Stereoselective plasma protein binding of amlodipine

Maddi, Srinivas; Yamsani, Madhusudan Rao; Seeling, Andreas; Scriba, Gerhard K. E.

doi:10.1002/chir.20738

Cited by 27 publications

(20 citation statements)

References 16 publications

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“…It has been recognized that preclinical data from animals cannot be extrapolated to humans 63 . Further studies also showed that stereoselective differences are dependent on species 28,29 . Nevertheless, mammalian results are occasionally consistent with human disposition 64 .…”

Section: Stereoselectivity Of Plasma Protein Binding To Chiral Drugsmentioning

confidence: 92%

“…To illustrate enantioselective drug-protein binding, classical methods, such as equilibrium dialysis (ED), ultrafiltration (UF) and ultracentrifugation (UC), are commonly combined with chiral separation techniques 27,28,29 . ED is an apparatus with two compartments separated by a semipermeable membrane, and only unbound drug molecules can permeate through the membrane.…”

Section: Methods and Modelsmentioning

confidence: 99%

“…The binding of bimoclomol to human plasma was stereoselective, and AGP was mainly responsible for the preference toward S -bimoclomol, whereas HSA did not play a role 62 . Another study showed that HSA and human plasma binding tended to be stereospecific in regard to S -amlodipine, whereas the opposite binding of its enantiomer was observed for AGP 29 .…”

Section: Stereoselectivity Of Plasma Protein Binding To Chiral Drugsmentioning

confidence: 99%

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Stereoselective binding of chiral drugs to plasma proteins

et al. 2013

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Chiral drugs show distinct biochemical and pharmacological behaviors in the human body. The binding of chiral drugs to plasma proteins usually exhibits stereoselectivity, which has a far-reaching influence on their pharmacological activities and pharmacokinetic profiles. In this review, the stereoselective binding of chiral drugs to human serum albumin (HSA), α1-acid glycoprotein (AGP) and lipoprotein, three most important proteins in human plasma, are detailed. Furthermore, the application of AGP variants and recombinant fragments of HSA for studying enantiomer binding properties is also discussed. Apart from the stereoselectivity of enantiomer-protein binding, enantiomer-enantiomer interactions that may induce allosteric effects are also described. Additionally, the techniques and methods used to determine drug-protein binding parameters are briefly reviewed.

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Section: Stereoselectivity Of Plasma Protein Binding To Chiral Drugsmentioning

confidence: 92%

Section: Methods and Modelsmentioning

confidence: 99%

Section: Stereoselectivity Of Plasma Protein Binding To Chiral Drugsmentioning

confidence: 99%

See 1 more Smart Citation

Stereoselective binding of chiral drugs to plasma proteins

et al. 2013

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“…Since the binding of drugs to plasma proteins can be stereoselective [11,12], the present study describes, for the first time, the analysis of unbound concentrations of the tramadol, M1 and M2 enantiomers in human plasma and the application of this method to pharmacokinetic studies on patients with neuropathic pain treated with a single dose of racemic tramadol. The method described is derived from a study recently published by our group in which total concentrations of the tramadol, M1 and M2 enantiomers were analyzed in rat plasma [13].…”

Section: Introductionmentioning

confidence: 99%

Enantioselective analysis of unbound tramadol, O-desmethyltramadol and N-desmethyltramadol in plasma by ultrafiltration and LC–MS/MS: Application to clinical pharmacokinetics

Moraes

Lauretti

Napolitano

et al. 2012

Journal of Chromatography B

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“…Binding of UK-390957 to human plasma proteins was determined by equilibrium dialysis. Human plasma protein binding values for propranolol (Rodgers and Rowland, 2007) and amlodipine (Maddi et al, 2010) were taken from the literature. BPR measurements for all three compounds were made using heparinized human blood (for further details, see Allan et al, 2008).…”

Section: Methodsmentioning

confidence: 99%

Measurement of Binding of Basic Drugs to Acidic Phospholipids Using Surface Plasmon Resonance and Incorporation of the Data into Mechanistic Tissue Composition Equations to Predict Steady-State Volume of Distribution

Small

Gardner²,

Jones³

et al. 2011

Drug Metab Dispos

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ABSTRACT:Acidic phospholipid binding plays an important role in determining the tissue distribution of basic drugs. This article describes the use of surface plasmon resonance to measure binding affinity (K D ) of three basic drugs to phosphatidylserine, a major tissue acidic phospholipid. The data are incorporated into mechanistic tissue composition equations to allow prediction of the steady-state volume of distribution (V ss ). The prediction accuracy of V ss using this approach is compared with the original methodology described by Rodgers et al. (J Pharm Sci 94:1259-1276), in which the binding to acidic phospholipids is calculated from the blood/plasma concentration ratio (BPR). The compounds used in this study [amlodipine, propranolol, and 3-dimethylaminomethyl-4-(4-methylsulfanylphenoxy)-benzenesulfonamide (UK-390957)] showed higher affinity binding to phosphatidylserine than to phosphatidylcholine. When the binding affinity to phosphatidylserine was incorporated into mechanistic tissue composition equations, the V ss was more accurately predicted for all three compounds by using the surface plasmon resonance measurement than by using the BPR to estimate acidic phospholipid binding affinity. The difference was particularly marked for UK-390957, a sulfonamide that has a high BPR due to binding to carbonic anhydrase. The novel approach described in this article allows the binding affinity of drugs to an acidic phospholipid (phosphatidylserine) to be measured directly and demonstrates the utility of the binding data in the prediction of V ss . IntroductionAlong with clearance, the volume of distribution at steady state (V ss ) is a key pharmacokinetic parameter that determines how long a drug remains in the body. Several approaches have been used to prospectively predict human V ss , including scaling in vivo data from preclinical species, scaling in vitro data, and various in silico calculation methods (Obach, 2007).An approach that has gained popularity in recent years is to use in vitro and physicochemical data for a particular compound to estimate its tissue/plasma partitioning and by accounting for the volumes of different tissues and their composition. This information is used to predict V ss of a compound in an integrated physiologically based manner (eq. 1).where V is physical tissue volume, T is tissue, Kp is tissue to plasma partition coefficient, and p is plasma.Prediction of Kp on the basis of tissue composition and the physicochemical properties of a compound was first described by Poulin and Theil (2000) for neutral compounds, with emphasis on lipophilicity and binding to neutral lipids. This approach has subsequently been used by various authors to predict V ss for different compound datasets (Jones et al., 2006;De Buck et al., 2007). An extension to this mechanistic PBPK model that incorporates pH and binding of the ionized base to acidic phospholipids as an additional component of tissue binding was proposed by Rodgers et al. (2005a), initially for ionized bases. The affinity of a compound t...

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Stereoselective plasma protein binding of amlodipine

Cited by 27 publications

References 16 publications

Stereoselective binding of chiral drugs to plasma proteins

Stereoselective binding of chiral drugs to plasma proteins

Enantioselective analysis of unbound tramadol, O-desmethyltramadol and N-desmethyltramadol in plasma by ultrafiltration and LC–MS/MS: Application to clinical pharmacokinetics

Measurement of Binding of Basic Drugs to Acidic Phospholipids Using Surface Plasmon Resonance and Incorporation of the Data into Mechanistic Tissue Composition Equations to Predict Steady-State Volume of Distribution

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