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CHEM 437- Midterm Exam Guide - Comprehensive Notes for the exam ( 36 pages long!)


Department
Chemistry
Course Code
CHEM 437
Professor
Hoff
Study Guide
Midterm

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UVic
CHEM 437
MIDTERM EXAM
STUDY GUIDE

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Chem 437!
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6.5 Pro-drugs:!
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-esters are the most widely used pro-drug functional group transformations!
-highly charged things may be had to get across membranes, but there ar many chemical, structural things you
cane o to make it better at transferring!
-some drugs aren't metabolized and get excreted in their active form!
-other drugs get more active once metabolized!
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6.5 Metabolism:
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Metabolism might:
"- make a drug "go away"!
"- make a drug more potent!
"- make a toxic form!
"- vary from person to person!
"- not happen at all!
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Causes an analytical chemist huge challenges!
potency is not end all be all--> e.g. change molecule to get a less potent molecule but the stability increases by a
lot, therefore, good tradeoff!
Optimization is very important!
Fluorine is poorly dealt with by natural enzymes!
30-50% of all drugs contain fluorine!
carbon fluorine bonds are relay stable --> teflon C-H!
by products of teflon, bad environmental pollutant!
C-F bonds can't be processed!
F is used to prevent metabolism
6.6 Predicting pharmacological properties from structure:
-predicting drug-likeness from structure (Lipinski "rules of 5")!
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c log P!
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logP = log ( [drug in octanal]/ [drug in H20])!
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"-more increase log P. increased in hydrophobic !
"-computer programs can predict clogP value!
4 structural features that look bad for drug likeness!
breaking two of the "rules of 5", gives a 90% chance the drug candidate will have poor absorption!
breaking both MW and logP rules creates a 99% failure rate "ref. slide for rules"!
Lipitor is an exception breaks two rules, in the 1% !
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clarification :!
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HBA= hydrogen bond aceeptor!
HBD= hydrogen bond donor!
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Vebers rules:!
nrot: # of rotatable bonds!
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higher nrot, more flexible, lower oral bioavailability!
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rotatable bond: single bond, not in a ring, not on a terminal group, not an amide C-N bond.!
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polar surface area = PSA!
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!
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