Latanoprost Lactol
[CAS# 352276-28-9]

Identification

• Classification: API >> Hormone and endocrine-regulating drugs >> Prostaglandins
• Name: Latanoprost Lactol
• Synonyms: (3aR,4R,5R,6aS)-Hexahydro-4-[(3R)-3-hydroxy-5-phenylpentyl]-2H-cyclopenta[b]furan-2,5-diol
• Molecular Formula: C₁₈H₂₆O₄
• Molecular Weight: 306.40
• CAS Registry Number: 352276-28-9
• EC Number: 807-848-8
• SMILES: C1[C@H]([C@@H]([C@@H]2[C@H]1OC(C2)O)CC[C@H](CCC3=CC=CC=C3)O)O

Properties

• Density: 1.207

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H317-H319
• Safety Statements: P280-P305+P351+P351

Discovery and Applications

Latanoprost lactol is a chemically modified derivative of latanoprost, a widely used prostaglandin F2α analogue. Latanoprost itself is recognized for its efficacy in the treatment of elevated intraocular pressure, commonly associated with conditions such as open-angle glaucoma and ocular hypertension. Latanoprost lactol, derived from the lactone form, features a lactol group in its molecular structure, which can influence its reactivity and potential interactions in biological systems.

The discovery of latanoprost lactol stems from continued efforts in the pharmaceutical industry to optimize prostaglandin analogues for therapeutic applications. Latanoprost was initially synthesized by modifying the natural prostaglandin F2α, targeting the receptors involved in lowering intraocular pressure. Through chemical modifications, including the formation of lactol derivatives, researchers aimed to improve the pharmacokinetic properties, such as bioavailability and metabolic stability, of these analogues. The lactol form, in particular, presents unique opportunities for further manipulation and conversion into more bioactive species.

Latanoprost lactol finds its primary application in research settings, where it serves as an intermediate for the synthesis of more advanced prostaglandin analogues. This compound can be utilized to explore the structure-activity relationships (SAR) of prostaglandin analogues, helping scientists understand how various functional groups impact biological activity, receptor binding, and metabolism.

In addition to research, latanoprost lactol has the potential to be used as a precursor in the development of new therapeutic agents targeting prostaglandin receptors. The presence of the lactol group can modify the chemical properties of the molecule, potentially leading to derivatives with improved potency or selectivity. Researchers are particularly interested in exploring the lactol form for its ability to act as a more stable or versatile scaffold in drug design.

Latanoprost lactol’s contribution to the field of ophthalmic treatments, while more focused on research than direct clinical use, remains significant. By facilitating the synthesis of novel analogues and offering insights into the chemical properties of prostaglandins, latanoprost lactol plays an important role in the ongoing development of treatments for glaucoma and other related eye disorders.

References

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