Latanoprost

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

Similar Structures

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 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

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Associated Conditions

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

Target	Actions	Organism
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.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

Hover over products below to view reaction partners

Latanoprost
- Latanoprost acid
  - 1, 2 Dinor Latanoprost Acid + 1,2,3,4 Tetranor Latanoprost Acid

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.^3,6 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.^6,8An 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.

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
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Aceclofenac	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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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

Name	Dosage	Strength	Route	Labeller	Marketing Start	Marketing End
Bl Latanoprost	Solution	50 mcg / mL	Ophthalmic	Bausch & Lomb Inc	Not applicable	Not applicable
Latanoprost	Solution	50 mcg / mL	Ophthalmic	Laboratoire Riva Inc	Not applicable	Not applicable
Latanoprost Ophthalmic Solution	Solution	50 mcg / mL	Ophthalmic	Sandoz Canada Incorporated	Not applicable	Not applicable
Latanoprost Ophthalmic Solution	Solution	50 mcg / mL	Ophthalmic	Hikma Canada Limited	2020-06-26	Not applicable
Latanoprost PF	Solution / drops	0.05 mg/1mL	Ophthalmic	ImprimisRx NJ	2018-01-01	Not applicable
M-latanoprost	Solution	50 mcg / mL	Ophthalmic	Mantra Pharma Inc	2021-11-10	Not applicable
Monoprost	Solution	50 mcg / mL	Ophthalmic	Laboratoires Thea	2018-01-03	Not applicable
Xalatan	Solution	50 ug/1mL	Ophthalmic	Pfizer Laboratories Div Pfizer Inc	1995-03-20	Not applicable
Xalatan	Solution	50 ug/1mL	Ophthalmic	Dispensing Solutions, Inc.	1995-03-20	Not applicable
Xalatan	Solution	50 mcg / mL	Ophthalmic	Upjohn Canada Ulc	1997-07-28	Not applicable

Generic Prescription Products

Name	Dosage	Strength	Route	Labeller	Marketing Start	Marketing End
Apo-latanoprost	Solution	50 mcg / mL	Ophthalmic	Apotex Corporation	2011-10-03	Not applicable
Gd-latanoprost	Solution	50 mcg / mL	Ophthalmic	Upjohn Canada Ulc	2011-10-03	Not applicable
Jamp Latanoprost	Solution	50 mcg / mL	Ophthalmic	Jamp Pharma Corporation	2020-02-07	Not applicable
Latanoprost	Solution / drops	50 ug/1mL	Ophthalmic	Nucare Pharmaceuticals,inc.	2011-03-22	2020-04-01
Latanoprost	Solution	50 ug/1mL	Ophthalmic	Mylan Pharmaceuticals	2011-03-22	2013-03-31
Latanoprost	Solution / drops	50 ug/1mL	Ophthalmic	Remedy Repack	2013-01-31	2016-09-16
Latanoprost	Solution	50 ug/1mL	Ophthalmic	Rising Pharmaceuticals, Inc.	2016-09-01	Not applicable
Latanoprost	Solution / drops	50 ug/1mL	Ophthalmic	Akorn	2012-07-01	Not applicable
Latanoprost	Solution / drops	50 ug/1mL	Ophthalmic	Nucare Pharmaceuticals,inc.	2019-12-03	Not applicable
Latanoprost	Solution / drops	50 ug/1mL	Ophthalmic	Direct Rx	2017-03-27	Not applicable

Mixture Products

Name	Ingredients	Dosage	Route	Labeller	Marketing Start	Marketing End
Act Latanoprost/timolol	Latanoprost (50 mcg / mL) + Timolol maleate (5 mg / mL)	Solution	Ophthalmic	TEVA Canada Limited	2015-09-29	Not applicable
Apo-latanoprost-timop	Latanoprost (50 mcg / mL) + Timolol maleate (5 mg / mL)	Solution	Ophthalmic	Apotex Corporation	2014-07-02	Not applicable
ARUCOM	Latanoprost (0.05 mg/mL) + Timolol maleate (5 mg/mL)	Solution / drops; Suspension / drops	Ophthalmic		2017-01-01	Not applicable
ARUCOM	Latanoprost (0.05 mg/mL) + Timolol maleate (5 mg/mL)	Solution / drops; Suspension / drops	Ophthalmic		2017-01-01	2021-11-15
ARUCOM	Latanoprost (0.05 mg/mL) + Timolol maleate (5 mg/mL)	Solution / drops; Suspension / drops	Ophthalmic		2017-01-01	Not applicable
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
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
FIXAPROST 50UG/ML+5MG/ML	Latanoprost (0.01 mg) + Timolol maleate (1 mg)	Solution / drops; Suspension / drops	Ophthalmic		2017-01-01	Not applicable
FIXAPROST 50UG/ML+5MG/ML	Latanoprost (0.01 mg) + Timolol maleate (1 mg)	Solution / drops; Suspension / drops	Ophthalmic		2017-01-01	Not applicable
Gd-latanoprost/timolol	Latanoprost (50 mcg / mL) + Timolol maleate (5 mg / mL)	Solution	Ophthalmic	Upjohn Canada Ulc	2013-05-01	Not applicable

Unapproved/Other Products

Name	Ingredients	Dosage	Route	Labeller	Marketing Start	Marketing End
Latanoprost PF	Latanoprost (0.05 mg/1mL)	Solution / drops	Ophthalmic	ImprimisRx NJ	2018-01-01	Not applicable
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
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
Tim-Lat -PF	Latanoprost (0.05 mg/1mL) + Timolol maleate (5 mg/1mL)	Solution / drops	Ophthalmic	ImprimisRx NJ	2018-01-01	Not applicable

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]
Xalatan FDA label [Link]
Caymanchem MSDS [Link]
Latanoprost, drugs.com [Link]
Xalatan, Canadian monograph [Link]
Rocklatan FDA label [Link]
Sandoz Latanoprost monograph [Link]

External Links

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

FDA label

Download (502 KB)

MSDS

Download (21.1 KB)

Clinical Trials

Clinical Trials

Phase	Status	Purpose	Conditions	Count
4	Active Not Recruiting	Treatment	NonSegmental 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
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
Solution	Ophthalmic	0.05 mg/ml
Solution	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	50 mcg/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)
US5296504	No	1994-03-22	2011-03-22
US6429226	No	2002-08-06	2009-09-06
CA1339132	No	1997-07-29	2014-07-29
US8394826	No	2013-03-12	2030-11-10
US9096569	No	2015-08-04	2026-07-11
US8450344	No	2013-05-28	2026-07-11
US9415043	No	2016-08-16	2034-03-14
US9931336	No	2018-04-03	2034-03-14
US9539262	No	2017-01-10	2035-04-20
US9629852	No	2017-04-25	2029-09-12
US9993470	No	2018-06-12	2034-03-14
US10174017	No	2019-01-08	2030-01-27
US10532993	No	2020-01-14	2026-07-11
US10588901	No	2020-03-17	2034-03-14
US10654844	No	2020-05-19	2030-11-10
US10882840	No	2021-01-05	2026-07-11
US11028081	No	2021-06-08	2030-01-27
US11021456	No	2021-06-01	2026-07-11
US11197853	No	2021-12-14	2034-03-14
US11185538	No	2021-11-30	2034-03-14

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

ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

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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Property	Measurement	pH	Temperature (°C)	References
EC 50 (nM)	34.4	N/A	N/A	A28723
Ki (nM)	2.8	N/A	N/A	A28722
Ki (nM)	555	N/A	N/A	A28722

Details1. Prostaglandin F2-alpha receptor

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]
Xalatan FDA label [Link]
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

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]
Xalatan FDA label [Link]

Transporters

Details1. Solute carrier organic anion transporter family member 2A1

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]

Details2. Solute carrier family 22 member 6

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

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]

Details3. Solute carrier family 22 member 8

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 24, 2022 08:21

Latanoprost

Identification

Structure for Latanoprost (DB00654)

Pharmacology

Interactions

Products

Categories

Chemical Identifiers

References

Clinical Trials

Pharmacoeconomics

Properties

Spectra

Targets

References

Enzymes

References

Transporters

References

References

References