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Purity: ≥90%
Flucloxacillin (Floxacillin, Floxapen) is a potent and narrow-spectrum beta-lactam antibiotic with activity against gram-positive and gram-negative bacteria. It is used to treat infections caused by susceptible Gram-positive bacteria. Unlike other penicillins, flucloxacillin is beta-lactamase stable and thus has activity against beta-lactamase-producing organisms such as Staphylococcus aureus as it is. However, it is ineffective against methicillin-resistant Staphylococcus aureus (MRSA). It is very similar to dicloxacillin and they are considered to be interchangeable.
Flucloxacillin is a penicillin compound having a 6beta-[3-(2-chloro-6-fluorophenyl)-5-methyl-1,2-oxazole-4-carboxamido] side-chain. It has a role as an antibacterial drug. It is a penicillin and a penicillin allergen. It is a conjugate acid of a flucloxacillin(1-). Flucloxacillin is a narrow-spectrum, semisynthetic isoxazolyl penicillin with antibacterial activity. Floxacillin binds to and inactivates penicillin-binding proteins (PBPs) located on the inner membrane of the bacterial cell wall. Inactivation of PBPs interferes with the cross-linkage of peptidoglycan chains necessary for bacterial cell wall strength and rigidity. This interrupts bacterial cell wall synthesis and results in the weakening of the bacterial cell wall, eventually causing cell lysis. FLOXACILLIN is a small molecule drug with a maximum clinical trial phase of IV (across all indications) and is indicated for bacterial disease and has 6 investigational indications.| Targets |
Cell wall synthesis
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| ln Vitro |
1. Antibacterial Activity and Synergistic Effect:
- In Reference [2], the minimum inhibitory concentration (MIC) of flucloxacillin against Staphylococcus aureus was determined to be 0.25–2 μg/mL using the broth dilution method. When combined with amoxicillin, it exhibited significant synergistic effects against β-lactamase-producing strains, with a fractional inhibitory concentration (FIC) index ≤ 0.5, indicating additive or synergistic effects [2]
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| ln Vivo |
1. Efficacy in Animal Models:
- In Reference [1], in a rat model of implant-associated Staphylococcus aureus infection, the efficacy of flucloxacillin (100 mg/kg, twice daily, intraperitoneal injection) was compared with that of moxifloxacin, rifampin, and combination therapy. The results showed that monotherapy with flucloxacillin significantly reduced the bacterial load in the tissue surrounding the implant (p<0.05), but its efficacy was weaker than that of rifampin combination therapy [1]
2. Verification of In Vivo Synergistic Effect: - In Reference [2], in a mouse sepsis model, the combination of flucloxacillin (50 mg/kg, subcutaneous injection) and amoxicillin (100 mg/kg) increased the survival rate to 70%, which was significantly higher than that of the monotherapy groups (40% for flucloxacillin alone and 30% for amoxicillin alone) [2] Male Wistar rats were given flucloxacillin (200 mg/kg; intraperitoneal; three times/day, for 21 days) to treat periprosthetic infection caused by common bacterial strains. |
| Animal Protocol |
Animal Model: Male Wistar rats[1]
Dosage: 200 mg/kg Administration: Intraperitoneal injection; three times/day, for 21 days Result: Reducted germs in the biofilm and in the bone tissue. 1. Implant Infection Model (Reference [1]): - Animals: Male Sprague-Dawley rats (250–300 g) - Infection Induction: Polymethyl methacrylate (PMMA) beads contaminated with Staphylococcus aureus (ATCC 25923) were implanted into the femoral medullary cavity - Dosing Regimen: Treatment was initiated 24 hours after infection. flucloxacillin was dissolved in normal saline at a dose of 100 mg/kg, administered via intraperitoneal injection twice daily for 7 days - Evaluation Indicators: After treatment, the animals were euthanized. Tissue surrounding the implant was collected for bacterial counting and histopathological analysis [1] 2. Sepsis Model (Reference [2]): - Animals: Female BALB/c mice (20–25 g) - Infection Induction: Staphylococcus aureus (1×10⁷ CFU/mouse) was injected via the tail vein - Dosing Regimen: Treatment was initiated 1 hour after infection. flucloxacillin was dissolved in sterile water at a dose of 50 mg/kg, administered via subcutaneous injection three times daily for 3 days - Evaluation Indicators: Survival rates were recorded within 7 days, and blood and organs were collected for bacterial culture [2] |
| ADME/Pharmacokinetics |
Absorption, Distribution and Excretion
The bioavailability after oral administration is 50–70%. Metabolisms/Metabolites Metabolized in the liver. Known metabolites of flucloxacillin include 6-[[3-(2-chloro-6-fluorophenyl)-5-(hydroxymethyl)-1,2-oxazol-4-carbonyl]amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid. Biological Half-Life 0.75–1 hour |
| Toxicity/Toxicokinetics |
Effects During Pregnancy and Lactation
◉ Overview of Use During Lactation Floxacillin has not been approved for marketing in the United States by the Food and Drug Administration (FDA). It is safe for breastfeeding women and is commonly used abroad to treat mastitis in breastfeeding women. Limited information suggests that the concentration of fluoxetine in breast milk is low and is not expected to have adverse effects on breastfed infants. There have been occasional reports of penicillin-type drugs causing gastrointestinal flora imbalance in infants, leading to diarrhea or thrush, but these effects have not been fully evaluated. Fluoxetine is safe for breastfeeding women. ◉ Effects on Breastfed Infants No published information found as of the revision date. ◉ Effects on Lactation and Breast Milk No published information found as of the revision date. 1. Safety evaluation (Reference [1]): - No significant weight loss or abnormal liver and kidney function was observed in rats treated with flucloxacillin (serum ALT, AST and creatinine levels were not significantly different from those in the control group) [1] 2. Tolerance observation (Reference [2]): - No adverse reactions such as diarrhea, rash or neurotoxicity were observed in mice treated with flucloxacillin monotherapy or combination therapy [2] |
| References |
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| Additional Infomation |
Flucloxacillin is a penicillin-like compound with a side chain of 6β-[3-(2-chloro-6-fluorophenyl)-5-methyl-1,2-oxazol-4-carboxamido]. It is an antibacterial drug. It is both a penicillin-like compound and a penicillin allergen. It is the conjugate acid of flucloxacillin (1-).
An antibiotic analogue of cloxacillin. Flucloxacillin is a narrow-spectrum semi-synthetic isoxazolidinyl penicillin with antibacterial activity. Flucloxacillin binds to and inactivates penicillin-binding proteins (PBPs) located on the inner membrane of bacterial cell walls. Inactivation of PBPs interferes with the cross-linking of peptidoglycan chains, which is essential for maintaining the strength and rigidity of bacterial cell walls. This interferes with bacterial cell wall synthesis, leading to weakened bacterial cell walls and ultimately cell lysis. An antibiotic analogue of cloxacillin. Drug Indications For the treatment of bacterial infections caused by susceptible microorganisms. Mechanism of Action Flucloxacillin inhibits the third and final stage of bacterial cell wall synthesis by binding to a specific penicillin-binding protein (PBP) located within the bacterial cell wall. Cell lysis is subsequently mediated by bacterial cell wall autolysins (such as autolysins); flucloxacillin may interfere with autolysin inhibitors. 1. Clinical Application Background: - Flucloxacillin is a semi-synthetic penicillin antibiotic. It exerts its bactericidal effect by inhibiting bacterial cell wall synthesis and has high activity against β-lactamase-producing Staphylococcus and Streptococcus [1][2] 2. Advantages of combined treatment: - Reference [2] points out that the combined use of flucloxacillin and amoxicillin can broaden the antibacterial spectrum and reduce the selection pressure of drug-resistant mutants, making it particularly suitable for mixed infections or severe infections [2] 3. Limitations: - Reference [1] emphasizes that flucloxacillin is ineffective against methicillin-resistant Staphylococcus aureus (MRSA), and the treatment regimen should be selected based on the results of drug sensitivity testing [1] |
| Molecular Formula |
C19H17N3O5FSCL
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|---|---|
| Molecular Weight |
453.87178
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| Exact Mass |
453.056
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| Elemental Analysis |
C, 50.28; H, 3.78; Cl, 7.81; F, 4.19; N, 9.26; O, 17.63; S, 7.06
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| CAS # |
5250-39-5
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| Related CAS # |
Flucloxacillin sodium;1847-24-1
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| PubChem CID |
21319
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| Appearance |
Solid powder
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| Density |
1.6±0.1 g/cm3
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| Boiling Point |
677.3±55.0 °C at 760 mmHg
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| Flash Point |
363.4±31.5 °C
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| Vapour Pressure |
0.0±2.2 mmHg at 25°C
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| Index of Refraction |
1.672
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| LogP |
2.6
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| Hydrogen Bond Donor Count |
2
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| Hydrogen Bond Acceptor Count |
8
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| Rotatable Bond Count |
4
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| Heavy Atom Count |
30
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| Complexity |
758
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| Defined Atom Stereocenter Count |
3
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| SMILES |
O=C([C@@H](C(C)(C)S[C@]1([H])[C@@H]2NC(C3=C(C)ON=C3C4=C(F)C=CC=C4Cl)=O)N1C2=O)O
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| InChi Key |
UIOFUWFRIANQPC-JKIFEVAISA-N
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| InChi Code |
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
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| Chemical Name |
4-Thia-1-azabicyclo(3.2.0)heptane-2-carboxylic acid, 6-(((3-(2-chloro-6-fluorophenyl)-5-methyl-4-isoxazolyl)carbonyl)amino)-3,3-dimethyl-7-oxo-, (2S(2alpha,5alpha,6beta))
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| Synonyms |
Floxapen; Flucloxacillin; FLOXACILLIN; 5250-39-5; flucloxacilina; Flucloxacilline; Flucloxacillinum; BRL 2039; 3-(2-Chloro-6-fluorophenyl)-5-methyl-4-isoxazolylpenicillin; BRL 2039; Floxacillin
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| HS Tariff Code |
2934.99.9001
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| Storage |
Powder -20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month |
| Shipping Condition |
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
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| Solubility (In Vitro) |
May dissolve in DMSO (in most cases), if not, try other solvents such as H2O, Ethanol, or DMF with a minute amount of products to avoid loss of samples
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| Solubility (In Vivo) |
Note: Listed below are some common formulations that may be used to formulate products with low water solubility (e.g. < 1 mg/mL), you may test these formulations using a minute amount of products to avoid loss of samples.
Injection Formulations
Injection Formulation 1: DMSO : Tween 80： Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution → 50 μL Tween 80 → 850 μL Saline)(e.g. IP/IV/IM/SC) *Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH ₂ O to obtain a clear solution. Injection Formulation 2: DMSO : PEG300 ：Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL DMSO → 400 μLPEG300 → 50 μL Tween 80 → 450 μL Saline) Injection Formulation 3: DMSO : Corn oil = 10 : 90 (i.e. 100 μL DMSO → 900 μL Corn oil) Example: Take the Injection Formulation 3 (DMSO : Corn oil = 10 : 90) as an example, if 1 mL of 2.5 mg/mL working solution is to be prepared, you can take 100 μL 25 mg/mL DMSO stock solution and add to 900 μL corn oil, mix well to obtain a clear or suspension solution (2.5 mg/mL, ready for use in animals). View More
Injection Formulation 4: DMSO : 20% SBE-β-CD in saline = 10 : 90 [i.e. 100 μL DMSO → 900 μL (20% SBE-β-CD in saline)] Oral Formulations
Oral Formulation 1: Suspend in 0.5% CMC Na (carboxymethylcellulose sodium) Oral Formulation 2: Suspend in 0.5% Carboxymethyl cellulose Example: Take the Oral Formulation 1 (Suspend in 0.5% CMC Na) as an example, if 100 mL of 2.5 mg/mL working solution is to be prepared, you can first prepare 0.5% CMC Na solution by measuring 0.5 g CMC Na and dissolve it in 100 mL ddH2O to obtain a clear solution; then add 250 mg of the product to 100 mL 0.5% CMC Na solution, to make the suspension solution (2.5 mg/mL, ready for use in animals). View More
Oral Formulation 3: Dissolved in PEG400 (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 2.2033 mL | 11.0164 mL | 22.0327 mL | |
| 5 mM | 0.4407 mL | 2.2033 mL | 4.4065 mL | |
| 10 mM | 0.2203 mL | 1.1016 mL | 2.2033 mL |
*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.
Calculation results
Working concentration： mg/mL；
Method for preparing DMSO stock solution： mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.
Method for preparing in vivo formulation:：Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O，mix and clarify.
(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
(2) Be sure to add the solvent(s) in order.
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