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%\usepackage{opensans}          % Can't make this work so far. Shame. Would be lovely.
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% Document Info
\author{sam219}
\pdfinfo{
  /Title (metabolism-biotransformation.pdf)
  /Creator (Cheatography)
  /Author (sam219)
  /Subject (Metabolism/Biotransformation Cheat Sheet)
}

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\noindent
\begin{multicols}{3}
\begin{tabulary}{5.8cm}{C}
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    \vspace{-7pt}
    {\parbox{\dimexpr\textwidth-2\fboxsep\relax}{\noindent
        \hspace*{-6pt}\includegraphics[width=5.8cm]{/web/www.cheatography.com/public/images/cheatography_logo.pdf}}
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\begin{tabulary}{11cm}{L}
    \vspace{-2pt}\large{\bf{\textcolor{DarkBackground}{\textrm{Metabolism/Biotransformation Cheat Sheet}}}} \\
    \normalsize{by \textcolor{DarkBackground}{sam219} via \textcolor{DarkBackground}{\uline{cheatography.com/201893/cs/45383/}}}
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\noindent
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  \mymulticolumn{2}{p{5.377cm}}{\bf\textcolor{white}{Cheatographer}}  \\
  \vspace{-2pt}sam219 \\
  \uline{cheatography.com/sam219} \\
  \end{tabulary}
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  \mymulticolumn{1}{p{5.377cm}}{\bf\textcolor{white}{Cheat Sheet}}  \\
   \vspace{-2pt}Not Yet Published.\\
   Updated 5th January, 2025.\\
   Page {\thepage} of \pageref{LastPage}.
\end{tabulary}
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  \vspace{-5pt}
  %\includegraphics[width=48px,height=48px]{dave.jpeg}
  Measure your website readability!\\
  www.readability-score.com
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\begin{document}
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\begin{tabularx}{17.67cm}{x{5.9045 cm} x{5.061 cm} x{5.9045 cm} }
\SetRowColor{DarkBackground}
\mymulticolumn{3}{x{17.67cm}}{\bf\textcolor{white}{Phae 1: Functionalization reactions}}  \tn
% Row 0
\SetRowColor{LightBackground}
Oxidative pathways\{\{ac\}\} & Reduction\{\{ac\}\} & Hydrolytic reactions \{\{ac\}\} \tn 
% Row Count 2 (+ 2)
% Row 1
\SetRowColor{white}
{\bf{1. Alcohols \& Aldehydes}}\{\{ac\}\} & {\bf{1. Aldehydes}}\{\{ac\}\} & {\bf{1. Esters}}\{\{ac\}\} \tn 
% Row Count 5 (+ 3)
% Row 2
\SetRowColor{LightBackground}
Ex: pyridoxine becoming pyridoxal & Become alcohols from H addition. & Ex: Cocaine, Aspirin, Mepiridine, Procaine \tn 
% Row Count 8 (+ 3)
% Row 3
\SetRowColor{white}
Aliphatic \seqsplit{hydroxylation:} addition of OH. & {\bf{2. Azo-reduction}}\{\{ac\}\} & The ester (COO) gp becomes an acid. \tn 
% Row Count 11 (+ 3)
% Row 4
\SetRowColor{LightBackground}
{\bf{2. Oxidative N-demethylation}}\{\{ac\}\} & Ex: Sulfasalazine-{}-\textgreater{} \seqsplit{Sulfapyridine} & {\bf{2. Amides}}\{\{ac\}\} \tn 
% Row Count 14 (+ 3)
% Row 5
\SetRowColor{white}
Ex: \seqsplit{Methamphetamine}, Lidocaine, Epinephrine & {\bf{3. Nitroreduction}}\{\{ac\}\} & Ex: Procainamide \tn 
% Row Count 18 (+ 4)
% Row 6
\SetRowColor{LightBackground}
N with a CH3 (or other) get replaced by =O & Ex: Nitrazepam, \seqsplit{Chloramphenicol} & {\bf{3. Glycosides}}\{\{ac\}\} \tn 
% Row Count 21 (+ 3)
% Row 7
\SetRowColor{white}
{\bf{3. Oxidative deamination}}\{\{ac\}\} & NO2 becomes NH2. & Ex: Digoxin -{}-\textgreater{} Digoxin aglycone \tn 
% Row Count 24 (+ 3)
% Row 8
\SetRowColor{LightBackground}
Ex: \seqsplit{Norepinephrine}, Histamine, Mescaline & {\bf{4. Dehalogenation}} & {\bf{4. Epoxides}}\{\{ac\}\} \tn 
% Row Count 27 (+ 3)
% Row 9
\SetRowColor{white}
Removal of NH2 and its release as ammonia gas. Gets replaced by =O. & Ex: Halothane, \seqsplit{Ethchlovynol} & Ex: DES metabolite-{}-\textgreater{} DES \tn 
% Row Count 32 (+ 5)
\end{tabularx}
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\begin{tabularx}{17.67cm}{x{5.9045 cm} x{5.061 cm} x{5.9045 cm} }
\SetRowColor{DarkBackground}
\mymulticolumn{3}{x{17.67cm}}{\bf\textcolor{white}{Phae 1: Functionalization reactions (cont)}}  \tn
% Row 10
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\mymulticolumn{3}{x{17.67cm}}{{\bf{4. Oxidative O-dealkylation}}\{\{ac\}\}} \tn 
% Row Count 1 (+ 1)
% Row 11
\SetRowColor{white}
\mymulticolumn{3}{x{17.67cm}}{Ex: Phenacetin, Codeine, Mescaline, Papaverine} \tn 
% Row Count 2 (+ 1)
% Row 12
\SetRowColor{LightBackground}
\mymulticolumn{3}{x{17.67cm}}{O-alkyl becomes -OH.} \tn 
% Row Count 3 (+ 1)
% Row 13
\SetRowColor{white}
\mymulticolumn{3}{x{17.67cm}}{{\bf{5. N-Oxidation}}\{\{ac\}\}} \tn 
% Row Count 4 (+ 1)
% Row 14
\SetRowColor{LightBackground}
\mymulticolumn{3}{x{17.67cm}}{Ex: Imipramine.} \tn 
% Row Count 5 (+ 1)
% Row 15
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\mymulticolumn{3}{x{17.67cm}}{Coordinate bond between tert-N and O.} \tn 
% Row Count 6 (+ 1)
% Row 16
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\mymulticolumn{3}{x{17.67cm}}{{\bf{6. S-Oxidation}}\{\{ac\}\}} \tn 
% Row Count 7 (+ 1)
% Row 17
\SetRowColor{white}
\mymulticolumn{3}{x{17.67cm}}{Ex: Chlorpromazine; S-O (sulfoxide) then becomes (S=O) Sulfone.} \tn 
% Row Count 9 (+ 2)
% Row 18
\SetRowColor{LightBackground}
\mymulticolumn{3}{x{17.67cm}}{{\bf{7. Desulfuration}} \{\{ac\}\}} \tn 
% Row Count 10 (+ 1)
% Row 19
\SetRowColor{white}
\mymulticolumn{3}{x{17.67cm}}{Ex: Thiobarbital, Parathion} \tn 
% Row Count 11 (+ 1)
% Row 20
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\mymulticolumn{3}{x{17.67cm}}{=S is replaced by =O} \tn 
% Row Count 12 (+ 1)
% Row 21
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\mymulticolumn{3}{x{17.67cm}}{{\bf{8. Epoxidation}}\{\{ac\}\}} \tn 
% Row Count 13 (+ 1)
% Row 22
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\mymulticolumn{3}{x{17.67cm}}{Ex: DES; O in a strained tricyclic structure.} \tn 
% Row Count 14 (+ 1)
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\begin{tabularx}{17.67cm}{x{5.7358 cm} x{5.5671 cm} x{5.5671 cm} }
\SetRowColor{DarkBackground}
\mymulticolumn{3}{x{17.67cm}}{\bf\textcolor{white}{Phase 1: Functionalisation cont.}}  \tn
% Row 0
\SetRowColor{LightBackground}
\seqsplit{Decarboxylation} \{\{ac\}\} & Oxidative pathways catalysed by other oxidoreductases\{\{ac\}\} & Reductive pathways by \seqsplit{oxidoreductases} \{\{ac\}\} \tn 
% Row Count 5 (+ 5)
% Row 1
\SetRowColor{white}
Ex: Histidine, a-methyldopa, L-Dopa. & {\bf{Alcohol dehydrogenases}} & Less significant \tn 
% Row Count 8 (+ 3)
% Row 2
\SetRowColor{LightBackground}
Removal of carboxylic acid. & 1ry alcohol \seqsplit{(benzylalcohol}, phenethanol, retinol)-{}-\textgreater{} Aldehydes & Include reactions on: \tn 
% Row Count 13 (+ 5)
% Row 3
\SetRowColor{white}
Histidine-{}-\textgreater{} Histamine; L-Dopa-{}-\textgreater{} dopamine. & 2ry alcohols-{}-{}-\textgreater{} Ketones & 1) C=O compounds 2) Olefins 3) \seqsplit{Dehalogenation} 4) other atoms \tn 
% Row Count 18 (+ 5)
% Row 4
\SetRowColor{LightBackground}
 & 3ry alcohols do not react. & Hydrolytic pathways\{\{ac\}\} \tn 
% Row Count 20 (+ 2)
% Row 5
\SetRowColor{white}
 & {\bf{Aldehyde dehydrogenases}} & include hydrolyses enzymes \tn 
% Row Count 23 (+ 3)
% Row 6
\SetRowColor{LightBackground}
 & Aldehydes-{}-\textgreater{} Acid & They add a water to functional groups. \tn 
% Row Count 26 (+ 3)
% Row 7
\SetRowColor{white}
 & {\bf{Monoamine oxidase (MAO)}} &  \tn 
% Row Count 29 (+ 3)
% Row 8
\SetRowColor{LightBackground}
 & Has 2 \seqsplit{forms/isozymes} A \& B, that deaminate \seqsplit{catecholamines}. &  \tn 
% Row Count 34 (+ 5)
\end{tabularx}
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\begin{tabularx}{17.67cm}{x{5.7358 cm} x{5.5671 cm} x{5.5671 cm} }
\SetRowColor{DarkBackground}
\mymulticolumn{3}{x{17.67cm}}{\bf\textcolor{white}{Phase 1: Functionalisation cont. (cont)}}  \tn
% Row 9
\SetRowColor{LightBackground}
 & Treats Parkinson's  (esp MAO B). &  \tn 
% Row Count 3 (+ 3)
\hhline{>{\arrayrulecolor{DarkBackground}}---}
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\begin{tabularx}{17.67cm}{x{5.7358 cm} x{5.5671 cm} x{5.5671 cm} }
\SetRowColor{DarkBackground}
\mymulticolumn{3}{x{17.67cm}}{\bf\textcolor{white}{Phase 2: conjugation reaction}}  \tn
% Row 0
\SetRowColor{LightBackground}
Methylation \{\{ac\}\} & Acetylation \& Acylation & Amino acid conjugation reactions\{\{ac\}\} \tn 
% Row Count 3 (+ 3)
% Row 1
\SetRowColor{white}
A methyl group on carrier (SAM) adds the methyl to O/N/S on the drug or phase 1 metabolite. & \seqsplit{Acyl-coenzyme} A is required & Glycine is used to conjugate COOH gp in xenobiotics. \tn 
% Row Count 10 (+ 7)
% Row 2
\SetRowColor{LightBackground}
\seqsplit{O-methylation} by COMT. & Ex: \seqsplit{Sulfamethoxazole} where COCH3 gp is added. & Carrier is glycine \seqsplit{N-acyltransferase}. \tn 
% Row Count 14 (+ 4)
% Row 3
\SetRowColor{white}
\seqsplit{N-methylation} by \seqsplit{N-methyltransferase}. & Some people are fast or slow acetylators and thus drug dose metabolized here should be adjusted. &  \tn 
% Row Count 22 (+ 8)
% Row 4
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\mymulticolumn{3}{x{17.67cm}}{S-methylation by thiol or thiopurine methyltransferases.} \tn 
% Row Count 24 (+ 2)
% Row 5
\SetRowColor{white}
\mymulticolumn{3}{x{17.67cm}}{Thiol containing drugs (captopril, mercaptopurine, propylthiouracil) are subjected to S-methylation.} \tn 
% Row Count 26 (+ 2)
% Row 6
\SetRowColor{LightBackground}
\mymulticolumn{3}{x{17.67cm}}{Captopril is unique in that phase 2 S-methylation occurs first, then phase 1.} \tn 
% Row Count 28 (+ 2)
\hhline{>{\arrayrulecolor{DarkBackground}}---}
\end{tabularx}
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\begin{tabularx}{17.67cm}{x{4.1175 cm} x{4.1175 cm} x{4.1175 cm} x{4.1175 cm} }
\SetRowColor{DarkBackground}
\mymulticolumn{4}{x{17.67cm}}{\bf\textcolor{white}{Phase 2: conjugation reaction cont.}}  \tn
% Row 0
\SetRowColor{LightBackground}
Glucuronidation\{\{ac\}\} & Sulfate \seqsplit{conjugation} \{\{ac\}\} & \seqsplit{Glutathione} (GSH) \seqsplit{conjugation} \{\{ac\}\} & \seqsplit{Miscellaneous} \seqsplit{conjugation} reactions\{\{ac\}\} \tn 
% Row Count 5 (+ 5)
% Row 1
\SetRowColor{white}
\seqsplit{Conjugation} with \seqsplit{glucuronic} acid with carrier UDPG. & A sulfate molecule is \seqsplit{transferred} from carrier, PAPS, to the \seqsplit{substrate/drug} by  enzyme cytosolic \seqsplit{sulfotransferases}. & In its reduced form, its the \seqsplit{tripeptide} GSH. But it becomes in the oxidized form GS-SG and the SG attachs to drug & 1) \seqsplit{Phosphorylation} via \seqsplit{phosphotransferase} \tn 
% Row Count 17 (+ 12)
% Row 2
\SetRowColor{LightBackground}
The enzyme, \seqsplit{UDP-glucouronosyl} \seqsplit{transferase}, acts on O, N, S in the compound. &  &  & Ex: \seqsplit{Zidovudine}. \tn 
% Row Count 25 (+ 8)
% Row 3
\SetRowColor{white}
 &  &  & 2) \seqsplit{Endogenous} carbonyl + Exogenous drug with \seqsplit{hydrazines} or hydrazides-{}-{}-\textgreater{} \seqsplit{Hydrazones}. \tn 
% Row Count 34 (+ 9)
\hhline{>{\arrayrulecolor{DarkBackground}}----}
\end{tabularx}
\par\addvspace{1.3em}



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