Latanoprost

Latanoprost

Cat Number
API130209824
CAS Number
130209-82-4

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CAS Number
130209-82-4
EINECS
634-172-9
Storage
Store at 2-8℃
Synonyms
Xalatan; PhXA41; latanoprostum; propan-2-yl (Z)-7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-[(3R)-3-hydroxy-5-phenylpentyl]cyclopentyl]hept-5-enoate; 6Z5B6HVF6O
Molecular Formula
C26H40O5
Molecular Weight
432.6
Smiles
CC(C)OC(=O)CCC/C=C\C[C@H]1[C@H](C[C@H]([C@@H]1CC[C@H](CCC2=CC=CC=C2)O)O)O
Appearance
Light yellow oily liquid
Boiling Point
583.8℃
General Description
Latanoprost is a synthetic prostaglandin F2-alpha analogue and a first-line topical agent for the reduction of intraocular pressure. It is formulated as a sterile ophthalmic solution administered once daily, representing one of the most widely prescribed medications for glaucoma worldwide. The compound is a prodrug designed to enhance corneal penetration through esterification of the parent prostaglandin.
Mechanism of Action
Following corneal absorption, latanoprost is hydrolyzed to its biologically active free acid, which selectively activates the prostaglandin F receptor. This activation increases uveoscleral outflow by inducing matrix metalloproteinase synthesis and remodeling of the extracellular matrix within the ciliary muscle. The resultant reduction in aqueous humor drainage resistance lowers intraocular pressure without significantly affecting conventional trabecular outflow or aqueous production.
Application
It is indicated for the reduction of elevated intraocular pressure in patients with open-angle glaucoma and ocular hypertension. As a first-line agent, it offers the advantage of once-daily dosing with excellent 24-hour efficacy, including consistent pressure control during the nocturnal period. Common adverse effects include dose-dependent increases in iris pigmentation, eyelash growth, and periorbital fat atrophy.

A phase 3 open‑label study evaluated once‑daily omidenepag isopropyl (OMDI) 0.002% in 107 patients with primary open‑angle glaucoma or ocular hypertension who were low/nonresponders to latanoprost. After an 8‑week latanoprost run‑in, OMDI treatment for 3 months produced an additional mean diurnal intraocular pressure reduction of 2.96 mm Hg from baseline (23.34 mm Hg; P<0.0001). No significant safety issues were reported. The authors conclude that OMDI is effective and safe in latanoprost low/nonresponders, making it a viable treatment option in this population.

Fig. 1 Mean diurnal IOP change from the start of run-in period (week −8) to month 3 by analysis visit. (Panarelli JF, <i>et al</i>., 2023) Fig. 1 Mean diurnal IOP change from the start of run-in period (week −8) to month 3 by analysis visit. (Panarelli JF, et al., 2023)

References

  1. Panarelli JF, et al. Omidenepag Isopropyl in Latanoprost Low/Nonresponders With Primary Open Angle Glaucoma or Ocular Hypertension: A Phase 3, Nonrandomized, Two-Phase, Open-Label Study. J Glaucoma. 2023; 32(12):999-1005.

A novel conjunctival‑contact drug delivery device was developed using freeze‑dried hyaluronic acid tablets loaded with latanoprost (HA‑latanoprost) and tested in a mouse model. Compared to standard latanoprost eye drops (Xalatan™), HA‑latanoprost achieved significantly greater intraocular pressure reduction by day 10 and caused less ocular irritation (fewer scratching motions). Gene expression analysis revealed lower inflammatory cytokine levels and higher expression of IOP‑lowering proteins in the HA‑latanoprost group. No significant side effects were observed. This hyaluronic acid‑based conjunctival contact device effectively lowers IOP with improved tolerability over conventional eye drops, though further development is needed for clinical translation.

Fig. 2 Scanning electron microscopy images of freeze-dried HA and HA-latanoprost. (Lee S, <i>et al</i>., 2025) Fig. 2 Scanning electron microscopy images of freeze-dried HA and HA-latanoprost. (Lee S, et al., 2025)

References

  1. Lee S, et al. Development of a conjunctival contact-type drug delivery device for latanoprost using hyaluronic acid. Drug Deliv. 2025; 32(1):2459775.

Does Latanoprost require refrigerated storage as a prostaglandin analog?

Yes, it must be stored at 2-8°C. The isopropyl ester is susceptible to hydrolysis at room temperature, leading to loss of potency and formation of latanoprost free acid.

Is Latanoprost sensitive to light during long-term storage?

Yes, it is photosensitive. Prolonged exposure to light can cause isomerization and degradation. Store in light-resistant containers and protect from UV light.

What is the stability of Latanoprost in ophthalmic solution formulations?

Formulated solutions are typically stored under refrigeration before opening.

How is the degradation product latanoprost free acid monitored?

We use a validated HPLC method to specifically quantify the free acid impurity, ensuring it remains well below pharmacopoeial limits throughout the product's shelf life.
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