Information about Flucloxacillin
Flucloxacillin (INN) or floxacillin (USAN) is a narrow spectrum beta-lactam antibiotic of the penicillin class. It is used to treat infections caused by susceptible Gram-positive bacteria. Notably, it is active against beta-lactamase-producing organisms such as Staphylococcus aureus, which would otherwise be resistant to most penicillins. It is very similar to dicloxacillin and these two agents are considered interchangeable. Flucloxacillin is available under a variety of trade names including Flopen (CSL) and Floxapen (GSK).
Like other β-lactam antibiotics, flucloxacillin acts by inhibiting the synthesis of bacterial cell walls. It inhibits cross-linkage between the linear peptidoglycan polymer chains that make up a major component of the cell wall of Gram-positive bacteria.
Flucloxacillin has similar pharmacokinetics, antibacterial activity and indications to dicloxacillin and the two agents are considered interchangeable. It is believed to have higher incidence of severe hepatic adverse effects than dicloxacillin, but a lower incidence of renal adverse effects.[1]
It should be used with caution in the elderly, patients with renal impairment, where a reduced dose is required; and those with hepatic impairment, due to the risk of cholestatic hepatitis.<ref name="AMH2006" />
Rarely, cholestatic jaundice (also referred to as cholestatic hepatitis) has been associated with flucloxacillin therapy. The reaction may occur up to several weeks after treatment has stopped, and takes weeks to resolve. The estimated incidence is 1 in 15,000 exposures, and is more frequent in people >55 years, females, and those with treatment longer than 2 weeks.<ref name="AMH2006" /><ref name="BNF50" />
Mode of action
Like other β-lactam antibiotics, flucloxacillin acts by inhibiting the synthesis of bacterial cell walls. It inhibits cross-linkage between the linear peptidoglycan polymer chains that make up a major component of the cell wall of Gram-positive bacteria.
Medicinal chemistry
Flucloxacillin is insensitive to beta-lactamase (also known as penicillinase) enzymes secreted by many penicillin-resistant bacteria. The presence of the isoxazolyl group on the side chain of the penicillin nucleus facilitates the β-lactamase resistance, since they are relatively intolerant of side-chain steric hindrance. Thus it is able to bind to penicillin binding proteins (PBPs) and inhibit peptidoglycan crosslinking, but is not bound by or inactivated by β-lactamases.Clinical use
Flucloxacillin is more acid-stable than many other penicillins and can be given orally, in addition to parenteral routes. However, like methicillin, it is less potent than benzylpenicillin against non-β-lactamase-producing Gram-positive bacteria.Flucloxacillin has similar pharmacokinetics, antibacterial activity and indications to dicloxacillin and the two agents are considered interchangeable. It is believed to have higher incidence of severe hepatic adverse effects than dicloxacillin, but a lower incidence of renal adverse effects.[1]
Available forms
Flucloxacillin is commercially available as the sodium salt flucloxacillin sodium, in capsules (250 or 500 mg), oral suspensions (125 mg/5 mL or 250 mg/5 mL), and injections (powder for reconstitution, 250, 500 and 1000 mg per vial).Indications
Flucloxacillin is indicated for the treatment of infections caused by susceptible bacteria. Specific approved indications include:<ref name="AMH2006" />[2]- Staphylococcal skin infections and cellulitis – including impetigo, otitis externa, folliculitis, boils, carbuncles, and mastitis
- Pneumonia (adjunct)
- Osteomyelitis, septic arthritis
- Septicaemia
- Empirical treatment for endocarditis
- Surgical prophylaxis
Precautions/contraindications
Flucloxacillin is contraindicated in those with a previous history of allergy to penicillins, cephalosporins or carbapenems. It should also not be used in the eye, or those with a history of cholestatic hepatitis associated with the use of dicloxacillin or flucloxacillin.<ref name="AMH2006" />It should be used with caution in the elderly, patients with renal impairment, where a reduced dose is required; and those with hepatic impairment, due to the risk of cholestatic hepatitis.<ref name="AMH2006" />
Adverse effects
Common adverse drug reactions (ADRs) associated with the use of flucloxacillin include: diarrhoea, nausea, rash, urticaria, pain and inflammation at injection site, superinfection (including candidiasis), allergy, and transient increases in liver enzymes and bilirubin.<ref name="AMH2006" />Rarely, cholestatic jaundice (also referred to as cholestatic hepatitis) has been associated with flucloxacillin therapy. The reaction may occur up to several weeks after treatment has stopped, and takes weeks to resolve. The estimated incidence is 1 in 15,000 exposures, and is more frequent in people >55 years, females, and those with treatment longer than 2 weeks.<ref name="AMH2006" /><ref name="BNF50" />
Resistance
Despite flucloxacillin being insensitive to beta-lactamases, some organisms have developed resistance to it and other narrow-spectrum β-lactam antibiotics including methicillin. Such organisms include methicillin-resistant Staphylococcus aureus (MRSA).See also
References
1. ^ Rossi S, editor. Australian Medicines Handbook 2006. Adelaide: Australian Medicines Handbook; 2006.
2. ^ Joint Formulary Committee. British National Formulary, 50th edition. London: British Medical Association and Royal Pharmaceutical Society of Great Britain; 2005.
2. ^ Joint Formulary Committee. British National Formulary, 50th edition. London: British Medical Association and Royal Pharmaceutical Society of Great Britain; 2005.
Antibacterials for systemic use: beta-lactam antibiotics - penicillins (J01C) | |
|---|---|
| Antibiotics | Amoxicillin • Ampicillin • Azlocillin • Carbenicillin • Cloxacillin • Dicloxacillin • Flucloxacillin • Mezlocillin • Nafcillin • Piperacillin • Pivampicillin • Ticarcillin |
| Beta-lactamase inhibitors | Sulbactam • Tazobactam • Clavulanic acid |
| Combinations | Ampicillin/sulbactam (Sultamicillin) • Co-amoxiclav |
An International Nonproprietary Name (INN; also known as rINN, for recommended International Nonproprietary Name) is the official non-proprietary or generic name given to a pharmaceutical substance, as designated by the World Health Organization (WHO).
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United States Adopted Names are unique nonproprietary names assigned to pharmaceuticals marketed in the United States. Each name is assigned by the USAN Council, which is co-sponsored by the American Medical Association (AMA), the United States Pharmacopoeial Convention (USP), and
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antibiotic is a chemotherapeutic agent that inhibits or abolishes the growth of micro-organisms, such as bacteria, fungi, or protozoans. The term originally referred to any agent with biological activity against living organisms; however, "antibiotic" now is used to refer to
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β-lactam antibiotics are a broad class of antibiotics which include penicillin derivatives, cephalosporins, monobactams, carbapenems and β-lactamase inhibitors; basically any antibiotic agent which contains a β-lactam nucleus in its molecular structure.
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Penicillin (sometimes abbreviated PCN) is a group of beta-lactam antibiotics used in the treatment of bacterial infections caused by susceptible, usually Gram-positive, organisms.
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Gram-positive bacteria are those that retain a crystal violet dye during the Gram stain process.[1] Gram-positive bacteria appear blue or violet under a microscope, while Gram-negative bacteria appear red or pink.
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Bacteria
Phyla
Actinobacteria
Aquificae
Chlamydiae
Bacteroidetes/Chlorobi
Chloroflexi
Chrysiogenetes
Cyanobacteria
Deferribacteres
Deinococcus-Thermus
Dictyoglomi
Fibrobacteres/Acidobacteria
Firmicutes
Fusobacteria
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Phyla
Actinobacteria
Aquificae
Chlamydiae
Bacteroidetes/Chlorobi
Chloroflexi
Chrysiogenetes
Cyanobacteria
Deferribacteres
Deinococcus-Thermus
Dictyoglomi
Fibrobacteres/Acidobacteria
Firmicutes
Fusobacteria
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Beta-lactamase is an enzyme (EC 3.5.2.6 ) produced by some bacteria that is responsible for their resistance to beta-lactam antibiotics like penicillins, cephalosporins, cephamycins and carbapenems.
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S. aureus
Binomial name
Staphylococcus aureus
Rosenbach 1884
Staphylococcus aureus /ˌstæf.ə.loˈko.
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Binomial name
Staphylococcus aureus
Rosenbach 1884
Staphylococcus aureus /ˌstæf.ə.loˈko.
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Penicillin (sometimes abbreviated PCN) is a group of beta-lactam antibiotics used in the treatment of bacterial infections caused by susceptible, usually Gram-positive, organisms.
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Dicloxacillin (INN) is a narrow spectrum beta-lactam antibiotic of the penicillin class. It is used to treat infections caused by susceptible Gram-positive bacteria. Notably, it is active against beta-lactamase-producing organisms such as Staphylococcus aureus
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CSL Limited
Public
ASX: CSL
Founded 1994 (privatised), 1916 (government department)
Headquarters Melbourne, Australia Australia
Key people Brian A McNamee (CEO)
Industry medicine
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Public
ASX: CSL
Founded 1994 (privatised), 1916 (government department)
Headquarters Melbourne, Australia Australia
Key people Brian A McNamee (CEO)
Industry medicine
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GlaxoSmithKline
Public (LSE: GSK
NYSE: GSK )
Founded 2000, by merger of Glaxo Wellcome and SmithKline Beecham
Headquarters London, England, UK
Key people Sir Chris Gent, Chairman
Dr Jean-Pierre Garnier, Chief Executive
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Public (LSE: GSK
NYSE: GSK )
Founded 2000, by merger of Glaxo Wellcome and SmithKline Beecham
Headquarters London, England, UK
Key people Sir Chris Gent, Chairman
Dr Jean-Pierre Garnier, Chief Executive
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β-lactam antibiotics are a broad class of antibiotics which include penicillin derivatives, cephalosporins, monobactams, carbapenems and β-lactamase inhibitors; basically any antibiotic agent which contains a β-lactam nucleus in its molecular structure.
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cell wall is a fairly rigid layer surrounding a cell, located external to the cell membrane, which provides the cell with structural support, protection, and acts as a filtering mechanism. The cell wall also prevents over-expansion when water enters the cell.
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Peptidoglycan, also known as murein, is a polymer consisting of sugars and amino acids that forms a mesh-like layer outside the plasma membrane of eubacteria. The sugar component consists of alternating residues of β-(1,4) linked N-acetylglucosamine and N-acetylmuramic
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Gram-positive bacteria are those that retain a crystal violet dye during the Gram stain process.[1] Gram-positive bacteria appear blue or violet under a microscope, while Gram-negative bacteria appear red or pink.
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Beta-lactamase is an enzyme (EC 3.5.2.6 ) produced by some bacteria that is responsible for their resistance to beta-lactam antibiotics like penicillins, cephalosporins, cephamycins and carbapenems.
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Isoxazole is an azole with an oxygen atom next to the nitrogen.
Isoxazoles are found in some natural products, such as ibotenic acid. Isoxazoles also form the basis for a number of drugs, including the COX-2 inhibitor valdecoxib (Bextra).
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Isoxazoles are found in some natural products, such as ibotenic acid. Isoxazoles also form the basis for a number of drugs, including the COX-2 inhibitor valdecoxib (Bextra).
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side chain in organic chemistry and biochemistry is a part of a molecule that is attached to a core structure. An R group is a generic label for a side chain which can be anything; however, it is typically stable and covalently linked to the adjoining atom.
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Steric effects arise from the fact that each atom within a molecule occupies a certain amount of space. If atoms are brought too close together, there is an associated cost in energy due to overlapping electron clouds (Pauli or Born repulsion), and this may affect the molecule's
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Penicillin binding proteins (PBPs) are a group of proteins which are characterized by their affinity for and binding of penicillin. They do not just bind penicillin but all beta-lactam antibiotics which are a family of antibiotics sharing a four membered lactam ring (beta-lactam
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Peptidoglycan, also known as murein, is a polymer consisting of sugars and amino acids that forms a mesh-like layer outside the plasma membrane of eubacteria. The sugar component consists of alternating residues of β-(1,4) linked N-acetylglucosamine and N-acetylmuramic
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In pharmacology and toxicology, a route of administration is the path by which a drug, fluid, poison or other substance is brought into contact with the body.[1]
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Methicillin (USAN) or meticillin (INN, BAN) is a narrow spectrum beta-lactam antibiotic of the penicillin class. It was developed by Beecham in 1959. It was previously used to treat infections caused by susceptible Gram-positive bacteria, particularly
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Penicillin (sometimes abbreviated PCN) is a group of beta-lactam antibiotics used in the treatment of bacterial infections caused by susceptible, usually Gram-positive, organisms.
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Gram-positive bacteria are those that retain a crystal violet dye during the Gram stain process.[1] Gram-positive bacteria appear blue or violet under a microscope, while Gram-negative bacteria appear red or pink.
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Pharmacokinetics (in Greek: "pharmacon" meaning drug and "kinetikos" meaning putting in motion, the study of time dependency) is a branch of pharmacology dedicated to the determination of the fate of substances administered externally to a living organism.
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In medicine, an adverse effect is a harmful and undesired effect resulting from a medication or other intervention such as chemotherapy or surgery. An adverse effect may be termed a "side-effect" (when judged to be secondary to a main or therapeutic effect) and may result from an
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tablet is a mixture of active substances and excipients, usually in powder form, pressed or compacted into a solid. The excipients include binders, glidants (flow aids) and lubricants to ensure efficient tabletting; disintegrants to ensure that the tablet breaks up in the digestive
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