstaglandin F2-alpha receptor
agonist
Human
Absorption

Latanoprost 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 distribution
Not Available
Protein binding
Not 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 elimination
Not Available
Half life

17 minutes

Clearance
  • 7 mL/min/kg
Toxicity

Symptoms of overdose include bloodshot eyes and eye irritation.

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

Interactions

Drug Interactions
DrugInteraction
AcebutololLatanoprost may increase the hypotensive activities of Acebutolol.
AceclofenacThe therapeutic efficacy of Latanoprost can be decreased when used in combination with Aceclofenac.
AcemetacinThe therapeutic efficacy of Latanoprost can be decreased when used in combination with Acemetacin.
Acetylsalicylic acidThe therapeutic efficacy of Latanoprost can be decreased when used in combination with Acetylsalicylic acid.
AlclofenacThe therapeutic efficacy of Latanoprost can be decreased when used in combination with Alclofenac.
AliskirenLatanoprost may increase the hypotensive activities of Aliskiren.
AlminoprofenThe therapeutic efficacy of Latanoprost can be decreased when used in combination with Alminoprofen.
AlprenololLatanoprost may increase the hypotensive activities of Alprenolol.
AmbrisentanLatanoprost may increase the hypotensive activities of Ambrisentan.
AminophenazoneThe therapeutic efficacy of Latanoprost can be decreased when used in combination with Aminophenazone.
Food Interactions
Not 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
Human Metabolome Database
HMDB0014792
KEGG Drug
D00356
PubChem Compound
5311221
PubChem Substance
46506279
ChemSpider
4470740
BindingDB
50240648
ChEBI
6384
ChEMBL
CHEMBL1051
Therapeutic Targets Database
DAP001216
PharmGKB
PA164774763
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
PDRhealth
PDRhealth Drug Page
Wikipedia
Latanoprost
ATC Codes
S01EE01 — Latanoprost
AHFS Codes
  • 52:40.28 — Prostaglandin Analogs
FDA label
Download (502 KB)
MSDS
Download (21.1 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
1CompletedNot AvailableGlaucoma / Ocular Hypertension2
1CompletedTreatmentGlaucoma1
1CompletedTreatmentOcular Hypertension / Open-angle Glaucoma (OAG)1
1CompletedTreatmentOpen Angle Glaucoma -Ocular Hypertension1
1TerminatedTreatmentGlaucoma, Primary Open Angle (POAG) / Ocular Hypertension1
1, 2CompletedTreatmentGlaucoma, Primary Open Angle (POAG) / Ocular Hypertension1
1, 2CompletedTreatmentGlaucoma / Ocular Hypertension1
1, 2CompletedTreatmentOcular Hypertension / Open-angle Glaucoma (OAG)1
2Active Not RecruitingTreatmentChildhood Glaucoma1
2Active Not RecruitingTreatmentMenière's Disease1
2CompletedScreeningIntraocular Pressure1
2CompletedTreatmentElevated Intraocular Pressure / Glaucoma, Primary Open Angle (POAG) / Ocular Hypertension1
2CompletedTreatmentGlaucoma3
2CompletedTreatmentGlaucoma, Primary Open Angle (POAG)2
2CompletedTreatmentGlaucoma, Primary Open Angle (POAG) / Ocular Hypertension4
2CompletedTreatmentGlaucoma, Primary Open Angle (POAG) / Ocular Hypertension / Pigmentary Glaucoma / Pseudoexfoliative Glaucoma1
2CompletedTreatmentGlaucoma / Glaucoma or Ocular Hypertension and / Ocular Hypertension / Ocular Surface Disease1
2CompletedTreatmentGlaucoma / Ocular Hypertension1
2CompletedTreatmentOcular Hypertension / Open Angle Glaucoma (OAG)2
2CompletedTreatmentOcular Hypertension / Open Angle-glaucoma1
2CompletedTreatmentOcular Hypertension / Open-angle Glaucoma (OAG)11
2CompletedTreatmentOpen-angle Glaucoma or Ocular Hypertension1
2RecruitingTreatmentOcular Hypertension / Open-angle Glaucoma (OAG)1
2RecruitingTreatmentOpen-angle Glaucoma, Ocular Hypertension1
2TerminatedTreatmentGlaucoma1
2Unknown StatusTreatmentGlaucoma1
2WithdrawnTreatmentOcular Hypertension / Open-angle Glaucoma (OAG)1
2, 3CompletedTreatmentGlaucoma, Primary Open Angle (POAG) / Ocular Hypertension1
2, 3Not Yet RecruitingTreatmentVitiligo1
3CompletedTreatmentGlaucoma3
3CompletedTreatmentGlaucoma, Angle-Closure / Ocular Hypertension1
3CompletedTreatmentGlaucoma, Primary Open Angle (POAG) / Ocular Hypertension3
3CompletedTreatmentGlaucoma / Ocular Hypertension2
3CompletedTreatmentGlaucoma / Ocular Hypertension / Open Angle Glaucoma (OAG)1
3CompletedTreatmentGlaucoma / Ocular Hypertension / Open-angle Glaucoma (OAG)1
3CompletedTreatmentOcular Hypertension / Open Angle Glaucoma (OAG)6
3CompletedTreatmentOcular Hypertension / Open-angle Glaucoma (OAG)10
3CompletedTreatmentPrimary Open Angle Glaucoma or Ocular Hypertension1
3RecruitingPreventionGlaucoma1
3RecruitingTreatmentGlaucoma, Primary Open Angle (POAG) / Ocular Hypertension2
3RecruitingTreatmentOpen Angle Glaucoma or Ocular Hypertension1
3TerminatedTreatmentOcular Hypertension / Open Angle Glaucoma (OAG)1
3Unknown StatusTreatmentGlaucoma1
3WithdrawnTreatmentOcular Hypertension / Open Angle Glaucoma (OAG)1
3WithdrawnTreatmentOcular Hypertension / Open-angle Glaucoma (OAG)1
4CompletedNot AvailableGlaucoma / Ocular Hypertension1
4CompletedNot AvailableOpen-angle Glaucoma (OAG)1
4CompletedBasic ScienceOcular Hypertension / Open Angle Glaucoma (OAG)1
4CompletedSupportive CareDry Eye Syndrome (DES)1
4CompletedTreatmentAlopecia Areata (AA)1
4CompletedTreatmentAnterior Uveitis (AU) / Cystoid Macular Edema1
4CompletedTreatmentApplication Site Pigmentation Changes / Glaucoma1
4CompletedTreatmentEye Diseases / Glaucoma / Open-angle Glaucoma (OAG)1
4CompletedTreatmentGlaucoma8
4CompletedTreatmentGlaucoma / Healthy Volunteers1
4CompletedTreatmentGlaucoma / Ocular Hypertension10
4CompletedTreatmentOcular Hypertension1
4CompletedTreatmentOcular Hypertension / Open Angle Glaucoma (OAG)3
4CompletedTreatmentOcular Hypertension / Open-angle Glaucoma (OAG)9
4CompletedTreatmentOpen-angle Glaucoma (OAG)3
4CompletedTreatmentRetinopathy, Diabetic1
4Not Yet RecruitingTreatmentOpen-angle Glaucoma (OAG)1
4RecruitingTreatmentGlaucoma1
4RecruitingTreatmentGlaucoma, Primary Open Angle (POAG) / Ocular Hypertension1
4RecruitingTreatmentGlaucoma, Primary Open Angle (POAG) / Ocular Hypertension / POAG1
4TerminatedTreatmentGlaucoma1
4TerminatedTreatmentGlaucoma, Angle-Closure1
4Unknown StatusTreatmentGlaucoma1
4Unknown StatusTreatmentGlaucoma, Primary Open Angle (POAG) / Ocular Hypertension1
4WithdrawnPreventionGlaucoma / Ocular Hypertension / Thyroid Eye Disease1
Not AvailableCompletedNot AvailableGlaucoma1
Not AvailableCompletedNot AvailableGlaucoma / Ocular Hypertension2
Not AvailableCompletedNot AvailableOcular Hypertension / Open-angle Glaucoma (OAG)1
Not AvailableCompletedBasic ScienceDrug Effect (Glaucoma Drugs)1
Not AvailableCompletedOtherIntraocular Pressure1
Not AvailableCompletedPreventionRetinopathy, Diabetic1
Not AvailableCompletedTreatmentAlopecia Areata (AA)1
Not AvailableCompletedTreatmentGlaucoma / Ocular Hypertension1
Not AvailableCompletedTreatmentNormal Tension Glaucoma1
Not AvailableCompletedTreatmentPhysiology, Ocular / Retina1
Not AvailableCompletedTreatmentPrimary Vascular Dysregulation1
Not AvailableNot Yet RecruitingTreatmentGlaucoma / IOP / Ocular Hypertension1
Not AvailableRecruitingDiagnosticGlaucoma1
Not AvailableUnknown StatusHealth Services ResearchOpen Angle Glaucoma (OAG)1
Not AvailableUnknown StatusTreatmentGlaucoma1
Not AvailableUnknown StatusTreatmentGlaucoma, Angle-Closure1
Not AvailableUnknown StatusTreatmentOcular Hypertension1
Not AvailableUnknown StatusTreatmentOcular Hypertension / Primary Glaucoma1

Pharmacoeconomics

Manufacturers
  • Pharmacia and upjohn co
Packagers
  • Assia Chemical Industries Ltd.
  • Cardinal Health
  • Pfizer Inc.
  • Pharmacia Inc.
Dosage forms
FormRouteStrength
SolutionOphthalmic50 ug/1mL
Solution / dropsOphthalmic50 ug/1mL
Solution / dropsOphthalmic0.05 mg/1mL
Solution / dropsOphthalmic
SolutionOphthalmic
SolutionOphthalmic50 mcg
Solution / dropsOphthalmic; Topical0.05 mg/1mL
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)
US5296504No1994-03-222011-03-22Us
US6429226No1992-09-062009-09-06Us
CA1339132No1997-07-292014-07-29Canada
US9539262No2015-04-202035-04-20Us
US9629852No2009-09-122029-09-12Us

Properties

State
Liquid
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 FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
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)

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
LC-MS/MS Spectrum - LC-ESI-qTof , PositiveLC-MS/MSNot Available
MS/MS Spectrum - , positiveLC-MS/MSsplash10-052r-1958000000-c694c9459db45a20b9af

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
Fatty acid esters / Cyclopentanols / Benzene and substituted derivatives / Cyclic alcohols and derivatives / Carboxylic acid esters / Monocarboxylic acids and derivatives / Organic oxides / Hydrocarbon derivatives / Carbonyl compounds
Substituents
Prostaglandin skeleton / Fatty acid ester / Monocyclic benzene moiety / Cyclopentanol / Benzenoid / Cyclic alcohol / Carboxylic acid ester / Secondary alcohol / Carboxylic acid derivative / Monocarboxylic acid or derivatives
Molecular Framework
Aromatic homomonocyclic compounds
External Descriptors
carboxylic ester, prostaglandins Falpha, triol (CHEBI:6384)

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. 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
Uniprot Name
Solute carrier organic anion transporter family member 2B1
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-methylnico...
Gene Name
SLC22A1
Uniprot ID
O15245
Uniprot Name
Solute carrier family 22 member 1
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]

Drug created on June 13, 2005 07:24 / Updated on November 14, 2018 12:44