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Effect of pH on the complexation of irbesartan with β -, hydroxypropyl-β -, and γ -cyclodextrin: Solubility enhancement and physicochemical characterization

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The affinity of irbesartan (IRB) to form inclusion complexes with β-cyclodextrin (β-CD), hydroxypropylβ-cyclodextrin (HP-β -CD), and γ-cyclodextrin (γ-CD) was investigated in aqueous buffered solutions at pH 1.7, 4.1, and 7.0. Analysis of the UV absorption-pH profiles revealed that IRB has two pKa values: pKa1 = 3.60 (imidazolinone ring moiety) and pKa2 = 4.70 (tetrazole moiety). In the presence of 5.0 mmol L−1β-CD, the tetrazole moiety became more acidic, indicating its inclusion within the β-CD cavity. Phase-solubility diagrams (PSDs) were obtained for IRB in aqueous buffered solutions of β-CD, HP-β -CD, and γ-CD at pH 4.1 (zwitterionic IRB), pH 1.7 (protonated IRB), and pH 7.0 (deprotonated IRB). |

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