Cloxacillin-13C4 SodiuM Salt

Cloxacillin-13C4 SodiuM Salt Basic information
Product Name:Cloxacillin-13C4 SodiuM Salt
Synonyms:austrastaph;prostaphlina;sodiumorbenin;sodiumsyntarpen;staphybiotic;syntarpensodiumsalt;tegopen;CLOXACILLIN SODIUM SALT HYDRATE
CAS:642-78-4
MF:C19H19ClN3NaO5S
MW:459.88
EINECS:211-390-9
Product Categories:API;Inhibitors;Amines;Aromatics;Intermediates & Fine Chemicals;Pharmaceuticals;A - KAntibiotics;Antibacterial;Antibiotics A to;Antibiotics A-FAntibiotics;Chemical Structure Class;Interferes with Cell Wall SynthesisAntibiotics;Chiral Reagents;Heterocycles;Mechanism of Action;Penicillins and Cephalosporins (beta-Lactams);Spectrum of Activity
Mol File:642-78-4.mol
Cloxacillin-13C4 SodiuM Salt Structure
Cloxacillin-13C4 SodiuM Salt Chemical Properties
Melting point 170°C
storage temp. 2-8°C
solubility H2O: 50 mg/mL, clear, colorless
form Solid
color White to Off-White
Water Solubility Soluble in water
BCS Class3
Stability:Stable. Incompatible with strong oxidizing agents. Refrigerate.
CAS DataBase Reference642-78-4(CAS DataBase Reference)
Safety Information
Hazard Codes Xn
Risk Statements 36/37/38-42/43
Safety Statements 26-36-22
WGK Germany 2
RTECS XH8920000
MSDS Information
ProviderLanguage
SigmaAldrich English
Cloxacillin-13C4 SodiuM Salt Usage And Synthesis
DescriptionCloxacillin is a β-lactam antibiotic and a derivative of oxacillin . 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 (Kis = 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.
Chemical PropertiesWhite Crystalline Powder
OriginatorOrbenin,Beecham,UK,1962
UsesCloxacillin-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.
UsesCloxacillin-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.
UsesLabelled S-Form of Dropropizine. Cough suppressive phenylpiperazine derivative. Antitussive.
UsesRopivacaine (R675000) metabolite.
DefinitionChEBI: Cloxacillin sodium is an organic sodium salt. It contains a cloxacillin(1-).
Manufacturing ProcessThe 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.
Brand nameCloxapen (GlaxoSmithKline); Tegopen (Apothecon).
Therapeutic FunctionAntibacterial
Purification MethodsPurify 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}
Cloxacillin-13C4 SodiuM Salt Preparation Products And Raw materials
Raw materials6-Aminopenicillanic acid-->Ethyl acetoacetate
Preparation ProductsSodium cloxacillin monohydrate
Methylparaben Sodium acetate Sodium dichromate dihydrate Bensulfuron methyl PYRAZOPHOS Methyl cellulose Trisodium phosphate Cloxacillin-13C4 SodiuM Salt Kresoxim-methyl Cloxacillin Methanol Sodium hydroxide Methyl acrylate Methyl bromide METSULFURON METHYL Oxacillin sodium monohydrate N,N-Dimethyl-1,4-phenylenediamine 8-CHLOROADENOSINE-3',5'-CYCLIC MONOPHOSPHOROTHIOATE, RP-ISOMER SODIUM SALT

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