Nafcillin

Base Information

• Chemical Name: Nafcillin
• CAS No.: 147-52-4
• Molecular Formula: C₂₁H₂₂N₂O₅S
• Molecular Weight: 414.482
• European Community (EC) Number: 205-690-9
• UNII: 4CNZ27M7RV
• DSSTox Substance ID: DTXSID8023343
• Nikkaji Number: J10.134F
• Wikipedia: Nafcillin
• Wikidata: Q1638852
• NCI Thesaurus Code: C62053
• RXCUI: 7233
• Metabolomics Workbench ID: 42936
• ChEMBL ID: CHEMBL1443
• Mol file: 147-52-4.mol

Synonyms:Nafcil;Nafcillin;Nafcillin Sodium;Nafcillin, Monosodium Salt, Anhydrous;Nafcillin, Sodium;Naphthamidopenicillin;Sodium Nafcillin;Sodium, Nafcillin

Chemical Property of Nafcillin

Chemical Property:

• Vapor Pressure: 4.28E-21mmHg at 25°C
• Boiling Point: 714.1 °C at 760 mmHg
• PKA: 2.44±0.50(Predicted)
• Flash Point: 385.7 °C
• PSA: 121.24000
• Density: 1.42 g/cm³
• LogP: 2.81260
• XLogP3: 2.9
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 5
• Exact Mass: 414.12494298
• Heavy Atom Count: 29
• Complexity: 699

Purity/Quality:

99.9% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Drug Classes: Penicillin (Penicillinase-Resistant)
• Canonical SMILES: CCOC1=C(C2=CC=CC=C2C=C1)C(=O)NC3C4N(C3=O)C(C(S4)(C)C)C(=O)O
• Isomeric SMILES: CCOC1=C(C2=CC=CC=C2C=C1)C(=O)N[C@H]3[C@@H]4N(C3=O)[C@H](C(S4)(C)C)C(=O)O
• Recent ClinicalTrials: DOTS: Dalbavancin as an Option for Treatment of Staphylococcus Aureus Bacteremia
• Uses: Antibacterial.
• Therapeutic Function: Antibacterial

Technology Process of Nafcillin

There total 8 articles about Nafcillin which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 79.6%

nafcillin triethylamine → naphcillin (147-52-4)

Guidance literature:

With formic acid; In diethyl ether; acetone; at 10 ℃; for 4h; pH=1; Reagent/catalyst; Temperature; Solvent; pH-value; Large scale;

Reference yield:

6β-[(2-ethoxy-naphthalene-1-carbonyl)-phenylacetyl-amino]-penicillanic acid 2-(4-bromo-phenyl)-2-oxo-ethyl ester (53388-50-4) → naphcillin (147-52-4)

Guidance literature:

With sodium thiophenolate; In ethyl acetate; N,N-dimethyl-formamide;

Reference yield:

2-ethoxy-naphthalene-1-carboxylic acid; sodium salt (53446-67-6) → naphcillin (147-52-4)

Guidance literature:

Multi-step reaction with 2 steps

1: (i) Py, PCl₅, CHCl₃, (ii) /BRN= 5397971/

2: NaSPh / ethyl acetate; dimethylformamide

With sodium thiophenolate; In ethyl acetate; N,N-dimethyl-formamide;

upstream raw materials:

6-Aminopenicillanic Acid

2-ethoxynaphthalenyl-1-carbonyl chloride

6β-[(2-ethoxy-naphthalene-1-carbonyl)-phenylacetyl-amino]-penicillanic acid 2-(4-bromo-phenyl)-2-oxo-ethyl ester

2-ethoxy-naphthalene-1-carboxylic acid; sodium salt

Refernces

• 1、 -. "Apparatus And Methods For Delivering A Plurality Of Medicaments For Management Of Co-Morbid Diseases, Illnesses Or Conditions". . . Retrieved 2010/09/07.
• 2、 -. "Method of using deuterated calcium channel blockers". . . Retrieved 2008/06/13.