sodium (2S,5R,6R)-6-(2-ethoxynaphthalene-1-amido)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate hydrate

• ChemBase ID: 155373
• Molecular Formular: C21H23N2NaO6S
• Molecular Mass: 454.47189
• Monoisotopic Mass: 454.11745175
• SMILES: CCOc1ccc2ccccc2c1C(=O)N[C@H]1[C@@H]2N(C1=O)[C@H](C(S2)(C)C)C(=O)[O-].O.[Na+]
• Canonical SMILES: CCOc1ccc2c(c1C(=O)N[C@@H]1C(=O)N3[C@@H]1SC([C@@H]3C(=O)[O-])(C)C)cccc2.O.[Na+]
• InChI: 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
• InChIKey: OCXSDHJRMYFTMA-KMFBOIRUSA-M

NAMES AND DATABASE IDS

Names

• IUPAC name: sodium (2S,5R,6R)-6-(2-ethoxynaphthalene-1-amido)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate hydrate
• IUPAC Traditional name: sodium nafcillin(1-) hydrate
• Synonyms: 6-(2-Ethoxy-1-naphthamido)penicillin; Nafcillin sodium salt monohydrate

Database IDs

• CAS Number: 7177-50-6
• MDL Number: MFCD01941128
• PubChem SID: 162249511; 24897636
• PubChem CID: 23704143

CALCULATED PROPERTIES

• Acid pKa: 3.3094113
• H Acceptors: 5
• H Donor: 1
• LogD (pH = 5.5): 0.11520102
• LogD (pH = 7.4): -1.1349657
• Log P: 2.289126
• Molar Refractivity: 118.9755 cm^3
• Polarizability: 42.997944 Å^3
• Polar Surface Area: 98.77 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

PROPERTIES

Safety Information

• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 36/37/38-42/43
• Safety Statements: 26-36
• GHS Pictograms: GHS07; GHS08
• GHS Signal Word: Danger
• GHS Hazard statements: H315-H317-H319-H334-H335
• GHS Precautionary statements: P261-P280-P305 + P351 + P338-P342 + P311
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Faceshields, Gloves
• Storage Temperature: 2-8°C

Product Information

• Impurities: ~3.5% Sodium citrate
• Linear Formula: C21H21N2O5SNa · H2O

DETAILS

Sigma Aldrich - N3269

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. Nafcillin is used to study penicillin binding proteins (PBPs). It has been used to study penicillin-binding proteins 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.