642-78-4

Cloxacillin is a β-lactam antibiotic and a derivative of oxacillin (Item No. 23954). It is active against clinical isolates of the Gram-positive bacteria S. aureus and S. epidermidis (MICs = 0.004-0.4 and 0.1-0.8 μg/ml, respectively) but not 34 Gram-negative bacteria (MICs = >128 μg/ml for all). Cloxacillin binds to S. aureus penicillin-binding protein 1 (PBP1), PBP2, PBP3, and PBP4 (IC₅₀s = 0.04, 0.12, 0.21, and 2.5 μg/ml, respectively). It also binds to recombinant type Ib penicillinase, as well as P. vulgaris and C. freundii cephalosporinase (K_is = 15, 0.27, and 0.027 μM, respectively). Cloxacillin decreases the number of staphylococci in the mammary gland in a mouse model of acute, but not chronic, mastitis induced by Staphylococcus infection.

White Crystalline Powder

Orbenin,Beecham,UK,1962

Cloxacillin-13C4 SodiuM Salt is an antibiotic that belongs to the group of the isoxazolylpenicillins. Cloxacillin is used to treat infections caused by species of staphylococci that produce beta-lactamase due to its inhibitory effects on beta-lactamase binding.

Cloxacillin-13C4 SodiuM Salt, an antibiotic that belongs to the group of the isoxazolylpenicillins. Cloxacillin is used to treat infections caused by species of staphylococci that produce beta-lac tamase due to its inhibitory effects on beta-lactamase binding.

Labelled S-Form of Dropropizine. Cough suppressive phenylpiperazine derivative. Antitussive.

Ropivacaine (R675000) metabolite.

ChEBI: Cloxacillin sodium is an organic sodium salt. It contains a cloxacillin(1-).

The reaction between 6-aminopenicillanic acid (6.5 g) and 3-o-chlorophenyl-5- methylisoxazole4-carbonyl chloride (7.66 g) gave the sodium salt of 3-ochlorophenyl-5-methyl-4-isoxazolylpenicillin (9.98 g) as a pale yellow solid. Colorimetric assay with hydroxylamine against a benzylpenicillin standard indicated a purity of 68%.
The 3-o-chlorophenyl-5-methylisoxazole-4-carboxylic acid, from which the acid chloride was prepared, was obtained by hydrolysis of the ester product of the reaction between o-chlorobenzohydroxamic chloride and ethyl acetoacetate in methanolic sodium methoxide. Reaction with thionyl chloride gave the starting material.

Cloxapen (GlaxoSmithKline); Tegopen (Apothecon).

Antibacterial

Purify cloxacillin sodium salt by dissolving it in isoPrOH containing 20% of H2O, and diluting with isoPrOH to a water content of 5% and chilling. Recrystallise it again in this manner. The sodium salt is collected and dried at 40o in air to give the colourless monohydrate. It is soluble in H2O (5%), MeOH, EtOH, pyridine and ethylene glycol. [Doyle et al. J Chem Soc 5838 1963, Naylor et al. Nature 195 1264 1962.] (
) -Cocaine {ecogonine methyl ester benzoate, 2 -carbomethoxy-3--benzoxytropane, methyl 1R -(exo,exo)]-3-(benzoyloxy)-2-methyl-8-azabicyclo[3.2.1]octane-2-carboxylate}

[1] D. GIBBS C T. Susceptibility of Gram-negative bacteria to β-lactam antibiotics and rapid characterization of β-lactamase activity[J]. Current Microbiology, 1979, 2 1: 239-244. DOI: 10.1007/bf02601720
[2] L D SABATH. Susceptibility of Staphylococcus aureus and Staphylococcus epidermidis to 65 antibiotics.[J]. Antimicrobial Agents and Chemotherapy, 1976, 9 6: 962-969. DOI: 10.1128/aac.9.6.962
[3] KENJI OKONOG . The Possible Physiological Roles of Penicillin-Binding Proteins of Methicillin-Susceptible and Methicillin-Resistant Staphylococcus aureus[J]. Journal of Infection and Chemotherapy, 1995, 1 1: Pages 50-58. DOI: 10.1007/bf02347729
[4] A YAMAGUCHI. Conversion of cloxacillin into a progressive inhibitor of beta-lactamases by sulfonation and its activity against various types of these enzymes.[J]. Journal of Antibiotics, 1985, 38 1: 83-93. DOI: 10.7164/antibiotics.38.83
[5] N CRAVEN  J C A. Therapy of experimental staphylococcal mastitis in the mouse with cloxacillin and rifampicin, alone and in combination.[J]. Research in veterinary science, 1981, 31 3: 295-300.