Studies on the hydrolysis of clavulanic acid

Finn, M. J.; Harris, Michael A.; Hunt, Eric; Zomaya, Iskander I.

doi:10.1039/p19840001345

Cited by 28 publications

(23 citation statements)

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“…1; ii). For clavu lanic acid the chemistry is much more complex, and based on studies by Finn et al [1984] and Haginaka et al [1985], it is probable that a sequence of reactions as shown in figure lb would occur on reaction with pro tein amino groups. The oxazolidine derivative ( fig.…”

Section: Discussionmentioning

confidence: 99%

Immunogenicity and Allergenicity Studies on Two Beta-Lactam Structures, a Clavam, Clavulanic Acid, and a Carbapenem: Structure-Activity Relationships

Edwards¹,

Dewdney²,

Dobrzanski³

et al. 1988

Int Arch Allergy Immunol

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Two newer β-lactam-containing structures, a clavam, clavulanic acid, and a carbapenem, MM22383, have been studied for their intrinsic immunogenicity and allergenicity. Clavulanic acid has a very low immunogenic and allergenic potential, in contrast to MM22383 which is a contact sensitiser in guinea pigs and an immunogen in rabbits. Evidence for the allergenic potential of MM22383 in man through occupational exposure is also presented. Consideration of the chemistry of these two compounds with respect to their reactivity with protein provides a rationale for the marked difference in their behaviour. The importance of stable hapten-protein conjugates and epitope density is discussed in relation to immunogenicity.

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Section: Discussionmentioning

confidence: 99%

Immunogenicity and Allergenicity Studies on Two Beta-Lactam Structures, a Clavam, Clavulanic Acid, and a Carbapenem: Structure-Activity Relationships

Edwards¹,

Dewdney²,

Dobrzanski³

et al. 1988

Int Arch Allergy Immunol

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“…CA is one of the active ingredients in Augmentin 1 and acts as a potent inhibitor of b-lactamases produced by some b-lactam resistant pathogenic microorganism to enable efficient treatment of infectious diseases. 1 The production as well as the downstream processing is accompanied by the compound's degradation, initiated by hydrolysis, which is around 10 times faster than the one of penicillin G. 2 Hydrolysis of CA under neutral or basic conditions proceeds via the reactive amino ketone (2) to pyrazine end-products (3)(4)(5) (Fig. 1), 3,4 which are part of a complex product mixture.…”

Section: Introductionmentioning

confidence: 99%

Clavulanic Acid Decomposition Is Catalyzed by the Compound Itself and by Its Decomposition Products

Brethauer

Held

Panke

2008

Journal of Pharmaceutical Sciences

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“…The signals that indicate the presence of potassium clavulanate are described in Hirata et al (2009) and were compared here with the signals observed in the 1 H-NMR spectrum ( Figure 9). No signal of aminoketone (one of its degradation products) (Finn et al, 1984) was detected, thus demonstrating that this reaction offers the advantage of yielding potassium clavulanate with no subsequent degradation, unlike other CA purification processes in which solvent or water is evaporated, leading to marked degradation of CA and therefore low yields.…”

Section: Figurementioning

confidence: 91%

Optimization of the precipitation of clavulanic acid from fermented broth using t-octylamine as intermediate

Hirata

Oliveira

Leão

et al. 2013

Braz. J. Chem. Eng.

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-This work describes the use of clavulanic acid (CA) precipitation as the final step in the process of purification of CA from fermentation broth as an alternative to conventional methods employed traditionally. The purpose of this study was to use a stable intermediate (t-octylamine) between the conversion of CA to its salt form (potassium clavulanate), thereby enabling the resulting intermediate (amine salt of clavulanic acid) to improve the purification process and maintain the stability of the resulting potassium clavulanate. To this end, response surface methodology was employed to optimize the precipitation step. For the first reaction, five temperatures (6.6 to 23.4 °C), concentrations of clavulanic acid in organic solvent (6.6 to 23.4 mg/mL) and t-octylamine inflow rates (0.33 to 1.17 drop/min) were selected based on a central composite rotatable design (CCRD). For the second reaction, five temperatures (11.6 to 28.4 °C), concentrations of clavulanic acid amine salt in organic solvent (8.2 to 41.8 mg/mL) and concentrations of potassium 2-ethylhexanoate (0.2 to 1.2 molar) were also selected using CCRD. From these results, precipitation conditions were selected and applied to the purification of CA from the fermentation broth, obtaining a yield of 72.37%.

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Studies on the hydrolysis of clavulanic acid

Cited by 28 publications

References 0 publications

Immunogenicity and Allergenicity Studies on Two Beta-Lactam Structures, a Clavam, Clavulanic Acid, and a Carbapenem: Structure-Activity Relationships

Immunogenicity and Allergenicity Studies on Two Beta-Lactam Structures, a Clavam, Clavulanic Acid, and a Carbapenem: Structure-Activity Relationships

Clavulanic Acid Decomposition Is Catalyzed by the Compound Itself and by Its Decomposition Products

Optimization of the precipitation of clavulanic acid from fermented broth using t-octylamine as intermediate

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