A β-lactam antibiotic
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Labeled Version(s)
28801Cloxacillin-13C4 (sodium salt)
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Cloxacillin (sodium salt)

Item No. 22249

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(2S,5R,6R)-6-[[[3-(2-chlorophenyl)-5-methyl-4-isoxazolyl]carbonyl]amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid, monosodium salt
CAS Number
642-78-4
Molecular Formula
C19H17ClN3O5S • Na
Formula Weight
457.9
Purity
≥95%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 20 mg/mlDMSO: 16 mg/mLEthanol: 2 mg/mLPBS (pH 7.2): 10 mg/mL
SMILES
CC1(C)[C@H](C([O-])=O)N2C([C@@H](NC(C3=C(C)ON=C3C4=CC=CC=C4Cl)=O)[C@@]2([H])S1)=O.[Na+]
InChi Code
InChI=1S/C19H18ClN3O5S.Na/c1-8-11(12(22-28-8)9-6-4-5-7-10(9)20)15(24)21-13-16(25)23-14(18(26)27)19(2,3)29-17(13)23;/h4-7,13-14,17H,1-3H3,(H,21,24)(H,26,27);/q;+1/p-1/t13-,14+,17-;/m1./s1
InChi Key
SCLZRKVZRBKZCR-SLINCCQESA-M
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    Product 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

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Gibbs, D.L., and Thornsberry, C. Susceptibility of gram-negative bacteria to β-lactam antibiotics and rapid characterization of β-lactamase activity. Curr. Microbiol. 2(4), 239-244 (1979).

    2. Sabath, L.D., Garner, C., Wilcox, C., et al. Susceptibility of Staphylococcus aureus and Staphylococcus epidermidis to 65 antibiotics. Antimicrob. Agents Chemother. 9(6), 962-969 (1976).

    3. Okonogi, K., Noji, Y., Nakao, M., et al. The possible physiological roles of penicillin-binding proteins of methicillin-susceptible and methicillin-resistant Staphylococcus aureus. J. Infect. Chemother. 1(1), 50-58 (1995).

    4. Yamaguchi, A., Adachi, A., Hirata, T., et al. Conversion of cloxacillin into a progressive inhibitor of beta-lactamases by sulfonation and its activity against various types of these enzymes. J. Antibiot. (Tokyo) 38(1), 83-93 (1985).

    5. Craven, N., and Anderson, J.C. Therapy of experimental staphylococcal mastitis in the mouse with cloxacillin and rifampicin, alone and in combination. Res. Vet. Sci. 31(3), 295-300 (1981).