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Merck

L1167

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
NACRES:
NA.77
PubChem Substance ID:
24724523
UNSPSC Code:
12352200
MDL number:
MFCD00216074

Product Name

Latanoprost, ≥98% (HPLC)

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

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 key

GGXICVAJURFBLW-CEYXHVGTSA-N

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

Quality Level

100

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

Storage Class

10 - Combustible liquids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Faceshields, Gloves, type N95 (US)

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Certificates of Analysis (COA)

Lot/Batch Number
0000507883
0000507891
0000507883
0000507891
0000504536

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Masahiko Ayaki et al.
PloS one, 14(1), e0211631-e0211631 (2019-02-01)
Prostaglandin analogues (PG) reduce intra-ocular pressure by enhancing uveoscleral flow at the ciliary body, which controls accommodation via the ciliary muscle. We investigated the effect of PG on accommodation and presbyopia progression in glaucoma patients. We conducted a clinic-based, retrospective
Jean-François Rouland et al.
The British journal of ophthalmology, 97(2), 196-200 (2012-12-04)
To compare efficacy (intraocular pressure (IOP) reduction) and safety of preservative-free latanoprost (T2345) to benzalkonium chloride (BAK)-preserved latanoprost (BPL; Xalatan) in ocular hypertension (OHT) or primary open angle glaucoma (POAG) patients. Prospective, international, multicentre, randomised, investigator-masked, parallel-group trial. After a
0.005% Preservative-free latanoprost induces dry eye-like ocular surface damage via promotion of inflammation in mice
Yang Y, et al.
Investigative Ophthalmology & Visual Science, 59(8), 3375-3384 (2018)
Aude Pauly et al.
Investigative ophthalmology & visual science, 53(13), 8172-8180 (2012-11-15)
To compare in vitro, on the human reconstituted corneal epithelial SkinEthics model, and in vivo, using an acute rabbit toxicological model, the effects of a benzalkonium chloride (BAK)-preserved solution of latanoprost and a preservative-free (PF) latanoprost solution. In vitro, the
David F Garway-Heath et al.
Ophthalmology, 120(1), 68-76 (2012-09-19)
Elevated intraocular pressure (IOP) is a major risk factor for the deterioration of open-angle glaucoma (OAG); medical IOP reduction is the standard treatment, yet no randomized placebo-controlled study of medical IOP reduction has been undertaken previously. The United Kingdom Glaucoma
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