LatanoprostAcid

Names

[ Name ]:
LatanoprostAcid

[Synonym ]:
(5Z)-7-{(1R,2R,3R,5S)-3,5-Dihydroxy-2-[(3R)-3-hydroxy-5-phenylpentyl]cyclopentyl}hept-5-enoic acid
Latanoprost acid
latanoprost free acid
5-Heptenoic acid, 7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-[(3R)-3-hydroxy-5-phenylpentyl]cyclopentyl]-, (5Z)-
LatanoprostAcid
(5Z)-7-{(1R,2R,3R,5S)-3,5-Dihydroxy-2-[(3R)-3-hydroxy-5-phenylpentyl]cyclopentyl}-5-heptenoic acid

Biological Activity

[Description]:

Latanoprost acid, an analog of prostaglandin (PG) F2α, is an selective prostanoid receptor (FP) agonist that specifically activates the FP-PG receptor[1]. Latanoprost acid inhibits RANKL-induced osteoclastgenesis and function by inhibiting ERK, AKT, JNK, and p38 cascade, following by the c-fos/NFATc1 pathway. Latanoprost acid is a medication which works to lower pressure inside the eyes[2].

[Related Catalog]:

Signaling Pathways >> GPCR/G Protein >> Prostaglandin Receptor

Research Areas >> Inflammation/Immunology

[Target]

[In Vitro]

Latanoprost acid (10-20 μM;24 hours) reduces he protein expressions of c-fos and NFATc1[1]. Latanoprost acid (10μM with 50ng/ml RANKL) significantly inhibits ERK, p38, AKT and JNK[1]. Latanoprost acid (10 μM, 20 μM) significantly inhibits the mature osteoclast formation[1]. Western Blot Analysis[1] Cell Line: Bone marrow-derived macrophages cells (BMMs) Concentration: 10 μM, 20 μM Incubation Time: 24 hours Result: Reduced he protein expressions of c-fos and NFATc1.

[In Vivo]

Latanoprost acid (i.p.; 20 mg/kg; once a day for 7 days) notably prevents LPS-induced bone destruction at a dose of 20mg/kg[1]. Animal Model: 8-week-old C57BL/6J mice[1] Dosage: 20 mg/kg Administration: Intraperitoneally injected; once a day for 7 days Result: Notably prevented LPS-induced bone destruction at a dose of 20mg/kg.

[References]

[1]. Weinreb RN, et al. Effects of prostaglandins on the aqueous humor outflow pathways. Surv Ophthalmol. 2002 Aug;47 Suppl 1:S53-64.

[2]. Xu X, et al. The prevention of latanoprost on osteoclastgenesis in vitro and lipopolysaccharide-induced murine calvaria osteolysis in vivo. J Cell Biochem. 2018 Jun;119(6):4680-4691.

Chemical & Physical Properties

[ Density]:
1.2±0.1 g/cm3

[ Boiling Point ]:
609.1±50.0 °C at 760 mmHg

[ Molecular Formula ]:
C₂₃H₃₄O₅

[ Molecular Weight ]:
390.513

[ Flash Point ]:
336.2±26.6 °C

[ Exact Mass ]:
390.240631

[ PSA ]:
97.99000

[ LogP ]:
2.22

[ Vapour Pressure ]:
0.0±1.8 mmHg at 25°C

[ Index of Refraction ]:
1.564

[ Storage condition ]:
-20°C

MSDS

Click to get detail MSDS

Safety Information

[ Personal Protective Equipment ]:
Eyeshields;Gloves

[ RIDADR ]:
NONH for all modes of transport

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Articles

New prostaglandin analog formulation for glaucoma treatment containing cyclodextrins for improved stability, solubility and ocular tolerance.

Eur. J. Pharm. Biopharm. 95 , 203-14, (2015)

Latanoprost is a practically insoluble prostaglandin F2α analog considered a first-line agent for glaucoma treatment. From a pharmaceutical point of view, latanoprost is challenging to be formulated a...

Effect of prostaglandins A(2), E(1), F(2 alpha)and latanoprost on cultured human iridal melanocytes.

Exp. Eye Res. 70(1) , 113-20, (2000)

The effect of various prostaglandins on the growth, melanogenesis and dendrification of cultured iridal melanocytes were studied. Iridal melanocytes were isolated and cultured with medium supplemented...

Prostaglandins increase matrix metalloproteinase release from human ciliary smooth muscle cells.

Invest. Ophthalmol. Vis. Sci. 38(13) , 2772-80, (1997)

To identify matrix metalloproteinases (MMPs) released by ciliary smooth muscle cells in vitro and to determine whether MMP release is altered by exposure to prostaglandins (PGs).Human ciliary smooth m...