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Erythromycin
M.Sc. Biotechnology Part II (Sem III)
Paper III - Unit III
Mumbai University
BY: Mayur D. Chauhan
1
Introduction
• Erythromycin belongs to the group of Macrolide
antibiotics.
• Macrolide antibiotics slow the growth of, or
sometimes kill sensitive bacteria by reducing the
production of important proteins needed by the
bacteria to survive.
• It has an antimicrobial spectrum similar to or
slightly wider than that of penicillin and is often
used for people who have allergy to penicillin.
2
• It is used to treat many different types of
infections caused by various bacteria.
• It is used to prevent bacterial endocarditis and
attacks of rheumatic fever.
• Also used to prevent outbreaks of sexually
transmitted diseases like chlamydia, syphilis
and gonorrhea. Prevents respiratory tract
infections.
• Erythromycin is produced from the strain of
actinomycete Saccharopolyspora erythraea
formerly known as Streptomyces erythraeus.
3
Structure
• It is a macrocyclic compound containing 14-
membered lactone ring with 10 asymmetric
centers and two sugars – L-Cladinose and D-
Desoamine.
• Trade name is E-mycin or Erythrocin
4
5
Mechanism of Action
• Erythromycin displays a bacteriocidal activity
particularly at higher concentrations.
• It prevents the growth of bacteria by inhibiting
their protein synthesis.
• Erythromycin binds to the 23s rRNA molecule
in the 50S ribosomal subunit.
• This binding blocks thee exit of the growing
peptide thus inhibiting the translocation of
the peptides.
6
Erythromycin interferes with the aminoacyl translocation preventing the transfer of the
tRNA bound at the A site to the P site of the rRNA complex.
7
Pharmacokinetics
• Erythromycin is easily inactivated by gastric acids,
therefore all orally administered formulations are
given as either enteric coated or more stable salts
or esters, such as erythromycin ethylsuccinate.
• It is rapidly absorbed and diffused into most
tissues and phagocytes.
• Due to high concentration in phagocytes,
erythromycin is actively transported to the site of
infection, where during active phagocytosis, large
concentration of erythromycin is released.
8
Metabolism
• It is mostly metabolised by demethylation in
the liver.
• It’s main elimination route is Bile and a small
portion in Urine
• It’s half-life is 1.5 hours
9
Production Process
2 steps
Production
phase
Biomass
accumulation
10
Biomass Accumulation
• The sporulating culture of Streptomyces
erythraeus is done on Trypton agar slant.
• Cells are harvested from agar plates and the
suspension is taken in Sterile water.
• The suspension is then stored at 4o C.
11
Production Phase
• Media which used in a stirred tank fermenter
consists of,
• Sucrose – 5%
• Corn steep liquor – 0.5%
• Soyabean oil meal – 1.5%
• Yeast – 1.0%
• NaCl – 0.5%
• CaCo3 precipitate – 0.3%
• pH – 7.0 -7.2
12
• Production of Erythromycin production occurs
when froth reaches stationary phase.
• Addition of n-propanol as precursor increases
the production of erythromycin..
13
Isolation and Extraction
Mycelium is separated from the broth by
centrifugation or drum filtration
Acidic condition is maintained by addition of
Butyl acetate which favors the separation of
the mycelium. Also it dissolves the antibiotic
Wash with water
14
pH is adjusted at 9.5
using Acetone
Precipitate formed in the
form of Crystals
Erythromycin is obtained
as a dihydrate salt
15
Available Forms of Erythromycin
• Erythromycin is available in enteric coated
tablets, slow release capsules, oral
suspensions, opthalmic solutions, ointments,
gels and injections.
• Erythromycin base (Capsules, tablets)
• Erythromycin ethylsuccinate (Oral suspension,
tablets)
• Erythromycin stearate (Oral suspension,
tablets).
16
Injections
• Erythromycin Gluceptate
• Erythromycin lactobionate
17
18

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Erythromycin- Structure and Production

  • 1. Erythromycin M.Sc. Biotechnology Part II (Sem III) Paper III - Unit III Mumbai University BY: Mayur D. Chauhan 1
  • 2. Introduction • Erythromycin belongs to the group of Macrolide antibiotics. • Macrolide antibiotics slow the growth of, or sometimes kill sensitive bacteria by reducing the production of important proteins needed by the bacteria to survive. • It has an antimicrobial spectrum similar to or slightly wider than that of penicillin and is often used for people who have allergy to penicillin. 2
  • 3. • It is used to treat many different types of infections caused by various bacteria. • It is used to prevent bacterial endocarditis and attacks of rheumatic fever. • Also used to prevent outbreaks of sexually transmitted diseases like chlamydia, syphilis and gonorrhea. Prevents respiratory tract infections. • Erythromycin is produced from the strain of actinomycete Saccharopolyspora erythraea formerly known as Streptomyces erythraeus. 3
  • 4. Structure • It is a macrocyclic compound containing 14- membered lactone ring with 10 asymmetric centers and two sugars – L-Cladinose and D- Desoamine. • Trade name is E-mycin or Erythrocin 4
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  • 6. Mechanism of Action • Erythromycin displays a bacteriocidal activity particularly at higher concentrations. • It prevents the growth of bacteria by inhibiting their protein synthesis. • Erythromycin binds to the 23s rRNA molecule in the 50S ribosomal subunit. • This binding blocks thee exit of the growing peptide thus inhibiting the translocation of the peptides. 6
  • 7. Erythromycin interferes with the aminoacyl translocation preventing the transfer of the tRNA bound at the A site to the P site of the rRNA complex. 7
  • 8. Pharmacokinetics • Erythromycin is easily inactivated by gastric acids, therefore all orally administered formulations are given as either enteric coated or more stable salts or esters, such as erythromycin ethylsuccinate. • It is rapidly absorbed and diffused into most tissues and phagocytes. • Due to high concentration in phagocytes, erythromycin is actively transported to the site of infection, where during active phagocytosis, large concentration of erythromycin is released. 8
  • 9. Metabolism • It is mostly metabolised by demethylation in the liver. • It’s main elimination route is Bile and a small portion in Urine • It’s half-life is 1.5 hours 9
  • 11. Biomass Accumulation • The sporulating culture of Streptomyces erythraeus is done on Trypton agar slant. • Cells are harvested from agar plates and the suspension is taken in Sterile water. • The suspension is then stored at 4o C. 11
  • 12. Production Phase • Media which used in a stirred tank fermenter consists of, • Sucrose – 5% • Corn steep liquor – 0.5% • Soyabean oil meal – 1.5% • Yeast – 1.0% • NaCl – 0.5% • CaCo3 precipitate – 0.3% • pH – 7.0 -7.2 12
  • 13. • Production of Erythromycin production occurs when froth reaches stationary phase. • Addition of n-propanol as precursor increases the production of erythromycin.. 13
  • 14. Isolation and Extraction Mycelium is separated from the broth by centrifugation or drum filtration Acidic condition is maintained by addition of Butyl acetate which favors the separation of the mycelium. Also it dissolves the antibiotic Wash with water 14
  • 15. pH is adjusted at 9.5 using Acetone Precipitate formed in the form of Crystals Erythromycin is obtained as a dihydrate salt 15
  • 16. Available Forms of Erythromycin • Erythromycin is available in enteric coated tablets, slow release capsules, oral suspensions, opthalmic solutions, ointments, gels and injections. • Erythromycin base (Capsules, tablets) • Erythromycin ethylsuccinate (Oral suspension, tablets) • Erythromycin stearate (Oral suspension, tablets). 16
  • 17. Injections • Erythromycin Gluceptate • Erythromycin lactobionate 17
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