Identification

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

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

Structure
Thumb
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
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Bl LatanoprostSolutionOphthalmicBausch & Lomb IncNot applicableNot applicableCanada
LatanoprostSolution50 mcgOphthalmicLaboratoire Riva IncNot applicableNot applicableCanada
Latanoprost Ophthalmic SolutionSolutionOphthalmicSandoz Canada IncorporatedNot applicableNot applicableCanada
Latanoprost Ophthalmic SolutionSolutionOphthalmicTeligent Canada IncNot applicableNot applicableCanada
Latanoprost PFSolution / drops0.05 mg/1mLOphthalmicImprimisRx NJ2018-01-01Not applicableUs
MonoprostSolutionOphthalmicLaboratoires Thea2018-01-03Not applicableCanada
XalatanSolution50 ug/1mLOphthalmicPharmacia and Upjohn Company1995-03-202010-06-25Us
XalatanSolution50 mcgOphthalmicPfizer Canada Ulc1997-07-28Not applicableCanada
XalatanSolution50 ug/1mLOphthalmicDispensing Solutions, Inc.1995-03-20Not applicableUs
XalatanSolution50 ug/1mLOphthalmicPharmacia and Upjohn Company LLC1995-03-20Not applicableUs
Additional Data Available
  • Application Number
    Application Number

    A unique ID assigned by the FDA when a product is submitted for approval by the labeller.

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  • Product Code
    Product Code

    A governmentally-recognized ID which uniquely identifies the product within its regulatory market.

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Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Apo-latanoprostSolutionOphthalmicApotex Corporation2011-10-03Not applicableCanada
Gd-latanoprostSolutionOphthalmicGenmed A Division Of Pfizer Canada Ulc2011-10-03Not applicableCanada
Jamp-latanoprostSolutionOphthalmicJamp Pharma CorporationNot applicableNot applicableCanada
LatanoprostSolution / drops50 ug/1mLOphthalmicA-S Medication Solutions2012-07-01Not applicableUs
LatanoprostSolution50 ug/1mLOphthalmicPaddock Laboratories, Inc.2011-10-172012-10-01Us
LatanoprostSolution / drops50 ug/1mLOphthalmicNucare Pharmaceuticals,inc.2011-03-22Not applicableUs
LatanoprostSolution50 ug/1mLOphthalmicMylan Pharmaceuticals2011-03-222013-03-31Us
LatanoprostSolution / drops50 ug/1mLOphthalmicMwi2015-04-08Not applicableUs
LatanoprostSolution / drops50 ug/1mLOphthalmicAurobindo Pharma Limited2019-09-03Not applicableUs
LatanoprostSolution / drops50 ug/1mLOphthalmicNucare Pharmaceuticals,inc.2011-03-22Not applicableUs
Additional Data Available
  • Application Number
    Application Number

    A unique ID assigned by the FDA when a product is submitted for approval by the labeller.

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  • Product Code
    Product Code

    A governmentally-recognized ID which uniquely identifies the product within its regulatory market.

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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 Ulc2013-05-01Not applicableCanada
Jamp-latanoprost/timololLatanoprost (50 mcg) + Timolol (5 mg)SolutionOphthalmicJamp Pharma CorporationNot applicableNot applicableCanada
Latanoprost and Timolol Ophthalmic SolutionLatanoprost (50 mcg) + Timolol (5 mg)SolutionOphthalmicTeligent Canada IncNot 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 Inc2017-01-032018-08-28Canada
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)
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

Latanoprost is indicated for the reduction of elevated intraocular pressure in patients who have been diagnosed with open-angle glaucoma or ocular hypertension.6 Latanoprost may be combined in a product with Netarsudil, a rho kinase inhibitor, for the same indications.10 In addition to the above indications, the Canadian monograph for this drug also approves latanoprost for the treatment of elevated intraocular pressure as a result of angle-closure glaucoma that has been treated with peripheral iridotomy or laser iridoplasty.9

Associated Conditions
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
Additional Data Available
Adverse Effects

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Additional Data Available
Contraindications

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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.11

Protein binding

Latanoprost is about 90% plasma protein-bound.11

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

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.11

Half life

The elimination half-life of latanoprost from the plasma is about 17 minutes.3 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

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.6,8An intravenous infusion of 3 μg/kg of latanoprost in healthy volunteers led to mean plasma concentrations of 200 times higher than a normally administered therapeutic dose and no adverse effects were noted.6 One study suggested that an overdose of latanoprost lead 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 the management of a latanoprost overdose.

Affected organisms
  • Humans and other mammals
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.
AlminoprofenThe therapeutic efficacy of Latanoprost can be decreased when used in combination with Alminoprofen.
AminophenazoneThe therapeutic efficacy of Latanoprost can be decreased when used in combination with Aminophenazone.
AntipyrineThe therapeutic efficacy of Latanoprost can be decreased when used in combination with Antipyrine.
AntrafenineThe therapeutic efficacy of Latanoprost can be decreased when used in combination with Antrafenine.
AzapropazoneThe therapeutic efficacy of Latanoprost can be decreased when used in combination with Azapropazone.
BalsalazideThe therapeutic efficacy of Latanoprost can be decreased when used in combination with Balsalazide.
Additional Data Available
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    Extended Description

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  • Severity
    Severity

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  • Evidence Level
    Evidence Level

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  • Action
    Action

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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]
  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. [PubMed:8922563]
  3. Alm A: Latanoprost in the treatment of glaucoma. Clin Ophthalmol. 2014 Sep 26;8:1967-85. doi: 10.2147/OPTH.S59162. eCollection 2014. [PubMed:25328381]
  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. [PubMed:29921209]
  5. Sjoquist B, Stjernschantz J: Ocular and systemic pharmacokinetics of latanoprost in humans. Surv Ophthalmol. 2002 Aug;47 Suppl 1:S6-12. [PubMed:12204697]
  6. Xalatan FDA label [Link]
  7. Caymanchem MSDS [Link]
  8. Latanoprost, drugs.com [Link]
  9. Xalatan, Canadian monograph [Link]
  10. Rocklatan FDA label [Link]
  11. Sandoz Latanoprost monograph [Link]
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
1Not Yet RecruitingTreatmentOpen Angle Glaucoma (OAG)1
1TerminatedTreatmentGlaucoma, Primary Open Angle (POAG) / Ocular Hypertension1
1, 2CompletedTreatmentGlaucoma, Primary Open Angle (POAG) / Ocular Hypertension1
1, 2CompletedTreatmentGlaucoma / Ocular Hypertension1
1, 2CompletedTreatmentOcular Hypertension1
1, 2CompletedTreatmentOcular Hypertension / Open Angle Glaucoma (OAG)1
1, 2CompletedTreatmentOcular Hypertension / Open-angle Glaucoma (OAG)1
2Active Not RecruitingTreatmentMenière's Disease1
2CompletedScreeningIntraocular Pressure1
2CompletedTreatmentChildhood Glaucoma1
2CompletedTreatmentGlaucoma3
2CompletedTreatmentGlaucoma, Primary Open Angle (POAG)2
2CompletedTreatmentGlaucoma, Primary Open Angle (POAG) / Ocular Hypertension6
2CompletedTreatmentGlaucoma, Primary Open Angle (POAG) / Ocular Hypertension / Pigmentary Glaucoma / Pseudoexfoliative Glaucoma1
2CompletedTreatmentGlaucoma / Glaucoma or Ocular Hypertension and / Ocular Hypertension / Ocular Surface Disease1
2CompletedTreatmentGlaucoma / Ocular Hypertension6
2CompletedTreatmentOcular Hypertension / Open Angle Glaucoma (OAG)3
2CompletedTreatmentOcular Hypertension / Open Angle-glaucoma1
2CompletedTreatmentOcular Hypertension / Open-angle Glaucoma (OAG)12
2CompletedTreatmentOpen-angle Glaucoma or Ocular Hypertension1
2RecruitingTreatmentGlaucoma, Primary Open Angle (POAG) / Ocular Hypertension1
2RecruitingTreatmentOcular Hypertension / Open-angle Glaucoma (OAG)1
2RecruitingTreatmentOpen Angle Glaucoma and Cataract1
2RecruitingTreatmentOpen-angle Glaucoma, Ocular Hypertension1
2TerminatedTreatmentGlaucoma1
2Unknown StatusTreatmentGlaucoma1
2WithdrawnTreatmentGlaucoma / Ocular Hypertension1
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 Hypertension4
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)12
3CompletedTreatmentOpen Angle Glaucoma or Ocular Hypertension1
3CompletedTreatmentPrimary Open Angle Glaucoma or Ocular Hypertension1
3Not Yet RecruitingTreatmentGlaucoma, Primary Open Angle (POAG) / Ocular Hypertension1
3RecruitingPreventionGlaucoma1
3RecruitingTreatmentGlaucoma, Primary Open Angle (POAG) / Ocular Hypertension1
3RecruitingTreatmentOcular Hypertension / Open Angle Glaucoma (OAG)1
3TerminatedTreatmentOcular Hypertension / Open Angle Glaucoma (OAG)1
3Unknown StatusTreatmentGlaucoma1
3WithdrawnTreatmentOcular Hypertension / Open Angle Glaucoma (OAG)1
3WithdrawnTreatmentOcular Hypertension / Open-angle Glaucoma (OAG)1
4CompletedNot AvailableGlaucoma2
4CompletedNot AvailableGlaucoma / Ocular Hypertension1
4CompletedNot AvailableOpen-angle Glaucoma (OAG)1
4CompletedBasic ScienceOcular Hypertension / Open Angle Glaucoma (OAG)1
4CompletedDiagnosticGlaucoma / Ocular Hypertension1
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
4CompletedTreatmentGlaucoma10
4CompletedTreatmentGlaucoma, Primary Open Angle (POAG)1
4CompletedTreatmentGlaucoma, Primary Open Angle (POAG) / Ocular Hypertension2
4CompletedTreatmentGlaucoma / Healthy Volunteers1
4CompletedTreatmentGlaucoma / Ocular Hypertension10
4CompletedTreatmentOcular Hypertension1
4CompletedTreatmentOcular Hypertension / Open Angle Glaucoma (OAG)3
4CompletedTreatmentOcular Hypertension / Open-angle Glaucoma (OAG)10
4CompletedTreatmentOpen-angle Glaucoma (OAG)4
4CompletedTreatmentRetinopathy, Diabetic1
4Not Yet RecruitingBasic ScienceOpen-angle Glaucoma (OAG)1
4Not Yet RecruitingTreatmentOpen-angle Glaucoma (OAG)1
4RecruitingBasic ScienceGlaucoma / Ocular Hypertension1
4RecruitingTreatmentGlaucoma1
4RecruitingTreatmentGlaucoma, Primary Open Angle (POAG)1
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
4Unknown StatusTreatmentIntraocular Pressure (IOP) / Tear Break-Up Time1
4WithdrawnPreventionGlaucoma / Ocular Hypertension / Thyroid Eye Disease1
Not AvailableCompletedNot AvailableGlaucoma1
Not AvailableCompletedNot AvailableGlaucoma / Ocular Hypertension2
Not AvailableCompletedNot AvailableOcular Dryness / Ocular Hypertension / Ocular Irritation / Open-angle Glaucoma (OAG)1
Not AvailableCompletedNot AvailableOcular Hypertension / Open-angle Glaucoma (OAG)1
Not AvailableCompletedBasic ScienceDrug Effect (Glaucoma Drugs)1
Not AvailableCompletedDiagnosticIntraocular Pressure / Physiology, Ocular / Regional Blood Flow1
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 StatusTreatmentExfoliation Syndrome / Glaucoma / Ocular Hypertension1
Not AvailableUnknown StatusTreatmentGlaucoma1
Not AvailableUnknown StatusTreatmentGlaucoma, Angle-Closure1
Not AvailableUnknown StatusTreatmentOcular Hypertension1
Not AvailableUnknown StatusTreatmentOcular Hypertension / Open-angle Glaucoma (OAG)1
Not AvailableUnknown StatusTreatmentOcular Hypertension / Primary Glaucoma1
Not AvailableWithdrawnNot AvailableOcular Hypertension / Open-angle Glaucoma (OAG)1

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
SolutionOphthalmic
Solution / dropsOphthalmic; Topical
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
US6429226No2002-08-062009-09-06Us
CA1339132No1997-07-292014-07-29Canada
US8394826No2013-03-122030-11-10Us
US9096569No2015-08-042026-07-11Us
US8450344No2013-05-282026-07-11Us
US9415043No2016-08-162034-03-14Us
US9931336No2018-04-032034-03-14Us
US9539262No2017-01-102035-04-20Us
US9629852No2017-04-252029-09-12Us
US9993470No2018-06-122034-03-14Us
US10174017No2019-01-082030-01-27Us
Additional Data Available
  • Filed On
    Filed On

    The date on which a patent was filed with the relevant government.

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Properties

State
Liquid
Experimental Properties
PropertyValueSource
boiling point (°C)583.8https://www.lookchem.com/Latanoprost/
logP2.18https://www.ebi.ac.uk/chembl/compound_report_card/CHEMBL448/
pKa7.93https://www.ebi.ac.uk/chembl/compound_report_card/CHEMBL448/
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
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. [PubMed:14646172]
  2. Alm A: Latanoprost in the treatment of glaucoma. Clin Ophthalmol. 2014 Sep 26;8:1967-85. doi: 10.2147/OPTH.S59162. eCollection 2014. [PubMed:25328381]
  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. [PubMed:8922563]
  4. Xalatan FDA label [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. [PubMed:8922563]
  2. Alm A: Latanoprost in the treatment of glaucoma. Clin Ophthalmol. 2014 Sep 26;8:1967-85. doi: 10.2147/OPTH.S59162. eCollection 2014. [PubMed:25328381]
  3. Xalatan FDA label [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. [PubMed:20019365]
  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. [PubMed:19843975]
  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. [PubMed:22013971]
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. [PubMed:11907186]
  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. [PubMed:16338963]
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. [PubMed:16338963]
  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. [PubMed:11907186]

Drug created on June 13, 2005 07:24 / Updated on October 12, 2019 09:59