Summary

DescriptionAlbendazole metabolism.svg	English: Albendazole is metabolized into R(+)-albendazole sulfoxide and S(-)-albendazole sulfoxide. Both are metabolized to albendazole sulfone.
Date	7 August 2017
Source	Own work
Author	Prof. Squirrel
Other versions
SVG development InfoField	The SVG code is valid.   This structural formula was created with Adobe Illustrator.

References:

• Capece, Bettencourt P. S.; Virkel, Guillermo L.; Lanusse, Carlos E. (2009). "Enantiomeric behaviour of albendazole and fenbendazole sulfoxides in domestic animals: Pharmacological implications". The Veterinary Journal 181 (3): 241-250. DOI:10.1016/j.tvjl.2008.11.010. ISSN 1090-0233.
• Rawden, Helen C.; Kokwaro, Gilbert O.; Ward, Stephen A.; Edwards, Geoffrey (2004). "Relative contribution of cytochromes P-450 and flavin-containing monoxygenases to the metabolism of albendazole by human liver microsomes". British Journal of Clinical Pharmacology 49 (4): 313-322. DOI:10.1046/j.1365-2125.2000.00170.x. ISSN 1365-2125.

Made using the chemfig package in LaTex:

 

This W3C-unspecified vector image was created with LaTeX.

}

\renewcommand{\familydefault}{\sfdefault}

\begin{document} \hspace{-1.5in} \schemestart % ALBENDAZOLE @c1 \chemname{

   \chemfig{
   -[:30] -[:-30] -[:30]S -[:-30] 
   *6( =  %bottom
       - 
       = *5(-N
            = ( -\chembelow{N}{H} -[:60]( =[:120]O ) -O -[:60] )
            -\chemabove{N}{H}  
            -
            -
            )
       - %top
       =
       -
       )
   }

}{albendazole} \arrow(.mid east--.mid west){<->[FMO][]}[30,2] % alb -> + alb sulfoxide \setlewis{}{}{magenta} %ALBENDAZOLE SULFOXIDE (+) \chemname{

   \chemfig{
   -[:30] -[:-30] -[:30]S ( <[:120,1.25,,,,magenta]\color{magenta}{O} ) ( <:[:50,1.25,,,,magenta]\color{white}{\Lewis{1:,.}} ) -[:-30] 
   *6( =  %bottom
       - 
       = *5(-N
            = ( -\chembelow{N}{H} -[:60]( =[:120]O ) -O -[:60] )
            -\chemabove{N}{H}  
            -
            -
            )
       - %top
       =
       -
       )
   }

}{R(+)-albendazole sulfoxide} \arrow(@c1.mid east--.mid west){<->[][CYP]}[-30,2] % alb -> - alb sulfoxide \arrow(@c2.east--@c4.west){->[\sf{CYP}]}[30,2] \setlewis{}{}{magenta} %ALBENDAZOLE SULFOXIDE (-) \chemname {

   \chemfig{
   -[:30] -[:-30] -[:30]S ( <[:120,1.25,,,,magenta]\color{white}{\Lewis{3:,.}} ) ( <:[:50,1.25,,,,magenta]\color{magenta}{O} ) -[:-30] 
   *6( =  %bottom
       - 
       = *5(-N
            = ( -\chembelow{N}{H} -[:60]( =[:120]O ) -O -[:60] )
            -\chemabove{N}{H}  
            -
            -
            )
       - %top
       =
       -
       )
   }

}{S(-)-albendazole sulfoxide} \arrow(.east--.west){->[][CYP]}[30,2] %ALBENDAZOLE SULFONE \chemname {

   \chemfig{
   -[:30] -[:-30] -[:30]S ( =[:60,,,,,magenta]\color{magenta}{O} )( =[:120,,,,,magenta]\color{magenta}{O} ) -[:-30] 
   *6( =  %bottom
       - 
       = *5(-N
            = ( -\chembelow{N}{H} -[:60]( =[:120]O ) -O -[:60] )
            -\chemabove{N}{H}  
            -
            -
            )
       - %top
       =
       -
       )
   }

}{albendazole sulfone} \schemestop \end{document} }}

Licensing

This image of a simple structural formula is ineligible for copyright and therefore in the public domain, because it consists entirely of information that is common property and contains no original authorship.