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Cloxacillin-13C4 SodiuM Salt

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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
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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 Class
3
Stability:
Stable. Incompatible with strong oxidizing agents. Refrigerate.
CAS DataBase Reference
642-78-4(CAS DataBase Reference)
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Safety Information

Hazard Codes 
Xn
Risk Statements 
36/37/38-42/43
Safety Statements 
26-36-22
WGK Germany 
2
RTECS 
XH8920000

MSDS

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Cloxacillin-13C4 SodiuM Salt Usage And Synthesis

Description

Cloxacillin 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 Properties

White Crystalline Powder

Originator

Orbenin,Beecham,UK,1962

Uses

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

Uses

Ropivacaine (R675000) metabolite.

Uses

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.

Uses

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.

Definition

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

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.

brand name

Cloxapen (GlaxoSmithKline); Tegopen (Apothecon).

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}

Cloxacillin-13C4 SodiuM Salt Preparation Products And Raw materials

Preparation Products

Cloxacillin sodium

Cloxacillin-13C4 SodiuM SaltSupplier

J & K SCIENTIFIC LTD.
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