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Flucloxacillin sodium

Alias: Floxapen;Floxacillin;Flucloxacillin; Floxacillin sodium; Floxapen sodium; Sodium flucloxacillin; Monosodium flucloxacillin; Stafopen sodium salt; Staphylex Sodium salt; MFI-PC; ...; 1847-24-1; Fluorochloroxacillin
Cat No.:V21108 Purity: ≥98%
Flucloxacillin sodium (Floxacillin, Floxapen) is a potentnarrow-spectrum beta-lactam antibiotic used to treat infections caused by susceptible Gram-positive bacteria.
Flucloxacillin sodium
Flucloxacillin sodium Chemical Structure CAS No.: 1847-24-1
Product category: Bacterial
This product is for research use only, not for human use. We do not sell to patients.
Size Price Stock Qty
250mg
500mg
1g
2g
5g
Other Sizes

Other Forms of Flucloxacillin sodium:

  • 5-Hydroxymethyl flucloxacillin
  • Flucloxacillin
Official Supplier of:
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Purity & Quality Control Documentation

Purity: ≥98%

Product Description

Flucloxacillin sodium (Floxacillin, Floxapen) is a potent narrow-spectrum beta-lactam antibiotic 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.

Biological Activity I Assay Protocols (From Reference)
Targets
Cell wall synthesis
ln Vitro
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
ln Vivo
The serum elimination half-life of flucloxacillin is 1.31-1.39 hours, and six hours after administration of a single 250 mg dose the serum concentration of flucloxacillin is 0.46 micrograms/mL[1]. Oral flucloxacillin does not affect sweat electrolytes and is not a contraindication to sweat testing[2]. Flucloxacillin has been reported to be metabolized in man to the penicilloic acid, the antibacterially active 5-hydroxymethyl derivative and the penicilloic acid of the 5-hydroxymethyl derivative. The metabolism of flucloxacillin in the rat is similar[3].
Animal Protocol
Rats: On the day of the experiment the animal is given an intravenous bolus injection of 200 mg/kg as pure free acid sodium flucloxacillin (dose volume: 1 mL sterile water per kg) and then return to the metabolism cage. Urine is collected directly into individual CO2 cooled containers for a period of 24 h before dosing and then at frequent intervals after dosing[3].
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.
References

[1].Paton DM, et al. Bioavailability and half-life of two preparations of flucloxacillin. N Z Med J. 1982 Nov 10;95(719):766-8.

[2].Williams J, et al.Sweat tests and flucloxacillin. Arch Dis Child. 1988 Jul;63(7):847-8.

[3].Everett JR, et al. 19F NMR spectroscopy study of the metabolites of flucloxacillin in rat urine. J Pharm Pharmacol. 1985 Dec;37(12):869-73.

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.
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C19H16CLFN3NAO5S
Molecular Weight
475.8512
Exact Mass
475.038
Elemental Analysis
C, 47.96; H, 3.39; Cl, 7.45; F, 3.99; N, 8.83; Na, 4.83; O, 16.81; S, 6.74
CAS #
1847-24-1
Related CAS #
Flucloxacillin;5250-39-5
PubChem CID
21319
Appearance
Solid powder
Boiling Point
677.3ºC at 760 mmHg
Melting Point
176-178ºC
Flash Point
363.4ºC
Vapour Pressure
2.86E-19mmHg at 25°C
LogP
1.681
Hydrogen Bond Donor Count
2
Hydrogen Bond Acceptor Count
8
Rotatable Bond Count
4
Heavy Atom Count
30
Complexity
758
Defined Atom Stereocenter Count
3
SMILES
ClC1=C([H])C([H])=C([H])C(=C1C1C(=C(C([H])([H])[H])ON=1)C(N([H])[C@]1([H])C(N2[C@@]([H])(C(=O)[O-])C(C([H])([H])[H])(C([H])([H])[H])S[C@@]21[H])=O)=O)F.[Na+]
InChi Key
OTEANHMVDHZOPB-SLINCCQESA-M
InChi Code
InChI=1S/C19H17ClFN3O5S.Na/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)/q+1/p-1/t13-,14+,17-/m1./s1
Chemical Name
Sodium (2S-(2alpha,5alpha,6beta))-6-(((3-(2-chloro-6-fluorophenyl)-5-methylisoxazol-4-yl)carbonyl)amino)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo(3.2.0)heptane-2-carboxylate
Synonyms
Floxapen;Floxacillin;Flucloxacillin; Floxacillin sodium; Floxapen sodium; Sodium flucloxacillin; Monosodium flucloxacillin; Stafopen sodium salt; Staphylex Sodium salt; MFI-PC; ...; 1847-24-1; Fluorochloroxacillin
HS Tariff Code
2934.99.9001
Storage

Powder      -20°C    3 years

                     4°C     2 years

In solvent   -80°C    6 months

                  -20°C    1 month

Note: Please store this product in a sealed and protected environment, avoid exposure to moisture.
Shipping Condition
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
Solubility Data
Solubility (In Vitro)
H2O : ~100 mg/mL (~210.15 mM )
DMSO : ≥ 100 mg/mL (~210.15 mM)
Solubility (In Vivo)
Solubility in Formulation 1: ≥ 2.5 mg/mL (5.25 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL.
Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution.

Solubility in Formulation 2: ≥ 2.5 mg/mL (5.25 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly.
Preparation of 20% SBE-β-CD in Saline (4°C,1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution.

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Solubility in Formulation 3: ≥ 2.5 mg/mL (5.25 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of corn oil and mix evenly.


Solubility in Formulation 4: 10% DMSO+40% PEG300+5% Tween-80+45% Saline: ≥ 2.5 mg/mL (5.25 mM)

Solubility in Formulation 5: 100 mg/mL (210.15 mM) in PBS (add these co-solvents sequentially from left to right, and one by one), clear solution; with ultrasonication.

 (Please use freshly prepared in vivo formulations for optimal results.)
Preparing Stock Solutions 1 mg 5 mg 10 mg
1 mM 2.1015 mL 10.5075 mL 21.0150 mL
5 mM 0.4203 mL 2.1015 mL 4.2030 mL
10 mM 0.2102 mL 1.0508 mL 2.1015 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.

Calculator

Molarity Calculator allows you to calculate the mass, volume, and/or concentration required for a solution, as detailed below:

  • Calculate the Mass of a compound required to prepare a solution of known volume and concentration
  • Calculate the Volume of solution required to dissolve a compound of known mass to a desired concentration
  • Calculate the Concentration of a solution resulting from a known mass of compound in a specific volume
An example of molarity calculation using the molarity calculator is shown below:
What is the mass of compound required to make a 10 mM stock solution in 5 ml of DMSO given that the molecular weight of the compound is 350.26 g/mol?
  • Enter 350.26 in the Molecular Weight (MW) box
  • Enter 10 in the Concentration box and choose the correct unit (mM)
  • Enter 5 in the Volume box and choose the correct unit (mL)
  • Click the “Calculate” button
  • The answer of 17.513 mg appears in the Mass box. In a similar way, you may calculate the volume and concentration.

Dilution Calculator allows you to calculate how to dilute a stock solution of known concentrations. For example, you may Enter C1, C2 & V2 to calculate V1, as detailed below:

What volume of a given 10 mM stock solution is required to make 25 ml of a 25 μM solution?
Using the equation C1V1 = C2V2, where C1=10 mM, C2=25 μM, V2=25 ml and V1 is the unknown:
  • Enter 10 into the Concentration (Start) box and choose the correct unit (mM)
  • Enter 25 into the Concentration (End) box and select the correct unit (mM)
  • Enter 25 into the Volume (End) box and choose the correct unit (mL)
  • Click the “Calculate” button
  • The answer of 62.5 μL (0.1 ml) appears in the Volume (Start) box
g/mol

Molecular Weight Calculator allows you to calculate the molar mass and elemental composition of a compound, as detailed below:

Note: Chemical formula is case sensitive: C12H18N3O4  c12h18n3o4
Instructions to calculate molar mass (molecular weight) of a chemical compound:
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Definitions of molecular mass, molecular weight, molar mass and molar weight:
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  • Molar mass (molar weight) is the mass of one mole of a substance and is expressed in g/mol.
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Reconstitution Calculator allows you to calculate the volume of solvent required to reconstitute your vial.

  • Enter the mass of the reagent and the desired reconstitution concentration as well as the correct units
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  • The answer appears in the Volume (to add to vial) box
In vivo Formulation Calculator (Clear solution)
Step 1: Enter information below (Recommended: An additional animal to make allowance for loss during the experiment)
Step 2: Enter in vivo formulation (This is only a calculator, not the exact formulation for a specific product. Please contact us first if there is no in vivo formulation in the solubility section.)
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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.

Clinical Trial Information
Dalbavancin for the Treatment of Acute Bacterial Skin and Skin Structure Infections in Children, Known or Suspected to be Caused by Susceptible Gram-positive Organisms, Including MRSA
CTID: NCT02814916
Phase: Phase 3
Status: Completed
Date: 2024-09-19
Penicillin Against Flucloxacillin Treatment Evaluation
CTID: NCT03632642
Phase: Phase 4
Status: Withdrawn
Date: 2022-11-16
Comparing the Intravenous Treatment of Skin Infections in Children, Home Versus Hospital
CTID: NCT02334124
Phase: N/A
Status: Completed
Date: 2022-11-08
Adjunctive Clindamycin for Cellulitis: C4C Trial.
CTID: NCT01876628
Phase: Phase 4
Status: Completed
Date: 2022-08-17
Flucloxacillin as an Inducer of CYP-enzymes
CTID: NCT04840641
Phase: Phase 1
Status: Completed
Date: 2022-01-11
Flucloxacillin as an inducer of CYP-enzymes
EudraCT: 2020-004044-28
Phase: Phase 1, Phase 2
Status: Completed
Date: 2020-12-18
Safe shortening of antibiotic treatment duration for complicated Staphylococcus aureus bacteremia
EudraCT: 2019-004921-25
Phase: Phase 4
Status: Trial now transitioned
Date: 2020-08-17
Use of repeated Multiple Breath Washout to detect and treat pulmonary exacerbation in children with Cystic Fibrosis, a multicenter randomized controlled study.
EudraCT: 2019-003501-10
Phase: Phase 4
Status: Ongoing, Prematurely Ended, Completed
Date: 2020-04-08
ABSORB 2:An exploratie study determining the oral antibiotic drug absorption in patients with short bowel syndrome.
EudraCT: 2019-002587-28
Phase: Phase 4
Status: Completed
Date: 2020-02-25
Effects of antibiotics on micobiota, pulmonary immune response and incidence of ventilator-associated infections
EudraCT: 2018-000492-32
Phase: Phase 4
Status: Prematurely Ended
Date: 2019-01-14
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