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Revision as of 12:28, 17 November 2011 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Saving copy of the {{drugbox}} taken from revid 456155649 of page Flucloxacillin for the Chem/Drugbox validation project (updated: 'DrugBank').  Latest revision as of 06:45, 2 October 2024 edit Azn bookworm10 (talk | contribs)Extended confirmed users1,273 editsm →Skin: MOS:ITALSCINAMES and WP:NOPIPE 
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{{Short description|Penicillin}}
{{ambox | text = This page contains a copy of the infobox ({{tl|drugbox}}) taken from revid of page ] with values updated to verified values.}}
{{Use dmy dates|date=June 2022}}
{{Drugbox
{{cs1 config |name-list-style=vanc |display-authors=6}}
| verifiedrevid = 443820900
{{Infobox drug
| IUPAC_name = (2''S'',5''R'',6''R'')-6-({carbonyl}amino)-3,3-dimethyl-7-oxo-4-thia-1-azabicycloheptane-2-carboxylic acid
| Watchedfields = changed
| verifiedrevid = 461101078
| image = Flucloxacillin.svg | image = Flucloxacillin.svg
| alt =
| image2 = Flucloxacillin-from-xtal-1980-3D-balls.png | image2 = Flucloxacillin-from-xtal-1980-3D-balls.png
| alt2 =
| caption =


<!--Clinical data--> <!-- Clinical data -->
| tradename = | pronounce =
| tradename = Floxapen, others<ref name=Drugs.com>{{cite web |title=Flucloxacillin |url=https://www.drugs.com/international/flucloxacillin.html |website=Drugs.com |access-date=11 December 2020 }}</ref>
| Drugs.com = {{drugs.com|CONS|flucloxacillin}}
| Drugs.com = {{drugs.com|international|flucloxacillin}}
| MedlinePlus =
| DailyMedID = <!-- DailyMed may use generic or brand name (generic name preferred) -->
| pregnancy_AU = B1 | pregnancy_AU = B1
| pregnancy_AU_comment =
| pregnancy_US =
| pregnancy_category=
| routes_of_administration = ], ], ], ], ]
| class =
| ATC_prefix = J01
| ATC_suffix = CF05
| ATC_supplemental =

<!-- Legal status -->
| legal_AU = S4 | legal_AU = S4
| legal_AU_comment = <ref>{{cite web | title=Flucloxacillin Baxter (Baxter Healthcare Pty Ltd) | website=Therapeutic Goods Administration (TGA) | date=13 September 2024 | url=https://www.tga.gov.au/resources/prescription-medicines-registrations/flucloxacillin-baxter-baxter-healthcare-pty-ltd | access-date=15 September 2024}}</ref><ref>https://www.tga.gov.au/resources/prescription-medicines-registrations/eug-flucloxacillin-eugia-pharma-australia-pty-ltd</ref>
| legal_BR = <!-- OTC, A1, A2, A3, B1, B2, C1, C2, C3, C4, C5, D1, D2, E, F -->
| legal_BR_comment =
| legal_CA = <!-- OTC, Rx-only, Schedule I, II, III, IV, V, VI, VII, VIII -->
| legal_CA_comment =
| legal_DE = <!-- Anlage I, II, III or Unscheduled -->
| legal_DE_comment =
| legal_NZ = <!-- Class A, B, C -->
| legal_NZ_comment =
| legal_UK = POM | legal_UK = POM
| legal_UK_comment =
| legal_US =
| legal_US = <!-- OTC / Rx-only / Schedule I, II, III, IV, V -->
| routes_of_administration = Oral, ], ], ], ]
| legal_US_comment =
| legal_EU = Rx-only
| legal_EU_comment =<ref name=EMA2020>. European Medicines Agency. November 2020</ref>
| legal_UN = <!-- N I, II, III, IV / P I, II, III, IV -->
| legal_UN_comment =
| legal_status = <!-- For countries not listed above -->


<!--Pharmacokinetic data--> <!-- Pharmacokinetic data -->
| bioavailability = 50–70% | bioavailability = 50–70%
| protein_bound =
| metabolism = ]
| metabolism = ]
| elimination_half-life = 0.75–1 hour
| metabolites =
| excretion = ]
| onset =
| elimination_half-life = 0.75–1 hour<ref name=Hitchings2015>{{Cite book| vauthors = Hitchings A, Lonsdale D, Burrage D, Baker E |url=https://books.google.com/books?id=oeYjAwAAQBAJ&pg=PA180|title=The Top 100 Drugs e-book: Clinical Pharmacology and Practical Prescribing|date=2015|publisher=Churchill Livingstone; Elsevier|isbn=978-0-7020-5516-4|pages=181|language=en}}</ref>
| duration_of_action =
| excretion = ]<ref name=Hitchings2015/>


<!--Identifiers--> <!-- Identifiers -->
| CASNo_Ref = {{cascite|correct|CAS}} | CAS_number_Ref = {{cascite|correct|CAS}}
| CAS_number = 5250-39-5 | CAS_number = 5250-39-5
| ATC_prefix = J01
| ATC_suffix = CF05
| ATC_supplemental = {{ATCvet|J51|CF05}}
| PubChem = 21319
| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
| DrugBank = DB00301
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 20037
| UNII_Ref = {{fdacite|correct|FDA}} | UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 43B2M34G2V | UNII = 43B2M34G2V
| CAS_supplemental =
| KEGG_Ref = {{keggcite|correct|kegg}}
| PubChem = 21319
| IUPHAR_ligand =
| DrugBank_Ref =
| DrugBank = DB00301
| ChemSpiderID_Ref =
| ChemSpiderID =
| KEGG_Ref =
| KEGG = D04196 | KEGG = D04196
| ChEBI_Ref = {{ebicite|correct|EBI}} | ChEBI_Ref =
| ChEBI = 5098 | ChEBI = 5098
| ChEMBL_Ref = {{ebicite|correct|EBI}} | ChEMBL_Ref =
| ChEMBL = 222645 | ChEMBL = 222645
| NIAID_ChemDB =
| PDB_ligand =
| synonyms = BRL-2039


<!--Chemical data--> <!-- Chemical and physical data -->
| IUPAC_name = (2''S'',5''R'',6''R'')-6-({carbonyl}amino)-3,3-dimethyl-7-oxo-4-thia-1-azabicycloheptane-2-carboxylic acid
| C=19 | H=17 | Cl=1 | F=1 | N=3 | O=5 | S=1
| C=19 | H=17 | Cl=1 | F=1 | N=3 | O=5 | S=1
| molecular_weight = 453.87 g/mol
| smiles = O=C(O)3N4C(=O)(NC(=O)c2c(onc2c1c(F)cccc1Cl)C)4SC3(C)C | SMILES = O=C(O)3N4C(=O)(NC(=O)c2c(onc2c1c(F)cccc1Cl)C)4SC3(C)C
| InChI = 1/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
| InChIKey = UIOFUWFRIANQPC-JKIFEVAIBS
| StdInChI_Ref = {{stdinchicite|correct|chemspider}} | StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 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 | StdInChI = 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
| StdInChI_comment =
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = UIOFUWFRIANQPC-JKIFEVAISA-N | StdInChIKey = UIOFUWFRIANQPC-JKIFEVAISA-N
| density =
| density_notes =
| melting_point =
| melting_high =
| melting_notes =
| boiling_point =
| boiling_notes =
| solubility =
| sol_units =
| specific_rotation =
}} }}

<!-- Definition and medical uses -->
'''Flucloxacillin''', also known as '''floxacillin''', is an ] used to treat ], ], infections of leg ulcers, diabetic foot infections, and ].<ref name=BNF80>{{cite book | title=]|date= September 2020 – March 2021|publisher=BMJ Group and the Pharmaceutical Press|isbn=978-0-85711-369-6|edition=80|pages=582–587|chapter=5.2 Bacterial Infection}}</ref> It may be used together with other medications to treat ], and ].<ref name=BNF80/> It may also be used prior to surgery to prevent '']'' infections.<ref name=BNF80/> It is not effective against ] (MRSA).<ref>{{cite web |title=Methicillin-resistant Staphylococcus aureus (MRSA) |url=https://www.nhs.uk/conditions/mrsa/documents/rcn%20mrsa%20guidelines.pdf |website=NHS |access-date=11 December 2020 |page=3 |year=2005 |archive-date=12 December 2020 |archive-url=https://web.archive.org/web/20201212081203/https://www.nhs.uk/conditions/mrsa/documents/rcn%20mrsa%20guidelines.pdf |url-status=dead }}</ref> It is taken by mouth or given by injection into a vein or muscle.<ref name=BNF80/>

<!-- Side effects and mechanism -->
Common side effects include an upset stomach.<ref name=BNF80/> Other side effects may include muscle or joint pains, shortness of breath, and liver problems.<ref name=BNF80/><ref name="Wu2011">{{cite book |url=https://books.google.com/books?id=5v-Qa5BRKH0C&pg=PA240 |title=Pharmacogenomic Testing in Current Clinical Practice: Implementation in the Clinical Laboratory |vauthors=Wu AH, Yeo KT |date=2011 |publisher=Springer Science & Business Media |isbn=978-1-60761-283-4 |language=en}}</ref> It appears to be safe during pregnancy and breastfeeding.<ref name=BNF80/> It should not be used in those who are allergic to ].<ref name=BNF80/> It is a ] ] of the ] class.<ref name=Wu2011/> It is similar in effect to ] and ], being active against ] forming bacteria.<ref name=Weller2014>{{cite book | vauthors = Weller RB, Hunter HJ, Mann MW |title=Clinical Dermatology |date=2014 |publisher=John Wiley & Sons |isbn=978-1-118-85097-8 |page=411 |url=https://books.google.com/books?id=4sJoBQAAQBAJ&pg=PA411|language=en}}</ref>

<!-- Society and culture -->
Flucloxacillin was patented in 1961.<ref name="Alapi2006">{{cite book | vauthors = Alapi EM, Fischer J | veditors = Fischer J, Ganellin CR |title=Analogue-based Drug Discovery |date=2006 |publisher=Wiley-VCH |isbn=978-3-527-31257-3 |page=491 |chapter-url=https://books.google.com/books?id=FjKfqkaKkAAC&pg=PA491 |language=en |chapter=Part III. Table of Selected Analogue Classes}}</ref> It is not commonly used in the United States or Canada as of 2011.<ref>{{cite journal | vauthors = Devereaux BM, Crawford DH, Purcell P, Powell LW, Roeser HP | title = Flucloxacillin associated cholestatic hepatitis. An Australian and Swedish epidemic? | journal = European Journal of Clinical Pharmacology | volume = 49 | issue = 1–2 | pages = 81–85 | date = 1995 | pmid = 8751026 | doi = 10.1007/BF00192363 | s2cid = 1259750 }}</ref>

==Medical uses==
Flucloxacillin is an ] used to treat ], ], infections of leg ulcers, ]s, and ].<ref name=BNF80/>

===Skin===
Flucloxacillin is used for both ] and ] skin infections.<ref name=Stanway>Stanway, Amy. {{cite web|url=http://www.dermnetnz.org/topics/streptococcal-skin-infections/|title=Streptococcal skin infection – DermNet New Zealand|website=www.dermnetnz.org|date=26 October 2023 }}</ref> These include ], ],<ref name=Gould2016>{{Cite book| vauthors = Gould K | chapter-url=https://books.google.com/books?id=uM6SDAAAQBAJ&pg=PA177|title=Oxford Textbook of Fundamentals of Surgery |date=2016|publisher=Oxford University Press|isbn=978-0-19-966554-9| veditors = Thomas WE, Reed MW, Wyatt MG |pages=176–177|language=en|chapter=1.6 Applied surgical microbiology}}</ref> ], ], ], ], ], and infections of skin conditions such as ], ], ulcers and ].<ref name=BNF80/><ref name=Stanway/><ref name="EMC125">{{cite web |title=Flucloxacillin 125mg/5ml Oral solution – Summary of Product Characteristics (SmPC) – (emc) |url=https://www.medicines.org.uk/emc/product/527/smpc |website=medicines.org.uk |access-date=16 December 2020 |archive-date=2 March 2021 |archive-url=https://web.archive.org/web/20210302053327/https://www.medicines.org.uk/emc/product/527/smpc |url-status=dead }}</ref> 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 ] for more severe cellulitis.<ref name=Hitchings2015/> However, support for this practice has lessened since findings in a study published in the '']'' in 2005 did not show this combination to give additional clinical benefit.<ref name=Leman2005>{{cite journal | vauthors = Leman P, Mukherjee D | title = Flucloxacillin alone or combined with benzylpenicillin to treat lower limb cellulitis: a randomised controlled trial | journal = Emergency Medicine Journal | volume = 22 | issue = 5 | pages = 342–6 | date = May 2005 | pmid = 15843702 | pmc = 1726763 | doi = 10.1136/emj.2004.019869 }}</ref><ref name="Sark2011">{{Cite book| vauthors = Sarkar R, Nair V, Sinha S, Garg VK, Rodriguez DA |chapter-url=https://books.google.com/books?id=ERVywKMMqAsC&pg=PA121|title=Treatments for Skin of Color E-Book|date=2011|publisher=Saunders Elsevier|isbn=978-1-4377-0859-2| veditors = Taylor S, Gathers RC, Callender VD, Rodriguez DA, Badreshia-Bansal SC |pages=121|language=en|chapter=7. Infectious diseases}}</ref><ref name="Cox2009">{{Cite book| vauthors = Cox NH |chapter-url=https://books.google.com/books?id=SbsQij5xkfYC&q=Flucloxacillin+alone+or+combined+with+benzylpenicillin&pg=PA409|title=Evidence-Based Dermatology|date=2009|publisher=Blackwell Publishing|isbn=978-1-4051-4518-3| veditors = Williams H, Bigby M, Diepgen T, Herxheimer A, Naldi L, Rzany B |edition=2nd|pages=409|language=en|chapter=41. Streptococcal Cellulitis/Erysipelas of the lower leg}}</ref> In the UK, using flucloxacillin alone is the first choice for treating cellulitis. Some other countries vary.<ref name=Sullivan2018>{{cite journal | vauthors = Sullivan T, de Barra E | title = Diagnosis and management of cellulitis | journal = Clinical Medicine | volume = 18 | issue = 2 | pages = 160–163 | date = March 2018 | pmid = 29626022 | pmc = 6303460 | doi = 10.7861/clinmedicine.18-2-160 }}</ref>
<gallery mode="packed" widths="160px" heights="120">

File:Impetigo2020.jpg|Impetigo
File:Facial erysipelas.jpg|Erysipelas
File:Folliculitis2.jpg|Folliculitis
File:Cellulitis1.jpg|Cellulitis
File:Carbuncle.jpg|Carbuncle
</gallery>

===Wounds===
Infections of leg ulcers can be treated with flucloxacillin.<ref name=BNF80/> With diabetic foot infections the dose is adjusted according to whether the infection appears mild, moderate or severe.<ref name=BNF80/>

===Bone===
Despite having a lower than optimum drug penetration into bone ratio of 10–20%, flucloxacillin appears effective in treating ].<ref name=Preiss2020>{{cite journal | vauthors = Preiss H, Kriechling P, Montrasio G, Huber T, Janssen İ, Moldovan A, Lipsky BA, Uçkay İ | display-authors = 6 | title = Oral Flucloxacillin for Treating Osteomyelitis: A Narrative Review of Clinical Practice | journal = Journal of Bone and Joint Infection | volume = 5 | issue = 1 | pages = 16–24 | date = 1 January 2020 | pmid = 32117685 | pmc = 7045523 | doi = 10.7150/jbji.40667 }}</ref><ref>{{cite journal | vauthors = Thabit AK, Fatani DF, Bamakhrama MS, Barnawi OA, Basudan LO, Alhejaili SF | title = Antibiotic penetration into bone and joints: An updated review | language = en | journal = International Journal of Infectious Diseases | volume = 81 | pages = 128–136 | date = April 2019 | pmid = 30772469 | doi = 10.1016/j.ijid.2019.02.005 | url = https://www.ijidonline.com/article/S1201-9712(19)30069-4/abstract | doi-access = free }}</ref>

Depending on local guidance it may be used in the treatment of ] while waiting for culture results.<ref name=Hitchings2015/><ref name="KumarClark2011">{{cite book| vauthors = Kumar P, Clark ML |title=Kumar & Clark's Medical Management and Therapeutics – E-Book|chapter-url=https://books.google.com/books?id=RUHFAAAAQBAJ&pg=PA322|year=2011|publisher=Elsevier|isbn=978-0-7020-2765-9|page=322|chapter=9. Drugs in Rheumatology}}</ref>

===Other===
It may be used in combination with other antibiotics to treat ] and can be used to prevent infection before surgery, particularly heart, lung, or bone surgery.<ref name=BNF80/><ref name="EMC125"/> When used to treat ], in combination with other antibiotics or alone, the dose of flucloxacillin may need to exceed the usual dose.<ref name=BNF80/>

===Resistance===
Despite flucloxacillin being insensitive to beta-lactamases, some organisms have developed resistance to it and other narrow-spectrum β-lactam antibiotics including ]. Such organisms include ], which has developed resistance to flucloxacillin and other penicillins by having an altered penicillin-binding protein.<ref>{{cite journal | vauthors = Harvey K, Pavillard R | title = Methicillin resistance in Staphylococcus aureus with particular reference to Victorian strains | journal = The Medical Journal of Australia | volume = 1 | issue = 11 | pages = 465–467 | date = May 1982 | pmid = 7048040 | doi = 10.5694/j.1326-5377.1982.tb132417.x | s2cid = 204066905 }}</ref>

==Side effects==
Common side effects associated with the use of flucloxacillin include: ], ], ], ], ] and ] at injection site, ] (including ]), ], and transient increases in liver enzymes and bilirubin.<ref name="AMH2006" />

Rarely, in fewer than 1 in 1,000 people, ] (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.<ref name="NHS"/> 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.<ref name=BNF80/><ref name="NHS"/><ref name="AMH2006" />

Flucloxacillin is contraindicated in those with a previous history of allergy to penicillins, ]s, or ]s. It should also not be used in the eye, or administered to those with a history of ] 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" />

It should be taken on an empty stomach, one half to one hour before food, as absorption is reduced when taken with food,<ref>{{cite web |title=New Zealand Consumer Medicine Information |url=http://www.medsafe.govt.nz/Consumers/CMI/f/flucloxacillin-aft.pdf |work=medsafe.govt.nz}}</ref> though some studies suggest that this does not compromise flucloxacillin plasma concentrations in most circumstances.<ref name="US National Library of Medicine">{{cite journal | vauthors = Gardiner SJ, Drennan PG, Begg R, Zhang M, Green JK, Isenman HL, Everts RJ, Chambers ST, Begg EJ | display-authors = 6 | title = In healthy volunteers, taking flucloxacillin with food does not compromise effective plasma concentrations in most circumstances | journal = PLOS ONE | volume = 13 | issue = 7 | pages = e0199370 | year = 2018 | pmid = 30001392 | pmc = 6042703 | doi = 10.1371/journal.pone.0199370 | bibcode = 2018PLoSO..1399370G | doi-access = free }}</ref>

The UK's ] recommends taking at least 30 minutes before food and at least 2 hours after.<ref name="NHS">{{Cite web|url=https://www.nhs.uk/medicines/flucloxacillin/|title=Flucloxacillin: antibiotic to treat infections|date=27 November 2018|website=nhs.uk}}</ref>

===Drug interactions===
Flucloxacillin can reduce the excretion of ], 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 ].<ref name=Weller2014/>

==Mechanism of action==
{{main article|Beta-lactam antibiotic}}
Flucloxacillin is a ] ] belonging to the ] group of ]s.<ref name=Wu2011/><ref name="NIH1">{{cite web |title=Flucloxacillin sodium salt|url=https://pubchem.ncbi.nlm.nih.gov/compound/Flucloxacillin-sodium-salt|access-date=13 December 2020|website=pubchem.ncbi.nlm.nih.gov|publisher=PubChem at the National Institutes of Health|language=en}}</ref> It works by breaking down the bacterial cell wall.<ref name="NIH1"/>

Like other β-lactam antibiotics, flucloxacillin <!-- ('''fluclox''') --> ] by inhibiting the synthesis of bacterial ]s. It inhibits cross-linkage between the linear ] polymer chains that make up a major component of the cell wall of ] bacteria.{{fact|date=November 2021}}

Flucloxacillin is more acid-stable than many other penicillins and can be given orally, in addition to ] routes. However, like ], it is less potent than ] against non-β-lactamase-producing Gram-positive bacteria.{{fact|date=November 2021}}

Flucloxacillin has similar ], antibacterial activity, and indications to dicloxacillin, and the two agents are considered interchangeable. It is reported to have higher, though rare, incidence of severe hepatic ] than dicloxacillin,<ref>{{cite book |title=LiverTox: Clinical and Research Information on Drug-Induced Liver Injury |date=2012 |publisher=National Institute of Diabetes and Digestive and Kidney Diseases |chapter-url=https://www.ncbi.nlm.nih.gov/books/NBK548106/ |chapter=Dicloxacillin |pmid=31643436 }}</ref> but a lower incidence of renal adverse effects.<ref name="AMH2006">Rossi S, editor. ] 2006. Adelaide: Australian Medicines Handbook; 2006.</ref>

==Chemistry==
Flucloxacillin is insensitive to ] (also known as penicillinase) enzymes secreted by many penicillin-resistant bacteria. The presence of the ] group on the ] of the penicillin nucleus facilitates the β-lactamase resistance, since they are relatively intolerant of side chain ]. Thus, it is able to bind to ]s and inhibit peptidoglycan crosslinking, but is not bound by or inactivated by β-lactamases.{{fact|date=November 2021}}

==History==
Flucloxacillin was developed in the 1960s following an increase in penicillin-resistant (] producing) staphylococcal infections due to the widespread use of ] by 1960.<ref name="White2010">{{cite book | vauthors = White RJ | veditors = Fischer J, Ganellin CR |title=Analogue-based Drug Discovery II |date=2010 |publisher=Wiley-VCH |isbn=978-1-4614-1399-8 |page=11 |url=https://books.google.com/books?id=h2Kd8ci4Ln8C |language=en}}</ref><ref name=Page2012>{{cite book |doi=10.1007/978-1-4614-1400-1_3 |chapter=Beta-Lactam Antibiotics |title=Antibiotic Discovery and Development |year=2012 | vauthors = Page MG |pages=79–117 |isbn=978-1-4614-1399-8 }}</ref> All the natural penicillins and first semi-synthetic penicillins were destroyed by staphylococcal beta-lactamase, leading ] (later ]) to search for more stable antibiotics. By 1962, a series of similarly structured acid-stable penicillins (], ], ] and flucloxacillin), with the potential for being taken by mouth, were developed. Flucloxacillin and dicloxacillin showed particular stability against the beta-lactamase enzyme of ''Staph. aureus'' and could withstand acid.<ref name="White2010"/><ref name=Page2012/> Beecham further developed cloxacillin and popularised flucloxacillin in the UK, while ] concentrated on marketing oxacillin and dicloxacillin in the United States, leading to the difference in use in both countries.<ref name=Greenwood2008>{{cite book| vauthors = Greenwood D |title=Antimicrobial Drugs: Chronicle of a Twentieth Century Medical Triumph|chapter-url=https://books.google.com/books?id=i4_FZHmzjzwC&pg=PA124|year=2008|publisher=]|location=Oxford|isbn=978-0-19-953484-5|page=124|chapter=4. Wonder Drugs}}</ref><ref name="Sutherland">{{cite journal | vauthors = Sutherland R, Croydon EA, Rolinson GN | title = Flucloxacillin, a new isoxazolyl penicillin, compared with oxacillin, cloxacillin, and dicloxacillin | journal = British Medical Journal | volume = 4 | issue = 5733 | pages = 455–60 | date = November 1970 | pmid = 5481218 | pmc = 1820086 | doi = 10.1136/bmj.4.5733.455 }}</ref> Flucloxacillin was first marketed in Europe in the 1970s.<ref name=Wu2011/>

==Available forms==
Both the oral and intravenous preparations of flucloxacillin are inexpensive and are available as the sodium salt flucloxacillin sodium, in ] (250 or 500&nbsp;mg), oral ]s (125&nbsp;mg/5 ml or 250&nbsp;mg/5 ml), and injections (powder for reconstitution, 250, 500, 1000 and 2000&nbsp;mg per vial).<ref name=Hitchings2015/><ref name="EMC">{{cite web |title=Search Results – Flucloxacillin |url=https://www.medicines.org.uk/emc/search?q=flucloxacillin |website=medicines.org.uk |access-date=16 December 2020}}</ref>

Flucloxacillin is not commonly used in the United States or Canada as of 2011.<ref name=Wu2011/> In several other countries however, it is supplied under a variety of trade names including Floxapen, Flopen, Flubex, Flupen, Phylopen, and Staphylex.<ref name=Drugs.com/>

===Combination===
{{main article|Co-fluampicil}}
Flucloxacillin is combined with ] in ].<ref name=BNF80/>
<gallery mode="packed" widths="360px" heights="260">

File:Flucloxacillin powder for oral solution.jpg|Flucloxacillin powder for oral solution 125&nbsp;mg/5ml, with measuring spoon
File:Flucloxacillin preparations.jpg|Selection of Flucloxacillin preparations found in the UK
File:Co-fluampicil capsules and container.jpg|Co-fluampicil: Flucloxacillin combined with ampicillin (UK)
</gallery>
{{-}}

== References ==
{{Reflist}}

{{PenicillinAntiBiotics}}
{{Xenobiotic-sensing receptor modulators}}
{{Portal bar | Medicine}}
{{Authority control}}

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]
]
]