Tazobactam
Chemical compound
- EU EMA: by INN
category
- B
administration
- J01CG02 (WHO)
- In general: ℞ (Prescription only)
- (2S,3S,5R)-3-Methyl-7-oxo-3-(1H-1,2,3-triazol-1-ylmethyl)-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid 4,4-dioxide
- 89786-04-9 Y
- 123630
- DB01606 Y
- 110216 Y
- SE10G96M8W
- D00660 Y
- CHEBI:9421 N
- ChEMBL404 Y
- DTXSID8023634
- Interactive image
- O=S2(=O)[C@]([C@@H](N1C(=O)C[C@H]12)C(=O)O)(Cn3nncc3)C
InChI
- InChI=1S/C10H12N4O5S/c1-10(5-13-3-2-11-12-13)8(9(16)17)14-6(15)4-7(14)20(10,18)19/h2-3,7-8H,4-5H2,1H3,(H,16,17)/t7-,8+,10+/m1/s1 Y
- Key:LPQZKKCYTLCDGQ-WEDXCCLWSA-N Y
Tazobactam is a pharmaceutical drug that inhibits the action of bacterial β-lactamases, especially those belonging to the SHV-1 and TEM groups. It is commonly used as its sodium salt, tazobactam sodium.
Tazobactam is combined with the extended spectrum β-lactam antibiotic piperacillin in the drug piperacillin/tazobactam, used in infections due to Pseudomonas aeruginosa. Tazobactam broadens the spectrum of piperacillin by making it effective against organisms that express β-lactamase and would normally degrade piperacillin.[1]
Tazobactam was patented in 1982 and came into medical use in 1992.[2]
See also
References
- ^ Yang Y, Rasmussen BA, Shlaes DM (August 1999). "Class A beta-lactamases--enzyme-inhibitor interactions and resistance". Pharmacology & Therapeutics. 83 (2): 141–151. doi:10.1016/S0163-7258(99)00027-3. PMID 10511459.
- ^ Fischer J, Ganellin CR (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 490. ISBN 9783527607495.
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(inhibit synthesis
of peptidoglycan
layer of bacterial
cell wall by binding
to and inhibiting
PBPs, a group of
D-alanyl-D-alanine
transpeptidases)
Penicillins (Penams) |
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Carbapenems / Penems | |||||||||||||||||
Cephems Cephalosporins Cephamycins Carbacephems |
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Monobactams | |||||||||||||||||
β-lactamase inhibitors |
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Combinations |
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Lipopeptides |
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Other |
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- Inhibit PG subunit synthesis and transport: NAM synthesis inhibition (Fosfomycin)
- DADAL/AR inhibitors (Cycloserine)
- bactoprenol inhibitors (Bacitracin)
- Hydrolyze NAM-NAG
- Tyrothricin
- Isoniazid#
- Teixobactin
- #WHO-EM
- ‡Withdrawn from market
- Clinical trials:
- †Phase III
- §Never to phase III
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