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28221

Sigma-Aldrich

Oxacillin sodium salt

815-950 μg/mg (Oxacillin)

Empirical Formula (Hill Notation):
C19H18N3NaO5S
CAS Number:
Molecular Weight:
423.42
Beilstein:
4098179
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.85

Quality Level

biological source

synthetic

assay

815-950 μg/mg (Oxacillin)

form

powder

color

white to off-white

antibiotic activity spectrum

Gram-negative bacteria
Gram-positive bacteria

Mode of action

cell wall synthesis | interferes

storage temp.

2-8°C

SMILES string

[Na+].Cc1onc(-c2ccccc2)c1C(=O)N[C@H]3C4SC(C)(C)[C@@H](N4C3=O)C([O-])=O

InChI

1S/C19H19N3O5S.Na/c1-9-11(12(21-27-9)10-7-5-4-6-8-10)15(23)20-13-16(24)22-14(18(25)26)19(2,3)28-17(13)22;/h4-8,13-14,17H,1-3H3,(H,20,23)(H,25,26);/q;+1/p-1/t13-,14+,17?;/m1./s1

InChI key

VDUVBBMAXXHEQP-ZTRPPZFVSA-M

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General description

Chemical structure: ß-lactam

Application

Oxacillin is used to study mechanisms of penicillinase resistance and antimicrobial susceptibility . It has been used to study autolysins

Biochem/physiol Actions

Oxacillin inhibits bacterial cell wall biosynthesis at the level of transpeptidation (PBP) of peptidoglycan. Used to study mechanisms of penicillinase resistance.

Packaging

1g, 5g

Other Notes

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

Storage Class Code

13 - Non 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

Certificate of Analysis

Certificate of Origin

M B Huang et al.
Journal of clinical microbiology, 31(10), 2683-2688 (1993-10-01)
The need to add NaCl to agar media to ensure accuracy of results when testing staphylococci with oxacillin was investigated. The results of four antimicrobial susceptibility testing methods (agar and broth dilution, E test, and disk diffusion) in which the
Sinisa Bratulic et al.
Nature communications, 8, 15410-15410 (2017-05-20)
Phenotypic mutations are amino acid changes caused by mistranslation. How phenotypic mutations affect the adaptive evolution of new protein functions is unknown. Here we evolve the antibiotic resistance protein TEM-1 towards resistance on the antibiotic cefotaxime in an Escherichia coli
De Novo Resistance to Arg10-Teixobactin Occurs Slowly and Is Costly.
Lloyd, et al.
Antimicrobial Agents and Chemotherapy, 65 (2021)
G K Best et al.
Antimicrobial agents and chemotherapy, 6(6), 825-830 (1974-12-01)
A comparison of the autolytic enzyme activity in Staphylococcus aureus strains that differ markedly in their rates of lysis and killing after exposure to oxacillin has been made. Log-phase cells of the clinical isolate that is tolerant to oxacillin inhibition
Natanel Iluz et al.
Lasers in surgery and medicine, 50(5), 535-551 (2018-01-16)
Staphylococcus aureus is a major pathogen in clinical microbiology. It is known to cause infections at various body sites and can be life-threatening. The development of resistance to many well-established antibiotic treatments and the prevalence of methicillin-resistant S. aureus (MRAS)

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