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27555

Sigma-Aldrich

Cloxacillin sodium salt

≥95.0% (HPLC)

Synonym(s):

3-(o-Chlorophenyl)-5-methyl-4-isoxazolylpenicillin sodium salt, Syntarpen sodium salt

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About This Item

Empirical Formula (Hill Notation):
C19H17ClN3NaO5S
CAS Number:
642-78-4
Molecular Weight:
457.86
Beilstein:
4103180
EC Number:
211-390-9
MDL number:
MFCD00063568
UNSPSC Code:
51102829
PubChem Substance ID:
57648259
NACRES:
NA.85

biological source

semisynthetic

Quality Level

200

Assay

≥95.0% (HPLC)

form

powder or crystals

impurities

≤5% Total impurities (anhydrous)

color

white to off-white

antibiotic activity spectrum

Gram-positive bacteria

Mode of action

cell wall synthesis | interferes

storage temp.

2-8°C

SMILES string

[Na+].Cc1onc(-c2ccccc2Cl)c1C(=O)N[C@H]3[C@H]4SC(C)(C)[C@@H](N4C3=O)C([O-])=O

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

General description

Chemical structure: ß-lactam

Application

Cloxacillin is a semisynthetic antibiotic in the same class as penicillin. Cloxacillin is used against staphylococci that produce β-lactamase. It is used to study the role of pH in antibiotic effectiveness and how oxgall, acid, and hydrogen peroxide stress effects the susceptibility of Bifidobacteria.

Biochem/physiol Actions

Cloxacillin interferes with the last stage of bacterial cell wall synthesis by binding to penicillin-binding proteins. This inhibits the necessary cross-linking and leads to autolysis of the bacteria by autolysins.

Other Notes

Keep container tightly closed in a dry and well-ventilated place.

Storage Class Code

11 - Combustible Solids

WGK

WGK 2

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Sandrine Lemaire et al.
Antimicrobial agents and chemotherapy, 51(5), 1627-1632 (2007-02-20)
Early studies showed that methicillin-resistant Staphylococcus aureus (MRSA) strains are susceptible to beta-lactams when they are exposed to pH < or = 5.5 in broth. Because S. aureus survives in the phagolysosomes of macrophages, where the pH may be acidic
E Kheadr et al.
Antimicrobial agents and chemotherapy, 51(1), 169-174 (2006-10-25)
The effects of acid, oxgall, and H(2)O(2) on susceptibilities to antibiotics and nisin were examined for 13 strains of bifidobacteria. Susceptibilities to ampicillin, cloxacillin, penicillin, vancomycin, kanamycin, neomycin, paramomycin, streptomycin, chloramphenicol, erythromycin, tetracycline, and nisin A were assayed by a
M Britzi et al.
Journal of veterinary pharmacology and therapeutics, 37(5), 445-450 (2014-03-29)
The pharmacokinetics of ampicillin in dogs was determined after intravenous (i.v.) bolus and constant rate infusion. Ampicillin was administered to six beagle dogs as an i.v. bolus at 20 mg/kg and as a constant rate i.v. infusion (CRI) at 20 mg/kg during

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