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| Clinical data | |
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| AHFS/Drugs.com | Monograph |
| MedlinePlus | a685017 |
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| Routes of administration | Oral |
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| Legal status | |
| Pharmacokinetic data | |
| Bioavailability | 60 to 80% |
| Protein binding | 98% |
| Metabolism | Hepatic |
| Eliminationhalf-life | 0.7 hours |
| Excretion | Renal and biliary |
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| CAS Number | |
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| ChEBI | |
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| CompTox Dashboard(EPA) | |
| ECHA InfoCard | 100.019.535 |
| Chemical and physical data | |
| Formula | C19H17Cl2N3O5S |
| Molar mass | 470.32 g·mol−1 |
| 3D model (JSmol) | |
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Dicloxacillin is anarrow-spectrumβ-lactam antibiotic of thepenicillin class.[1] It is used to treat infections caused by susceptible (non-resistant)Gram-positive bacteria.[1] It is active againstbeta-lactamase-producing organisms such asStaphylococcus aureus, which would otherwise be resistant to mostpenicillins. Dicloxacillin is available under a variety of trade names including Diclocil (BMS).[2]
It was patented in 1961 and approved for medical use in 1968.[3] It is available as ageneric medication.[4]
Dicloxacillin is used to treat mild-to-moderate staphylococcal infections.[5] To decrease the development of resistance, dicloxacillin is recommended to treat infections that are suspected or proven to be caused by beta-lactamase-producing bacteria.[5]
Dicloxacillin is similar inpharmacokinetics, antibacterial activity, and indications to flucloxacillin, and the two agents are considered interchangeable.[6] It is believed to have lower incidence of severe hepaticadverse effects than flucloxacillin, but a higher incidence of renal adverse effects.[6]
Dicloxacillin is used for the treatment of infections caused by susceptible bacteria. Specific approved indications include:[6]
Dicloxacillin is commercially available as the sodium salt,dicloxacillin sodium, incapsules and as a powder for reconstitution.[1][7]
Dicloxacillin is contraindicated in those with a previous history of allergy (hypersensitivity/anaphylactic reaction) to any penicillins.[1][8]
Commonadverse drug reactions (ADRs) associated with the use of dicloxacillin include:diarrhea,nausea,rash,urticaria,pain andinflammation at injection site,superinfection (includingcandidiasis),allergy, and transient increases in liver enzymes and bilirubin.[6]
On rare occasions,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 over 55 years old, females, and those with treatment longer than 2 weeks.[6]
It should be used with caution and monitored in the elderly, particularly with intravenous administration, due to a risk ofthrombophlebitis.[1]
Dicloxacillin can also lower the effectiveness of birth control pills and pass into breast milk.[9]
Dicloxacillin has potential interactions with following drugs:
Despite dicloxacillin being insensitive to beta-lactamases, some organisms have developed resistance to other narrow-spectrum β-lactam antibiotics including methicillin. Such organisms includemethicillin-resistantStaphylococcus aureus (MRSA).[13][better source needed]
Like other β-lactam antibiotics, dicloxacillin acts by inhibiting the synthesis of bacterialcell walls. It inhibits cross-linkage between the linearpeptidoglycan polymer chains that make up a major component of the cell wall ofGram-positive bacteria.[citation needed]
Dicloxacillin is insensitive tobeta-lactamase (also known as penicillinase) enzymes secreted by many penicillin-resistant bacteria. The presence of theisoxazolyl group on the side chain of the penicillin nucleus facilitates the β-lactamase resistance, since they are relatively intolerant of side-chainsteric hindrance. Thus, it is able to bind topenicillin-binding proteins (PBPs) and inhibitpeptidoglycan crosslinking, but is not bound by or inactivated by β-lactamase[citation needed]
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