Structure via PubChem · Public domain (PubChem)
flucloxacillin
Sign in to saveAlso known as BRL-2039, Floxapen, (2S,5R,6R)-6-({[3-(2-chloro-6-fluorophenyl)-5-methyl-1,2-oxazol-4-yl]carbonyl}amino)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid, 3-(2-Chloro-6-fluorophenyl)-5-methyl-4-isoxazolylpenicillin, Floxacillin, Flucloxacilina, Flucloxacilline
Flucloxacillin, also known as floxacillin, is an antibiotic used to treat skin infections, external ear infections, infections of leg ulcers, diabetic foot infections, and infection of bone. It may be used together with other medications to treat pneumonia, and endocarditis. It may also be used prior to surgery to prevent Staphylococcus infections. It is not effective against methicillin-resistant Staphylococcus aureus (MRSA). It is taken by mouth or given by injection into a vein or muscle.
Key facts
- Drug.Watchedfields
- changed
- Drug.verifiedrevid
- 461101078
- Drug.image
- Flucloxacillin skeletal formula labelled.svg
- Drug.image_class
- skin-invert-image
- Drug.image2
- Flucloxacillin-from-xtal-1980-3D-balls.png
- Drug.image_class2
- bg-transparent
- Drug.tradename
- Floxapen, others
- Drug.pregnancy_AU
- B1
- Drug.routes_of_administration
- By mouth, intramuscular, intravenous, intrapleural, intraarticular
- Drug.ATC_prefix
- J01
- Drug.ATC_suffix
- CF05
- Drug.legal_AU
- S4
- Drug.legal_NZ
- Prescription only
- Drug.legal_UK
- POM
- Drug.legal_EU
- Rx-only
- Drug.bioavailability
- 50–70%
- Drug.metabolism
- Liver
- Drug.elimination_half life
- 0.75–1 hour
via Wikipedia infobox
Chemical data
- Formula
- C19H17ClFN3O5S
- Molecular weight
- 453.9 g/mol
- IUPAC name
- (2S,5R,6R)-6-[[3-(2-chloro-6-fluorophenyl)-5-methyl-1,2-oxazole-4-carbonyl]amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
- SMILES
- CC1=C(C(=NO1)C2=C(C=CC=C2Cl)F)C(=O)N[C@H]3[C@@H]4N(C3=O)[C@H](C(S4)(C)C)C(=O)O
- InChIKey
- UIOFUWFRIANQPC-JKIFEVAISA-N
- XLogP
- 2.6
- Polar surface area
- 138 Ų
- H-bond donors
- 2
- H-bond acceptors
- 8
- Formal charge
- 0
via PubChem
Research
1,519 papers- [Flucloxacillin-induced hypokalemia].Nederlands tijdschrift voor geneeskunde · 2024
- Flucloxacillin-associated hepatic injury.Liver · 1994
- Flucloxacillin: A Review of Characteristics, Properties and Analytical Methods.Critical reviews in analytical chemistry · 2019
- Flucloxacillin-induced liver injury.Toxicology · 2008
- Therapeutic drug monitoring of flucloxacillin.The Netherlands journal of medicine · 2019
via PubMed
Wikidata facts
- Mass
- 453.056148
- Has use
- medication
Show 7 more facts
- chemical formula
- C₁₉H₁₇ClFN₃O₅S
- Commons category
- Flucloxacillin
- isomeric SMILES
- CC1=C(C(=NO1)C2=C(C=CC=C2Cl)F)C(=O)N[C@H]3[C@@H]4N(C3=O)[C@H](C(S4)(C)C)C(=O)O
- canonical SMILES
- CC1=C(C(=NO1)C2=C(C=CC=C2Cl)F)C(=O)NC3C4N(C3=O)C(C(S4)(C)C)C(=O)O
- subject has role
- bactericide
- World Health Organisation international non-proprietary name
- flucloxacillin
- medical condition treated
- meningitis
Sources (6)
via Wikidata · CC0
~11 min read
Encyclopedic overview
14 sectionsContents
- Medical uses
- Skin
- Wounds
- Bone
- Other
- Resistance
- Side effects
- Drug interactions
- Mechanism of action
- Chemistry
- History
- Available forms
- Combination
- References
{{Infobox drug | Watchedfields = changed | verifiedrevid = 461101078 | image = Flucloxacillin skeletal formula labelled.svg | image_class = skin-invert-image | alt = | image2 = Flucloxacillin-from-xtal-1980-3D-balls.png | image_class2 = bg-transparent | alt2 = | caption =
| pronounce = | tradename = Floxapen, others | Drugs.com = | MedlinePlus = | DailyMedID = | pregnancy_AU = B1 | pregnancy_AU_comment = | pregnancy_category= | routes_of_administration = By mouth, intramuscular, intravenous, intrapleural, intraarticular | class = | ATC_prefix = J01 | ATC_suffix = CF05 | ATC_supplemental =
Excerpted from Wikipedia’s “flucloxacillin” article, available under the CC BY-SA 4.0 licence.