July 17, 2024, 05:04:07 AM
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Topic: Similar structure = similar properties?  (Read 3579 times)

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Offline Justjules

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Similar structure = similar properties?
« on: February 17, 2024, 01:15:22 PM »
Hi all,
Recently, I started a new medication, with the molecular formula C17H11ClF3N5O3.  Previously, I took a now obsolete drug whose formula I looked up and appears very similar to my layperson eyes  C14H9ClF3NO2.  Is it right to presume both's metabolism/affects will be similar taken? Is this how pharmaceutical companies develop new drugs? 

Thank you in advance.

Jules

Offline Hunter2

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Re: Similar structure = similar properties?
« Reply #1 on: February 17, 2024, 02:04:34 PM »
A molecular formula says not so much. You need the structure of the molecule.

Offline Justjules

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Re: Similar structure = similar properties?
« Reply #2 on: February 18, 2024, 05:04:35 AM »
Hi Hunter, and thank you.  The structures look 'very different ', so I guess there's the answer.

Thank you.  I just assumed having a similar number of the same elements would produce the same effects.


Offline Justjules

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Re: Similar structure = similar properties?
« Reply #3 on: February 18, 2024, 05:07:39 AM »
Hi all,
Recently, I started a new medication, with the molecular formula C17H11ClF3N5O3.  Previously, I took a now obsolete drug whose formula I looked up and appears very similar to my layperson eyes  C14H9ClF3NO2.  Is it right to presume both's metabolism/affects will be similar taken? Is this how pharmaceutical companies develop new drugs? 

Thank you in advance.

Jules

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Offline BobfromNC

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Re: Similar structure = similar properties?
« Reply #4 on: February 19, 2024, 05:25:21 PM »
Yes, the same building blocks can make very different drugs.   Much like a pile of lumber can look alike, but you might build many different styles of house from the same basic lumber, ranch, 2 story, modern, federal, etc.   Often a single atom or a few can change major properties of a molecule, which is why drug discovery is not so easy, sometimes a small change will have huge, and unpredictable effects on its activity or metabolism.

Conversely, there are some drugs that look very different, but act similarly in the body or in other ways, ie morphine and fentanyl, benzene and thiophene, ethanol and valium.   

Offline Justjules

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Re: Similar structure = similar properties?
« Reply #5 on: February 20, 2024, 12:55:41 PM »
Hi Bob,

I'm super grateful for you taking the time to respond to my question and share your knowledge - as I am with Hunter.
 
Seeing there's people out there like you two makes me happier the world is a not so bad place.  Or at least, not as bad as we're led to believe.

Many thanks and hope you have a good day, or night, if it is where you are.

BW,
Jules



Offline DrCMS

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Re: Similar structure = similar properties?
« Reply #6 on: February 21, 2024, 12:19:01 PM »
I started a new medication, with the molecular formula C17H11ClF3N5O3.  Previously, I took a now obsolete drug whose formula I looked up and appears very similar to my layperson eyes  C14H9ClF3NO2. 

To a chemist these are quite different formulas and as others have pointed out they are shaped differently.  However, if you look here at the space filling models and rotate them they do have some similarities.  They are both reverse transcriptase inhibitors so do interact with the same biological active site, just with differing degrees of receptor site binding and specificity.

https://pubchem.ncbi.nlm.nih.gov/compound/Doravirine#section=3D-Conformer
https://pubchem.ncbi.nlm.nih.gov/compound/Efavirenz#section=3D-Conformer

Note both these drug are used to treat the same condition which a google search will link to your user name.  Sorry to hear your diagnosis; all the best.

Offline rolnor

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Re: Similar structure = similar properties?
« Reply #7 on: February 22, 2024, 03:48:54 AM »
I have synthesized efavirenz, it started with a large amount of sodium in liquid ammonia and at the end to separate isomers I ran multiple prep HPLC runs. It gives nightmares I believe?

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