Atorvastatin chemical structure
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Atorvastatin Chemical Structure: Molecular and Crystal Details
Atorvastatin Molecular Structure and Functional Groups
Atorvastatin is an aromatic compound with a complex structure that includes several functional groups. Its molecular formula is C33H34FN2O5, and it contains aromatic rings, a fluorine atom, carboxylic acid, and hydroxyl groups. These features are important for its biological activity as an HMG-CoA reductase inhibitor, which is the basis for its cholesterol-lowering effects 35.
Atorvastatin Calcium Salt: Crystal Structure
The most common pharmaceutical form of atorvastatin is its calcium salt, specifically atorvastatin calcium trihydrate. The crystal structure of this form has been determined using advanced X-ray powder diffraction and density functional theory (DFT) methods. Atorvastatin calcium trihydrate crystallizes in the P1 space group and features a hydrophilic layer parallel to the ab-plane. The calcium ion is coordinated in a distorted octahedral geometry, involving four carboxylate oxygens, one water molecule, and a hydroxyl group from one of the atorvastatin anions. The structure also includes a network of O–H···O hydrogen bonds, contributing to its stability 1.
Solid-State NMR and Local Structure Insights
Solid-state NMR studies have provided detailed information about the chemical environment of carbon, fluorine, and nitrogen atoms in atorvastatin calcium. These studies confirm that the asymmetric unit contains two atorvastatin molecules and help assign the positions of all resolvable carbon and fluorine atoms. The NMR data, combined with DFT calculations, support the proposed structure of atorvastatin calcium and reveal details about the local coordination of calcium ions 24.
Chemical Reactivity and Substitution Sites
Computational studies using DFT methods have identified the most reactive sites on the atorvastatin molecule, particularly for electrophilic substitution reactions such as iodination. The carboxylic acid O–H group is especially reactive, and this site is also important for the molecule’s antioxidant properties. Theoretical calculations confirm that the structure and reactivity of atorvastatin are closely linked to its functional groups and overall molecular geometry 35.
Conclusion
Atorvastatin’s chemical structure is defined by its aromatic rings, functional groups, and the way it coordinates with calcium in its pharmaceutical form. Advanced crystallographic and NMR techniques, supported by computational studies, have provided a detailed understanding of its molecular and crystal structure, which is essential for its function as a cholesterol-lowering drug 12345.
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