Latanoprost

Identification

Summary

Latanoprost is an isopropyl ester prodrug used to treat increased intraocular pressure.

Brand Names
Iyuzeh, Rocklatan, Xalacom, Xalatan, Xelpros
Generic Name
Latanoprost
DrugBank Accession Number
DB00654
Background

Latanoprost is a prodrug analog of prostaglandin F2 alpha that is used to treat elevated intraocular pressure (IOP). It was initially approved by the FDA in 1998. Latanoprost is the first topical prostaglandin F2 alpha analog used for glaucoma treatment.3 It has been found to be well-tolerated and its use does not normally result in systemic adverse effects like other drugs used to treat elevated intraocular pressure, such as Timolol. Another benefit latanoprost is that it can be administered once a day.2

Type
Small Molecule
Groups
Approved, Investigational
Structure
Weight
Average: 432.5928
Monoisotopic: 432.28757439
Chemical Formula
C26H40O5
Synonyms
  • isopropyl (Z)-7-((1R,2R,3R,5S)-3,5-dihydroxy-2-((3R)-3-hydroxy-5-phenylpentyl)cyclopentyl)-5-heptenoate
  • Latanoprost
  • Latanoprostum
  • 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

Pharmacology

Indication

Latanoprost is indicated for the reduction of elevated intraocular pressure in patients who have been diagnosed with open-angle glaucoma or ocular hypertension.6,10,11 It is available as monotherapy or in a combination product with netarsudil 9 or timolol.12

In Canada, latanoprost is also indicated to treat elevated intraocular pressure due to angle-closure glaucoma that has been treated with peripheral iridotomy or laser iridoplasty.10

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Associated Conditions
Indication TypeIndicationCombined Product DetailsApproval LevelAge GroupPatient CharacteristicsDose Form
Used in combination to manageIncreased intra ocular pressure (iop)Combination Product in combination with: Netarsudil (DB13931)••••••••••••
Used in combination to manageIncreased intra ocular pressure (iop)Combination Product in combination with: Netarsudil (DB13931)••••••••••••
Management ofIncreased intra ocular pressure (iop)••••••••••••
Management ofIncreased intra ocular pressure (iop)••••••••••••
Used in combination to treatOcular hypertensionCombination Product in combination with: Timolol (DB00373)•••••••••••••••••••••••• •••••••• •• ••••• •••••••••
Contraindications & Blackbox Warnings
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Pharmacodynamics

Latanoprost effectively decreases intraocular pressure by increasing uveoscleral outflow.2 A decrease in intraocular pressure has been measured within 3–4 hours post-administration, reaches a maximum decrease at 8–12 hours, and can be maintained for a period of 24 hours.3

A note on eye and periorbital changes

Between 3 to 10% of patients taking latanoprost have experienced iris pigmentation after about 3-4 months of latanoprost use.1,2 Patients should be notified of this risk before initiating treatment. It may occur in both patients with light-colored irides (green-brown or blue/grey-brown) or dark-colored (brown) irides, but is less pronounced in the latter group.1 This drug may also cause other ocular effects including infrequent conjunctival hyperemia, pigmentation of periocular tissues, eyelash changes, hypertrichosis, and ocular irritation.3,6

Mechanism of action

Elevated intraocular pressure leads to an increased risk of glaucomatous visual field loss. The higher the intraocular pressure, the higher the risk of damage to the optic nerve and loss of visual field.6 Latanoprost selectively stimulates the prostaglandin F2 alpha receptor and this results in a decreased intraocular pressure (IOP) via the increased outflow of aqueous humor, which is often implicated in cases of elevated intraocular pressure.2,6 Possible specific mechanisms of the abovementioned increased aqueous outflow are the remodeling of the extracellular matrix and regulation of matrix metalloproteinases. These actions result in higher tissue permeability related to humor outflow pathways, which likely change outflow resistance and/or outflow rates.3

TargetActionsOrganism
AProstaglandin F2-alpha receptor
agonist
Humans
Absorption

This drug is rapidly absorbed in the cornea as an isopropyl ester prodrug and is then activated by the process of hydrolysis. A small amount of this drug is systemically absorbed.2 The Cmax of latanoprost in the systemic circulation is reached after 5 minutes and is measured to be 53 pg/mL. The Cmax in the aqueous humor is attained within 2 hours after administration.3,6 and has been estimated to be 15-30 ng/mL.3

Volume of distribution

The volume of distribution of latanoprost is 0.16 ± 0.02 L/kg. The activated acid form of latanoprost can be measured in aqueous humor in the initial 4 hours post-administration, and it is measured in the plasma only for 1 hour following ophthalmic administration.6 This drug is more lipophilic than its parent prostaglandin and easily penetrates the cornea.2 It has been shown to cross the placenta in rats.10

Protein binding

Latanoprost is about 90% plasma protein-bound.10

Metabolism

After corneal uptake, this prodrug is hydrolyzed and activated by esterases to become a pharmacologically active drug. The small portion of this drug that is able to reach the circulation is found to be metabolized by the liver to the 1,2-dinor and 1,2,3,4-tetranor metabolites through fatty acid beta-oxidation.2,3,6

Hover over products below to view reaction partners

Route of elimination

After hepatic beta-oxidation, the metabolites of latanoprost are primarily found to be excreted by the kidneys. About 88% of the latanoprost dose is recovered in the urine after topical administration.2,6 About 15% of a dose is reported to be excreted in the feces.10

Half-life

The elimination half-life of latanoprost from the plasma is about 17 minutes.3,6 The elimination half-life of latanoprost from the eye is estimated at 2–3 hours.3

Clearance

The systemic clearance of latanoprost is 7 mL/min/kg.6

Adverse Effects
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Toxicity

The oral LD50 in the rat is > 50 mg/kg.7

An overdose of latanoprost is not expected to result in dangerous patient outcomes, however, conjunctival or episcleral hyperemia may occur.6 An intravenous infusion of 3 μg/kg of latanoprost in healthy volunteers led to mean plasma concentrations 200 times higher than a normally administered therapeutic dose and no adverse effects were noted.6 One study suggested that an overdose of latanoprost leads to cystoid macular edema after a large, unintended overdose. This resolved within 4 weeks after 4 weeks following treatment with nepafenac 0.3% eye drops in addition to oral acetazolamide.4 Contact the local poison control center for updated guidance on managing a latanoprost overdose.

Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
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.
AminophenazoneThe therapeutic efficacy of Latanoprost can be decreased when used in combination with Aminophenazone.
Food Interactions
No interactions found.

Products

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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)
Brand Name Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
Bl LatanoprostSolution50 mcg / mLOphthalmicBausch & Lomb IncNot applicableNot applicableCanada flag
IyuzehSolution / drops50 ug/1mLOphthalmicThea Pharma Inc.2023-07-14Not applicableUS flag
LatanoprostSolution50 mcg / mLOphthalmicLaboratoire Riva IncNot applicableNot applicableCanada flag
Latanoprost Ophthalmic SolutionSolution50 mcg / mLOphthalmicHikma Canada Limited2020-06-26Not applicableCanada flag
Latanoprost Ophthalmic SolutionSolution50 mcg / mLOphthalmicSandoz Canada IncorporatedNot applicableNot applicableCanada flag
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
Ag-latanoprostSolution50 mcg / mLOphthalmicAngita Pharma Inc.Not applicableNot applicableCanada flag
Apo-latanoprostSolution50 mcg / mLOphthalmicApotex Corporation2011-10-03Not applicableCanada flag
Jamp LatanoprostSolution50 mcg / mLOphthalmicJamp Pharma Corporation2020-02-07Not applicableCanada flag
LatanoprostSolution50 ug/1mLOphthalmicNucare Pharmaceuticals,inc.2016-09-01Not applicableUS flag
LatanoprostSolution50 ug/1mLOphthalmicMylan Pharmaceuticals2011-03-222013-03-31US flag
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
Act Latanoprost/timololLatanoprost (50 mcg / mL) + Timolol maleate (5 mg / mL)SolutionOphthalmicTEVA Canada Limited2015-09-29Not applicableCanada flag
Akistan Duo 50 Mikrogramm/ml + 5 mg/ml Augentropfen, LösungLatanoprost (50 mcg/ml) + Timolol maleate (6.8 mg/ml)Solution / dropsOphthalmicPharmaselect International Beteiligungs Gmb H2019-08-30Not applicableAustria flag
Apo-latanoprost-timopLatanoprost (50 mcg / mL) + Timolol maleate (5 mg / mL)SolutionOphthalmicApotex Corporation2014-07-02Not applicableCanada flag
ARUCOMLatanoprost (0.05 mg/mL) + Timolol maleate (5 mg/mL)Solution / drops; Suspension / dropsOphthalmic2017-01-01Not applicableGermany flag
ARUCOMLatanoprost (0.05 mg/mL) + Timolol maleate (5 mg/mL)Solution / drops; Suspension / dropsOphthalmic2017-01-01Not applicableGermany flag
Unapproved/Other Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
Latanoprost PFLatanoprost (0.05 mg/1mL)Solution / dropsOphthalmicImprimisRx NJ2018-01-01Not applicableUS flag
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 flag
Tim-Dor-LatLatanoprost (0.05 mg/1mL) + Dorzolamide hydrochloride (20 mg/1mL) + Timolol maleate (5 mg/1mL)Solution / dropsOphthalmicImprimisRx NJ2018-01-01Not applicableUS flag
Tim-Lat -PFLatanoprost (0.05 mg/1mL) + Timolol maleate (5 mg/1mL)Solution / dropsOphthalmicImprimisRx NJ2018-01-01Not applicableUS flag

Categories

ATC Codes
S01EE01 — LatanoprostS01EE51 — Latanoprost and netarsudil
Drug Categories
Chemical TaxonomyProvided by Classyfire
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
Alcohol / Aromatic homomonocyclic compound / Benzenoid / Carbonyl group / Carboxylic acid derivative / Carboxylic acid ester / Cyclic alcohol / Cyclopentanol / Fatty acid ester / Hydrocarbon derivative
Molecular Framework
Aromatic homomonocyclic compounds
External Descriptors
carboxylic ester, prostaglandins Falpha, triol (CHEBI:6384)
Affected organisms
  • Humans and other mammals

Chemical Identifiers

UNII
6Z5B6HVF6O
CAS number
130209-82-4
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

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. [Article]
  2. Patel SS, Spencer CM: Latanoprost. A review of its pharmacological properties, clinical efficacy and tolerability in the management of primary open-angle glaucoma and ocular hypertension. Drugs Aging. 1996 Nov;9(5):363-78. doi: 10.2165/00002512-199609050-00007. [Article]
  3. Alm A: Latanoprost in the treatment of glaucoma. Clin Ophthalmol. 2014 Sep 26;8:1967-85. doi: 10.2147/OPTH.S59162. eCollection 2014. [Article]
  4. Makri OE, Tsekouras IK, Plotas P, Tsapardoni F, Pallikari A, Georgakopoulos CD: Cystoid Macular Edema Due to Accidental Latanoprost Overdose After Uncomplicated Phacoemulsification. Curr Drug Saf. 2018;13(3):208-210. doi: 10.2174/1574886313666180619163845. [Article]
  5. Sjoquist B, Stjernschantz J: Ocular and systemic pharmacokinetics of latanoprost in humans. Surv Ophthalmol. 2002 Aug;47 Suppl 1:S6-12. [Article]
  6. FDA Approved Drug Products: Xalatan (latanoprost) Ophthalmic Solution [Link]
  7. Cayman Chemical: Latanoprost MSDS [Link]
  8. Drugs.com: Latanoprost ophthalmic [Link]
  9. FDA Approved Drug Products: ROCKLATAN (netarsudil and latanoprost) Ophthalmic Solution [Link]
  10. Health Canada Approved Drug Products: SANDOZ LATANOPROST (Latanoprost) Ophthalmic Solution [Link]
  11. FDA Approved Drug Products: IYUZEH (latanoprost ophthalmic solution) 0.005%, for topical ophthalmic use [Link]
  12. Health Canada Product Monograph: ACT LATANOPROST/TIMOLOL (Latanaprost and Timolol) Ophthalmic Solution [Link]
Human Metabolome Database
HMDB0014792
KEGG Drug
D00356
PubChem Compound
5311221
PubChem Substance
46506279
ChemSpider
4470740
BindingDB
50240648
RxNav
43611
ChEBI
6384
ChEMBL
CHEMBL1051
ZINC
ZINC000012468792
Therapeutic Targets Database
DAP001216
PharmGKB
PA164774763
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
PDRhealth
PDRhealth Drug Page
Wikipedia
Latanoprost

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
4Active Not RecruitingTreatmentNon-segmental Vitiligo1
4CompletedNot AvailableGlaucoma2
4CompletedBasic ScienceOcular Hypertension / Open Angle Glaucoma (OAG)1
4CompletedBasic ScienceOpen Angle Glaucoma (OAG)1
4CompletedDiagnosticGlaucoma / Ocular Hypertension1

Pharmacoeconomics

Manufacturers
  • Pharmacia and upjohn co
Packagers
  • Assia Chemical Industries Ltd.
  • Cardinal Health
  • Pfizer Inc.
  • Pharmacia Inc.
Dosage Forms
FormRouteStrength
Solution / drops; suspension / dropsOphthalmic50 MIKROGRAMM/ML
Solution / dropsOphthalmic
Solution / dropsOphthalmic50 mcg/ml
Solution / drops; suspension / dropsOphthalmic0.05 mg/mL
Solution / dropsOphthalmic0.005 % w/v
SolutionOphthalmic50 mcg
Solution / dropsOphthalmic0.005 %w/v
Solution / dropsOphthalmic50 g/ml
SolutionOphthalmic50.00 mcg
SolutionOphthalmic0.05 mg
SolutionConjunctival; Ophthalmic0.05 mg
SolutionOphthalmic0.005 % w/w
SolutionOphthalmic0.125 mg/2.5ml
SolutionOphthalmic0.050 mg
Solution / drops; suspension / dropsOphthalmic50 UG/ML
SolutionOphthalmic
Solution / drops; suspension / dropsOphthalmic
SolutionOphthalmic50 ug/1mL
Solution / dropsOphthalmic50 ug/1mL
SolutionConjunctival; Ophthalmic
Solution / drops; suspension / dropsOphthalmic0.05 mg
Solution / dropsOphthalmic0.05 mg/1mL
Solution / drops; suspension / dropsOphthalmic50 UG
SolutionOphthalmic0.05 mg/ml
LiquidOphthalmic50 mcg/1ml
SolutionOphthalmic0.005 % w/v
Solution / dropsOphthalmic50 Mikrogramm/ml
Solution / dropsOphthalmic0005 %
Solution / dropsOphthalmic0.05 MG/ML
EmulsionOphthalmic0.05 mg
SolutionConjunctival; Ophthalmic50 mcg
Solution / dropsOphthalmic50 MICROGRAMMI/ML
SprayNasal
SolutionOphthalmic50.000 mcg
SolutionOphthalmic0.050 mg/ml
Solution / dropsOphthalmic; Topical
Solution / dropsOphthalmic
SolutionOphthalmic0.05 mg/ml
SolutionOphthalmic
SolutionOphthalmic50 mcg/1ml
SolutionOphthalmic50 mcg / mL
Solution / drops; suspension / dropsOphthalmic0.005 %
Solution / dropsOphthalmic0.005 %
SolutionOphthalmic50 mcg/ml
SolutionOphthalmic0.005 %w/v
Solution / dropsOphthalmic; Topical0.05 mg/1mL
Solution / dropsOphthalmic50 mcg/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)Region
US5296504No1994-03-222011-03-22US flag
US6429226No2002-08-062009-09-06US flag
CA1339132No1997-07-292014-07-29Canada flag
US8394826No2013-03-122030-11-10US flag
US9096569No2015-08-042026-07-11US flag
US8450344No2013-05-282026-07-11US flag
US9415043No2016-08-162034-03-14US flag
US9931336No2018-04-032034-03-14US flag
US9539262No2017-01-102035-04-20US flag
US9629852No2017-04-252029-09-12US flag
US9993470No2018-06-122034-03-14US flag
US10174017No2019-01-082030-01-27US flag
US10532993No2020-01-142026-07-11US flag
US10588901No2020-03-172034-03-14US flag
US10654844No2020-05-192030-11-10US flag
US10882840No2021-01-052026-07-11US flag
US11028081No2021-06-082030-01-27US flag
US11021456No2021-06-012026-07-11US flag
US11197853No2021-12-142034-03-14US flag
US11185538No2021-11-302034-03-14US flag
US11618748No2010-01-272030-01-27US flag
US8637054No2011-07-082031-07-08US flag

Properties

State
Liquid
Experimental Properties
PropertyValueSource
boiling point (°C)583.8https://www.lookchem.com/Latanoprost/
logP3.98https://www.ebi.ac.uk/chembl/compound_report_card/CHEMBL1051/
pKa4.88https://www.tandfonline.com/doi/abs/10.1517/14656566.2012.662219?src=recsys&journalCode=ieop20
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
Polarizability50.9 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-MSsplash10-00kf-5469500000-3070e3312e2f54422eeb
LC-MS/MS Spectrum - LC-ESI-qTof , PositiveLC-MS/MSsplash10-052r-1958000000-c694c9459db45a20b9af
MS/MS Spectrum - , positiveLC-MS/MSsplash10-052r-1958000000-c694c9459db45a20b9af
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-00dj-0009000000-eb46deeacd0be69af238
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-001i-0005900000-6a67554997b398d3e095
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-05gj-1139100000-6785ad65f23e066d90dc
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0zfr-0019000000-7637f51e3bcf86095ff8
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-004j-4931100000-259ed8417a3298e43bb5
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0a4i-9838100000-0babebc7d3efa19da652
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-234.8277888
predicted
DarkChem Lite v0.1.0
[M-H]-242.2269888
predicted
DarkChem Lite v0.1.0
[M-H]-211.85632
predicted
DeepCCS 1.0 (2019)
[M+H]+235.0936888
predicted
DarkChem Lite v0.1.0
[M+H]+242.1008888
predicted
DarkChem Lite v0.1.0
[M+H]+214.10527
predicted
DeepCCS 1.0 (2019)
[M+Na]+233.7618888
predicted
DarkChem Lite v0.1.0
[M+Na]+242.3212888
predicted
DarkChem Lite v0.1.0
[M+Na]+220.0178
predicted
DeepCCS 1.0 (2019)

Targets

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insights and accelerate drug research.
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Kind
Protein
Organism
Humans
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. 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. [Article]
  2. Alm A: Latanoprost in the treatment of glaucoma. Clin Ophthalmol. 2014 Sep 26;8:1967-85. doi: 10.2147/OPTH.S59162. eCollection 2014. [Article]
  3. Patel SS, Spencer CM: Latanoprost. A review of its pharmacological properties, clinical efficacy and tolerability in the management of primary open-angle glaucoma and ocular hypertension. Drugs Aging. 1996 Nov;9(5):363-78. doi: 10.2165/00002512-199609050-00007. [Article]
  4. FDA Approved Drug Products: Xalatan (latanoprost) Ophthalmic Solution [Link]
  5. ChemBL compound report card [Link]

Enzymes

1. Corneal esterases
Kind
Group
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
Esterases in the cornea that metabolize drugs in the eye.
References
  1. Patel SS, Spencer CM: Latanoprost. A review of its pharmacological properties, clinical efficacy and tolerability in the management of primary open-angle glaucoma and ocular hypertension. Drugs Aging. 1996 Nov;9(5):363-78. doi: 10.2165/00002512-199609050-00007. [Article]
  2. Alm A: Latanoprost in the treatment of glaucoma. Clin Ophthalmol. 2014 Sep 26;8:1967-85. doi: 10.2147/OPTH.S59162. eCollection 2014. [Article]
  3. FDA Approved Drug Products: Xalatan (latanoprost) Ophthalmic Solution [Link]

Transporters

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Sodium-independent organic anion transmembrane transporter activity
Specific Function
May mediate the release of newly synthesized prostaglandins from cells, the transepithelial transport of prostaglandins, and the clearance of prostaglandins from the circulation. Transports PGD2, a...
Gene Name
SLCO2A1
Uniprot ID
Q92959
Uniprot Name
Solute carrier organic anion transporter family member 2A1
Molecular Weight
70043.33 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. [Article]
  2. Mandery K, Bujok K, Schmidt I, Wex T, Treiber G, Malfertheiner P, Rau TT, Amann KU, Brune K, Fromm MF, Glaeser H: Influence of cyclooxygenase inhibitors on the function of the prostaglandin transporter organic anion-transporting polypeptide 2A1 expressed in human gastroduodenal mucosa. J Pharmacol Exp Ther. 2010 Feb;332(2):345-51. doi: 10.1124/jpet.109.154518. Epub 2009 Oct 20. [Article]
  3. Roth M, Obaidat A, Hagenbuch B: OATPs, OATs and OCTs: the organic anion and cation transporters of the SLCO and SLC22A gene superfamilies. Br J Pharmacol. 2012 Mar;165(5):1260-87. doi: 10.1111/j.1476-5381.2011.01724.x. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
Inhibitor
General Function
Sodium-independent organic anion transmembrane transporter activity
Specific Function
Involved in the renal elimination of endogenous and exogenous organic anions. Functions as organic anion exchanger when the uptake of one molecule of organic anion is coupled with an efflux of one ...
Gene Name
SLC22A6
Uniprot ID
Q4U2R8
Uniprot Name
Solute carrier family 22 member 6
Molecular Weight
61815.78 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. [Article]
  2. Sauvant C, Holzinger H, Gekle M: Prostaglandin E2 inhibits its own renal transport by downregulation of organic anion transporters rOAT1 and rOAT3. J Am Soc Nephrol. 2006 Jan;17(1):46-53. doi: 10.1681/ASN.2005070727. Epub 2005 Dec 7. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Sodium-independent organic anion transmembrane transporter activity
Specific Function
Plays an important role in the excretion/detoxification of endogenous and exogenous organic anions, especially from the brain and kidney. Involved in the transport basolateral of steviol, fexofenad...
Gene Name
SLC22A8
Uniprot ID
Q8TCC7
Uniprot Name
Solute carrier family 22 member 8
Molecular Weight
59855.585 Da
References
  1. Sauvant C, Holzinger H, Gekle M: Prostaglandin E2 inhibits its own renal transport by downregulation of organic anion transporters rOAT1 and rOAT3. J Am Soc Nephrol. 2006 Jan;17(1):46-53. doi: 10.1681/ASN.2005070727. Epub 2005 Dec 7. [Article]
  2. 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. [Article]

Drug created at June 13, 2005 13:24 / Updated at May 25, 2024 22:42