N3269

Nafcillin sodium salt monohydrate

Name: Nafcillin sodium salt monohydrate
Brand: SIGMA

Sinonimo/i:

6-(2-Ethoxy-1-naphthamido)penicillin

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Informazioni su questo articolo

Formula condensata:

C₂₁H₂₁N₂O₅SNa · H₂O

Numero CAS:

7177-50-6

Peso molecolare:

454.47

NACRES:

NA.85

PubChem Substance ID:

24897636

UNSPSC Code:

51283515

MDL number:

MFCD01941128

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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

SMILES string

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

InChI key

OCXSDHJRMYFTMA-KMFBOIRUSA-M

form

solid

antibiotic activity spectrum

Gram-positive bacteria

mode of action

cell wall synthesis | interferes

storage temp.

2-8°C

Quality Level

200

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Questo articolo	A9518	C9393	28221
Sigma-Aldrich N3269 Nafcillin sodium salt monohydrate	Sigma-Aldrich A9518 Ampicillina	Sigma-Aldrich C9393 Cloxacillin sodium salt monohydrate	Sigma-Aldrich 28221 Oxacillin sodium salt
antibiotic activity spectrum Gram-positive bacteria	antibiotic activity spectrum Gram-negative bacteria, Gram-positive bacteria	antibiotic activity spectrum Gram-positive bacteria	antibiotic activity spectrum Gram-negative bacteria, Gram-positive bacteria
mode of action cell wall synthesis \| interferes	mode of action cell wall synthesis \| interferes	mode of action cell wall synthesis \| interferes	mode of action cell wall synthesis \| interferes
Quality Level 200	Quality Level 200	Quality Level 200	Quality Level 200
form solid	form powder	form powder or crystals	form powder
storage temp. 2-8°C	storage temp. 2-8°C	storage temp. 2-8°C	storage temp. 2-8°C

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[1]. It is a potential therapy of meningitis due to Staphylococcus aureus[2].

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.

General description

Chemical structure: ß-lactam

Other Notes

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

pictograms

GHS08,GHS07

signalword

Danger

hcodes

H315,H317,H319,H334,H335

pcodes

P280 - P302 + P352 - P305 + P351 + P338

Hazard Classifications

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

target_organs

Respiratory system

Classe di stoccaggio

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Faceshields, Gloves

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Co-trimoxazole versus nafcillin in the therapy of experimental meningitis due to Staphylococcus aureus.

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

Effect of NaCl and nafcillin on penicillin-binding protein 2a and heterogeneous expression of methicillin resistance in Staphylococcus aureus.

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

Virtual mutation and directional evolution of anti-amoxicillin ScFv antibody for immunoassay of penicillins in milk.

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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