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Encyclopedia > Dicloxacillin
Chemical structure of Dicloxacillin.

Dicloxacillin
6-((S)-3-(2,6-dichlorophenyl)-5-methylisoxazole-
4-carboxamido)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo
[3.2.0]heptane-2-carboxylic acid
CAS number
3116-76-5
ATC code
J01CF01
PubChem
CID 3041
DrugBank
APRD00916
Chemical formula C19H17CI2N3O5S
Molecular weight 470.33
Bioavailability 60–80%
Metabolism hepatic
Elimination half-life 0.7 hours
Excretion renal
Pregnancy category B2 (Aust)
Legal status Schedule 4 (Aust)
Routes of administration oral, IV

Dicloxacillin (INN) is a narrow spectrum beta-lactam antibiotic. 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 flucloxacillin and these two agents are considered interchangeable. Dicloxacillin is available under a variety of trade names including Diclocil (BMS). CAS registry numbers are unique numerical identifiers for chemical compounds, polymers, biological sequences and alloys. ... The Anatomical Therapeutic Chemical Classification System is used for the classification of drugs. ... PubChem is a database of chemical molecules . ... DrugBank is a database available at the University of Alberta that provides information about thousands of products. ... A chemical formula (also called molecular formula) is a concise way of expressing information about the atoms that constitute a particular chemical compound. ... The molecular mass of a substance (less accurately called molecular weight and abbreviated as MW) is the mass of one molecule of that substance, relative to the unified atomic mass unit u (equal to 1/12 the mass of one atom of carbon-12). ... In pharmacology, bioavailability is used to describe the fraction of an administered dose of medication that reaches the systemic circulation, one of the principal pharmacokinetic properties of drugs. ... Santorio Santorio (1561-1636) in his steelyard balance, from Ars de statica medecina, first published 1614 Metabolism (from μεταβολισμος (metabolismos)), the Greek word for change, or overthrow (Etymonline)), is the biochemical modification of chemical compounds in living organisms and cells. ... The elimination half-life of a drug (or any xenobiotic agent) refers to the timecourse necessary for the quantity of the xenobiotic agent in the body (or plasma concentration) to be reduced to half of its original level through various elimination processes. ... Excretion is the biological process by which an organism chemically separates waste products from its body. ... The pregnancy category of a pharmaceutical agent is an assessment of the risk of fetal injury due to the pharmaceutical, if it is used as directed by the mother. ... Motto: none (formerly Advance Australia) Anthem: Advance Australia Fair Capital Canberra Largest city Sydney Official language(s) English (de facto)1 Government  â€¢ Queen  â€¢ Governor-General  â€¢ Prime Minister Const. ... The regulation of therapeutic goods, that is drugs and therapeutic devices, varies by jurisdiction. ... Motto: none (formerly Advance Australia) Anthem: Advance Australia Fair Capital Canberra Largest city Sydney Official language(s) English (de facto)1 Government  â€¢ Queen  â€¢ Governor-General  â€¢ Prime Minister Const. ... An intravenous drip in a hospital Intravenous therapy or IV therapy is the administration of liquid substances directly into a vein. ... An International Nonproprietary Name (INN) is the official non-proprietary or generic name given to a pharmaceutical substance, as designated by the World Health Organization. ... A narrow-spectrum antibiotic is an antibiotic that is useful for a restricted group of microorganisms. ... β-lactam antibiotics are a broad class of antibiotics including penicillin derivatives, cephalosporins, monobactams, carbapenems and β-lactamase inhibitors; basically any antibiotic agent which contains a β-lactam nucleus in its molecular structure. ... Gram-positive bacteria are those that are stained dark blue or violet by gram staining, in contrast to gram-negative bacteria, which are not affected by the stain. ... Kingdoms/Phyla/Divisions Actinobacteria Aquificae Bacteroidetes/Chlorobi Chlamydiae/Verrucomicrobia Chloroflexi Chrysiogenetes Cyanobacteria Deferribacteres Deinococcus-Thermus Dictyoglomi Fibrobacteres/Acidobacteria Firmicutes Fusobacteria Gemmatimonadetes Nitrospirae Planctomycetes Proteobacteria Spirochaetes Thermodesulfobacteria Thermomicrobia Thermotogae Bacteria (singular: bacterium) are a major group of living organisms. ... Beta-lactamase is a type of enzyme (EC 3. ... Binomial name Staphylococcus aureus Rosenbach, 1884 Staphylococcus aureus (which is occasionally given the nickname golden staph) is a bacterium, frequently living on the skin or in the nose of a healthy person, that can cause illnesses ranging from minor skin infections (such as pimples, boils, and cellulitis) and abscesses, to... Penicillin refers to a group of β-lactam antibiotics used in the treatment of bacterial infections caused by susceptible, usually Gram-positive, organisms. ... Flucloxacillin is a narrow-spectrum antibiotic in the penicillin group. ... Bristol-Myers Squibb NYSE: BMY, colloquially referred to as BMS, is a pharmaceutical corporation, formed by a 1989 merger between pharmaceutical companies Bristol-Myers Company and Squibb Corporation. ...

Contents


Mode of action

Main article: Beta-lactam antibiotic β-lactam antibiotics are a broad class of antibiotics including penicillin derivatives, cephalosporins, monobactams, carbapenems and β-lactamase inhibitors; basically any antibiotic agent which contains a β-lactam nucleus in its molecular structure. ...


Like other β-lactam antibiotics, dicloxacillin 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. A cell wall is a more or less solid layer surrounding a cell. ... Peptidoglycan, also known as murein, is a substance that forms a homogeneous layer lying outside the plasma membrane in bacteria. ... Gram-positive bacteria are those that are stained dark blue or violet by gram staining, in contrast to gram-negative bacteria, which are not affected by the stain. ...


Medicinal chemistry

Dicloxacillin 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. Beta-lactamase is a type of enzyme (EC 3. ... Steric effects are the interaction of molecules dictated by their shape and/or spatial relationships. ... Peptidoglycan, also known as murein, is a substance that forms a homogeneous layer lying outside the plasma membrane in bacteria. ...


Clinical use

Dicloxacillin 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. 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. ... Methicillin is an antibiotic related to penicillin and other beta-lactam containing antibiotics. ... Gram-positive bacteria are those that are stained dark blue or violet by gram staining, in contrast to gram-negative bacteria, which are not affected by the stain. ...


Dicloxacillin has similar pharmacokinetics, 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 than flucloxacillin, but a higher incidence of renal adverse effects. (Rossi, 2006) Pharmacokinetics is a branch of pharmacology dedicated to the study of the time course of substances and their relationship with an organism or system. ... Adverse effect, in medicine, is an abnormal, harmful, undesired and/or unintended side-effect, although not necessarily unexpected, which is obtained as the result of a therapy or other medical intervention, such as drug/chemotherapy, physical therapy, surgery, medical procedure, use of a medical device, etc. ...


Available forms

Dicloxacillin is commercially available as the sodium salt dicloxacillin sodium in capsules (250 or 500 mg) and injections (powder for reconstitution, 500 and 1000 mg per vial). The word capsule (from the Latin capsula, a small box), has many similar meanings in English: In botany, a capsule is a type of dry fruit as in the poppy, iris, foxglove, etc. ... The milligram (symbol mg) is an SI unit of mass. ...


Indications

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

Species S. aureus S. caprae S. epidermidis S. haemolyticus S. hominis S. lugdunensis S. saprophyticus S. warneri S. xylosus Staphylococcus (in Greek staphyle means bunch of grapes and coccos means granule) is a genus of gram-positive bacteria. ... Folliculitis is inflammation of one or more hair follicles. ... Boil or furuncle is a skin disease caused by the inflammation of hair follicles, thus resulting in the localized accumulation of pus and dead tissues. ... A carbuncle is an abscess larger than a boil, usually with one or more openings draining pus onto the skin. ... Mastitis is the inflammation of the mammalian breast caused by the blocking of the milk ducts while the mother is lactating (see breastfeeding). ... Pneumonia is an illness of the lungs and respiratory system in which the microscopic, air-filled sacs (alveoli) responsible for absorbing oxygen from the atmosphere become inflamed and flooded with fluid. ... Osteomyelitis is an infection of bone, usually caused by pyogenic bacteria or mycobacteria. ... Septic arthritis is the proliferation of bacteria in joints and resultant inflammation. ... Sepsis (in Greek Σήψις) is a serious medical condition caused by a severe systemic infection leading to a systemic inflammatory response. ... Empirical is an adjective often used in conjunction with science, both the natural and social sciences, which means an observation or experiment based upon experience that is capable of being verified or disproved. ... Endocarditis is an inflammation of the inner layer of the heart, the endocardium. ... Prophylaxis refers to any medical or public health procedure whose purpose is to prevent, rather than treat or cure, disease. ...

Precautions/contraindications

Dicloxacillin 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 dicloxacillin. (Rossi, 2006) Penicillin refers to a group of β-lactam antibiotics used in the treatment of bacterial infections caused by susceptible, usually Gram-positive, organisms. ... The cephalosporins, are a class of β-lactam antibiotics. ... Carbapenems are a class of beta-lactam antibiotics. ... it relates to ciongetive pressures on the intestinal walls from blockage related to low fiber in the diet. ...


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 reactions (ADRs) associated with the use of dicloxacillin include: diarrhoea, nausea, rash, urticaria, pain and inflammation at injection site, superinfection (including candidiasis), allergy, and transient increases in liver enzymes and bilirubin. (Rossi, 2006) An adverse drug reaction (abbreviated ADR) is a term to describe the unwanted, negative consequences sometimes associated with the use of medications. ... Diarrhoea is the correct way to spell the word Diarrhoea. ... Nausea (Greek Ναυτεία) is the sensation of unease and discomfort in the stomach with an urge to vomit. ... RASH (Red and Anarchist Skinheads) is a left-wing anti-racist, anti-fascist skinhead group. ... Pain is an unpleasant sensation which may be associated with actual or potential tissue damage and which may have physical and emotional components. ... Inflammation is the first response of the immune system to infection or irritation and may be referred to as the innate cascade. ... In virology, superinfection describes the process by which a cell that has previously been infected by one virus gets coinfected with another virus at a later point in time. ... An allergy or Type I hypersensitivity is an immune malfunction whereby a persons body is hypersensitised to react immunologically to typically nonimmunogenic substances. ...


Rarely, cholestatic jaundice (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) it relates to ciongetive pressures on the intestinal walls from blockage related to low fiber in the diet. ...


Resistance

Despite dicloxacillin being insensitive to beta-lactamses, some organisms have developed resistance to it and other narrow-spectrum β-lactam antibiotics including methicillin. Such organisms include methicillin-resistant Staphylococcus aureus (MRSA). Electron micrograph of MRSA Methicillin-resistant Staphylococcus aureus, (MRSA) is a specific strain of the Staphylococcus aureus bacterium that has developed antibiotic resistance, first to penicillin since 1947, and later to methicillin and related anti-staphylococcal drugs. ...


See also

β-lactam antibiotics are a broad class of antibiotics including penicillin derivatives, cephalosporins, monobactams, carbapenems and β-lactamase inhibitors; basically any antibiotic agent which contains a β-lactam nucleus in its molecular structure. ... Flucloxacillin is a narrow-spectrum antibiotic in the penicillin group. ...

References


  Results from FactBites:
 
Dicloxacillin - Drugs & Vitamins - Drug Library - DrugDigest (561 words)
Dicloxacillin kills certain bacteria that cause infection, or stops their growth.
Dicloxacillin treats infections of the skin and soft tissues, joints, urinary and respiratory tracts.
Take dicloxacillin 1 to 2 hours before or at least 2 hours after eating; taking it with food can make it less effective.
dicloxacillin - [Medication] (1189 words)
Dicloxacillin is in the FDA pregnancy category B. This means that it is not expected to be harmful to an unborn baby.
Dicloxacillin should be taken at evenly spaced intervals throughout the day and night to keep the medicine level in your blood high enough to treat the infection.
Symptoms of an dicloxacillin overdose include muscle spasms or weakness, pain or twitching, pain in the fingers or toes, loss of feeling in the fingers or toes, seizures, confusion, coma, or agitation.
  More results at FactBites »


 

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