Travoprost Impurity 20
[CAS# 208114-58-3]

Identification

• Classification: API >> Hormone and endocrine-regulating drugs >> Prostaglandins
• Name: Travoprost Impurity 20
• Synonyms: [(3aS,4S,5S,6aR)-4-[(E,3R)-3-hydroxy-4-[3-(trifluoromethyl)phenoxy]but-1-enyl]-2-oxo-3,3a,4,5,6,6a-hexahydrocyclopenta[b]furan-5-yl] benzoate
• Molecular Formula: C₂₅H₂₃F₃O₆
• Molecular Weight: 476.44
• CAS Registry Number: 208114-58-3
• SMILES: C1[C@@H]2[C@@H](CC(=O)O2)[C@@H]([C@H]1OC(=O)C3=CC=CC=C3)/C=C/[C@H](COC4=CC=CC(=C4)C(F)(F)F)O

Properties

• Density: 1.38±0.1 g/cm³, Calc.^*
• Boiling Point: 620.0±55.0 °C, Calc.

Discovery and Applications

Travoprost Impurity 20 is a chemical compound that arises as a byproduct during the synthesis of travoprost, a prostaglandin analog used primarily in the treatment of glaucoma and ocular hypertension. The discovery of impurities such as Travoprost Impurity 20 typically occurs during the development and refinement of pharmaceutical manufacturing processes. Impurities are often identified through advanced analytical techniques such as high-performance liquid chromatography (HPLC) and mass spectrometry. The identification of Travoprost Impurity 20 allows researchers and manufacturers to improve the purity and safety of the final drug product.

Travoprost is synthesized through multi-step chemical processes involving the esterification of a prostaglandin derivative. During these complex reactions, side products such as Impurity 20 can form. Travoprost Impurity 20 is structurally related to the active ingredient, but its presence in pharmaceutical preparations must be carefully monitored. Regulatory authorities such as the FDA and EMA require stringent control of impurities to ensure that they do not exceed acceptable limits, which is crucial for patient safety.

In pharmaceutical applications, the identification and control of impurities like Travoprost Impurity 20 are vital for drug quality. The presence of even trace amounts of impurities can affect the safety, efficacy, and shelf life of medications. As such, manufacturers develop purification techniques and establish acceptable thresholds for these substances. Travoprost Impurity 20 is typically removed or reduced to acceptable levels during purification stages, ensuring the final product meets regulatory standards.

The role of Travoprost Impurity 20 in pharmaceutical development highlights the importance of impurity profiling in drug synthesis. By understanding the formation pathways of such impurities, chemists can optimize reaction conditions to minimize their presence. This contributes to the overall improvement of manufacturing efficiency and product safety. Additionally, the study of impurities like Travoprost Impurity 20 can provide insights into the stability and degradation pathways of the parent drug, which is essential for developing better formulations and improving drug performance.

References

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