N3269

Nafcillin sodium salt monohydrate

• Synonym(s): 6-(2-Ethoxy-1-naphthamido)penicillin
• Linear Formula: C₂₁H₂₁N₂O₅SNa · H₂O
• CAS Number: 7177-50-6
• Molecular Weight: 454.47
• NACRES: NA.85
• PubChem Substance ID: 24897636
• UNSPSC Code: 51283515
• MDL number: MFCD01941128

Properties

• form: solid
• antibiotic activity spectrum: Gram-positive bacteria
• mode of action: cell wall synthesis | interferes
• 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

Description

General description

Chemical structure: β-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.

Safety Information

• 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
• Storage Class: 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