642-78-4 Usage
Description
Sodium cloxacillin, also known as Cloxacillin-13C4 Sodium Salt, is a β-lactam antibiotic and a derivative of oxacillin. It is characterized by its white crystalline powder appearance and is known by the brand names Cloxapen (GlaxoSmithKline) and Tegopen (Apothecon). Sodium cloxacillin is active against clinical isolates of the Gram-positive bacteria S. aureus and S. epidermidis but not against Gram-negative bacteria. It binds to various penicillin-binding proteins and inhibits the binding of beta-lactamase, making it effective against infections caused by species of staphylococci that produce this enzyme.
Uses
Used in Pharmaceutical Industry:
Sodium cloxacillin is used as an antibiotic for treating infections caused by species of staphylococci that produce beta-lactamase. Its inhibitory effects on beta-lactamase binding make it a valuable treatment option for such infections.
Used in Antimicrobial Applications:
Sodium cloxacillin is employed as an antimicrobial agent, particularly against clinical isolates of the Gram-positive bacteria S. aureus and S. epidermidis. It binds to penicillin-binding proteins and inhibits the binding of beta-lactamase, effectively decreasing the number of staphylococci in the affected area.
Used in Research and Development:
Sodium cloxacillin, in its labeled form, is used as a research tool for studying the mechanisms of action and interactions with penicillin-binding proteins and beta-lactamases. This helps in understanding the antibiotic's effectiveness and potential improvements in its design and application.
Originator
Orbenin,Beecham,UK,1962
Manufacturing Process
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.
Therapeutic Function
Antibacterial
Purification Methods
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}
Check Digit Verification of cas no
The CAS Registry Mumber 642-78-4 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 6,4 and 2 respectively; the second part has 2 digits, 7 and 8 respectively.
Calculate Digit Verification of CAS Registry Number 642-78:
(5*6)+(4*4)+(3*2)+(2*7)+(1*8)=74
74 % 10 = 4
So 642-78-4 is a valid CAS Registry Number.
InChI:InChI=1/C19H17Cl2N3O5S.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
642-78-4Relevant articles and documents
IMPROVED PROCESS FOR PREPARING PENICILLINS AND INTERMEDIATE COMPOUNDS
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, (2013/02/27)
Disclosed is an improved process for the preparation of isoxazolyl penicillins of formula (I), wherein X1 and X2 can be independently selected from the group comprising hydrogen, chlorine or fluorine, and its pharmaceutically suitable salts. The process is economic in -situ synthetic method without isolation of any intermediate. (I).
