Cloxacillin-13C4 SodiuM Salt

Cloxacillin-13C4 SodiuM Salt Property

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)

Safety

Hazard Codes 

Xn

Risk Statements 

36/37/38-42/43

Safety Statements 

26-36-22

WGK Germany 

2

RTECS 

XH8920000

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Danger

Hazard statements

H317May cause an allergic skin reaction

H334May cause allergy or asthma symptoms or breathing difficulties if inhaled

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P272Contaminated work clothing should not be allowed out of the workplace.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P285In case of inadequate ventilation wear respiratory protection.

P302+P352IF ON SKIN: wash with plenty of soap and water.

P304+P341IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.

P321Specific treatment (see … on this label).

P333+P313IF SKIN irritation or rash occurs: Get medical advice/attention.

P342+P311IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician.

P363Wash contaminated clothing before reuse.

P501Dispose of contents/container to..…

Cloxacillin-13C4 SodiuM Salt Chemical Properties,Usage,Production

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 (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.

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}

References

[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.