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Increase in Solubility of Poorly-Ionizable Pharmaceuticals by Salt Formation: A Case of Agomelatine Sulfonates

The result's identifiers

  • Result code in IS VaVaI

    <a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F61388963%3A_____%2F17%3A00480929" target="_blank" >RIV/61388963:_____/17:00480929 - isvavai.cz</a>

  • Alternative codes found

    RIV/60461373:22310/17:43914798 RIV/60461373:22340/17:43914798 RIV/00216208:11320/17:10370291

  • Result on the web

    <a href="http://dx.doi.org/10.1021/acs.cgd.7b00805" target="_blank" >http://dx.doi.org/10.1021/acs.cgd.7b00805</a>

  • DOI - Digital Object Identifier

    <a href="http://dx.doi.org/10.1021/acs.cgd.7b00805" target="_blank" >10.1021/acs.cgd.7b00805</a>

Alternative languages

  • Result language

    angličtina

  • Original language name

    Increase in Solubility of Poorly-Ionizable Pharmaceuticals by Salt Formation: A Case of Agomelatine Sulfonates

  • Original language description

    The search for new solid forms of an active pharmaceutical ingredient (API) is an important step in drug development. Often, an API has a low water solubility, which then leads to low oral bioavailability. For basic or acidic APIs, the rational solution is the preparation of salts. For neutral, poorly ionizable, compounds, the cocrystallization is often the only choice. Agomelatine, a poorly soluble ”nonionizable” amide acting as a melatonergic antidepressant is a typical representative of such class of compounds. Until recently, the only multicomponent forms of agomelatine were cocrystals. In this work, we report the preparation of three salts of agomelatine (hydrogensulfate, mesylate, and besylate) and their solvated forms, along with their crystallographic characterization. Interestingly, the crystal structures of the solvated and nonsolvated hydrogensulfates were determined from the same crystal via a topotactic transformation. In all of the structures, the agomelatine molecule was positively charged with the amide oxygen being protonated. The salt formation was also confirmed by solid state nuclear magnetic resonance measurements and density functional theory calculations. By sulfonate salt formation, up to similar to 200-times faster dissolution of agomelatine was achieved, which proves that salts might be an attractive alternative even for the poorly ionizable compounds.

  • Czech name

  • Czech description

Classification

  • Type

    J<sub>imp</sub> - Article in a specialist periodical, which is included in the Web of Science database

  • CEP classification

  • OECD FORD branch

    10403 - Physical chemistry

Result continuities

  • Project

    Result was created during the realization of more than one project. More information in the Projects tab.

  • Continuities

    I - Institucionalni podpora na dlouhodoby koncepcni rozvoj vyzkumne organizace

Others

  • Publication year

    2017

  • Confidentiality

    S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů

Data specific for result type

  • Name of the periodical

    Crystal Growth & Design

  • ISSN

    1528-7483

  • e-ISSN

  • Volume of the periodical

    17

  • Issue of the periodical within the volume

    10

  • Country of publishing house

    US - UNITED STATES

  • Number of pages

    12

  • Pages from-to

    5283-5294

  • UT code for WoS article

    000412718100035

  • EID of the result in the Scopus database

    2-s2.0-85042508930