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![Aztreonam
2-[(Z)-[1-(2-Amino-1,3-thiazol-4-yl)-2-[[(2S,3S)-2-methyl-4-oxo-1-sulfoazetidin-3-
yl]amino]-2-oxoethylidene]amino]oxy-2-methylpropanoic acid](https://image.slidesharecdn.com/07antibiotics-monobactams-220613055731-d5b8e030/75/Monobactams-6-2048.jpg)
![Tigemonam
2-[[1-(2-Amino-1,3-thiazol-4-yl)- 2-[[(3S)-2,2-dimethyl-4-oxo-1- sulfooxyazetidin-3-
yl]amino]-2- oxoethylidene]amino]oxyacetic acid](https://image.slidesharecdn.com/07antibiotics-monobactams-220613055731-d5b8e030/75/Monobactams-7-2048.jpg)
![Nocardicin A
(2R)-2-Amino-4-[4-[N-hydroxy-C-[[(3S)-1- [(1R)-2-hydroxy-1-(4-hydroxyphenyl)-2-
oxoethyl]-2-oxoazetidin-3- yl]carbamoyl]carbonimidoyl]phenoxy]butanoic acid](https://image.slidesharecdn.com/07antibiotics-monobactams-220613055731-d5b8e030/75/Monobactams-8-2048.jpg)
![Tabtoxin
also known as wildfire toxin
(2S,3R)-2-{(2S)-2-Amino-4-[(3S)-3-hydroxy-2-oxoazetidin-3-yl]butanamido}-3-
hydroxybutanoic acid](https://image.slidesharecdn.com/07antibiotics-monobactams-220613055731-d5b8e030/75/Monobactams-9-2048.jpg)
Uploaded byDr. Ajmer Singh Grewal
Monobactams
Monobactams are a class of β-lactam antibiotics that contain a single β-lactam ring, unlike penicillins and cephalosporins which have the ring fused to another. Aztreonam was the first to be approved in 1986. Monobactams are effective against gram-negative bacteria and show promise in treating multi-drug resistant pathogens. They work by inhibiting cell wall synthesis through binding to penicillin-binding proteins. Side effects are generally mild but can include rashes, liver problems, and seizures in susceptible individuals.
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Monobactams
- 1.
- 2. Introduction Monobactams is asubgroup of β-lactam antibiotics wherein the β-lactam ring is alone and not fused to another ring, in contrast to most other β-lactams (such as penicillins, cephalosporins, and carbapenems). Monobactams were discovered in 1980s. Aztreonam was approved for medical use in the United States in 1986.
- 4. Monobactams are effectiveonly against aerobic Gram-negative bacteria (e.g., Neisseria, Pseudomonas). Siderophore-conjugated monobactams show promise for the treatment of multi drug-resistant pathogens. (Siderophores: iron-chelating compounds)
- 5. Classification Aztreonam is commerciallyavailable monobactam antibiotic. Other examples of monobactams are tigemonam, nocardicin A, and tabtoxin.
- 6.
- 7. Tigemonam 2-[[1-(2-Amino-1,3-thiazol-4-yl)- 2-[[(3S)-2,2-dimethyl-4-oxo-1- sulfooxyazetidin-3- yl]amino]-2-oxoethylidene]amino]oxyacetic acid
- 8. Nocardicin A (2R)-2-Amino-4-[4-[N-hydroxy-C-[[(3S)-1- [(1R)-2-hydroxy-1-(4-hydroxyphenyl)-2- oxoethyl]-2-oxoazetidin-3-yl]carbamoyl]carbonimidoyl]phenoxy]butanoic acid
- 9. Tabtoxin also known aswildfire toxin (2S,3R)-2-{(2S)-2-Amino-4-[(3S)-3-hydroxy-2-oxoazetidin-3-yl]butanamido}-3- hydroxybutanoic acid
- 10. Mechanism of action Theyinhibit synthesis of the bacterial cell wall, by blocking peptidoglycan crosslinking. They have a very high affinity for penicillin-binding protein-3 and mild affinity for penicillin-binding protein-1a. They bind the penicillin-binding proteins of Gram-positive and anaerobic bacteria very poorly and are largely ineffective against them.
- 13. In absence ofmonobactams
- 14. In presence ofmonobactams
- 15.
- 16. Therapeutic Uses Aztreonam, soldunder the brand name Azactam used primarily to treat infections caused by gram-negative bacteria such as Pseudomonas aeruginosa.
- 17. Mycobacterial disease Infections inpeople who have received lung transplants Bone infections Endometritis Intra-abdominal infections Pneumonia Urinary tract infections Sepsis
- 18.
- 20. Stereochemistry of 4-methylgroup should be identical to the penicillin and cephalosporin antibiotics. Beta lactam ring is essential for antibacterial activity. Any modification in the beta lactam ring ring result in loss of activity. Removal/ replacement of hetero N-atom by any other atom (such as C, S, or O) result in loss of activity.
- 21. Adverse Effects Skin rash Occasionalabnormal liver functions Monobactams can trigger seizures in patients with history of seizures, although the risk is lower than with penicillins.
- 22. Common side effectswhen given by injection include pain at the site of injection, vomiting, skin rash, rarely toxic epidermal necrolysis. Common side effects when inhaled include wheezing, cough, and vomiting. Serious side effects include Clostridium difficile infection and allergic reactions including anaphylaxis. Gastrointestinal side effects generally include diarrhoea, nausea and vomiting. There may be drug-induced eosinophilia. Those who are allergic to other β-lactams have a low rate of allergy to aztreonam. Use in pregnancy appears to be safe.
- 23.