5250-39-5 Usage
Description
Flucloxacillin, also known as 3(2-chloro-6-fluorophenyl)-5-methyl-4-isoxazolyl penicillin, is a semi-synthetic antibiotic belonging to the penicillin group of drugs. It is chemically distinguished from dicloxacillin by the substitution of a fluorine atom for a chlorine atom. Flucloxacillin is effective against a range of bacterial infections and is available in various forms, including oral capsules, suspensions, and injectable formulations.
Uses
Used in Pharmaceutical Industry:
Flucloxacillin is used as an antibacterial agent for treating various bacterial infections. It is particularly effective against gram-positive bacteria, such as Staphylococcus and Streptococcus species. The antibiotic works by inhibiting bacterial cell wall synthesis, leading to cell lysis and death.
In addition to its primary use as an antibacterial agent, flucloxacillin may also be utilized in other applications within the pharmaceutical industry, such as:
1. Combination Therapy: Flucloxacillin can be combined with other antibiotics, like beta-lactamase inhibitors, to enhance its effectiveness against a broader range of bacteria and to minimize the development of antibiotic resistance.
2. Drug Development: Researchers may use flucloxacillin as a starting point for the development of new antibiotics with improved properties, such as increased potency, better pharmacokinetics, or reduced side effects.
3. Research and Diagnostics: Flucloxacillin can be employed in laboratory settings for studying bacterial growth, antibiotic susceptibility, and the mechanisms of action of various antibiotics.
Originator
Floxapen,Beecham,UK,1970
Manufacturing Process
3-(2-chloro-6-fluorophenyl)-5-methylisoxazole-4-carboxylicacid, MP 206° to
207°C, was obtained by chlorinating 2-chloro-6-fluorobenzaldoxime, then
condensing the resulting hydroxamoyl chloride with methyl acetoacetate in
methanolic sodium methoxide and hydrolyzing the resulting ester with hot
alkali. The acid chloride resulted from treatment of the acid with thionyl
chlorideA suspension of 6-aminopenicillanic acid (36.4 grams) in water was adjusted
to pH 7.2 by the addition of N aqueous sodium hydroxide and the resulting
solution was treated with a solution of 3-(2-chloro-6-fluorophenyl)-5-
methylisoxazole-4-carbonyl chloride (46.1 grams) in isobutyl methyl ketone.
The mixture was stirred vigorously for 1? hours and then filtered through Dicalite. The layers were separated and the isobutyl methyl ketone layer was
shaken with saturated brine. Then, precipitation of the sodium salt only took
place after dilution of the mixture with ether. In this way there was obtained
60.7 grams of the penicillin sodium salt having a purity of 88% as determined
by alkalimetric assay.
Therapeutic Function
Antibacterial
Antimicrobial activity
There is complete cross-resistance with other
penicillinase-stable penicillins.
Pharmacokinetics
Oral absorption: c. 80%
Cmax 250 mg (oral): 11 mg/L after 0.5–1 h
Plasma half-life: 2 h
Plasma protein binding: 95%
Absorption and distribution
It is well absorbed after oral administration and penetrates rapidly into extravascular exudates. Its high protein binding limits its diffusion, notably into the normal CSF.
Metabolism and excretion
Flucloxacillin is partly metabolized in the liver and about 10% of the plasma concentration is made up of metabolites. It is more slowly eliminated than cloxacillin. Some appears in the bile but about 50–80% of an oral dose is recovered from the urine, about 20% as metabolites.
Clinical Use
Uses are those of group 3 penicillins.
Side effects
In patients treated by intravenous infusion, about 5% developed
phlebitis by the first and 15% by the second day, after
which the proportion rose dramatically. Side effects are otherwise
those common to penicillins.
Drug interactions
Potentially hazardous interactions with other drugs
Reduces excretion of methotrexate.
Metabolism
In normal subjects approximately 10% of the flucloxacillin
administered is metabolised to penicilloic acid. Excretion
occurs mainly through the kidney. Between 65.5%
(oral route) and 76.1% (parenteral route) of the dose
administered is recovered in unaltered active form in
the urine within 8 hours. A small portion of the dose
administered is excreted in the bile.
Check Digit Verification of cas no
The CAS Registry Mumber 5250-39-5 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 5,2,5 and 0 respectively; the second part has 2 digits, 3 and 9 respectively.
Calculate Digit Verification of CAS Registry Number 5250-39:
(6*5)+(5*2)+(4*5)+(3*0)+(2*3)+(1*9)=75
75 % 10 = 5
So 5250-39-5 is a valid CAS Registry Number.
InChI:InChI=1/C19H17ClFN3O5S.Na.H2O/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);;1H2/q;+1;/p-1/t13-,14+,17-;;/m1../s1
5250-39-5Relevant articles and documents
Flucloxacillin sodium monohydrate synthetic method
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Paragraph 0032-0036; 0038-0042; 0043-0047; 0048-0051, (2017/09/01)
The invention discloses a method for compounding flucloxacillin sodium-hydrate, which belongs to the technical field of drug synthesis, and comprises the steps: 6-aminopenicillanic acid (6-APA) is salified, then 3-(2-chloro-6-fluorophenyl)-5- methyl isoxazole-4-formyl chloride or equivalents thereof are added to do an acylation reaction, and then acids are added drop by drop to adjust a potential of hydrogen (pH) value to obtain flucloxacillin acid aqueous solutions. Organic solution is used to extract, and organic phases are washed, dried and filtered to obtain flucloxacillin acid solutions through saturated salt water, then white solids are dissolved out in the flucloxacillin acid solutions which are added with sodium iso-octoate solutions, and products are obtained by controlling temperature and crystallizing. The method for compounding the flucloxacillin sodium-hydrate does not separate intermediate flucloxacillin acids, obtained flucloxacillin acids are directly salified with sodium iso-octoate after being extracted trough the organic solution, reduces separation steps and operation process, also reduces usage amount and times of organic solution simultaneously, greatly reduces discharge amount of organic solution relative to patent documentation CN 102964356A, reduces production cost above 20%, and obviously improves economic and environmental values.
