October 24, 2021, 02:18:08 AM
Forum Rules: Read This Before Posting


Topic: Regarding functional groups of a medicine (drug)  (Read 1570 times)

0 Members and 1 Guest are viewing this topic.

Offline MathewConnors1999

  • Regular Member
  • ***
  • Posts: 13
  • Mole Snacks: +0/-0
Regarding functional groups of a medicine (drug)
« on: February 04, 2021, 10:48:40 AM »
I've working with Alzeihemers and more specifically its medicine treatments. I've been tasked with finding the functional groups of Sertindole (C24H26ClFN4O) and describe its build with perspective towards acting as a drug. If anyone could help me, I would really appreciate it, as I have no idea of where to even start.
Regards
Matthew Conner

Offline Babcock_Hall

  • Chemist
  • Sr. Member
  • *
  • Posts: 4930
  • Mole Snacks: +288/-22
Re: Regarding functional groups of a medicine (drug)
« Reply #1 on: February 04, 2021, 10:59:01 AM »
I assume that you have found the structure at some appropriate site, such as PubChem or elsewhere.  Do you recognize any functional groups from your organic chemistry classes?

Offline AWK

  • Retired Staff
  • Sr. Member
  • *
  • Posts: 7982
  • Mole Snacks: +555/-93
  • Gender: Male
Re: Regarding functional groups of a medicine (drug)
« Reply #2 on: February 04, 2021, 11:12:01 AM »
Begin by drawing the structure of your chemical, then look for its mechanism of action. Draw a chemical compound with which the drug is competing for the receptor and compare the structural elements.
AWK

Offline MathewConnors1999

  • Regular Member
  • ***
  • Posts: 13
  • Mole Snacks: +0/-0
Re: Regarding functional groups of a medicine (drug)
« Reply #3 on: February 04, 2021, 11:54:26 AM »
Begin by drawing the structure of your chemical, then look for its mechanism of action. Draw a chemical compound with which the drug is competing for the receptor and compare the structural elements.
Thank you for your answer. The drug binds with the (along others) D2 dopamin receptor. I don't see any similarities between the two, except for there being a benzene ring and nitrogen present.

I assume that you have found the structure at some appropriate site, such as PubChem or elsewhere.  Do you recognize any functional groups from your organic chemistry classes?
Thank you for your answer. I have found the structure on PubChem yes. I do recognise a huge number of benzene rings along with ethyl chains? Is that right? And I also think that there is something about hydrogen bonding.
The problem is, to my knowledge I am just not sure what seperates a group.

Offline AWK

  • Retired Staff
  • Sr. Member
  • *
  • Posts: 7982
  • Mole Snacks: +555/-93
  • Gender: Male
Re: Regarding functional groups of a medicine (drug)
« Reply #4 on: February 04, 2021, 12:07:42 PM »
And I can see fragments in the molecule similar to dopamine and serotonin.
AWK

Offline Babcock_Hall

  • Chemist
  • Sr. Member
  • *
  • Posts: 4930
  • Mole Snacks: +288/-22
Re: Regarding functional groups of a medicine (drug)
« Reply #5 on: February 04, 2021, 12:44:57 PM »
Let me just focus on the organic chemistry perspective (I am not sure it is even necessary to do so), inasmuch as AWK has nicely covered it from a medicinal angle.  One of the functional groups present is an amine.  What kind of amine is it, primary, secondary, or tertiary?

Offline MathewConnors1999

  • Regular Member
  • ***
  • Posts: 13
  • Mole Snacks: +0/-0
Re: Regarding functional groups of a medicine (drug)
« Reply #6 on: February 04, 2021, 12:56:23 PM »
Let me just focus on the organic chemistry perspective (I am not sure it is even necessary to do so), inasmuch as AWK has nicely covered it from a medicinal angle.  One of the functional groups present is an amine.  What kind of amine is it, primary, secondary, or tertiary?
Thank you for your time. If I am not mistaken I can see a secondary amine at the very "top" of the molecule and three tertiary aminegroups throughout.

Offline MathewConnors1999

  • Regular Member
  • ***
  • Posts: 13
  • Mole Snacks: +0/-0
Re: Regarding functional groups of a medicine (drug)
« Reply #7 on: February 04, 2021, 12:58:19 PM »
And I can see fragments in the molecule similar to dopamine and serotonin.
Thank you for your time. Yes I can see that as well. Could it be that when metabolished the drug could alter to apear more like dopamine or serotonin, or is the simple resemblance enough to attach?

Offline Babcock_Hall

  • Chemist
  • Sr. Member
  • *
  • Posts: 4930
  • Mole Snacks: +288/-22
Re: Regarding functional groups of a medicine (drug)
« Reply #8 on: February 04, 2021, 01:46:28 PM »
I was thinking of the one nitrogen in the six-membered ring as being a tertiary amine.  Regarding the two nitrogen atoms that are in the five-membered ring, I would consider those two nitrogen atoms and the intervening carbonyl (C=O) to be a single functional group that is related to a common substance found in many biochemistry laboratories.  One might consider the entirety of the lone nitrogen in the five-membered ring fused with a six-membered ring to be a single group also.

Offline MathewConnors1999

  • Regular Member
  • ***
  • Posts: 13
  • Mole Snacks: +0/-0
Re: Regarding functional groups of a medicine (drug)
« Reply #9 on: February 04, 2021, 03:58:48 PM »
I was thinking of the one nitrogen in the six-membered ring as being a tertiary amine.  Regarding the two nitrogen atoms that are in the five-membered ring, I would consider those two nitrogen atoms and the intervening carbonyl (C=O) to be a single functional group that is related to a common substance found in many biochemistry laboratories.  One might consider the entirety of the lone nitrogen in the five-membered ring fused with a six-membered ring to be a single group also.

Oh okay I think I see. Regarding naming these groups, would that be by solely looking at them as if they were an isolated molecule and naming them thereafter?
And lastly what about the fluorobenzene. Is that of importance?

Offline Babcock_Hall

  • Chemist
  • Sr. Member
  • *
  • Posts: 4930
  • Mole Snacks: +288/-22
Re: Regarding functional groups of a medicine (drug)
« Reply #10 on: February 04, 2021, 04:49:04 PM »
I would name them that way, but perhaps others would do it differently.  I am not sure exactly what the reason for the fluorine is.
EDT
Obviously I agree with what AWK wrote about fluorine, and all that I can think to add is that one drug, flunitrazepam, has an aromatic fluorine in the ortho-position.
« Last Edit: February 04, 2021, 05:36:22 PM by Babcock_Hall »

Offline AWK

  • Retired Staff
  • Sr. Member
  • *
  • Posts: 7982
  • Mole Snacks: +555/-93
  • Gender: Male
Re: Regarding functional groups of a medicine (drug)
« Reply #11 on: February 04, 2021, 05:27:05 PM »
Fluoride is very common in synthetic drugs but must be present in non-reactive groups as p-fluorophenyl or trifluoromethyl.
The radius of the van der Waals of fluorine is only about 20% greater than the radius of hydrogen, therefore enzymes and receptors do not notice a difference in size, but enzymes are unable to metabolize such a group, e.g. oxidize the phenolic group, especially in the para position or to a carboxyl group.
In addition, fluoride has a beneficial effect when drugs overcome lipid barriers, i.e. the drug gets to places where it would not reach due to the rapid metabolism of the unsubstituted compound.
AWK

Offline MathewConnors1999

  • Regular Member
  • ***
  • Posts: 13
  • Mole Snacks: +0/-0
Re: Regarding functional groups of a medicine (drug)
« Reply #12 on: February 05, 2021, 05:26:21 AM »
I would name them that way, but perhaps others would do it differently.  I am not sure exactly what the reason for the fluorine is.
EDT
Obviously I agree with what AWK wrote about fluorine, and all that I can think to add is that one drug, flunitrazepam, has an aromatic fluorine in the ortho-position.
Thank you very much for your *delete me*

Fluoride is very common in synthetic drugs but must be present in non-reactive groups as p-fluorophenyl or trifluoromethyl.
The radius of the van der Waals of fluorine is only about 20% greater than the radius of hydrogen, therefore enzymes and receptors do not notice a difference in size, but enzymes are unable to metabolize such a group, e.g. oxidize the phenolic group, especially in the para position or to a carboxyl group.
In addition, fluoride has a beneficial effect when drugs overcome lipid barriers, i.e. the drug gets to places where it would not reach due to the rapid metabolism of the unsubstituted compound.
This is a very detailed answer. Thank you for that.
You would agree that this drug is competetive antagonistic, right? I am having a hard time getting how a drug as Sertindole, big and heavy and looks only a bit simmilar with dopamine can sit on the D2-dopamine receptors. I get that, as you mentioned the Van Der Waals radius of flourine is small and does not contribute to its size in the eyes of the receptors, but even if we don't consider the floruide, the drugs still seem rather unsimmilar to sit on the receptors. Could pH level have an effect?

Offline rolnor

  • Chemist
  • Sr. Member
  • *
  • Posts: 1610
  • Mole Snacks: +113/-8
Re: Regarding functional groups of a medicine (drug)
« Reply #13 on: February 05, 2021, 06:21:31 AM »
It is not uncommon that drugs are much bigger then the natural compound they mimic.

Offline Babcock_Hall

  • Chemist
  • Sr. Member
  • *
  • Posts: 4930
  • Mole Snacks: +288/-22
Re: Regarding functional groups of a medicine (drug)
« Reply #14 on: February 05, 2021, 08:48:24 AM »
If you look at the side chain of the amino acid tryptophan, you will see an heterocyclic aromatic structure that shows up in many drugs.  The name of this functional group is included in the name of this compound.  With respect to naming the other functional group, the one with two nitrogens and a carbonyl group, I would think about a major constituent of urine, the same compound often found in biochemistry labs to denature proteins.
EDT
In general the effect of pH can either be on the receptor or the drug itself, because either one might gain or lose a proton.  Which functional group on this compound is capable of gaining or losing a proton?
« Last Edit: February 05, 2021, 10:15:56 AM by Babcock_Hall »

Sponsored Links