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Antibiotics
+ In this presentation we are going to talk
about 4 molecules used as antibiotics, these
include azithromycin by Jacob,
ciprofloxacin by James, doxycycline by
Molly, and rifampicin by Tiffany.
+ As an overview, an antibiotic is defined as
a medicine that inhibits or stops the growth
of a microorganism
+ Antibiotics have a wide variety of uses in
medicine and their treatments, especially
treating bacterial infections
Azithromycin - Antibiotic
About the molecule
Azithromycin is semi-synthetic and it belongs to a
group known as “macrolides” however it is just an
analogue of the more commonly known macrolide
erythromycin.
Unlike the other analogues clarithromycin and
roxithromycin which are 14 membered macrocyclic
rings, azithromycin contains a 15 membered
macrocyclic ring. 1 (Macrocycles are compounds
containing 12 or more membered ring)
It can be synthesized from erythromycin through the
introduction of a nitrogen into the ring.
Other names for azithromycin include Zithromax
(Zmax) and Sumamed.
Structure of azithromycin
Structure of erythromycin
How it treats bacterial infections
Azithromycin binds to the 50s subunit of the 70s
ribosome found in bacteria.
This inhibits peptidyl transferase to bind which leads
to interference in the amino acid translocation
during translation.
This means the bacteria can no longer produce new
proteins. 2
Now the bacteria cannot grow therefore it cannot
undergo binary fission and divide.
References:
1 https://www.ncbi.nlm.nih.gov/pcm/articles/PMC5509991/#bib1 (accessed – 1/12/2020)
2 https://medlineplus.gov/druginfo/meds/a697037.html (accessed - 30/10/2020)
3 https://slideplayer.com/slide/13465378/ (accessed – 20/11/2020)
shows azithromycin “the
macrolide” binding to the 50s
subunit 3
Ciprofloxacin
• Ciprofloxacin is used for treating infections due to it having a
low minimum inhibitory concentration for infection causing
bacteria and a very low chance of random mutations in
bacteria.
• It is from a group of antibiotics called quinolones but more
specifically fluoroquinolones.
• They were discovered in the early 60s with fluoroquinolones
being developed between 1970-1980.
• Fluoroquinolones like ciprofloxacin were a big step up as they
offered a broader spectrum of activity and improved pharma
kinetics.
• They are very active against Gram-positive, Gram-negative
pathogens and importantly, the causation agent for
tuberculosis.
• Ciprofloxacin is used for Gram-negative pathogens and is
used even today over newer quinolones due to it having a
higher potency.
• Its potency against Gram-negative pathogen is due to it
having a piperazine ring.
Figure 1 – base structure of a quinolone
Figure 2 - ciprofloxacin
1
2
3
Treatment
• When it comes to using Ciprofloxacin for infections it needs to be used
on infections caused by Gram- negative organisms and not Gram-positive
due to it having poor activity.
• Examples of Gram-negative bacteria infections would include E-coil
infections, Cholera and typhoid fever.
• It is often used with other drugs such as Diazepam and Ropinirole as it
can increase the effectiveness of the drugs.
• Ciprofloxacin comes with a long list of side effects most uncommon and
rare so they are highly unlikely to occur, but it is common to get nausea
or diarrhoea. The rarer side effects are very deadly and could potentially
kill the person using it such as, seizures and thrombocytopenia.
• Some bacterial infections such as E Coli and pseudomonas aeruginosa,
long-term exposure to ciprofloxacin can cause a resistance to it.
Synthesis
• One way ciprofloxacin is synthesised is The Bayer or Grohe synthesis
which was patented in 1981 by Klaus Grohe. Its an 7 Step process which
uses 2,4-dichloro-5-fluorobenzoylchloride as its starting material. Figure 3 – The Bayer synthesis of ciprofloxacin
4).Andrew Dickman, Drugs in Palliative Care, Oxford University Press, 2010-03-25
5)Ciprofloxacin: A Two Step Process, Veera Reddy Arava, Pailla Umareddy, R & D Centre Suven Life Sciences Ltd, Plot No #18, Phase-III, Jeedimetla, Hyderabad-500055, India, Der Pharma Chemica, 2018, 10(3): 174-
178
Rifampicin
What is Rifampicin ?
• A Bactericidal antibiotic
• Red crystals with a macrocyclic structure
• A semi-synthetic derivative of rifamycin B
• Most commonly known for treating Tuberculosis but also treats many other infections
• When used alone rapid resistance can arise so it is usually prescribed along with other drugs
How does it work ?
• Inhibits the enzyme DNA dependant
RNA polymerase (RNAP)
• Forms a stable complex with RNA
polymerase
• Prevents DNA from being transcribed to
RNA
• Therefore inhibiting protein synthesis in
the bacterium
https://www.ncbi.nlm.nih.gov/books/NBK557488/ (accessed – 10/11/2020)
https://www.webmd.com/drugs/2/drug-1744/rifampin-oral/details/list-conditions (accessed - 12/11/2020)
Doxycycline
WHAT IS DOXYCYCLINE?
• It is a semi synthetic derivative of tetracycline.
• It is bacteriostatic (meaning that it prevents the growth of bacteria)
• It is a broad-spectrum antibiotic synthetically derived form
oxytetracycline
Skeletal structure of
Doxycycline molecule
• It is used to treat a wide range of bacterial infections, due to its
bacteriostatic properties
• It acts by inhibiting bacterial protein synthesis due to the
disruption of transfer and messenger RNA1
• Its used to treat bacterial infection such as cholera, urinary tract
infections and typhus fever and many more!2
WHAT IS IT USED FOR AND HOW DOES IT WORK?
Skeletal structure of tetracycline
HOW IS IT
SYNTHESISED?
+ Doxycycline is an isomer of tetracycline and differs
on in the placement of 1 hydroxyl group.
+ It can be formed by dehydrating oxytetracycline at
C6 by reducing the tertiary hydroxyl group with
hydrogen using a rhodium on carbon catalyst (see
figure 2)
Synthesis of doxycycline from oxytetracycline
+ 1. Clinical Infectious Diseases, Volume 38, Issue 6, 15 March 2004, Pages
864–870
+ 2. https://reference.medscape.com/drug/vibramycin-monodox-doxycycline-
References:
Thank you for listening to our presentation on
these 4 specific antibiotics!
To conclude, each of these antibiotics even
though somewhat different in their molecular
structure and synthesis, they are still widely
used to treat common and uncommon
infections today.
Does anyone have any questions?
azithromycin
Doxycycline
ciprofloxacin
Rifampicin

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Antibiotics presentation

  • 1. Antibiotics + In this presentation we are going to talk about 4 molecules used as antibiotics, these include azithromycin by Jacob, ciprofloxacin by James, doxycycline by Molly, and rifampicin by Tiffany. + As an overview, an antibiotic is defined as a medicine that inhibits or stops the growth of a microorganism + Antibiotics have a wide variety of uses in medicine and their treatments, especially treating bacterial infections
  • 2. Azithromycin - Antibiotic About the molecule Azithromycin is semi-synthetic and it belongs to a group known as “macrolides” however it is just an analogue of the more commonly known macrolide erythromycin. Unlike the other analogues clarithromycin and roxithromycin which are 14 membered macrocyclic rings, azithromycin contains a 15 membered macrocyclic ring. 1 (Macrocycles are compounds containing 12 or more membered ring) It can be synthesized from erythromycin through the introduction of a nitrogen into the ring. Other names for azithromycin include Zithromax (Zmax) and Sumamed. Structure of azithromycin Structure of erythromycin
  • 3. How it treats bacterial infections Azithromycin binds to the 50s subunit of the 70s ribosome found in bacteria. This inhibits peptidyl transferase to bind which leads to interference in the amino acid translocation during translation. This means the bacteria can no longer produce new proteins. 2 Now the bacteria cannot grow therefore it cannot undergo binary fission and divide. References: 1 https://www.ncbi.nlm.nih.gov/pcm/articles/PMC5509991/#bib1 (accessed – 1/12/2020) 2 https://medlineplus.gov/druginfo/meds/a697037.html (accessed - 30/10/2020) 3 https://slideplayer.com/slide/13465378/ (accessed – 20/11/2020) shows azithromycin “the macrolide” binding to the 50s subunit 3
  • 4. Ciprofloxacin • Ciprofloxacin is used for treating infections due to it having a low minimum inhibitory concentration for infection causing bacteria and a very low chance of random mutations in bacteria. • It is from a group of antibiotics called quinolones but more specifically fluoroquinolones. • They were discovered in the early 60s with fluoroquinolones being developed between 1970-1980. • Fluoroquinolones like ciprofloxacin were a big step up as they offered a broader spectrum of activity and improved pharma kinetics. • They are very active against Gram-positive, Gram-negative pathogens and importantly, the causation agent for tuberculosis. • Ciprofloxacin is used for Gram-negative pathogens and is used even today over newer quinolones due to it having a higher potency. • Its potency against Gram-negative pathogen is due to it having a piperazine ring. Figure 1 – base structure of a quinolone Figure 2 - ciprofloxacin 1 2 3
  • 5. Treatment • When it comes to using Ciprofloxacin for infections it needs to be used on infections caused by Gram- negative organisms and not Gram-positive due to it having poor activity. • Examples of Gram-negative bacteria infections would include E-coil infections, Cholera and typhoid fever. • It is often used with other drugs such as Diazepam and Ropinirole as it can increase the effectiveness of the drugs. • Ciprofloxacin comes with a long list of side effects most uncommon and rare so they are highly unlikely to occur, but it is common to get nausea or diarrhoea. The rarer side effects are very deadly and could potentially kill the person using it such as, seizures and thrombocytopenia. • Some bacterial infections such as E Coli and pseudomonas aeruginosa, long-term exposure to ciprofloxacin can cause a resistance to it. Synthesis • One way ciprofloxacin is synthesised is The Bayer or Grohe synthesis which was patented in 1981 by Klaus Grohe. Its an 7 Step process which uses 2,4-dichloro-5-fluorobenzoylchloride as its starting material. Figure 3 – The Bayer synthesis of ciprofloxacin 4).Andrew Dickman, Drugs in Palliative Care, Oxford University Press, 2010-03-25 5)Ciprofloxacin: A Two Step Process, Veera Reddy Arava, Pailla Umareddy, R & D Centre Suven Life Sciences Ltd, Plot No #18, Phase-III, Jeedimetla, Hyderabad-500055, India, Der Pharma Chemica, 2018, 10(3): 174- 178
  • 6. Rifampicin What is Rifampicin ? • A Bactericidal antibiotic • Red crystals with a macrocyclic structure • A semi-synthetic derivative of rifamycin B • Most commonly known for treating Tuberculosis but also treats many other infections • When used alone rapid resistance can arise so it is usually prescribed along with other drugs How does it work ? • Inhibits the enzyme DNA dependant RNA polymerase (RNAP) • Forms a stable complex with RNA polymerase • Prevents DNA from being transcribed to RNA • Therefore inhibiting protein synthesis in the bacterium https://www.ncbi.nlm.nih.gov/books/NBK557488/ (accessed – 10/11/2020) https://www.webmd.com/drugs/2/drug-1744/rifampin-oral/details/list-conditions (accessed - 12/11/2020)
  • 7. Doxycycline WHAT IS DOXYCYCLINE? • It is a semi synthetic derivative of tetracycline. • It is bacteriostatic (meaning that it prevents the growth of bacteria) • It is a broad-spectrum antibiotic synthetically derived form oxytetracycline Skeletal structure of Doxycycline molecule • It is used to treat a wide range of bacterial infections, due to its bacteriostatic properties • It acts by inhibiting bacterial protein synthesis due to the disruption of transfer and messenger RNA1 • Its used to treat bacterial infection such as cholera, urinary tract infections and typhus fever and many more!2 WHAT IS IT USED FOR AND HOW DOES IT WORK? Skeletal structure of tetracycline
  • 8. HOW IS IT SYNTHESISED? + Doxycycline is an isomer of tetracycline and differs on in the placement of 1 hydroxyl group. + It can be formed by dehydrating oxytetracycline at C6 by reducing the tertiary hydroxyl group with hydrogen using a rhodium on carbon catalyst (see figure 2) Synthesis of doxycycline from oxytetracycline + 1. Clinical Infectious Diseases, Volume 38, Issue 6, 15 March 2004, Pages 864–870 + 2. https://reference.medscape.com/drug/vibramycin-monodox-doxycycline- References:
  • 9. Thank you for listening to our presentation on these 4 specific antibiotics! To conclude, each of these antibiotics even though somewhat different in their molecular structure and synthesis, they are still widely used to treat common and uncommon infections today. Does anyone have any questions? azithromycin Doxycycline ciprofloxacin Rifampicin