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Dicloxacillin
 
 
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Dicloxacillin (INN
International Nonproprietary Name

An International Nonproprietary Name is the official non-proprietary or generic name given to a pharmaceutical substance, as designated by the World Health Organization ....
) is a narrow spectrum beta-lactam antibiotic
Beta-lactam antibiotic

?-lactam antibiotics are a broad class of antibiotics that include penicillin derivatives, cephalosporins, monobactams, carbapenems, and Beta-lactamase inhibitors, that is, any antibiotic agent that contains a beta-lactam nucleus in its molecular structure....
 of the penicillin
Penicillin

Penicillin is a group of antibiotics derived from Penicillium fungi. They are Beta-lactam antibiotics used in the treatment of bacterial infections caused by susceptible, usually Gram-positive, organisms....
 class. It is used to treat infections caused by susceptible Gram-positive
Gram-positive

Gram-positive Bacteria are those that are stained dark blue or violet by Gram staining. This is in contrast to Gram-negative bacteria, which cannot retain the crystal violet stain, instead taking up the counterstain and appearing red or pink....
 bacteria
Bacteria

The Bacteria are a large group of unicellular microorganisms. Typically a few micrometres in length, bacteria have a wide range of shapes, ranging from spheres to rods and spirals....
. Notably, it is active against beta-lactamase
Beta-lactamase

Beta-lactamases are enzymes produced by some bacteria and are responsible for their antibiotic resistance to beta-lactam antibiotics like penicillins, cephalosporins , cephamycins, and carbapenems ....
-producing organisms such as Staphylococcus aureus
Staphylococcus aureus

Staphylococcus aureus is the most common cause of staph infections. It is a spherical Bacteria, frequently found in the nose and skin of a person....
, which would otherwise be resistant to most penicillin
Penicillin

Penicillin is a group of antibiotics derived from Penicillium fungi. They are Beta-lactam antibiotics used in the treatment of bacterial infections caused by susceptible, usually Gram-positive, organisms....
s. It is very similar to flucloxacillin
Flucloxacillin

Flucloxacillin or floxacillin is a narrow-spectrum antibiotic beta-lactam antibiotic of the penicillin class. It is used to treat infections caused by susceptible Gram-positive bacteria....
 and these two agents are considered interchangeable. Dicloxacillin is available under a variety of trade names including Diclocil (BMS
Bristol-Myers Squibb

Bristol-Myers Squibb , colloquially referred to as BMS, is a pharmaceutical corporation, formed by a 1989 merger between pharmaceutical companies Bristol-Myers Company, founded in 1887 by William McLaren Bristol and John Ripley Myers in Clinton, NY , and E.R....
).

Mode of action
Like other ß-lactam antibiotics, dicloxacillin acts by inhibiting the synthesis of bacterial cell wall
Cell wall

A cell wall is a tough, flexible and sometimes fairly rigid layer that surrounds some types of cell . It is located outside the cell membrane and provides these cells with structural support and protection, and also acts as a filtering mechanism....
s.






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Dicloxacillin (INN
International Nonproprietary Name

An International Nonproprietary Name is the official non-proprietary or generic name given to a pharmaceutical substance, as designated by the World Health Organization ....
) is a narrow spectrum beta-lactam antibiotic
Beta-lactam antibiotic

?-lactam antibiotics are a broad class of antibiotics that include penicillin derivatives, cephalosporins, monobactams, carbapenems, and Beta-lactamase inhibitors, that is, any antibiotic agent that contains a beta-lactam nucleus in its molecular structure....
 of the penicillin
Penicillin

Penicillin is a group of antibiotics derived from Penicillium fungi. They are Beta-lactam antibiotics used in the treatment of bacterial infections caused by susceptible, usually Gram-positive, organisms....
 class. It is used to treat infections caused by susceptible Gram-positive
Gram-positive

Gram-positive Bacteria are those that are stained dark blue or violet by Gram staining. This is in contrast to Gram-negative bacteria, which cannot retain the crystal violet stain, instead taking up the counterstain and appearing red or pink....
 bacteria
Bacteria

The Bacteria are a large group of unicellular microorganisms. Typically a few micrometres in length, bacteria have a wide range of shapes, ranging from spheres to rods and spirals....
. Notably, it is active against beta-lactamase
Beta-lactamase

Beta-lactamases are enzymes produced by some bacteria and are responsible for their antibiotic resistance to beta-lactam antibiotics like penicillins, cephalosporins , cephamycins, and carbapenems ....
-producing organisms such as Staphylococcus aureus
Staphylococcus aureus

Staphylococcus aureus is the most common cause of staph infections. It is a spherical Bacteria, frequently found in the nose and skin of a person....
, which would otherwise be resistant to most penicillin
Penicillin

Penicillin is a group of antibiotics derived from Penicillium fungi. They are Beta-lactam antibiotics used in the treatment of bacterial infections caused by susceptible, usually Gram-positive, organisms....
s. It is very similar to flucloxacillin
Flucloxacillin

Flucloxacillin or floxacillin is a narrow-spectrum antibiotic beta-lactam antibiotic of the penicillin class. It is used to treat infections caused by susceptible Gram-positive bacteria....
 and these two agents are considered interchangeable. Dicloxacillin is available under a variety of trade names including Diclocil (BMS
Bristol-Myers Squibb

Bristol-Myers Squibb , colloquially referred to as BMS, is a pharmaceutical corporation, formed by a 1989 merger between pharmaceutical companies Bristol-Myers Company, founded in 1887 by William McLaren Bristol and John Ripley Myers in Clinton, NY , and E.R....
).

Mode of action


Like other ß-lactam antibiotics, dicloxacillin acts by inhibiting the synthesis of bacterial cell wall
Cell wall

A cell wall is a tough, flexible and sometimes fairly rigid layer that surrounds some types of cell . It is located outside the cell membrane and provides these cells with structural support and protection, and also acts as a filtering mechanism....
s. It inhibits cross-linkage between the linear peptidoglycan
Peptidoglycan

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 bacteria, forming the cell wall....
 polymer chains that make up a major component of the cell wall of Gram-positive
Gram-positive

Gram-positive Bacteria are those that are stained dark blue or violet by Gram staining. This is in contrast to Gram-negative bacteria, which cannot retain the crystal violet stain, instead taking up the counterstain and appearing red or pink....
 bacteria.

Medicinal chemistry

Dicloxacillin is insensitive to beta-lactamase
Beta-lactamase

Beta-lactamases are enzymes produced by some bacteria and are responsible for their antibiotic resistance to beta-lactam antibiotics like penicillins, cephalosporins , cephamycins, and carbapenems ....
 (also known as penicillinase) enzymes secreted by many penicillin-resistant bacteria. The presence of the isoxazolyl
Isoxazole

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 ....
 group on the side chain of the penicillin nucleus facilitates the ß-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
Peptidoglycan

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 bacteria, forming the cell wall....
 crosslinking, but is not bound by or inactivated by ß-lactamases.

Clinical use

Dicloxacillin is more acid-stable than many other penicillins and can be given orally, in addition to parenteral
Parenteral

Parenteral refers to a route of administration that involves piercing the skin or mucous membrane.Total parenteral nutrition refers to providing nutrition via the veins....
 routes. However, like methicillin
Methicillin

Meticillin or methicillin is a narrow-spectrum antibiotic beta-lactam antibiotic of the penicillin class. It was developed by Beecham in 1959....
, it is less potent than benzylpenicillin
Benzylpenicillin

Benzylpenicillin, commonly known as penicillin G, is the Gold standard penicillin. Penicillin G is typically given by a route of administration because it is unstable in the hydrochloric acid of the stomach....
 against non-ß-lactamase-producing Gram-positive
Gram-positive

Gram-positive Bacteria are those that are stained dark blue or violet by Gram staining. This is in contrast to Gram-negative bacteria, which cannot retain the crystal violet stain, instead taking up the counterstain and appearing red or pink....
 bacteria.

Dicloxacillin has similar pharmacokinetics
Pharmacokinetics

Pharmacokinetics is a branch of pharmacology dedicated to the determination of the fate of substances administered externally to a living organism....
, antibacterial activity and indications to flucloxacillin and the two agents are considered interchangeable. It is believed to have lower incidence of severe hepatic adverse effects
Adverse effect (medicine)

In medicine, an adverse effect is a harmful and undesired effect resulting from a medication or other intervention such as chemotherapy or surgery....
 than flucloxacillin, but a higher incidence of renal adverse effects. (Rossi, 2006)

Available forms

Dicloxacillin is commercially available as the sodium salt dicloxacillin sodium in capsule
Capsule

The word capsule, or encapsulation, may refer to:* Capsule , a cover or envelope partly or wholly surrounding a structure.* Capsule , a type of dry fruit like the poppy, iris or foxglove....
s (250 or 500 mg) and injections (powder for reconstitution, 500 and 1000 mg per vial).

Indications

Dicloxacillin is indicated for the treatment of infections caused by susceptible bacteria. Specific approved indications include: (Rossi, 2006)
  • Staphylococcal skin infections
    Staphylococcus

    Staphylococcus is a genus of Gram-positive Bacterium. Under the microscope they appear round , and form in grape-like clusters.The Staphylococcus genus include just thirty-three species....
     and cellulitis
    Cellulitis

    Cellulitis is a diffuse infection of connective tissue with severe inflammation of dermal and subcutaneous layers of the skin. Cellulitis can be caused by normal skin Flora or by exogenous bacteria, and often occurs where the skin has previously been broken: cracks in the skin, cuts, blisters, burn , insect bites, surgical wounds, or sites o...
     – including impetigo
    Impetigo

    Impetigo is a superficial bacterial skin infection most common among children 2 to 6 years old. People who play close contact sports such as rugby football, American football and wrestling are also susceptible, regardless of age....
    , otitis externa
    Otitis externa

    Otitis externa is an inflammation of the outer ear and ear canal. Along with otitis media, external otitis is one of the two human conditions commonly called "earache"....
    , folliculitis
    Folliculitis

    Folliculitis is the inflammation of one or more hair follicles. The condition may occur anywhere on the skin....
    , boil
    Boil

    Boil is a skin disease caused by the infection of hair follicles, resulting in the localized accumulation of pus and dead tissue. Individual boils can cluster together and form an interconnected network of boils called carbuncles....
    s, carbuncles, and mastitis
    Mastitis

    Mastitis is the inflammation of the parenchyma of the mammary gland . It is called wikt:puerperal mastitis when it occurs in lactating mothers and non-puerperal otherwise....
  • Pneumonia
    Pneumonia

    Pneumonia is an Inflammation illness of the lung. Frequently, it is described as lung parenchyma/alveolus inflammation and abnormal alveolar filling with fluid ....
     (adjunct)
  • Osteomyelitis
    Osteomyelitis

    Osteomyelitis is an infection of bone or bone marrow, usually caused by pyogenic bacteria or mycobacteria. It can be usefully subclassified on the basis of the causative organism, the route, duration and anatomic location of the infection....
    , septic arthritis
    Septic arthritis

    Septic arthritis is the purulent invasion of a joint by an infectious agent which produces arthritis....
  • Septicaemia
  • Empirical
    Empirical

    The word empirical denotes information gained by means of observation, experience, or experiment, as opposed to theory. A central concept in science and the scientific method is that all evidence must be empirical, or empirically based, that is, dependent on evidence or Logical consequence that are observable by the senses....
     treatment for endocarditis
    Endocarditis

    Endocarditis is an inflammation of the inner layer of the heart, the endocardium. It usually involves the heart valves . Other structures which may be involved include the interventricular septum, the chordae tendinae, the mural endocardium, or even on intracardiac devices....
  • Surgical prophylaxis
    Prophylaxis

    Prophylaxis is any medical or public health procedure whose purpose is to prevent, rather than treat or cure a disease. Roughly, prophylactic measures are divided between primary prophylaxis and secondary prophylaxis ....


Precautions/contraindications

Dicloxacillin is contraindicated in those with a previous history of allergy to penicillin
Penicillin

Penicillin is a group of antibiotics derived from Penicillium fungi. They are Beta-lactam antibiotics used in the treatment of bacterial infections caused by susceptible, usually Gram-positive, organisms....
s, cephalosporin
Cephalosporin

The cephalosporins are a class of beta-lactam antibiotic originally derived from Acremonium, which was previously known as "Cephalosporium"....
s or carbapenem
Carbapenem

Carbapenems are a class of beta-lactam antibiotics with a broad spectrum of antibacterial activity, and have a structure which renders them highly resistant to beta-lactamases....
s. It should also not be used in the eye, or those with a history of cholestatic hepatitis
Cholestasis

In medicine, cholestasis is a condition where bile cannot flow from the liver to the duodenum. Bile formation is a secretory function of the liver....
 associated with the use of dicloxacillin or dicloxacillin. (Rossi, 2006)

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. (Rossi, 2006)

Adverse effects

Common adverse drug reaction
Adverse drug reaction

An adverse drug reaction or adverse drug event is an expression that describes the unwanted, negative consequences associated with the use of given medications....
s (ADRs) associated with the use of dicloxacillin include: diarrhoea, nausea
Nausea

Nausea is the sensation of unease and discomfort in the stomach with an urge to vomit....
, rash
Rash

A rash is a change of the skin which affects its color, appearance, or texture. A rash may be localized in one part of the body, or affect all the skin....
, urticaria
Urticaria

Urticaria are a kind of skin rash notable for dark red, raised, itchy bumps. Hives are frequently caused by allergic reactions, however there are many non-allergic causes....
, pain
Pain

Pain, in the sense of physical pain, is a typical sensory experience that may be described as the unpleasant awareness of a noxious stimulus or bodily harm....
 and inflammation
Inflammation

Inflammation is the complex biological response of Blood vessel tissues to harmful stimuli, such as pathogens, damaged cells, or irritants. It is a protective attempt by the organism to remove the injurious stimuli as well as initiate the healing process for the tissue....
 at injection site, superinfection
Superinfection

In virology, superinfection is the process by which a cell , that has previously been infected by one virus, gets coinfection with a different strain of the virus, or another virus at a later point in time....
 (including candidiasis
Candidiasis

Candidiasis, commonly called yeast infection or thrush, is a fungal infection of any of the Candida species, of which Candida albicans is the most common....
), allergy
Allergy

Allergy is a Disorder of the immune system often also referred to as atopy. Allergic reactions occur to Natural environmental substances known as allergens; these reactions are Acquired disorder, predictable and rapid....
, and transient increases in liver enzymes and bilirubin. (Rossi, 2006)Some other affects are also vomiting & cold sweats.(emma 2008)

Rarely, cholestatic jaundice
Cholestasis

In medicine, cholestasis is a condition where bile cannot flow from the liver to the duodenum. Bile formation is a secretory function of the liver....
 (also referred to as cholestatic hepatitis) has been associated with dicloxacillin 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. (Joint Formulary Committee, 2005; Rossi, 2006)

Resistance

Despite dicloxacillin being insensitive to beta-lactamses, some organisms have developed resistance to it and other narrow-spectrum ß-lactam antibiotics including methicillin. Such organisms include methicillin-resistant Staphylococcus aureus
Methicillin-resistant Staphylococcus aureus

Methicillin-resistant Staphylococcus aureus is a Bacteria responsible for difficult-to-treat infections in humans. It may also be referred to as multidrug-resistant Staphylococcus aureus or oxacillin-resistant Staphylococcus aureus ....
 (MRSA).

See also

  • Beta-lactam antibiotic
    Beta-lactam antibiotic

    ?-lactam antibiotics are a broad class of antibiotics that include penicillin derivatives, cephalosporins, monobactams, carbapenems, and Beta-lactamase inhibitors, that is, any antibiotic agent that contains a beta-lactam nucleus in its molecular structure....
  • Flucloxacillin
    Flucloxacillin

    Flucloxacillin or floxacillin is a narrow-spectrum antibiotic beta-lactam antibiotic of the penicillin class. It is used to treat infections caused by susceptible Gram-positive bacteria....
  • Amoxicillin
    Amoxicillin

    Amoxicillin or amoxycillin is a moderate-spectrum, bacteriolytic, beta-lactam antibiotic used to treat bacterial infections caused by susceptible microorganisms....
     formerly Beecham
    Beecham

    Stemming from the French name and place BeauchampBeecham can refer to:...
     and Glaxo Laboratories now GlaxoSmithKline
    GlaxoSmithKline

    GlaxoSmithKline plc is a United Kingdom-based pharmaceutical industry, biological, and healthcare company. GSK is the world's second largest pharmaceutical company and a research-based company with a wide portfolio of pharmaceutical products covering anti-infectives, central nervous system, respiratory, gastro-intestinal/metabolic,...