Clavulanic acid. Medical search

Clavulanic acid and its salts and esters. The acid is a suicide inhibitor of bacterial beta-lactamase enzymes from Streptomyces clavuligerus. Administered alone, it has only weak antibacterial activity against most organisms, but given in combination with other beta-lactam antibiotics it prevents antibiotic inactivation by microbial lactamase.

Acids, salts, and derivatives of clavulanic acid (C8H9O5N). They consist of those beta-lactam compounds that differ from penicillin in having the sulfur of the thiazolidine ring replaced by an oxygen. They have limited antibacterial action, but block bacterial beta-lactamase irreversibly, so that similar antibiotics are not broken down by the bacterial enzymes and therefore can exert their antibacterial effects.

A fixed-ratio combination of amoxicillin trihydrate and potassium clavulanate.

An antibiotic derived from penicillin similar to CARBENICILLIN in action.

A broad-spectrum semisynthetic antibiotic similar to AMPICILLIN except that its resistance to gastric acid permits higher serum levels with oral administration.

Enzymes found in many bacteria which catalyze the hydrolysis of the amide bond in the beta-lactam ring. Well known antibiotics destroyed by these enzymes are penicillins and cephalosporins.

A beta-lactamase inhibitor with very weak antibacterial action. The compound prevents antibiotic destruction of beta-lactam antibiotics by inhibiting beta-lactamases, thus extending their spectrum activity. Combinations of sulbactam with beta-lactam antibiotics have been used successfully for the therapy of infections caused by organisms resistant to the antibiotic alone.

A building block of penicillin, devoid of significant antibacterial activity. (From Merck Index, 11th ed)

Four-membered cyclic AMIDES, best known for the PENICILLINS based on a bicyclo-thiazolidine, as well as the CEPHALOSPORINS based on a bicyclo-thiazine, and including monocyclic MONOBACTAMS. The BETA-LACTAMASES hydrolyze the beta lactam ring, accounting for BETA-LACTAM RESISTANCE of infective bacteria.

Naturally occurring family of beta-lactam cephalosporin-type antibiotics having a 7-methoxy group and possessing marked resistance to the action of beta-lactamases from gram-positive and gram-negative organisms.

Substances that reduce the growth or reproduction of BACTERIA.

A genus of bacteria that form a nonfragmented aerial mycelium. Many species have been identified with some being pathogenic. This genus is responsible for producing a majority of the ANTI-BACTERIAL AGENTS of practical value.

Any tests that demonstrate the relative efficacy of different chemotherapeutic agents against specific microorganisms (i.e., bacteria, fungi, viruses).

A group of antibiotics that contain 6-aminopenicillanic acid with a side chain attached to the 6-amino group. The penicillin nucleus is the chief structural requirement for biological activity. The side-chain structure determines many of the antibacterial and pharmacological characteristics. (Goodman and Gilman's The Pharmacological Basis of Therapeutics, 8th ed, p1065)

Cyclic AMIDES formed from aminocarboxylic acids by the elimination of water. Lactims are the enol forms of lactams.

Nonsusceptibility of bacteria to the action of the beta-lactam antibiotics. Mechanisms responsible for beta-lactam resistance may be degradation of antibiotics by BETA-LACTAMASES, failure of antibiotics to penetrate, or low-affinity binding of antibiotics to targets.

A beta-lactamase preferentially cleaving penicillins. (Dorland, 28th ed) EC 3.5.2.-.

Electrophoresis in which a pH gradient is established in a gel medium and proteins migrate until they reach the site (or focus) at which the pH is equal to their isoelectric point.

Single preparations containing two or more active agents, for the purpose of their concurrent administration as a fixed dose mixture.

A group of broad-spectrum antibiotics first isolated from the Mediterranean fungus ACREMONIUM. They contain the beta-lactam moiety thia-azabicyclo-octenecarboxylic acid also called 7-aminocephalosporanic acid.

Semisynthetic, broad-spectrum, AMPICILLIN derived ureidopenicillin antibiotic proposed for PSEUDOMONAS infections. It is also used in combination with other antibiotics.

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. They are unstable chemically, but have a very broad antibacterial spectrum. Thienamycin and its more stable derivatives are proposed for use in combinations with enzyme inhibitors.

Semi-synthetic derivative of penicillin that functions as an orally active broad-spectrum antibiotic.

A monocyclic beta-lactam antibiotic originally isolated from Chromobacterium violaceum. It is resistant to beta-lactamases and is used in gram-negative infections, especially of the meninges, bladder, and kidneys. It may cause a superinfection with gram-positive organisms.

Nonsusceptibility of an organism to the action of penicillins.

Gram-negative, non-motile, capsulated, gas-producing rods found widely in nature and associated with urinary and respiratory infections in humans.

Semisynthetic, broad-spectrum antibacterial derived from CEPHALORIDINE and used especially for Pseudomonas and other gram-negative infections in debilitated patients.

One of the PENICILLINS which is resistant to PENICILLINASE.

A penicillin derivative commonly used in the form of its sodium or potassium salts in the treatment of a variety of infections. It is effective against most gram-positive bacteria and against gram-negative cocci. It has also been used as an experimental convulsant because of its actions on GAMMA-AMINOBUTYRIC ACID mediated synaptic transmission.

Therapy with two or more separate preparations given for a combined effect.

A semisynthetic ampicillin-derived acylureido penicillin.

A family of gram-negative, facultatively anaerobic, rod-shaped bacteria that do not form endospores. Its organisms are distributed worldwide with some being saprophytes and others being plant and animal parasites. Many species are of considerable economic importance due to their pathogenic effects on agriculture and livestock.

Semisynthetic thienamycin that has a wide spectrum of antibacterial activity against gram-negative and gram-positive aerobic and anaerobic bacteria, including many multiresistant strains. It is stable to beta-lactamases. Clinical studies have demonstrated high efficacy in the treatment of infections of various body systems. Its effectiveness is enhanced when it is administered in combination with CILASTATIN, a renal dipeptidase inhibitor.

Broad-spectrum semisynthetic penicillin derivative used parenterally. It is susceptible to gastric juice and penicillinase and may damage platelet function.

A species of gram-negative, obligately aerobic rods. Motility occurs by peritrichous flagella. (From Bergey's Manual of Determinative Bacteriology, 9th ed)

The ability of bacteria to resist or to become tolerant to chemotherapeutic agents, antimicrobial agents, or antibiotics. This resistance may be acquired through gene mutation or foreign DNA in transmissible plasmids (R FACTORS).

A genus of gram-negative, facultatively anaerobic, rod-shaped bacteria whose organisms arrange singly, in pairs, or short chains. This genus is commonly found in the intestinal tract and is an opportunistic pathogen that can give rise to bacteremia, pneumonia, urinary tract and several other types of human infection.

A semi-synthetic antibiotic that is a chlorinated derivative of OXACILLIN.

Monocyclic, bacterially produced or semisynthetic beta-lactam antibiotics. They lack the double ring construction of the traditional beta-lactam antibiotics and can be easily synthesized.

Extrachromosomal, usually CIRCULAR DNA molecules that are self-replicating and transferable from one organism to another. They are found in a variety of bacterial, archaeal, fungal, algal, and plant species. They are used in GENETIC ENGINEERING as CLONING VECTORS.

The action of a drug in promoting or enhancing the effectiveness of another drug.

Preliminary administration of a drug preceding a diagnostic, therapeutic, or surgical procedure. The commonest types of premedication are antibiotics (ANTIBIOTIC PROPHYLAXIS) and anti-anxiety agents. It does not include PREANESTHETIC MEDICATION.

Proteins found in any species of bacterium.

Gram-negative bacteria occurring in the lower intestinal tracts of man and other animals. It is the most common species of anaerobic bacteria isolated from human soft tissue infections.

The ability of microorganisms, especially bacteria, to resist or to become tolerant to chemotherapeutic agents, antimicrobial agents, or antibiotics. This resistance may be acquired through gene mutation or foreign DNA in transmissible plasmids (R FACTORS).

Infections by bacteria, general or unspecified.

A species of gram-negative, facultatively anaerobic, rod-shaped bacteria (GRAM-NEGATIVE FACULTATIVELY ANAEROBIC RODS) commonly found in the lower part of the intestine of warm-blooded animals. It is usually nonpathogenic, but some strains are known to produce DIARRHEA and pyogenic infections. Pathogenic strains (virotypes) are classified by their specific pathogenic mechanisms such as toxins (ENTEROTOXIGENIC ESCHERICHIA COLI), etc.

The functional hereditary units of BACTERIA.

One of the three domains of life (the others being Eukarya and ARCHAEA), also called Eubacteria. They are unicellular prokaryotic microorganisms which generally possess rigid cell walls, multiply by cell division, and exhibit three principal forms: round or coccal, rodlike or bacillary, and spiral or spirochetal. Bacteria can be classified by their response to OXYGEN: aerobic, anaerobic, or facultatively anaerobic; by the mode by which they obtain their energy: chemotrophy (via chemical reaction) or PHOTOTROPHY (via light reaction); for chemotrophs by their source of chemical energy: CHEMOLITHOTROPHY (from inorganic compounds) or chemoorganotrophy (from organic compounds); and by their source for CARBON; NITROGEN; etc.; HETEROTROPHY (from organic sources) or AUTOTROPHY (from CARBON DIOXIDE). They can also be classified by whether or not they stain (based on the structure of their CELL WALLS) with CRYSTAL VIOLET dye: gram-negative or gram-positive.

Descriptions of specific amino acid, carbohydrate, or nucleotide sequences which have appeared in the published literature and/or are deposited in and maintained by databanks such as GENBANK, European Molecular Biology Laboratory (EMBL), National Biomedical Research Foundation (NBRF), or other sequence repositories.

The rate dynamics in chemical or physical systems.

Nonsusceptibility of a microbe to the action of ampicillin, a penicillin derivative that interferes with cell wall synthesis.

A surgical specialty concerned with the diagnosis and treatment of disorders and abnormalities of the COLON; RECTUM; and ANAL CANAL.

A semisynthetic cephamycin antibiotic resistant to beta-lactamase.

A set of genes descended by duplication and variation from some ancestral gene. Such genes may be clustered together on the same chromosome or dispersed on different chromosomes. Examples of multigene families include those that encode the hemoglobins, immunoglobulins, histocompatibility antigens, actins, tubulins, keratins, collagens, heat shock proteins, salivary glue proteins, chorion proteins, cuticle proteins, yolk proteins, and phaseolins, as well as histones, ribosomal RNA, and transfer RNA genes. The latter three are examples of reiterated genes, where hundreds of identical genes are present in a tandem array. (King & Stanfield, A Dictionary of Genetics, 4th ed)

A cephalosporin antibiotic.

Non-susceptibility of an organism to the action of the cephalosporins.

A sulfanilamide that is used as an anti-infective agent.

A species of extremophilic bacteria in the family Thermotogaceae. Generally anaerobic but in the presence of OXYGEN, it can produce hydrogen gas as a byproduct of metabolism.

Broad-spectrum cephalosporin antibiotic resistant to beta-lactamase. It has been proposed for infections with gram-negative and gram-positive organisms, GONORRHEA, and HAEMOPHILUS.

A genus of gram-negative, facultatively anaerobic, rod-shaped bacteria that occurs in the intestines of humans and a wide variety of animals, as well as in manure, soil, and polluted waters. Its species are pathogenic, causing urinary tract infections and are also considered secondary invaders, causing septic lesions at other sites of the body.

Compounds or agents that combine with an enzyme in such a manner as to prevent the normal substrate-enzyme combination and the catalytic reaction.

Inflammation of the middle ear with purulent discharge.

Semisynthetic broad-spectrum cephalosporin.

A species of gram-negative, facultatively anaerobic, rod-shaped bacteria that occurs in water, sewage, soil, meat, hospital environments, and on the skin and in the intestinal tract of man and animals as a commensal.

A species of gram-negative bacteria causing URINARY TRACT INFECTIONS and SEPTICEMIA.

A multistage process that includes cloning, physical mapping, subcloning, determination of the DNA SEQUENCE, and information analysis.

Infections with bacteria of the genus BACTEROIDES.

Susceptibility of multidrug-resistant strains of Mycobacterium tuberculosis to amoxycillin in combination with clavulanic acid and ethambutol. (1/354)

Thirty clinical isolates of Mycobacterium tuberculosis, 20 of which were multidrug-resistant (MDR), were tested for susceptibility to different combinations of amoxycillin, clavulanic acid and subinhibitory concentrations of ethambutol. beta-Lactamase production was assessed semiquantitatively with the nitrocefin method and susceptibility testing was performed with the BACTEC method. All isolates were beta-lactamase positive and were resistant to 16 mg/L amoxycillin. The MIC of amoxycillin in combination with clavulanic acid was > or =2 mg/L for 27/30 (90%) isolates. Addition of subinhibitory concentrations of ethambutol significantly reduced the MIC of amoxycillin for all tested isolates. Twenty-nine (97%) isolates had an MIC of amoxycillin of < or =0.5 mg/L when subinhibitory concentrations of ethambutol were added; this is well below the concentrations achievable in serum and tissue. (+info)

Ampicillin-sulbactam and amoxicillin-clavulanate susceptibility testing of Escherichia coli isolates with different beta-lactam resistance phenotypes. (2/354)

The activities of ampicillin-sulbactam and amoxicillin-clavulanate were studied with 100 selected clinical Escherichia coli isolates with different beta-lactam susceptibility phenotypes by standard agar dilution and disk diffusion techniques and with a commercial microdilution system (PASCO). A fixed ratio (2:1) and a fixed concentration (clavulanate, 2 and 4 micrograms/ml; sulbactam, 8 micrograms/ml) were used in the agar dilution technique. The resistance frequencies for amoxicillin-clavulanate with different techniques were as follows: fixed ratio agar dilution, 12%; fixed concentration 4-micrograms/ml agar dilution, 17%; fixed ratio microdilution, 9%; and disk diffusion, 9%. Marked discrepancies were found when these results were compared with those obtained with ampicillin-sulbactam (26 to 52% resistance), showing that susceptibility to amoxicillin-clavulanic acid cannot be predicted by testing the isolate against ampicillin-sulbactam. Interestingly, the discrimination between susceptible and intermediate isolates was better achieved with 4 micrograms of clavulanate per ml than with the fixed ratio. In contrast, amoxicillin susceptibility was not sufficiently restored when 2 micrograms of clavulanate per ml was used, particularly in moderate (mean beta-lactamase activity, 50.8 mU/mg of protein) and high-level (215 mU/mg) TEM-1 beta-lactamase producer isolates. Four micrograms of clavulanate per milliliter could be a reasonable alternative to the 2:1 fixed ratio, because most high-level beta-lactamase-hyperproducing isolates would be categorized as nonsusceptible, and low- and moderate-level beta-lactamase-producing isolates would be categorized as nonresistant. This approach cannot be applied to sulbactam, either with the fixed 2:1 ratio or with the 8-micrograms/ml fixed concentration, because many low-level beta-lactamase-producing isolates would be classified in the resistant category. These findings call for a review of breakpoints for beta-lactam-beta-lactamase inhibitors combinations. (+info)

Clavulanate induces expression of the Pseudomonas aeruginosa AmpC cephalosporinase at physiologically relevant concentrations and antagonizes the antibacterial activity of ticarcillin. (3/354)

Although previous studies have indicated that clavulanate may induce AmpC expression in isolates of Pseudomonas aeruginosa, the impact of this inducer activity on the antibacterial activity of ticarcillin at clinically relevant concentrations has not been investigated. Therefore, a study was designed to determine if the inducer activity of clavulanate was associated with in vitro antagonism of ticarcillin at pharmacokinetically relevant concentrations. By the disk approximation methodology, clavulanate induction of AmpC expression was observed with 8 of 10 clinical isolates of P. aeruginosa. Quantitative studies demonstrated a significant induction of AmpC when clavulanate-inducible strains were exposed to the peak concentrations of clavulanate achieved in human serum with the 3.2- and 3.1-g doses of ticarcillin-clavulanate. In studies with three clavulanate-inducible strains in an in vitro pharmacodynamic model, antagonism of the bactericidal effect of ticarcillin was observed in some tests with regimens simulating a 3.1-g dose of ticarcillin-clavulanate and in all tests with regimens simulating a 3.2-g dose of ticarcillin-clavulanate. No antagonism was observed in studies with two clavulanate-noninducible strains. In contrast to clavulanate. No antagonism was observed in studies with two clavulanate-noninducible strains. In contrast to clavulanate, tazobactam failed to induce AmpC expression in any strains, and the pharmacodynamics of piperacillin-tazobactam were somewhat enhanced over those of piperacillin alone against all strains studied. Overall, the data collected from the pharmacodynamic model suggested that induction per se was not always associated with reduced killing but that a certain minimal level of induction by clavulanate was required before antagonism of the antibacterial activity of its companion drug occurred. Nevertheless, since clinically relevant concentrations of clavulanate can antagonize the bactericidal activity of ticarcillin, the combination of ticarcillin-clavulanate should be avoided when selecting an antipseudomonal beta-lactam for the treatment of P. aeruginosa infections, particularly in immunocompromised patients. For piperacillin-tazobactam, induction is not an issue in the context of treating this pathogen. (+info)

Genes specific for the biosynthesis of clavam metabolites antipodal to clavulanic acid are clustered with the gene for clavaminate synthase 1 in Streptomyces clavuligerus. (4/354)

Portions of the Streptomyces clavuligerus chromosome flanking cas1, which encodes the clavaminate synthase 1 isoenzyme (CAS1), have been cloned and sequenced. Mutants of S. clavuligerus disrupted in cvm1, the open reading frame located immediately upstream of cas1, were constructed by a gene replacement procedure. Similar techniques were used to generate S. clavuligerus mutants carrying a deletion that encompassed portions of the two open reading frames, cvm4 and cvm5, located directly downstream of cas1. Both classes of mutants still produced clavulanic acid and cephamycin C but lost the ability to synthesize the antipodal clavam metabolites clavam-2-carboxylate, 2-hydroxymethyl-clavam, and 2-alanylclavam. These results suggested that cas1 is clustered with genes essential and specific for clavam metabolite biosynthesis. When a cas1 mutant of S. clavuligerus was constructed by gene replacement, it produced lower levels of both clavulanic acid and most of the antipodal clavams except for 2-alanylclavam. However, a double mutant of S. clavuligerus disrupted in both cas1 and cas2 produced neither clavulanic acid nor any of the antipodal clavams, including 2-alanylclavam. This outcome was consistent with the contribution of both CAS1 and CAS2 to a common pool of clavaminic acid that is shunted toward clavulanic acid and clavam metabolite biosynthesis. (+info)

Aspartic acid for asparagine substitution at position 276 reduces susceptibility to mechanism-based inhibitors in SHV-1 and SHV-5 beta-lactamases. (5/354)

In SHV-type beta-actamases, position 276 (in Ambler's numbering scheme) is occupied by an asparagine (Asn) residue. The effect on SHV-1 beta-lactamase and its extended-spectrum derivative SHV-5 of substituting an aspartic acid (Asp) residue for Asn276 was studied. Mutations were introduced by a PCR-based site-directed mutagenesis procedure. Wild-type SHV-1 and -5 beta-lactamases and their respective Asn276-->Asp mutants were expressed under isogenic conditions by cloning the respective bla genes into the pBCSK(+) plasmid and transforming Escherichia coli DH5alpha. Determination of IC50 showed that SHV-1(Asn276-->Asp), compared with SHV-1, was inhibited by 8- and 8.8-fold higher concentrations of clavulanate and tazobactam respectively. Replacement of Asn276 by Asp in SHV-5 beta-lactamase caused a ten-fold increase in the IC50 of clavulanate; the increases in the IC50s of tazobactam and sulbactam were 10- and 5.5-fold, respectively. Beta-lactam susceptibility testing showed that both Asn276-->Asp mutant enzymes, compared with the parental beta-lactamases, conferred slightly lower levels of resistance to penicillins (amoxycillin, ticarcillin and piperacillin), cephalosporins (cephalothin and cefprozil) and some of the expanded-spectrum oxyimino beta-lactams tested (cefotaxime, ceftriaxone and aztreonam). The MICs of ceftazidime remained unaltered, while those of cefepime and cefpirome were slightly elevated in the clones producing the mutant beta-lactamases. The latter clones were also less susceptible to penicillin-inhibitor combinations. Asn276-->Asp mutation was associated with changes in the substrate profiles of SHV-1 and SHV-5 enzymes. Based on the structure of TEM-1 beta-lactamase, the potential effects of the introduced mutation on SHV-1 and SHV-5 are discussed. (+info)

In-vitro susceptibilities of species of the Bacteroides fragilis group to newer beta-lactam agents. (6/354)

The in-vitro activities of imipenem and four beta-lactam-beta-lactamase inhibitor combinations were tested against 816 strains of the Bacteroides fragilis group, and compared with other anti-anaerobic agents. None of the strains was resistant to metronidazole, and only one was resistant to chloramphenicol. Mezlocillin and piperacillin were moderately active, while clindamycin was the least active. Rates of resistance varied between various species. The new beta-lactam agents tested showed excellent activity; piperacillin-tazobactam and imipenem were the most active. The emergence of strains that are resistant to these agents, observed in this study, suggests there is a need to perform periodic antimicrobial susceptibility tests. (+info)

A double-blind comparison of empirical oral and intravenous antibiotic therapy for low-risk febrile patients with neutropenia during cancer chemotherapy. (7/354)

BACKGROUND: Among patients with fever and neutropenia during chemotherapy for cancer who have a low risk of complications, oral administration of empirical broad-spectrum antibiotics may be an acceptable alternative to intravenous treatment. METHODS: We conducted a randomized, double-blind, placebo-controlled study of patients (age, 5 to 74 years) who had fever and neutropenia during chemotherapy for cancer. Neutropenia was expected to be present for no more than 10 days in these patients, and they had to have no other underlying conditions. Patients were assigned to receive either oral ciprofloxacin plus amoxicillin-clavulanate or intravenous ceftazidime. They were hospitalized until fever and neutropenia resolved. RESULTS: A total of 116 episodes were included in each group (84 patients in the oral-therapy group and 79 patients in the intravenous-therapy group). The mean neutrophil counts at admission were 81 per cubic millimeter and 84 per cubic millimeter, respectively; the mean duration of neutropenia was 3.4 and 3.8 days, respectively. Treatment was successful without the need for modifications in 71 percent of episodes in the oral-therapy group and 67 percent of episodes in the intravenous-therapy group (difference between groups, 3 percent; 95 percent confidence interval, -8 percent to 15 percent; P=0.48). Treatment was considered to have failed because of the need for modifications in the regimen in 13 percent and 32 percent of episodes, respectively (P<0.001) and because of the patient's inability to tolerate the regimen in 16 percent and 1 percent of episodes, respectively (P<0.001). There were no deaths. The incidence of intolerance of the oral antibiotics was 16 percent, as compared with 8 percent for placebo (P=0.07). CONCLUSIONS: In hospitalized low-risk patients who have fever and neutropenia during cancer chemotherapy, empirical therapy with oral ciprofloxacin and amoxicillin-clavulanate is safe and effective. (+info)

Oral versus intravenous empirical antimicrobial therapy for fever in patients with granulocytopenia who are receiving cancer chemotherapy. International Antimicrobial Therapy Cooperative Group of the European Organization for Research and Treatment of Cancer. (8/354)

BACKGROUND: Intravenously administered antimicrobial agents have been the standard choice for the empirical management of fever in patients with cancer and granulocytopenia. If orally administered empirical therapy is as effective as intravenous therapy, it would offer advantages such as improved quality of life and lower cost. METHODS: In a prospective, open-label, multicenter trial, we randomly assigned febrile patients with cancer who had granulocytopenia that was expected to resolve within 10 days to receive empirical therapy with either oral ciprofloxacin (750 mg twice daily) plus amoxicillin-clavulanate (625 mg three times daily) or standard daily doses of intravenous ceftriaxone plus amikacin. All patients were hospitalized until their fever resolved. The primary objective of the study was to determine whether there was equivalence between the regimens, defined as an absolute difference in the rates of success of 10 percent or less. RESULTS: Equivalence was demonstrated at the second interim analysis, and the trial was terminated after the enrollment of 353 patients. In the analysis of the 312 patients who were treated according to the protocol and who could be evaluated, treatment was successful in 86 percent of the patients in the oral-therapy group (95 percent confidence interval, 80 to 91 percent) and 84 percent of those in the intravenous-therapy group (95 percent confidence interval, 78 to 90 percent; P=0.02). The results were similar in the intention-to-treat analysis (80 percent and 77 percent, respectively; P=0.03), as were the duration of fever, the time to a change in the regimen, the reasons for such a change, the duration of therapy, and survival. The types of adverse events differed slightly between the groups but were similar in frequency. CONCLUSIONS: In low-risk patients with cancer who have fever and granulocytopenia, oral therapy with ciprofloxacin plus amoxicillin-clavulanate is as effective as intravenous therapy. (+info)

... was patented in 1974. Amoxicillin-clavulanic acid is a first-line treatment for many types of infections, ... which produces clavulanic acid. The β-lactam like structure of clavulanic acid looks structurally similar to penicillin, but ... which is the first step of the clavulanic acid biosynthesis. Clavulanic acid was discovered around 1974-75 by British ... This restructures the clavulanic acid molecule, creating a much more reactive species that attacks another amino acid in the ...

https://en.wikipedia.org/wiki/Clavulanic_acid

It may also increase the risk of yeast infections and, when used in combination with clavulanic acid, diarrhea. It should not ... For this reason, it may be combined with clavulanic acid, a β-lactamase inhibitor. This drug combination is commonly called co- ... Use of the amoxicillin/clavulanic acid combination for more than one week has caused a drug-induced immunoallergic-type ... Cundiff J, Joe S (January 2007). "Amoxicillin-clavulanic acid-induced hepatitis". American Journal of Otolaryngology. 28 (1): ...

https://en.wikipedia.org/wiki/Amoxicillin

This enzyme participates in clavulanic acid biosynthesis. Salowe SP, Krol WJ, Iwata-Reuyl D, Townsend CA (1991). "Elucidation ... Townsend CA (2002). "New reactions in clavulanic acid biosynthesis". Curr. Opin. Chem. Biol. 6 (5): 583-9. doi:10.1016/S1367- ... of the gene encoding proclavaminate amidino hydrolase and characterization of protein function in clavulanic acid biosynthesis ...

https://en.wikipedia.org/wiki/Proclavaminate_amidinohydrolase

Townsend CA (October 2002). "New reactions in clavulanic acid biosynthesis". Current Opinion in Chemical Biology. 6 (5): 583-9 ... Clavaminate synthase (EC 1.14.11.21, clavaminate synthase 2, clavaminic acid synthase) is an enzyme with systematic name ... "Structural origins of the selectivity of the trifunctional oxygenase clavaminic acid synthase". Nature Structural Biology. 7 (2 ...

https://en.wikipedia.org/wiki/Clavaminate_synthase

Townsend CA (2002). "New reactions in clavulanic acid biosynthesis". Curr. Opin. Chem. Biol. 6 (5): 583-9. doi:10.1016/S1367- ... This enzyme participates in clavulanic acid biosynthesis. Miller, M. T.; Bachmann, B. O.; Townsend, C. A.; Rosenzweig, A. C. ( ...

https://en.wikipedia.org/wiki/(carboxyethyl)arginine_beta-lactam-synthase

Khaleeli N; Li R; Townsend CA (1999). "Origin of the beta-lactam carbons in clavulanic acid from an unusual thiamine ... This enzyme participates in clavulanic acid biosynthesis. As of late 2007, two structures have been solved for this class of ... the first enzyme in the clavulanic acid biosynthesis pathway". J. Biol. Chem. 279 (7): 5685-92. doi:10.1074/jbc.M310803200. ...

https://en.wikipedia.org/wiki/N2-(2-carboxyethyl)arginine_synthase

Proclavaminate amidinohydrolase is involved in clavulanic acid biosynthesis. Clavulanic acid acts as an inhibitor of a wide ... evolution of a hydrolytic enzyme in clavulanic acid biosynthesis". Biochem. J. 366 (Pt 2): 423-434. doi:10.1042/BJ20020125. PMC ... Clifton IJ, Elkins JM, Hernandez H (2002). "Oligomeric structure of proclavaminic acid amidino hydrolase: ...

https://en.wikipedia.org/wiki/Ureohydrolase

An example is clavulanic acid, from which this compound class receives its name. Clavulanic acid, a type of Clavam, has ... This class is divided into the clavulanic acid class and the 5S clavams class. Clavulanic acid is a broad-spectrum antibiotic ... Clavulanic acid strongly inhibits b-lactamase in bacteria, which is associated with its antibiotic properties. B - lactam ... This is essential for the cephamycin C and clavulanic acid but not the 5S claims. CcaR is important for the expression of ...

https://en.wikipedia.org/wiki/Clavam

Baggaley K, Brown A, Schofield C (1997). "Chemistry and biosynthesis of clavulanic acid and other clavams". Nat Prod Rep. 14 (4 ... Tahlan K, Anders C, Jensen S (2004). "The Paralogous Pairs of Genes Involved in Clavulanic Acid and Clavam Metabolite ... Streptomyces clavuligerus is a species of Gram-positive bacterium notable for producing clavulanic acid. S. clavuligerus ATCC ... Kirk S (2000). "The physiology of clavulanic acid production by Streptomyces clavuligerus (PhD thesis)". University of Surrey, ...

https://en.wikipedia.org/wiki/Streptomyces_clavuligerus

"APO-Amoxycillin and Clavulanic Acid 500mg/125 mg Tablets" (PDF). Retrieved November 27, 2014. Mechanism of Action of Bacitracin ... Piperacillin/tazobactam Ticarcillin/clavulanic acid Certain carbapenems and carbapenem-beta-lactamase-inhibitors combinations: ... "Amoxicillin-sulbactam versus amoxicillin-clavulanic acid for the treatment of non-recurrent-acute otitis media in Argentinean ... Clindamycin Dalbavancin Fusidic acid Mupirocin (topical) Omadacycline Oritavancin Tedizolid Telavancin Tigecycline (also covers ...

https://en.wikipedia.org/wiki/List_of_antibiotics

Amoxicillin and amoxicillin/clavulanic acid were the most frequently consumed. Antibiotics are screened for any negative ... For example, β-lactam antibiotics may be used in combination with β-lactamase inhibitors, such as clavulanic acid or sulbactam ... Methicillin-resistant Staphylococcus aureus infections may be treated with a combination therapy of fusidic acid and rifampicin ... and Amino Acids)". Applied Microbiology. Springer India. pp. 83-120. doi:10.1007/978-81-322-2259-0. ISBN 978-81-322-2258-3. ...

https://en.wikipedia.org/wiki/Antibiotic

Cephalosporins, amoxicillin/clavulanic acid, or a fluoroquinolone may also be used. However, antibiotic resistance to ...

https://en.wikipedia.org/wiki/Urinary_tract_infection

Mennink-Kersten MA, Warris A, Verweij PE (2006). "1,3-β-D-Glucan in patients receiving intravenous amoxicillin-clavulanic acid ... increasing fecal bulk and producing short-chain fatty acids as byproducts with wide-ranging physiological activities. This ...

https://en.wikipedia.org/wiki/Beta-glucan

Thus imipenem/cilastatin, like amoxicillin/clavulanic acid, is a commonly used combination product. Keynan S, Hooper NM, Felici ...

https://en.wikipedia.org/wiki/Cilastatin

A strain isolated from mangroves has been demonstrated to produce clavulanic acid and streptomycin. The genome of M. ... v t e (Articles with short description, Short description matches Wikidata, Articles with 'species' microformats, Acid-fast ...

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"X-ray crystal structure of ornithine acetyltransferase from the clavulanic acid biosynthesis gene cluster". Biochem. J. 385 (Pt ...

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It can be sold and used in combination with clavulanate as ticarcillin/clavulanic acid. Because it is a penicillin, it also ... Ticarcillin is also often paired with a β-lactamase inhibitor such as clavulanic acid (co-ticarclav). In molecular biology, ... One synthesis began by making the monobenzyl ester of 3-Thienylmalonic acid, converting this to the acid chloride with SOCl2, ... and condensing it with 6-Aminopenicillanic acid (6-APA). Hydrogenolysis (Pd/C) completed the synthesis of ticarcillin. Fischer ...

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However, HugA does not affect cephamycins or carbapenems and is inhibited by clavulanic acid. Similar to other Proteus species ... penneri LPS are the amide of D-galacturonic acid with L-lysine α-D-GalA-(L-Lys) (and the amide of D-galacturonic acid with L- ... penneri from the experiment were found to be multiple drug-resistant including resistance to amoxy-clavulanic acid combination ...

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These include ampicillin, chloramphenicol, amoxicillin-clavulanic acid, cefamandole, cefuroxime, cefotaxime, tetracycline, ... "Deoxyribonucleic acid relatedness between Haemophilus aegyptius and Haemophilus influenzae," Elsevier, 137B (1986): 155-163. ...

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Brown AG (August 1986). "Clavulanic acid, a novel beta-lactamase inhibitor--a case study in drug discovery and development". ...

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"Simultaneous determination of amoxicillin and clavulanic acid in human plasma by HPLC-ESI mass spectrometry". Journal of ...

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Spratt BG, Jobanputra V, Zimmermann W (1977). "Binding of Thienamycin and Clavulanic Acid to the Penicillin-Binding Proteins of ... and l-α-aminoadipic acid by ACV synthetase (ACVS, a nonribosomal peptide synthetase) and then cyclization of this formed ...

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Due to its clavulanic acid component, penicillin amoxicillin-clavulanate is the most common culprit of cholestatic liver injury ... The primary bile acids cholic acid (CA) and chenodeoxycholic acid (CDCA) are synthesized in the liver and undergo conjugation ... a bile acid analogue), simtuzumab (a monoclonal antibody), and 24-norursodeoxycholic acid (a synthetic bile acid). Although the ... In the treatment of ICP, current evidence suggests ursodeoxycholic acid (UDCA), a minor secondary bile acid in humans, is the ...

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The combination of amoxicillin and clavulanic acid is used to treat certain infections caused by bacteria, including infections of the ears, lungs, sinus, skin, and urinary tract. (medlineplus.gov)
The combination of amoxicillin and clavulanic acid comes as a tablet, a chewable tablet, an extended-release (long-acting) tablet, and a suspension (liquid) to take by mouth. (medlineplus.gov)
Take amoxicillin and clavulanic acid exactly as directed. (medlineplus.gov)
The 250 mg and 500 mg tablets of amoxicillin and clavulanic acid contain the same amount of clavulanic acid. (medlineplus.gov)
Take amoxicillin and clavulanic acid until you finish the prescription, even if you feel better. (medlineplus.gov)
If you stop taking amoxicillin and clavulanic too soon, or skip doses, your infection may not be completely treated and the bacteria may become resistant to antibiotics. (medlineplus.gov)
Amoxicillin and clavulanic acid also is used sometimes to treat certain sexually transmitted diseases (STD). (medlineplus.gov)
tell your doctor and pharmacist if you are allergic to amoxicillin (Amoxil, Trimox, Wymox), clavulanic acid, penicillin, cephalosporins, any other medications, or any of the ingredients in amoxicillin and clavulanic acid preparations. (medlineplus.gov)
you should know that amoxicillin and clavulanic acid may decrease the effectiveness of oral contraceptives (birth control pills). (medlineplus.gov)
Plan to use another form of birth control while taking amoxicillin and clavulanic acid. (medlineplus.gov)
If you become pregnant while taking amoxicillin and clavulanic acid, call your doctor. (medlineplus.gov)
Amoxicillin and clavulanic acid may cause side effects. (medlineplus.gov)
Skin and Skin Structure Infection,Appropriate culture and susceptibility studies should be performed to identify the causative organism(s) and determine its (their) susceptibility to Amoxicillin and clavulanic acid tablets. (healthdirect.gov.au)
The treatment of mixed infections caused by amoxicillin susceptible organisms and beta-lactamase producing organisms susceptible to Amoxicillin and clavulanic acid tablets should not require the addition of another antibiotic due to the amoxicillin content of these products. (healthdirect.gov.au)
Concentration of amoxicillin and clavulanic acid in blood serum at reception of a combination of drugs of amoxicillin/clavulanic acid are similar to those which are observed at oral separate administration of an equivalent dose of amoxicillin and clavulanic acid. (rxeli.com)
Amoxicillin and clavulanic acid get through a placental barrier. (rxeli.com)
The diagnosis of neutrophilic FDE was first described by Agnew and Oliver in 2001, and the event was associated with amoxicillin and clavulanic acid. (dermsinica.org)

Each concentration includes a different amount of clavulanic acid (Table). (patientcareonline.com)
About 25% of total amount of clavulanic acid and 18% of amoxicillin contact proteins in blood plasma. (rxeli.com)

Amoxycillin 500mg + Clavulanic Acid 125mg + LB Tablet - Available by the brand name AMRO CV 625 at Servocare Lifesciences, this tablet contains a unification of three rich components that treat certain infections caused by bacteria which includes Amoxycillin, Clavulanic Acid, and LB. Amoxycillin with the dosage of 500 mg is a penicillin antibiotic is used to treat bacterial infections which include urinary tract infections, chest infections, and dental abscesses. (servocarelifesciences.in)
Simultaneously, Clavulanic Acid is added to Amoxycillin with a dosage of 125mg which is also beneficial to stop the growth of the bacteria and to treat infections of the lungs, skin, ears, sinus, and urinary tract. (servocarelifesciences.in)
Clavulanic Acid 125mg. (biocorplifesciences.com)

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It is composed of two efficacious drugs: Amoxycillin (penicillin-like antibiotics) and Clavulanic Acid (beta-lactamase inhibitors). (apikospharma.com)
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Curam Oral Suspension contains a combination of the active ingredients amoxycillin 250mg and clavulanic acid 62.5mg in powder form for oral suspension, which are antibiotics used to treat a wide range of common bacterial infections. (inhousepharmacy.vu)
High doses of amoxicillin, or amoxicillin-clavulanic acid for patients with a high risk of infection by Beta-lactamase producing strains, remain the first-line antibiotics. (bvsalud.org)

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Gram negative isolates showed high resistance rate of 73.1% to ampicillin and 65.4% to amoxicillin-clavulanic acid while Gram-positive isolates showed high resistant rate of 94.1% to penicillin. (bvsalud.org)

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Clavulanic acid is in a class of medications called beta-lactamase inhibitors. (medlineplus.gov)
Clavulanic acid belongs to a class of beta-lactamase inhibitors. (skginternationals.com)

When reconstituted, each 5 mL contains amoxicillin trihydrate equivalent to 250 mg amoxicillin and potassium clavulanate equivalent to 62.5 mg clavulanic acid. (inhousepharmacy.vu)

Clavulanic acid is an antibiotic structurally related to the penicillins that is able to inactivate a wide range of beta-lactamase enzymes commonly found in amoxycillin-resistant bacteria. (inhousepharmacy.vu)

Antibiotic sensitivity tests carried out on the posi- tive culture samples showed high sensitivity to gentamicin, amoxicillin-clavulanic acid and fosfomycin. (who.int)

Our range of products include amoxycillin and clavulanic acid with lactobacillus tablets, cefpodoxime proextel and clavulanic acid tablets, cefpodoxime proxetil 100 dispersible tablets, cefpodoxime 200 mg dispersibal tablet, cefixime 100 dispersible tablets and cefixime 200 mg dispersible tablets. (innovexia.in)

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Clavulanic acid is not effective if given alone hence we give it in combination with amoxicillin and hence the dose reduces because two drugs are acting at the same time. (lybrate.com)

The 250 mg regular tablet and the 250 mg chewable tablet contain different amounts of clavulanic acid. (medlineplus.gov)
Owing to the different amoxicillin/clavulanic acid ratios in the 250-mg tablet (250/125) versus the 250-mg chewable tablet (250/62.5), do not use the 250-mg tablet until the child weighs more than 40 kg. (medscape.com)

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Antimicrobial resistance occurs through different mechanisms, which include spontaneous (natural) genetic mutations and horizontal transfer of resistant genes through deoxyribonucleic acid (DNA). (who.int)

to combinations of clavulanic acid & penicillins with certain antitubercular agents. (who.int)

We manufacture Cefpodoxime with Clavulanic Acid Tablets. (dwarkeshpharma.com)

This combination inhibits bacterial growth by inhibiting the synthesis of dihydrofolic acid. (medscape.com)

Known hypersensitivity to mycophenolate sodium, mycophenolic acid (MPA), mycophenolate mofetil, or to any of its excipients. (nih.gov)

Evolution of amoxicillin-clavulanic acid nonsusceptibility of Escherichia coli from blood isolates, Spain, 2003-2006. (cdc.gov)

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High-dose amoxicillin/clavulanic acid is an appropriate medication for managing otitis media in the pediatric population. (patientcareonline.com)
This potential medication error can be easily prevented by paying close attention to the amoxicillin to clavulanic acid ratio. (patientcareonline.com)

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Organisms12

Diseases3

Chemicals and Drugs38

Analytical, Diagnostic and Therapeutic Techniques and Equipment5

Phenomena and Processes11

Disciplines and Occupations1

Information Science1

Susceptibility of multidrug-resistant strains of Mycobacterium tuberculosis to amoxycillin in combination with clavulanic acid and ethambutol. (1/354)

Ampicillin-sulbactam and amoxicillin-clavulanate susceptibility testing of Escherichia coli isolates with different beta-lactam resistance phenotypes. (2/354)

Clavulanate induces expression of the Pseudomonas aeruginosa AmpC cephalosporinase at physiologically relevant concentrations and antagonizes the antibacterial activity of ticarcillin. (3/354)

Genes specific for the biosynthesis of clavam metabolites antipodal to clavulanic acid are clustered with the gene for clavaminate synthase 1 in Streptomyces clavuligerus. (4/354)

Aspartic acid for asparagine substitution at position 276 reduces susceptibility to mechanism-based inhibitors in SHV-1 and SHV-5 beta-lactamases. (5/354)

In-vitro susceptibilities of species of the Bacteroides fragilis group to newer beta-lactam agents. (6/354)

A double-blind comparison of empirical oral and intravenous antibiotic therapy for low-risk febrile patients with neutropenia during cancer chemotherapy. (7/354)

Oral versus intravenous empirical antimicrobial therapy for fever in patients with granulocytopenia who are receiving cancer chemotherapy. International Antimicrobial Therapy Cooperative Group of the European Organization for Research and Treatment of Cancer. (8/354)

Clavulanic Acid

Clavulanic Acids

Amoxicillin-Potassium Clavulanate Combination

Ticarcillin

Amoxicillin

beta-Lactamases

Sulbactam

Penicillanic Acid

beta-Lactams

Cephamycins

Anti-Bacterial Agents

Streptomyces

Microbial Sensitivity Tests

Ureohydrolases

Penicillins

Lactams

Cephalosporinase

beta-Lactam Resistance

Penicillinase

Isoelectric Focusing

Drug Combinations

Cephalosporins

Piperacillin

Thienamycins

Ampicillin

Aztreonam

Penicillin Resistance

Klebsiella pneumoniae

Ceftazidime

Dicloxacillin

Penicillin G

Drug Therapy, Combination

Azlocillin

Enterobacteriaceae

Imipenem

Carbenicillin

Aza Compounds

Ochrobactrum anthropi

Drug Resistance, Bacterial

Klebsiella

Cloxacillin

Monobactams

Plasmids

Drug Synergism

Premedication

Bacterial Proteins

Bacteroides fragilis

Drug Resistance, Microbial

Bacterial Infections

Escherichia coli

Genes, Bacterial

Bacteria

Molecular Sequence Data

Kinetics

Ampicillin Resistance

Colorectal Surgery

Cefoxitin

Multigene Family

Cephalothin

Cephalosporin Resistance

Sulfadimethoxine

Thermotoga neapolitana

Cefuroxime

Proteus

Enzyme Inhibitors

Otitis Media, Suppurative

Cefotaxime

Enterobacter cloacae

Klebsiella oxytoca

Sequence Analysis, DNA

Bacteroides Infections

Susceptibility of multidrug-resistant strains of Mycobacterium tuberculosis to amoxycillin in combination with clavulanic acid and ethambutol. (1/354)

Ampicillin-sulbactam and amoxicillin-clavulanate susceptibility testing of Escherichia coli isolates with different beta-lactam resistance phenotypes. (2/354)

Clavulanate induces expression of the Pseudomonas aeruginosa AmpC cephalosporinase at physiologically relevant concentrations and antagonizes the antibacterial activity of ticarcillin. (3/354)

Genes specific for the biosynthesis of clavam metabolites antipodal to clavulanic acid are clustered with the gene for clavaminate synthase 1 in Streptomyces clavuligerus. (4/354)

Aspartic acid for asparagine substitution at position 276 reduces susceptibility to mechanism-based inhibitors in SHV-1 and SHV-5 beta-lactamases. (5/354)

In-vitro susceptibilities of species of the Bacteroides fragilis group to newer beta-lactam agents. (6/354)

A double-blind comparison of empirical oral and intravenous antibiotic therapy for low-risk febrile patients with neutropenia during cancer chemotherapy. (7/354)

Oral versus intravenous empirical antimicrobial therapy for fever in patients with granulocytopenia who are receiving cancer chemotherapy. International Antimicrobial Therapy Cooperative Group of the European Organization for Research and Treatment of Cancer. (8/354)

Amoxicillin + Clavulanic Acid drug information | DrugsUpdate India