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L1167

Sigma-Aldrich

Latanoprost

≥98% (HPLC)

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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
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

Signal Word

Warning

Hazard Statements

H361d

Hazard Classifications

Repr. 2

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)
Thermosensitive chitosan-gelatin-based hydrogel containing curcumin-loaded nanoparticles and latanoprost as a dual-drug delivery system for glaucoma treatment
Cheng Y H, et al.
Experimental Eye Research, 179(4), 179-187 (2019)
Latanoprost could exacerbate the progression of presbyopia
Ayaki M, et al.
PLoS ONE, 14(1) (2019)
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
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
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