Flucloxacillin

Source: Wikipedia, the free encyclopedia.
Flucloxacillin
Clinical data
Trade namesFloxapen, others[1]
Other namesBRL-2039
AHFS/Drugs.comInternational Drug Names
Pregnancy
category
  • AU: B1
intraarticular
ATC code
Legal status
Legal status
  • AU: S4 (Prescription only)
  • UK: POM (Prescription only)
  • EU: Rx-only[2]
Pharmacokinetic data
Bioavailability50–70%
MetabolismLiver
Elimination half-life0.75–1 hour[3]
ExcretionKidney[3]
Identifiers
  • (2S,5R,6R)-6-({[3-(2-chloro-5-fluorophenyl)-5-methylisoxazol-4-yl]carbonyl}amino)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
JSmol)
  • O=C(O)[C@@H]3N4C(=O)[C@@H](NC(=O)c2c(onc2c1c(F)cccc1Cl)C)[C@H]4SC3(C)C
  • InChI=1S/C19H17ClFN3O5S/c1-7-10(12(23-29-7)11-8(20)5-4-6-9(11)21)15(25)22-13-16(26)24-14(18(27)28)19(2,3)30-17(13)24/h4-6,13-14,17H,1-3H3,(H,22,25)(H,27,28)/t13-,14+,17-/m1/s1 checkY
  • Key:UIOFUWFRIANQPC-JKIFEVAISA-N checkY
  (verify)

Flucloxacillin, also known as floxacillin, is an

skin infections, external ear infections, infections of leg ulcers, diabetic foot infections, and infection of bone.[4] It may be used together with other medications to treat pneumonia, and endocarditis.[4] It may also be used prior to surgery to prevent Staphylococcus infections.[4] It is not effective against methicillin-resistant Staphylococcus aureus (MRSA).[5] It is taken by mouth or given by injection into a vein or muscle.[4]

Common side effects include an upset stomach.

penicillinase forming bacteria.[7]

Flucloxacillin was patented in 1961.[8] It is not commonly used in the United States or Canada as of 2011.[9]

Medical uses

Flucloxacillin is an

skin infections, external ear infections, infections of leg ulcers, diabetic foot infections, and infection of bone.[4]

Skin

Flucloxacillin is used for both

eczema, scabies, ulcers and acne.[4][10][12] Due to the widespread belief that dual-therapy is needed to cover both Staphylococcus and Streptococcus in cellulitis, flucloxacillin is sometimes given with the addition of benzylpenicillin for more severe cellulitis.[3] However, support for this practice has lessened since findings in a study published in the Emergency Medicine Journal in 2005 did not show this combination to give additional clinical benefit.[13][14][15] In the UK, using flucloxacillin alone is the first choice for treating cellulitis. Some other countries vary.[16]

  • Impetigo
    Impetigo
  • Erysipelas
    Erysipelas
  • Folliculitis
    Folliculitis
  • Cellulitis
    Cellulitis
  • Carbuncle
    Carbuncle

Wounds

Infections of leg ulcers can be treated with flucloxacillin.[4] With diabetic foot infections the dose is adjusted according to whether the infection appears mild, moderate or severe.[4]

Bone

Despite having a lower than optimum drug penetration into bone ratio of 10–20%, flucloxacillin appears effective in treating osteomyelitis.[17][18]

Depending on local guidance it may be used in the treatment of infection of joints while waiting for culture results.[3][19]

Other

It may be used in combination with other antibiotics to treat pneumonia and can be used to prevent infection before surgery, particularly heart, lung, or bone surgery.[4][12] When used to treat endocarditis, in combination with other antibiotics or alone, the dose of flucloxacillin may need to exceed the usual dose.[4]

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, which has developed resistance to flucloxacillin and other penicillins by having an altered penicillin-binding protein.[20]

Side effects

Common side effects associated with the use of flucloxacillin include:

urticaria, pain and inflammation at injection site, superinfection (including candidiasis), allergy, and transient increases in liver enzymes and bilirubin.[21]

Rarely, in fewer than 1 in 1,000 people, cholestatic jaundice (also referred to as cholestatic hepatitis) has been associated with flucloxacillin therapy. It may appear as pale stool with dark urine, and yellowish eyes and skin.[22] The reaction may occur up to several weeks after treatment has stopped, and takes weeks to resolve. The estimated incidence is one in 15,000 exposures, and is more frequent in people over the age of 55, females, and those with a treatment duration of longer than two weeks.[4][22][21]

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 administered to those with a history of cholestatic hepatitis associated with the use of dicloxacillin or flucloxacillin.[21]

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.[21]

It should be taken on an empty stomach, one half to one hour before food, as absorption is reduced when taken with food,[23] though some studies suggest that this does not compromise flucloxacillin plasma concentrations in most circumstances.[24]

The UK's National Health Service recommends taking at least 30 minutes before food and at least 2 hours after.[22]

Drug interactions

Flucloxacillin can reduce the excretion of methotrexate, potentially resulting in a risk of methotrexate toxicity. The level of flucloxacillin in the blood may rise in kidney failure and with the use of probenecid.[7]

Mechanism of action

Main article:
Beta-lactam antibiotic

Flucloxacillin is a

antibiotic belonging to the penicillin group of antibiotics.[6][25] It works by breaking down the bacterial cell wall.[25]

Like other β-lactam antibiotics, flucloxacillin

Gram-positive bacteria.[citation needed
]

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.[citation needed
]

Flucloxacillin has similar

adverse effects than dicloxacillin,[26] but a lower incidence of renal adverse effects.[21]

Chemistry

Flucloxacillin is insensitive to

penicillin-binding proteins and inhibit peptidoglycan crosslinking, but is not bound by or inactivated by β-lactamases.[citation needed
]

History

Flucloxacillin was developed in the 1960s following an increase in penicillin-resistant (

Bristol Laboratories concentrated on marketing oxacillin and dicloxacillin in the United States, leading to the difference in use in both countries.[29][30] Flucloxacillin was first marketed in Europe in the 1970s.[6]

Available forms

Both the oral and intravenous preparations of flucloxacillin are inexpensive and are 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, 1000 and 2000 mg per vial).[3][31]

Flucloxacillin is not commonly used in the United States or Canada as of 2011.[6] In several other countries however, it is supplied under a variety of trade names including Floxapen, Flopen, Flubex, Flupen, Phylopen, and Staphylex.[1]

Combination

Main article:
Co-fluampicil

Flucloxacillin is combined with

co-fluampicil.[4]

  • Flucloxacillin powder for oral solution 125 mg/5ml, with measuring spoon
    Flucloxacillin powder for oral solution 125 mg/5ml, with measuring spoon
  • Selection of Flucloxacillin preparations found in the UK
    Selection of Flucloxacillin preparations found in the UK
  • Co-fluampicil: Flucloxacillin combined with ampicillin (UK)
    Co-fluampicil: Flucloxacillin combined with ampicillin (UK)

References

  1. ^ a b "Flucloxacillin". Drugs.com. Retrieved 11 December 2020.
  2. ^ List of nationally authorised medicinal products. European Medicines Agency. November 2020
  3. ^
    ISBN 978-0-7020-5516-4
    .
  4. ^
    ISBN 978-0-85711-369-6
    .
  5. ^ "Methicillin-resistant Staphylococcus aureus (MRSA)" (PDF). NHS. 2005. p. 3. Archived from the original (PDF) on 12 December 2020. Retrieved 11 December 2020.
  6. ^
    ISBN 978-1-60761-283-4
    .
  7. ^
    ISBN 978-1-118-85097-8
    .
  8. ISBN 978-3-527-31257-3
    .
  9. S2CID 1259750
    .
  10. ^ a b Stanway, Amy. "Streptococcal skin infection – DermNet New Zealand". www.dermnetnz.org.
  11. ISBN 978-0-19-966554-9
    .
  12. ^ a b "Flucloxacillin 125mg/5ml Oral solution – Summary of Product Characteristics (SmPC) – (emc)". medicines.org.uk. Archived from the original on 2 March 2021. Retrieved 16 December 2020.
  13. PMID 15843702
    .
  14. ISBN 978-1-4377-0859-2
    .
  15. ISBN 978-1-4051-4518-3
    .
  16. PMID 29626022
    .
  17. PMID 32117685
    .
  18. PMID 30772469
    .
  19. ISBN 978-0-7020-2765-9
    .
  20. S2CID 204066905
    .
  21. ^ a b c d e Rossi S, editor. Australian Medicines Handbook 2006. Adelaide: Australian Medicines Handbook; 2006.
  22. ^ a b c "Flucloxacillin: antibiotic to treat infections". nhs.uk. 27 November 2018.
  23. ^ "New Zealand Consumer Medicine Information" (PDF). medsafe.govt.nz.
  24. PMID 30001392
    .
  25. ^ a b "Flucloxacillin sodium salt". pubchem.ncbi.nlm.nih.gov. PubChem at the National Institutes of Health. Retrieved 13 December 2020.
  26. PMID 31643436
    .
  27. ^
    ISBN 978-1-4614-1399-8
    .
  28. ^
    ISBN 978-1-4614-1399-8
    .
  29. ISBN 978-0-19-953484-5
    .
  30. PMID 5481218
    .
  31. ^ "Search Results – Flucloxacillin". medicines.org.uk. Retrieved 16 December 2020.
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