A comparative study of the molecular structure, lipophilicity, solubility, acidity, absorption and polar surface area of coumarinic anticoagulants and direct thrombin inhibitors

RSC Advances ◽  
2014 ◽  
Vol 4 (16) ◽  
pp. 8072-8084 ◽  
Author(s):  
Milan Remko ◽  
Ria Broer ◽  
Anna Remková
Keyword(s):  
Molecular Structure ◽  
Comparative Study ◽  
Computational Chemistry ◽  
Surface Area ◽  
Molecular Properties ◽  
Thrombin Inhibitors ◽  
Direct Thrombin Inhibitors ◽  
Polar Surface Area ◽  
Polar Surface

The methods of computational chemistry have been used to elucidate the molecular properties of coumarinic anticoagulants (acenocoumarol, phenprocoumon, warfarin and tecarfarin) and direct thrombin inhibitors (melagatran, dabigatran and their prodrug forms).

scholarly journals The correlation of plasma protein binding and molecular properties of selected antifungal drugs

2020 ◽  
Vol 85 (7) ◽  
pp. 897-907
Author(s):  
Jadranka Odovic ◽  
Milkica Crevar-Sakac ◽  
Zorica Vujic
Keyword(s):  
Molecular Weight ◽  
Protein Binding ◽  
Surface Area ◽  
Plasma Protein Binding ◽  
Plasma Protein ◽  
Antifungal Drugs ◽  
Molecular Properties ◽  
Log P ◽  
Polar Surface Area ◽  
Polar Surface

Antifungal agents are the group of drugs commonly prescribed in the treatment of fungal infections, which are widely spread among the global population. Their properties, such as absorption, distribution, metabolism, route of elimination or plasma protein binding (PPB), considerably influence their therapeutic success, while a number of the molecular physicochemical properties of the drug notably influence all these processes. Lipophilicity (log P), molecular weight (Mw), volume (Vol), polar surface area (PSA) and solubility (log S) play important roles in drug absorption, penetration into tissues, distribution and route of elimination or the degree of plasma protein binding. In this study, the relationships between these five molecular properties of eight antifungal drugs and their plasma protein binding data obtained from relevant literature were investigated. The Selected physicochemical molecular descriptors of the drug were calculated using software packages. The established relationships between PPB and PSA; Mw; Vol and log S were showed relatively poor correlation (r < 0.35). The best correlation was obtained for the relationship between PPB data and the lipophilicity descriptor X log P3 (correlation coefficient r = 0.55). In further investigation, multiple linear regression analysis was applied. The best correlation was obtained with application of lipophilicity with polar surface area (r = 0.918) and volume (r = 0.916) or molecular weight (r = 0.896) as independent variables.

Discovery of a Potent Free Fatty Acid 1 Receptor Agonist with Low Lipophilicity, Low Polar Surface Area, and Robust in Vivo Efficacy

2016 ◽  
Vol 59 (6) ◽  
pp. 2841-2846 ◽  
Author(s):  
Steffen V. F. Hansen ◽  
Elisabeth Christiansen ◽  
Christian Urban ◽  
Brian D. Hudson ◽  
Claire J. Stocker ◽  
...  
Keyword(s):  
Fatty Acid ◽  
Free Fatty Acid ◽  
Surface Area ◽  
Receptor Agonist ◽  
Polar Surface Area ◽  
In Vivo Efficacy ◽  
Polar Surface

scholarly journals The effect of the solvent nature on the quinoline derivatives physicochemical characteristics

2019 ◽  
Vol 60 (11) ◽  
pp. 31-39
Author(s):  
Vladimir V. Shcherbakov ◽  
◽  
Svetlana V. Kurbatova ◽  
Margarita N. Zemtsova ◽  
◽  
...  
Keyword(s):  
Dipole Moment ◽  
Surface Area ◽  
Chemical Nature ◽  
Solvation Energy ◽  
Biologically Active ◽  
Quinoline Derivatives ◽  
Polar Surface Area ◽  
Polar Surface ◽  
Solvent Nature ◽  
Derivatives Of

The influence of the solvent nature on some physicochemical parameters of the quinoline derivatives molecules is investigated. It was noted that a variety of intermolecular interactions arising between the dissolved substance and the solvent and often accompanied by the phenomena of solvation, association, etc. leads to a variety of structural and energy changes in such systems and complicating their description. The most urgent problems of solutions include issues related to the solubility and bioavailability of biologically active compounds and drugs, the study of their ability to dissolve, the permeability of biological barriers, targeted delivery, etc., as well as the problems associated with the study of sorption of organic compounds from aqueous-organic eluents, for example, in liquid chromatography. Derivatives of quinoline (4-carboxy- and 4-aminoquinoline), known as potential drugs with various types of pharmacological action, were used as research objects. Using quantum chemical calculations, the dipole moment of the amino and carboxy derivatives of quinoline was determined, and the data obtained for vacuum and in solvents of various chemical nature were compared. A significant effect of solvent polarity on the dipole moment of quinoline derivatives dissolved in these solvents was found. The values of the solvation energy of quinoline derivatives in solvents of various chemical nature are calculated. It is shown that a change in the solvation energy is determined both by the structure of the molecules of the quinoline derivatives and by the polarity of the solvent. A nonlinear change in the energy of solvation with a change in the polarity of the solvent is established. A comparison is made of the values of the quinoline derivatives molecules polar surface area in solvents of various chemical nature. It was found that the polar surface area of the studied compounds changes slightly with a change in the nature of the solvent.

scholarly journals Effect of drug lipophilicity and polar surface area on iontophoretic transdermal absorption.

2001 ◽  
Vol 16 (5) ◽  
pp. 419-423
Author(s):  
Yoshikazu Tashiro ◽  
Mari Sami ◽  
Shozo Shichibe ◽  
Yasuki Kato ◽  
Eiji Hayakawa ◽  
...  
Keyword(s):  
Surface Area ◽  
Polar Surface Area ◽  
Polar Surface ◽  
Transdermal Absorption

Polar Surface Area

2016 ◽  
Author(s):  
Derek R. Buckle ◽  
Paul W. Erhardt ◽  
C. Robin Ganellin ◽  
Toshi Kobayashi ◽  
Thomas J. Perun ◽  
...  
Keyword(s):  
Surface Area ◽  
Polar Surface Area ◽  
Polar Surface
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