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28221

Sigma-Aldrich

Oxacillin sodium salt

815-950 μg/mg (Oxacillin)

Synonym(s):

Sodium 5-methyl-3-phenyl-4-isoxazolyl penicillin

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About This Item

Empirical Formula (Hill Notation):
C19H18N3NaO5S
CAS Number:
1173-88-2
Molecular Weight:
423.42
Beilstein:
4098179
EC Number:
214-636-3
MDL number:
MFCD00082382
UNSPSC Code:
51283505
PubChem Substance ID:
57648295
NACRES:
NA.85

biological source

synthetic

form

powder

concentration

815-950 μg/mg (Oxacillin)

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

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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Daniel G Lloyd et al.
Antimicrobial agents and chemotherapy, 65(1) (2020-10-14)
Bacterial pathogens are rapidly evolving resistance to all clinically available antibiotics. One part of the solution to this complex issue is to better understand the resistance mechanisms to new and existing antibiotics. Here, we focus on two antibiotics. Teixobactin is
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
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
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
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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