Identification
- Summary
Latanoprost is an isopropyl ester prodrug used to treat increased intraocular pressure.
- Brand Names
- 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
Structure for Latanoprost (DB00654)
- 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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- Contraindications & Blackbox Warnings
Avoid life-threatening adverse drug eventsImprove clinical decision support with information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events & improve clinical decision support.- 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
Target Actions Organism AProstaglandin F2-alpha receptor agonistHumans - 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
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- 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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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.
Drug Interaction Integrate drug-drug
interactions in your softwareAceclofenac The therapeutic efficacy of Latanoprost can be decreased when used in combination with Aceclofenac. Acemetacin The therapeutic efficacy of Latanoprost can be decreased when used in combination with Acemetacin. Acetylsalicylic acid The therapeutic efficacy of Latanoprost can be decreased when used in combination with Acetylsalicylic acid. Alclofenac The therapeutic efficacy of Latanoprost can be decreased when used in combination with Alclofenac. Aminophenazone The therapeutic efficacy of Latanoprost can be decreased when used in combination with Aminophenazone. Antipyrine The therapeutic efficacy of Latanoprost can be decreased when used in combination with Antipyrine. Antrafenine The therapeutic efficacy of Latanoprost can be decreased when used in combination with Antrafenine. Balsalazide The therapeutic efficacy of Latanoprost can be decreased when used in combination with Balsalazide. Baricitinib The serum concentration of Baricitinib can be increased when it is combined with Latanoprost. Benorilate The therapeutic efficacy of Latanoprost can be decreased when used in combination with Benorilate. 
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- No interactions found.
Products
Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.- 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
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Bl Latanoprost Solution 50 mcg / mL Ophthalmic Bausch & Lomb Inc Not applicable Not applicable Canada 
Latanoprost Solution 50 mcg / mL Ophthalmic Laboratoire Riva Inc Not applicable Not applicable Canada Latanoprost Ophthalmic Solution Solution 50 mcg / mL Ophthalmic Sandoz Canada Incorporated Not applicable Not applicable Canada Latanoprost Ophthalmic Solution Solution 50 mcg / mL Ophthalmic Hikma Canada Limited 2020-06-26 Not applicable Canada Latanoprost PF Solution / drops 0.05 mg/1mL Ophthalmic ImprimisRx NJ 2018-01-01 Not applicable US 
M-latanoprost Solution 50 mcg / mL Ophthalmic Mantra Pharma Inc 2021-11-10 Not applicable Canada Monoprost Solution 50 mcg / mL Ophthalmic Laboratoires Thea 2018-01-03 Not applicable Canada Xalatan Solution 50 ug/1mL Ophthalmic Pfizer Laboratories Div Pfizer Inc 1995-03-20 Not applicable US Xalatan Solution 50 ug/1mL Ophthalmic Dispensing Solutions, Inc. 1995-03-20 Not applicable US Xalatan Solution 50 mcg / mL Ophthalmic Upjohn Canada Ulc 1997-07-28 Not applicable Canada - Generic Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Ag-latanoprost Solution 50 mcg / mL Ophthalmic Angita Pharma Inc. Not applicable Not applicable Canada Apo-latanoprost Solution 50 mcg / mL Ophthalmic Apotex Corporation 2011-10-03 Not applicable Canada Gd-latanoprost Solution 50 mcg / mL Ophthalmic Upjohn Canada Ulc 2011-10-03 Not applicable Canada Jamp Latanoprost Solution 50 mcg / mL Ophthalmic Jamp Pharma Corporation 2020-02-07 Not applicable Canada Latanoprost Solution 50 ug/1mL Ophthalmic Mylan Pharmaceuticals 2011-03-22 2013-03-31 US Latanoprost Solution 50 ug/1mL Ophthalmic AMERICAN REGENT, INC. 2011-08-02 2014-09-30 US Latanoprost Solution / drops 50 ug/1mL Ophthalmic Nucare Pharmaceuticals,inc. 2011-03-22 Not applicable US Latanoprost Solution / drops 50 ug/1mL Ophthalmic Akorn 2012-07-01 Not applicable US Latanoprost Solution / drops 50 ug/1mL Ophthalmic Somerset Therapeutics, Llc 2019-12-03 Not applicable US Latanoprost Solution / drops 50 ug/1mL Ophthalmic Physicians Total Care, Inc. 2011-06-21 Not applicable US - Mixture Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image Act Latanoprost/timolol Latanoprost (50 mcg / mL) + Timolol maleate (5 mg / mL) Solution Ophthalmic TEVA Canada Limited 2015-09-29 Not applicable Canada Akistan Duo 50 Mikrogramm/ml + 5 mg/ml Augentropfen, Lösung Latanoprost (50 mcg/ml) + Timolol maleate (6.8 mg/ml) Solution / drops Ophthalmic Pharmaselect International Beteiligungs Gmb H 2019-08-30 Not applicable Austria 
Apo-latanoprost-timop Latanoprost (50 mcg / mL) + Timolol maleate (5 mg / mL) Solution Ophthalmic Apotex Corporation 2014-07-02 Not applicable Canada ARUCOM Latanoprost (0.05 mg/mL) + Timolol maleate (5 mg/mL) Solution / drops; Suspension / drops Ophthalmic 2017-01-01 Not applicable Germany 
ARUCOM Latanoprost (0.05 mg/mL) + Timolol maleate (5 mg/mL) Solution / drops; Suspension / drops Ophthalmic 2017-01-01 2021-11-15 Germany ARUCOM Latanoprost (0.05 mg/mL) + Timolol maleate (5 mg/mL) Solution / drops; Suspension / drops Ophthalmic 2017-01-01 Not applicable Germany ARUCOM % 0.005 + % 0.5 GÖZ DAMLASI, 2.5 ML Latanoprost (50 mcg/ml) + Timolol maleate (5 mg/ml) Solution / drops Ophthalmic GENVEON İLAÇ SAN. VE TİC. A.Ş. 2020-08-14 Not applicable Turkey 
DUOPROST GÖZ DAMLASI, 1 ADET Latanoprost (50 μg/ml) + Timolol (5 mg/ml) Solution / drops Ophthalmic ROMPHARM İLAÇ SAN. VE TİC. LTD. ŞTİ. 2020-08-14 Not applicable Turkey Fixapost 50 Mikrogramm/ml + 5 mg/ml Augentropfen, Lösung im Einzeldosisbehältnis Latanoprost (50 mcg/ml) + Timolol (5 mg/ml) Solution / drops Ophthalmic Laboratoires Thea 2018-06-25 Not applicable Austria FIXAPROST 50UG/ML+5MG/ML Latanoprost (0.01 mg) + Timolol maleate (1 mg) Solution / drops; Suspension / drops Ophthalmic 2017-01-01 Not applicable Germany - Unapproved/Other Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image Latanoprost PF Latanoprost (0.05 mg/1mL) Solution / drops Ophthalmic ImprimisRx NJ 2018-01-01 Not applicable US Tim-Brim-Dor-Lat Latanoprost (0.05 mg/1mL) + Brimonidine tartrate (1.5 mg/1mL) + Dorzolamide hydrochloride (20 mg/1mL) + Timolol maleate (5 mg/1mL) Solution / drops Ophthalmic ImprimisRx NJ 2018-01-01 Not applicable US Tim-Dor-Lat Latanoprost (0.05 mg/1mL) + Dorzolamide hydrochloride (20 mg/1mL) + Timolol maleate (5 mg/1mL) Solution / drops Ophthalmic ImprimisRx NJ 2018-01-01 Not applicable US Tim-Lat -PF Latanoprost (0.05 mg/1mL) + Timolol maleate (5 mg/1mL) Solution / drops Ophthalmic ImprimisRx NJ 2018-01-01 Not applicable US
Categories
- ATC Codes
- S01EE01 — Latanoprost
- S01EE — Prostaglandin analogues
- S01E — ANTIGLAUCOMA PREPARATIONS AND MIOTICS
- S01 — OPHTHALMOLOGICALS
- S — SENSORY ORGANS
- Drug Categories
- Antiglaucoma Preparations and Miotics
- Antihypertensive Agents
- Autacoids
- Biological Factors
- Compounds used in a research, industrial, or household setting
- Eicosanoids
- Fatty Acids
- Fatty Acids, Unsaturated
- Lipids
- OAT1/SLC22A6 inhibitors
- OAT3/SLC22A8 Inhibitors
- Ophthalmic Solutions
- Ophthalmologicals
- Pharmaceutical Preparations
- Pharmaceutical Solutions
- Prostaglandin analogs reducing intraocular pressure (IOP)
- Prostaglandins
- Prostaglandins F, Synthetic
- Prostaglandins, Synthetic
- Sensory Organs
- Solutions
- 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
- Hara T: [Increased iris pigmentation after use of latanoprost in Japanese brown eyes]. Nippon Ganka Gakkai Zasshi. 2001 May;105(5):314-21. [Article]
- 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]
- Alm A: Latanoprost in the treatment of glaucoma. Clin Ophthalmol. 2014 Sep 26;8:1967-85. doi: 10.2147/OPTH.S59162. eCollection 2014. [Article]
- 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]
- Sjoquist B, Stjernschantz J: Ocular and systemic pharmacokinetics of latanoprost in humans. Surv Ophthalmol. 2002 Aug;47 Suppl 1:S6-12. [Article]
- FDA Approved Drug Products: Xalatan (latanoprost) Ophthalmic Solution [Link]
- Cayman Chemical: Latanoprost MSDS [Link]
- Drugs.com: Latanoprost ophthalmic [Link]
- FDA Approved Drug Products: ROCKLATAN (netarsudil and latanoprost) Ophthalmic Solution [Link]
- Health Canada Approved Drug Products: SANDOZ LATANOPROST (Latanoprost) Ophthalmic Solution [Link]
- FDA Approved Drug Products: IYUZEH (latanoprost ophthalmic solution) 0.005%, for topical ophthalmic use [Link]
- Health Canada Product Monograph: ACT LATANOPROST/TIMOLOL (Latanaprost and Timolol) Ophthalmic Solution [Link]
- External Links
- Human Metabolome Database
- HMDB0014792
- KEGG Drug
- D00356
- PubChem Compound
- 5311221
- PubChem Substance
- 46506279
- ChemSpider
- 4470740
- BindingDB
- 50240648
- 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
Phase Status Purpose Conditions Count 4 Active Not Recruiting Treatment Non-segmental Vitiligo 1 4 Completed Not Available Glaucoma 2 4 Completed Basic Science Ocular Hypertension / Open Angle Glaucoma (OAG) 1 4 Completed Basic Science Open Angle Glaucoma (OAG) 1 4 Completed Diagnostic Glaucoma / Ocular Hypertension 1 4 Completed Supportive Care Dry Eye Syndrome (DES) 1 4 Completed Treatment Alopecia Areata (AA) 1 4 Completed Treatment Anterior Uveitis (AU) / Macular Edema, Cystoid 1 4 Completed Treatment Application Site Pigmentation Changes / Glaucoma 1 4 Completed Treatment Diabetic Retinopathy (DR) 1
Pharmacoeconomics
- Manufacturers
- Pharmacia and upjohn co
- Packagers
- Assia Chemical Industries Ltd.
- Cardinal Health
- Pfizer Inc.
- Pharmacia Inc.
- Dosage Forms
Form Route Strength Solution / drops; suspension / drops Ophthalmic 50 MIKROGRAMM/ML Solution / drops Ophthalmic Solution / drops Ophthalmic 50 mcg/ml Solution / drops; suspension / drops Ophthalmic 0.05 mg/mL Solution / drops Ophthalmic 0.005 % w/v Solution / drops Ophthalmic 0.005 %w/v Solution Conjunctival; Ophthalmic 0.05 mg Solution Ophthalmic 0.05 mg Solution Ophthalmic 0.005 % w/w Solution Ophthalmic 0.125 mg/2.5ml Solution Ophthalmic 0.050 mg Solution / drops; suspension / drops Ophthalmic 50 UG/ML Solution Ophthalmic Solution / drops; suspension / drops Ophthalmic Solution Ophthalmic 50 ug/1mL Solution / drops Ophthalmic 50 ug/1mL Solution / drops; suspension / drops Ophthalmic 0.05 mg Solution / drops Ophthalmic 0.05 mg/1mL Solution / drops; suspension / drops Ophthalmic 50 UG Solution Ophthalmic 0.05 mg/ml Liquid Ophthalmic 50 mcg/1ml Solution Ophthalmic 0.005 % w/v Solution / drops Ophthalmic 50 Mikrogramm/ml Solution / drops Ophthalmic 0005 % Solution / drops Ophthalmic 0.05 MG/ML Emulsion Ophthalmic 0.05 mg Solution Conjunctival; Ophthalmic 50 mcg Solution / drops Ophthalmic 50 MICROGRAMMI/ML Spray Nasal Solution Conjunctival; Ophthalmic Solution Ophthalmic 0.050 mg/ml Solution / drops Ophthalmic; Topical Solution / drops Ophthalmic Solution Ophthalmic 0.05 mg/ml Solution Ophthalmic Solution Ophthalmic 50 mcg/1ml Solution Ophthalmic 50 mcg / mL Solution Ophthalmic 50 mcg Solution / drops; suspension / drops Ophthalmic 0.005 % Solution / drops Ophthalmic 0.005 % Solution Ophthalmic 50 mcg/ml Solution Ophthalmic 0.005 %w/v Solution / drops Ophthalmic; Topical 0.05 mg/1mL Solution / drops Ophthalmic 50 mcg/1ml - Prices
Unit description Cost Unit Xalatan 0.005% Solution 2.5ml Bottle 93.59USD bottle Xalatan 0.005% eye drops 45.06USD ml Xalatan 0.005 % Solution 12.18USD ml DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.- Patents
Patent Number Pediatric Extension Approved Expires (estimated) Region US5296504 No 1994-03-22 2011-03-22 US US6429226 No 2002-08-06 2009-09-06 US CA1339132 No 1997-07-29 2014-07-29 Canada US8394826 No 2013-03-12 2030-11-10 US US9096569 No 2015-08-04 2026-07-11 US US8450344 No 2013-05-28 2026-07-11 US US9415043 No 2016-08-16 2034-03-14 US US9931336 No 2018-04-03 2034-03-14 US US9539262 No 2017-01-10 2035-04-20 US US9629852 No 2017-04-25 2029-09-12 US US9993470 No 2018-06-12 2034-03-14 US US10174017 No 2019-01-08 2030-01-27 US US10532993 No 2020-01-14 2026-07-11 US US10588901 No 2020-03-17 2034-03-14 US US10654844 No 2020-05-19 2030-11-10 US US10882840 No 2021-01-05 2026-07-11 US US11028081 No 2021-06-08 2030-01-27 US US11021456 No 2021-06-01 2026-07-11 US US11197853 No 2021-12-14 2034-03-14 US US11185538 No 2021-11-30 2034-03-14 US
Properties
- State
- Liquid
- Experimental Properties
Property Value Source boiling point (°C) 583.8 https://www.lookchem.com/Latanoprost/ logP 3.98 https://www.ebi.ac.uk/chembl/compound_report_card/CHEMBL1051/ pKa 4.88 https://www.tandfonline.com/doi/abs/10.1517/14656566.2012.662219?src=recsys&journalCode=ieop20 - Predicted Properties
Property Value Source Water Solubility 0.0129 mg/mL ALOGPS logP 4.16 ALOGPS logP 3.98 Chemaxon logS -4.5 ALOGPS pKa (Strongest Acidic) 14.47 Chemaxon pKa (Strongest Basic) -2.7 Chemaxon Physiological Charge 0 Chemaxon Hydrogen Acceptor Count 4 Chemaxon Hydrogen Donor Count 3 Chemaxon Polar Surface Area 86.99 Å2 Chemaxon Rotatable Bond Count 14 Chemaxon Refractivity 124.34 m3·mol-1 Chemaxon Polarizability 50.9 Å3 Chemaxon Number of Rings 2 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter No Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.9474 Blood Brain Barrier + 0.6512 Caco-2 permeable + 0.5337 P-glycoprotein substrate Substrate 0.5728 P-glycoprotein inhibitor I Non-inhibitor 0.8684 P-glycoprotein inhibitor II Non-inhibitor 0.7124 Renal organic cation transporter Non-inhibitor 0.8805 CYP450 2C9 substrate Non-substrate 0.7819 CYP450 2D6 substrate Non-substrate 0.8835 CYP450 3A4 substrate Substrate 0.5947 CYP450 1A2 substrate Non-inhibitor 0.8845 CYP450 2C9 inhibitor Non-inhibitor 0.7724 CYP450 2D6 inhibitor Non-inhibitor 0.8985 CYP450 2C19 inhibitor Non-inhibitor 0.7236 CYP450 3A4 inhibitor Non-inhibitor 0.7393 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.7405 Ames test Non AMES toxic 0.8324 Carcinogenicity Non-carcinogens 0.9379 Biodegradation Not ready biodegradable 0.6353 Rat acute toxicity 4.3748 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9071 hERG inhibition (predictor II) Non-inhibitor 0.8763
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted GC-MS Spectrum - GC-MS Predicted GC-MS Not Available Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS Not Available LC-MS/MS Spectrum - LC-ESI-qTof , Positive LC-MS/MS Not Available MS/MS Spectrum - , positive LC-MS/MS splash10-052r-1958000000-c694c9459db45a20b9af
Targets
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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
- 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]
- Alm A: Latanoprost in the treatment of glaucoma. Clin Ophthalmol. 2014 Sep 26;8:1967-85. doi: 10.2147/OPTH.S59162. eCollection 2014. [Article]
- 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]
- FDA Approved Drug Products: Xalatan (latanoprost) Ophthalmic Solution [Link]
- ChemBL compound report card [Link]
Enzymes
1. Corneal esterases
Unknown
Substrate
References
- 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]
- Alm A: Latanoprost in the treatment of glaucoma. Clin Ophthalmol. 2014 Sep 26;8:1967-85. doi: 10.2147/OPTH.S59162. eCollection 2014. [Article]
- 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
- 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]
- 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]
- 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
- SubstrateInhibitor
- 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
- 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]
- 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
- 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]
- 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 June 05, 2023 06:28