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L1167

Sigma-Aldrich

Latanoprost

≥98% (HPLC)

Synonym(s):

Isopropyl (5Z,9α,11α,15R)-9,11,15-trihydroxy-17-phenyl-18,19,20-trinor-prost-5-en-1-oate, Isopropyl (Z)-7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-[(3R)-3-hydroxy-5-phenylpentyl]cyclopentyl]hept-5-enoate, Xalatan

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About This Item

Empirical Formula (Hill Notation):
C26H40O5
CAS Number:
130209-82-4
Molecular Weight:
432.59
MDL number:
MFCD00216074
UNSPSC Code:
12352200
PubChem Substance ID:
24724523
NACRES:
NA.77

Quality Level

100

assay

≥98% (HPLC)

form

oil

color

colorless to yellow

solubility

DMSO: freely soluble
methanol: soluble

originator

Johnson & Johnson

shipped in

wet ice

storage temp.

−20°C

SMILES string

CC(C)OC(=O)CCC\C=C/C[C@H]1[C@@H](O)C[C@@H](O)[C@@H]1CC[C@@H](O)CCc2ccccc2

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

InChI key

GGXICVAJURFBLW-CEYXHVGTSA-N

Gene Information

human ... PTGFR(5737)

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Application

Latanoprost has been used:
  • in the preparation of thermo-sensitive hydrogel consisting of curcumin-loaded nanoparticles (CUR-NPs) to determine its therapeutic effects on human trabecular meshwork (TM) cells under oxidative stress.
  • as an ester pro-drug to study its effects on the murine ocular surface in mice.
  • in the preparation of thermo-sensitive hydrogel to study its effects on controlling ocular hypertension.

Biochem/physiol Actions

Latanoprost is a potent, selective prostaglandin F2α analog receptor agonist. It is hydrolyzed by esterases into its biologically active form latanoprost acid in the cornea. Latanoprostplays a role in reducing the intraocular pressure (IOP) due to which it has therapeutic effects in treating glaucoma.

Features and Benefits

This compound is featured on the Prostanoid Receptors page of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.
This compound was developed by Johnson & Johnson. To browse the list of other pharma-developed compounds and Approved Drugs/Drug Candidates, click here.

pictograms

Health hazard
GHS08

signalword

Warning

hcodes

H361d

Hazard Classifications

Repr. 2

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Faceshields, Gloves, type N95 (US)

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Kojic acid analytical standard

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Sigma-Aldrich

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F Honrubia et al.
The British journal of ophthalmology, 93(3), 316-321 (2008-11-21)
To conduct a meta-analysis of randomised clinical trials (RCTs) in order to evaluate the development of conjunctival hyperaemia after the use of latanoprost versus travoprost and bimatoprost, in patients with ocular hypertension or glaucoma. In order to identify the potentially
Matthew B Schlenker et al.
Journal of ophthalmology, 2015, 547960-547960 (2015-04-30)
Objective. Compare glaucoma medication costs between the United States (USA) and Canada. Methods. We modelled glaucoma brand name and generic medication annual costs in the USA and Canada based on October 2013 Costco prices and previously reported bottle overfill rates
Sanae Abe et al.
Journal of ocular pharmacology and therapeutics : the official journal of the Association for Ocular Pharmacology and Therapeutics, 29(1), 55-60 (2012-10-11)
To clarify the mechanism of prostaglandin (PG) analogue-dependent relaxation in ciliary arteries from wild-type (WT) and prostanoid receptor-deficient mice. The intracellular-free calcium concentration ([Ca(2+)](i)) in isolated WT mouse ciliary arteries was measured by fluorescence photometry. Reduction of [Ca(2+)](i) leading to
A T Fung et al.
The British journal of ophthalmology, 91(1), 62-68 (2006-09-08)
To compare the efficacy and tolerability of latanoprost versus brimonidine in the treatment of open-angle glaucoma, ocular hypertension or normal-tension glaucoma. Systematic review of randomised controlled trials comparing latanoprost and brimondine, identified by searches including Medline, Embase and Cochrane Controlled
Anastasios G P Konstas et al.
The British journal of ophthalmology, 97(12), 1510-1515 (2013-05-18)
To compare 24 h intraocular pressure (IOP) control obtained with preservative free (PF) tafluprost 0.0015% versus branded preservative containing latanoprost 0.005% administered as first choice monotherapy in patients with primary open angle glaucoma (POAG) or ocular hypertension (OHT). This prospective
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