Flucloxacillin

Base Information

• Chemical Name: Flucloxacillin
• CAS No.: 5250-39-5
• Molecular Formula: C₁₉H₁₇ClFN₃O₅S
• Molecular Weight: 453.878
• European Community (EC) Number: 226-051-0
• UNII: 43B2M34G2V
• DSSTox Substance ID: DTXSID8023056
• Nikkaji Number: J8.825K
• Wikipedia: Flucloxacillin
• Wikidata: Q1994556
• NCI Thesaurus Code: C80591
• Metabolomics Workbench ID: 42690
• ChEMBL ID: CHEMBL222645
• Mol file: 5250-39-5.mol

Synonyms:Floxacillin;Flucloxacillin;Fluorochloroxacillin

Chemical Property of Flucloxacillin

Chemical Property:

• Appearance/Colour: white to off white free flowing crystalline powder
• Vapor Pressure: 2.86E-19mmHg at 25°C
• Boiling Point: 677.3 °C at 760 mmHg
• PKA: pKa 2.7 (Uncertain)
• Flash Point: 363.4 °C
• PSA: 138.04000
• Density: 1.59 g/cm³
• LogP: 3.01660
• XLogP3: 2.6
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 4
• Exact Mass: 453.0561477
• Heavy Atom Count: 30
• Complexity: 758

Purity/Quality:

99% ^*data from raw suppliers

Flucloxacillin ^*data from reagent suppliers

Safty Information:

• Pictogram(s): UN NO.
• Hazard Codes: UN NO.

MSDS Files:

Useful:

• 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
• 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
• Recent ClinicalTrials: Penicillin Against Flucloxacillin Treatment Evaluation
• Recent EU Clinical Trials: Flucloxacillin as an inducer of CYP-enzymes
• Description: Chemically this is 3(2-chloro-6-fluorophenyl)-5-methyl-4-isoxazolyl penicillin; this differs from dicloxacillin only by the substitution of a fluorine for a chlorine atom (Sutherland et al., 1970). It comes as oral capsules of 250 and 500 mg, as a suspension of 25 and 50 mg/ml, and in an injectable formulation of 500 mg and 1 g.
• Uses: Antibacterial.
• Therapeutic Function: Antibacterial
• Clinical Use: Uses are those of group 3 penicillins.
• Drug interactions: Potentially hazardous interactions with other drugs Reduces excretion of methotrexate.

Technology Process of Flucloxacillin

There total 1 articles about Flucloxacillin which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

6-Aminopenicillanic Acid (551-16-6) + 3-(2-chloro-6-fluorophenyl)-5-methylisoxazole-4-carbonyl chloride (69399-79-7) → floxacillin (5250-39-5,24223-74-3)

Guidance literature:

6-Aminopenicillanic Acid; With sodium carbonate; In water; at 0 - 10 ℃;

3-(2-chloro-6-fluorophenyl)-5-methylisoxazole-4-carbonyl chloride; In water; at 20 - 25 ℃; for 5h; pH=2.5; Reagent/catalyst; Temperature;

Reference yield: 90.6%

floxacillin (5250-39-5,24223-74-3) → Flucloxacillin sodium (1847-24-1)

Guidance literature:

With sodium isooctanoate; In ethyl acetate; Solvent;

Reference yield:

floxacillin (5250-39-5,24223-74-3) → carbon dioxide (124-38-9,18923-20-1) + 5,5-dimethyl-thiazolidine-2,4-dicarboxlic acid (142185-31-7) + 3-(2-chloro-6-flourophenyl)-5-methyl-isoxazole-4-carboxylic acid (3919-74-2)

Guidance literature:

With potassium tellurite; sulfuric acid; at 14.84 ℃; Temperature; Kinetics; Thermodynamic data;

DOI:10.1016/j.molliq.2019.111436

upstream raw materials:

6-Aminopenicillanic Acid

3-(2-chloro-6-fluorophenyl)-5-methylisoxazole-4-carbonyl chloride

Downstream raw materials:

Flucloxacillin sodium

5-Hydroxymethylflucloxacillin

carbon dioxide

5,5-dimethyl-thiazolidine-2,4-dicarboxlic acid

Refernces