| Identification | More | [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 Properties | Back 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 | [InChIKey]
SCLZRKVZRBKZCR-SLINCCQESA-M | [SMILES]
[Na+].Cc1onc(-c2ccccc2Cl)c1C(=O)N[C@H]3[C@H]4SC(C)(C)[C@@H](N4C3=O)C([O-])=O | [CAS DataBase Reference]
642-78-4(CAS DataBase Reference) |
| Safety Data | Back 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
| [Storage Class]
11 - Combustible Solids |
| Hazard Information | Back Directory | [Description]
Cloxacillin is a β-lactam antibiotic and a derivative of oxacillin (Item No. 23954).1 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).1,2 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).3 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).4 Cloxacillin decreases the number of staphylococci in the mammary gland in a mouse model of acute, but not chronic, mastitis induced by Staphylococcus infection.5 | [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} | [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.
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