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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:
Molecular Weight:
432.59
MDL number:
UNSPSC Code:
12352200
PubChem Substance ID:
NACRES:
NA.77

Quality Level

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

Signal Word

Warning

Hazard Statements

Hazard Classifications

Repr. 2

Storage Class Code

10 - Combustible liquids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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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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
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
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
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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