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Hetrocyclic Rings of Carbapenems Antibiotics

The document discusses carbapenems, a class of beta-lactam antibiotics characterized by heterocyclic rings. Carbapenems have a broad spectrum of antibacterial activity and are effective against drug-resistant strains. Three specific carbapenem drugs are described: imipenem-cilastatin, meropenem, and biapenem. All three work by inhibiting bacterial cell wall synthesis through binding to penicillin-binding proteins. Imipenem and meropenem are used to treat various bacterial infections while biapenem has similar properties to meropenem and activity against metallo-beta-lactamases. In conclusion, the heterocyclic ring structure is part of what gives carbapenems their antibiotic properties as

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عبدالرحمن بسمان غانم
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65 views5 pages

Hetrocyclic Rings of Carbapenems Antibiotics

The document discusses carbapenems, a class of beta-lactam antibiotics characterized by heterocyclic rings. Carbapenems have a broad spectrum of antibacterial activity and are effective against drug-resistant strains. Three specific carbapenem drugs are described: imipenem-cilastatin, meropenem, and biapenem. All three work by inhibiting bacterial cell wall synthesis through binding to penicillin-binding proteins. Imipenem and meropenem are used to treat various bacterial infections while biapenem has similar properties to meropenem and activity against metallo-beta-lactamases. In conclusion, the heterocyclic ring structure is part of what gives carbapenems their antibiotic properties as

Uploaded by

عبدالرحمن بسمان غانم
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© © All Rights Reserved
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Al-Noor University College

Department of Pharmacy

Hetrocyclic Rings
Of Carbapenems antibiotics:

Carbapenems are a class of highly effective antibiotic agents


commonly used for the treatment of severe or high-risk bacterial
infections.

Similar to penicillins and cephalosporins, carbapenems are


members of the beta lactam class of antibiotics, which kill bacteria
by binding to penicillin-binding proteins, thus inhibiting bacterial
cell wall synthesis.

However, these agents individually exhibit a broader spectrum of


activity compared to most cephalosporins and penicillins.
Furthermore, carbapenems are typically unaffected by emerging
antibiotic resistance, even to other beta-lactams.

Structure of carbapenem

Contain of beta lactam part

and pyrroline part

pyrroline
beta lactam part

Or(2-Azetidinone)
Carbapenem drugs
1.Imipenem–Cilastatin
Imipenem is N-formimidoylthienamycin, the most successful of a
series of chemically stable derivatives of thienamycin in which the
primary amino group is converted to a nonnucleophilic basic
function.
Mechanism of action
Imipenem acts as an antimicrobial through the inhibition of cell
wall synthesis of various gram-positive and gram-negative
bacteria.
 This inhibition of cell wall synthesis in gram-negative bateria is
attained by binding to penicillin-binding proteins (PBPs).
Indication
Imipenem is indicated, in combination with cilastatin with or
without relebactam, for the treatment of bacterial infections
including respiratory, skin, bone, gynecologic, urinary tract, and
intra-abdominal as well as septicemia and endocarditis.

Imipenem structure
2.Meropenem
Meropenem is a broad-spectrum,second-generation carbapenem
that, to date, has undergone the most extensive clinical evaluation.
Mechanism of action
The bactericidal activity of meropenem results from the inhibition
of cell wall synthesis.
Meropenem readily penetrates the cell wall of most Gram-positive
and Gram-negative bacteria to reach penicillin-binding- protein
(PBP) targets. Its strongest affinities are toward PBPs 2, 3 and 4 of
Escherichia coli and Pseudomonas aeruginosa; and PBPs 1, 2 and
4 of Staphylococcus aureus.
Indication
It has recently been approved as Merrem for the treatment of
infections caused by multiply-resistant bacteria and for empirical
therapy for serious infections, such as bacterial meningitis,
septicemia, pneumonia, and peritonitis.

Meropenem structure
3.Biapenem
This compound belongs to the class of organic compounds known
as thienamycins. These are beta-lactam antibiotics that differ from
penicillins in having the thiazolidine sulfur atom replaced by
carbon, the sulfur then becoming the first atom in the side chain.

Biapenem is a newer second-generation carbapenem with chemical


and microbiological properties similar to those of meropenem.

Thus, it has broad-spectrum antibacterial activity that includes


most aerobic Gram-negative and Grampositive bacteria and
anaerobes.Biapenem is stable to DHP-I67 and resistant to most
lactamases.

It is claimed to be less susceptible to metallo lactamases than either


imipenem or meropenem. It is not active orally.

Biapenem structure

CONCLUUSION:

β-Lactams represent one of the most important groups of


antibiotics prescribed for antibacterial treatment today ,which is
Hetrocyclic Ring, part of the core structure of carbapenems.
References
Wilson and Gisvold’s ORGANIC MEDICINAL& PHARMACEUTICAL CHEMISTRY-12 edition 2011-Dr.Murtadha
https://www.drugbank.ca/
https://reference.medscape.com/
https://pubchem.ncbi.nlm.nih.gov/
https://en.wikipedia.org/wiki/Main_Page
Names
‫عبدالرحمن بسمان غانم محمد‬
‫سجاد عزيز سعدون‬
‫محبة خضير اسود‬
‫زكريا رياض رشاد‬
‫يزن عبدالقادر اسماعيل‬

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