Ticagrelor Acetonide: Properties, Synthesis & Research Use

Ticagrelor Acetonide is a protected acetonide intermediate derived from Ticagrelor, serving as a key synthetic building block in the preparation and quality research of the antiplatelet drug Ticagrelor.

Product Name

Ticagrelor Acetonide

Catalog / Batch Reference

BD291053

SKU

A588519

Compound Class

Acetonide-protected diol derivative; triazolopyrimidine scaffold

Primary Research Use

Synthetic intermediate and reference standard in Ticagrelor manufacturing and impurity profiling

Parent Drug

Ticagrelor (reversible P2Y12 ADP receptor antagonist)

Chemical Background and Relationship to Ticagrelor

Ticagrelor Acetonide is the acetonide (isopropylidene ketal) protected form of Ticagrelor, in which the vicinal diol moiety of the cyclopentane ring is masked as a cyclic acetal. Ticagrelor itself is a direct-acting, reversible antagonist of the platelet P2Y12 ADP receptor, belonging to the cyclopentyl triazolopyrimidine chemical class. The acetonide protecting group is commonly introduced during multi-step synthesis to selectively shield the diol functionality, thereby enabling downstream chemical transformations at other sites of the molecule without unwanted side reactions.

The removal of the acetonide group under mild acidic conditions regenerates the free diol of Ticagrelor, making this intermediate a pivotal step in convergent synthetic routes. Understanding the chemical behavior and stability of Ticagrelor Acetonide is therefore essential for medicinal chemists and process development scientists working on Ticagrelor API synthesis or analog preparation.

Synthetic Role and Laboratory Applications

In pharmaceutical research and process chemistry, Ticagrelor Acetonide (A588519) serves multiple roles:

• Synthetic Intermediate: It is a key intermediate in the total synthesis of Ticagrelor, enabling selective manipulation of the cyclopentane diol region while other functional groups are elaborated.
• Reference Standard: As an authentic characterized compound, it functions as a reference standard for HPLC, LC-MS, and NMR-based purity and identity confirmation during Ticagrelor quality control or process research.
• Impurity Profiling: Regulatory guidelines for API characterization require identification and quantification of process-related impurities. Ticagrelor Acetonide may be relevant as a potential process-related impurity in Ticagrelor batches, making it important for method development and validation studies.
• Analog Synthesis: Researchers designing novel P2Y12 receptor ligands or prodrug strategies may employ this scaffold as a synthetic starting point, leveraging the protected diol chemistry for structural diversification.

Handling, Storage and Laboratory Safety

As with all pharmaceutical intermediates and research reagents, appropriate handling practices should be followed when working with Ticagrelor Acetonide:

• Storage: Store according to the conditions specified on the product certificate of analysis. Acetonide-containing compounds are generally sensitive to prolonged exposure to strong acids, which can cause premature deprotection. Storage in a cool, dry environment away from acidic vapors is recommended.
• Handling: Use standard laboratory PPE including gloves, lab coat, and eye protection. Work in a well-ventilated area or fume hood when weighing or dissolving the compound.
• Solubility: Ticagrelor Acetonide, like Ticagrelor, is expected to show limited aqueous solubility; organic solvents such as DMSO, dichloromethane, or methanol are typically suitable for dissolution in research applications.
• Stability: Confirm stability data from the product-specific certificate of analysis (CoA) supplied with catalog number A588519 (batch reference BD291053).

Always consult the Safety Data Sheet (SDS) provided by Aladdin Scientific before use.

Regulatory and Quality Considerations

For researchers involved in API development or generic drug filing, Ticagrelor Acetonide may be required as a certified reference standard to satisfy regulatory agency requirements (e.g., ICH Q3A/Q3B guidelines on impurities, or pharmacopeial monograph development). When used in this context:

• Request a Certificate of Analysis (CoA) confirming identity, purity, and structural characterization data (e.g., NMR, HRMS) from Aladdin Scientific at time of order.
• Ensure the compound is sourced from a qualified supplier with documented quality management practices to support GMP-adjacent or regulatory submission workflows.
• Aladdin Scientific's catalog entry A588519 corresponds to batch reference BD291053; confirm current lot availability and specifications with the procurement team prior to ordering.

Frequently asked questions

What is Ticagrelor Acetonide and how does it differ from Ticagrelor?

Ticagrelor Acetonide is a chemically protected derivative of Ticagrelor in which the vicinal diol group on the cyclopentane ring is masked as a cyclic acetonide (isopropylidene acetal). Unlike Ticagrelor, which is the pharmacologically active P2Y12 receptor antagonist, the acetonide form is primarily used as a synthetic intermediate or reference standard rather than as an active pharmaceutical ingredient.

What is the catalog number and batch reference for Ticagrelor Acetonide at Aladdin Scientific?

Ticagrelor Acetonide is listed under SKU A588519 with a batch reference of BD291053 at Aladdin Scientific. Researchers should confirm current lot availability and request a Certificate of Analysis at the time of ordering.

What solvents are suitable for dissolving Ticagrelor Acetonide in laboratory use?

Based on the physicochemical properties of the Ticagrelor scaffold, Ticagrelor Acetonide is expected to have limited water solubility. Polar aprotic solvents such as DMSO, as well as organic solvents like dichloromethane and methanol, are generally suitable choices. Researchers should verify solubility experimentally and consult the product CoA for specific guidance.

Can Ticagrelor Acetonide be used as a reference standard for impurity testing?

Yes. Ticagrelor Acetonide can serve as an authentic reference standard for HPLC and LC-MS based impurity profiling and method development in the context of Ticagrelor API quality control. Regulatory guidelines such as ICH Q3A require identification of process-related impurities above specified thresholds, and an authenticated sample of this compound supports that workflow.

References

1. Springthorpe B. et al. From ATP to AZD6140: The discovery of an orally active reversible P2Y12 receptor antagonist for the prevention of thrombosis. Bioorganic & Medicinal Chemistry Letters, 2007.
2. ICH Harmonised Guideline Q3A(R2): Impurities in New Drug Substances. International Council for Harmonisation of Technical Requirements for Pharmaceuticals for Human Use, 2006.
3. Aladdin Scientific Product Page: Ticagrelor Acetonide, SKU A588519, Batch BD291053.

Products are supplied for research and development use only. Not for use in humans, animals, diagnosis, or therapy.