Prodrugs pp 1289-1297 | Cite as

Case Study: Moexipril Hydrochloride: A Prodrug of Moexiprilat

  • Bianca M. Liederer
Part of the Biotechnology: Pharmaceutical Aspects book series (PHARMASP, volume V)


Moexiprilat is an orally active, nonsulfhydryl, long-acting dipeptide angiotensin-converting enzyme (ACE) inhibitor used to lower blood pressure (Stimpel et al., 1995; Brogden and Wiseman, 1998; Chrysant and Chrysant, 2003). Moexipril hydrochloride shows improved bioavailability compared to moexiprilat, most likely because esterification reduces the charge of the molecule and the pKa of its amine group (pKa Moexprilat = 7.7; pKa Moexipril = 5.4). Based on the comparable oral bioavailabilities of various esters of enalapril with different lipophilicities, it appears that lipophilicity is not the only factor that enhances oral bioavailability (Wyvratt and Patchett, 1985).


Severe Essential Hypertension Male Human Volunteer Show Maximum Stability Isoquinolinecarboxylic Acid Additional Medical Benefit 
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© American Association of Pharmaceutical Scientists 2007

Authors and Affiliations

  • Bianca M. Liederer
    • 1
  1. 1.Department of Pharmaceutical ChemistryThe University of KansasLawrenceUSA

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