5250-39-5 Usage
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.
Originator
Floxapen,Beecham,UK,1970
Uses
Antibacterial.
Definition
ChEBI: A penicillin compound having a 6beta-[3-(2-chloro-6-fluorophenyl)-5-methyl-1,2-oxazole-4-carboxamido] side-chain.
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
-
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.
