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Quantitative Structure-Activity Relationship, Activity Prediction, and Molecular Dynamics of Non-nucleotide Reverse Transcriptase Inhibitors

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Lamivudine salts with improved solubilities.

Felipe T Martins¹, Rudy Bonfilio, Magali B De Araújo

¹Instituto de Química, Universidade Federal de Goiás, Campus Samambaia, Goiânia, Goiâs, Brazil. felipe@quimica.ufg.br

Journal of Pharmaceutical Sciences

|March 16, 2012

Summary

Crystal engineering significantly boosts lamivudine solubility. New salts and a unique duplex structure dramatically increase the anti-HIV drug’s water solubility, aiding therapeutic development.

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Area of Science:

Pharmaceutical Sciences
Solid-State Chemistry
Drug Discovery

Background:

Optimizing drug solubility is crucial for therapeutic efficacy.
Current strategies often involve engineering and screening of crystal phases.
Lamivudine is an essential anti-human immunodeficiency virus (HIV) medication.

Purpose of the Study:

To investigate the water solubility of novel lamivudine salts and a lamivudine duplex structure.
To evaluate the impact of crystal engineering on improving lamivudine's aqueous solubility.
To understand the structure-solubility relationships for enhanced drug delivery.

Main Methods:

Preparation and characterization of lamivudine hydrochloride and lamivudine hydrochloride monohydrate.
Crystallization screening to form lamivudine duplex, a DNA-mimic structure.
Measurement of aqueous solubility for different lamivudine forms at 299 ± 2 K.

Main Results:

Lamivudine hydrochloride solubility increased by a factor of 1.2 compared to lamivudine form II.
Lamivudine hydrochloride monohydrate showed a 3.3-fold increase in solubility.
Lamivudine duplex exhibited a significant 4.5-fold increase in aqueous solubility.
Solubility profiles correlated with structural features and solvent-solute interactions.

Conclusions:

Crystal engineering strategies, including salt formation and duplex structures, can substantially enhance lamivudine solubility.
The findings provide a rational basis for designing new lamivudine salts with improved physicochemical properties.
Enhanced solubility of lamivudine is critical for developing more effective anti-HIV therapies.