All Photos(1)

N3269

Sigma-Aldrich

Nafcillin sodium salt monohydrate

Synonym(s):
6-(2-Ethoxy-1-naphthamido)penicillin
Linear Formula:
C21H21N2O5SNa · H2O
CAS Number:
Molecular Weight:
454.47
MDL number:
PubChem Substance ID:
NACRES:
NA.85

Quality Level

Mode of action

cell wall synthesis | interferes

antibiotic activity spectrum

Gram-positive bacteria

storage temp.

2-8°C

SMILES string

O.[Na+].CCOc1ccc2ccccc2c1C(=O)N[C@H]3C4SC(C)(C)[C@@H](N4C3=O)C([O-])=O

InChI

1S/C21H22N2O5S.Na.H2O/c1-4-28-13-10-9-11-7-5-6-8-12(11)14(13)17(24)22-15-18(25)23-16(20(26)27)21(2,3)29-19(15)23;;/h5-10,15-16,19H,4H2,1-3H3,(H,22,24)(H,26,27);;1H2/q;+1;/p-1/t15-,16+,19-;;/m1../s1

InChI key

OCXSDHJRMYFTMA-KMFBOIRUSA-M

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General description

Chemical structure: ß-lactam

Application

Nafcillin sodium is a narrow-spectrum β-lactam antibiotic. It is used to treat infections caused by Gram-positive bacteria, in particular, species of Staphylococci that are resistant to other penicillins. It has been used to study penicillin-binding proteins (PBPs), such as 2a, and heterogeneous expression of methicillin resistance in Staphylococcus aureus. It is a potential therapy of meningitis due to Staphylococcus aureus.

Biochem/physiol Actions

Nafcillin inhibits bacterial cell wall formation by inhibiting PBPs. The irreversible inhibition of the PBPs prevents the final crosslinking (transpeptidation) of the nascent peptidoglycan layer, which disrupts cell wall synthesis.

Other Notes

5g
Keep container tightly closed in a dry and well-ventilated place.

Pictograms

Exclamation markHealth hazard

Signal Word

Danger

Hazard Classifications

Eye Irrit. 2 - Resp. Sens. 1 - Skin Irrit. 2 - Skin Sens. 1 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

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

H F Chambers et al.
Antimicrobial agents and chemotherapy, 31(12), 1982-1988 (1987-12-01)
Expression of methicillin resistance in heterogeneous strains of Staphylococcus aureus is enhanced by 2 to 5% NaCl in the medium and by selection with beta-lactam antibiotics. Resistance is associated with production of a penicillin-binding protein (PBP), PBP 2a, with low...
W M Scheld et al.
The Journal of antimicrobial chemotherapy, 19(5), 647-658 (1987-05-01)
Co-trimoxazole was compared with nafcillin against Staphylococcus aureus in vitro and in the therapy of experimental Staph. aureus meningitis in rabbits. Co-trimoxazole (trimethoprim:sulphamethoxazole in a 1:20 ratio) was synergistic against 22/24 strains of Staph. aureus in vitro. The MBC90 of...
Xin He et al.
Analytical biochemistry, 517, 9-17 (2016-10-27)
In this study, an anti-amoxicillin single chain variable fragment (ScFv) antibody was evolved by directional mutagenesis of a contact amino acid residue based on the analysis of virtual mutation. Comparison with its parental ScFv, the mutant showed highly improved affinity...

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