Clavulanic acid
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Clavulanic acid
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CAS No:
58001-44-8
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Formula:
C8H9NO5
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Chemical Name:
Clavulanic acid
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Synonyms:
4-Oxa-1-azabicyclo[3.2.0]heptane-2-carboxylic acid,3-(2-hydroxyethylidene)-7-oxo-,(2R,3Z,5R)-;4-Oxa-1-azabicyclo[3.2.0]heptane-2-carboxylic acid,3-(2-hydroxyethylidene)-7-oxo-,[2R-(2α,3Z,5α)]-;(2R,3Z,5R)-3-(2-Hydroxyethylidene)-7-oxo-4-oxa-1-azabicyclo[3.2.0]heptane-2-carboxylic acid;Clavulanic acid;Antibiotic MM 14151;MM 14151;BRL 14151;Z-(3R,5R)-2-(β-Hydroxyethylidene)clavam-3-carboxylic acid
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CAS No:
Description
ChEBI: Antibiotic isolated from Streptomyces clavuligerus. It acts as a suicide inhibitor of bacterial beta-lactamase enzymes.
Characteristics
87.1
-1.5
white to off-white powder
1.7±0.1 g/cm3
117.5 - 118 °C
545.8±50.0 °C at 760 mmHg
283.9±30.1 °C
1.644
3.37e+02 g/L
Clavulanic acid Use and Manufacturing
Method 1: Microbial synthesis, using soybean powder, glucose, starch or dextrin as raw materials, after fermentation. Method 2: Using 3-methylthiopropiolactam as the raw material, it is synthesized through the steps of alkylation and chlorination decarboxylation.
beta-lactamase inhibitor
Computed Properties
Molecular Weight:199.16
XLogP3:-1.2
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:5
Rotatable Bond Count:2
Exact Mass:199.04807239
Monoisotopic Mass:199.04807239
Topological Polar Surface Area:87.1
Heavy Atom Count:14
Complexity:324
Undefined Atom Stereocenter Count:2
Undefined Bond Stereocenter Count:1
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
Drug Function and Efficacy
It has a β-lactam structure similar to penicillin and has only weak antibacterial activity itself, but it can inactivate enzymes produced by many bacteria by blocking the active site of β-lactamase. It is especially effective against clinically important plasmid-mediated β-lactamases (these enzymes are usually associated with changes in resistance to penicillins and cephalosporins).
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