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ChemicalBook--->CAS DataBase List--->642-78-4

642-78-4

642-78-4 Structure

642-78-4 Structure
IdentificationMore
[Name]

Sodium cloxacillin
[CAS]

642-78-4
[Synonyms]

[5-METHYL-3-(O-CHLOROPHENYL)-4-ISOXAZOLYL]PENICILLIN SODIUM SALT MONOHYDRATE
CLOXACILLIN SODIUM SALT HYDRATE
CLOXACILLIN SODIUM SALT MONOHYDRATE
CLOXACILLIN SODIUM SALT N-HYDRATE
3-dimethyl-7-oxo-thyl-4-isoxazolecarboxamido)-monosodiumsalt
3-o-chlorophenyl-5-methyl-4-isoxazolylpenicillinsodium
ankerbin
austrastaph
brl-1621sodiumsalt
cloxapen
ekvacillin
gelstaph
monosodiumcloxacillin
orbeninsodium
prevencilinap
prostaphilina
prostaphlina
sodiumorbenin
sodiumsyntarpen
staphybiotic
[EINECS(EC#)]

211-390-9
[Molecular Formula]

C19H19ClN3NaO6S
[MDL Number]

MFCD00150735
[Molecular Weight]

475.88
[MOL File]

642-78-4.mol
Chemical PropertiesBack Directory
[Appearance]

White Crystalline Powder
[Melting point ]

170°C
[storage temp. ]

2-8°C
[solubility ]

H2O: 50 mg/mL, clear, colorless
[form ]

Solid
[color ]

White to Off-White
[Stability:]

Stable. Incompatible with strong oxidizing agents. Refrigerate.
[Water Solubility ]

Soluble in water
[BCS Class]

3
[CAS DataBase Reference]

642-78-4(CAS DataBase Reference)
Safety DataBack Directory
[Hazard Codes ]

Xn
[Risk Statements ]

R36/37/38:Irritating to eyes, respiratory system and skin .
R42/43:May cause sensitization by inhalation and skin contact .
[Safety Statements ]

S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36:Wear suitable protective clothing .
S22:Do not breathe dust .
[WGK Germany ]

2
[RTECS ]

XH8920000
Raw materials And Preparation ProductsBack Directory
[Raw materials]

6-Aminopenicillanic acid-->Ethyl acetoacetate
[Preparation Products]

Sodium cloxacillin monohydrate
Hazard InformationBack Directory
[Description]

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 (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]

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.
[Uses]

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

Ropivacaine (R675000) metabolite.
[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}
Well-known Reagent Company Product InformationBack Directory
[Sigma Aldrich]

642-78-4(sigmaaldrich)
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