Fosinopril: Emerging Considerations and Implications for Angiotensin‐Converting Enzyme Inhibitor Therapy

Sica, Domenic A.; Gehr, Todd W.B.; Kelleher, Nicole M.; Blumenthal, Mel

doi:10.1111/j.1527-3466.1998.tb00362.x

Cited by 5 publications

(6 citation statements)

References 92 publications

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“…We added 2.0Å for the C9-C14 pair and 1.1Å for CH 3 and CH 2 groups. 13 The minimum energy conformations within about 3 kcal mol 1 (1 kal D 4.184 kJ) relative to the global minimum conformation for conformer II and 1 kcal mol 1 for conformer I are summarized in Table 3. The differences between the C2-N-C6-C7 and P-C8-C9-C10 torsion angles were very small for the two conformers, but were consistent with the J couplings and NOE results.…”

Section: Molecular Dynamics Simulationsmentioning

confidence: 99%

“…1 A study of polymorphs of this compound in the solid state demonstrated that the two conformers are formed and arise due to cis-trans isomerization around the amide bond. 4 Concentration-dependent behavior was observed in aqueous solution.…”

Section: Introductionmentioning

confidence: 99%

“…As an orally active antihypertensive, the solution conformation exerts an influence on its physicochemical properties and consequently affect the absorption in the body. 1,3 Hence a study of the conformational dynamics of fosinopril sodium would not only be helpful for its preservation and formulation, but also be useful for studying interactions between proteins and the drug molecule and assist in drug design.…”

Section: Introductionmentioning

confidence: 99%

“…1,2 It is a pro-drug which is completely de-esterified either during or shortly after absorption to form an active diacid, fosinoprilat. 1 Recently, two conformers of fosinopril sodium, detected in methanol, were found in the course of our research. As an orally active antihypertensive, the solution conformation exerts an influence on its physicochemical properties and consequently affect the absorption in the body.…”

Section: Introductionmentioning

confidence: 99%

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Conformational study of fosinopril sodium in solution using NMR and molecular modeling

Liu

Shi

Zhang

et al. 2003

Magnetic Reson in Chemistry

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Two conformers of fosinopril sodium in methanol were unambiguously established using 2D NMR methods and variable-temperature NMR experiments. Differences in their conformational structure were shown to be related to the rotational energy barrier about the amide bond and hydrophobic interaction. The relationship between the 3D structure and activity is discussed. It is suggested that the trans-conformer may be more biologically active owing to its stacking structure and strong hydrophobic interaction and the cis-conformer could be more easily hydrolyzed because of its extended structure.

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Section: Molecular Dynamics Simulationsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 2 more Smart Citations

Conformational study of fosinopril sodium in solution using NMR and molecular modeling

Liu

Shi

Zhang

et al. 2003

Magnetic Reson in Chemistry

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“…However, once absorbed, it is rapidly converted to Fosinopril diacid. The time to peak concentration of FPD is reported to be 2.4–4.2 h (Sica, Gehr, Kelleher, & Blumenthal, 1998). Since Fosinopril rapidly converts to FPD and it is FPD which has the antihypertensive action, it was decided to analyze FPD in human plasma by liquid chromatography–tandem mass spectrometry (LC–MS/MS).…”

Section: Introductionmentioning

confidence: 99%

A sensitive and efficient LC–MS/MS method for the bioanalysis of fosinopril diacid from human plasma and its application for a bioequivalence study in humans

Bhende

Varanasi²,

Abbulu³

2021

Biomedical Chromatography

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Fosinopril diacid is an angiotensin converting enzyme inhibitor with efficient antihypertensive action. It is an active metabolic product formed in the body from hydrolysis of its prodrug Fosinopril. A sensitive, rapid method with high recovery for Fosinopril diacid from human plasma was developed. Solid‐phase extraction technique employing Waters Oasis SPE cartridges gave clean samples with very high recovery of 97%. The analyte along with its internal standard (Benazepril hydrochloride) were chromatographed on an XTerra RP8 column (4.6 × 50 mm, 5 μm) using methanol–ammonium acetate buffer (10 mm; 90:10, v/v) as the mobile phase. A triple quadrupole mass spectrometer equipped with electrospray ionization source operated in the negative ion mode was used for detection. Multiple reaction monitoring scan mode was used for monitoring the transitions from m/z 434.00 → 237.15 for Fosinopril diacid and m/z 423.10 → 174.00 for Benazepril hydrochloride. Beer–Lambert’s law was obeyed in the range of 0.50–1,500.00 ng/ml (r = 0.9993). The stability of the drugs in human plasma and in stock solution was proved by performing stability tests as per US Food and Drug Administration guidelines. The method was successfully applied for a bioequivalence study of Fosinopril diacid in 36 healthy, adult, male volunteers under fasting conditions.

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Silicon Mimics of Unstable Carbon

Sieburth

2014

Topics in Medicinal Chemistry

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Fosinopril: Emerging Considerations and Implications for Angiotensin‐Converting Enzyme Inhibitor Therapy

Cited by 5 publications

References 92 publications

Conformational study of fosinopril sodium in solution using NMR and molecular modeling

Conformational study of fosinopril sodium in solution using NMR and molecular modeling

A sensitive and efficient LC–MS/MS method for the bioanalysis of fosinopril diacid from human plasma and its application for a bioequivalence study in humans

Silicon Mimics of Unstable Carbon

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