Oxacillin

Base Information

• Chemical Name: Oxacillin
• CAS No.: 66-79-5
• Molecular Formula: C₁₉H₁₉N₃O₅S
• Molecular Weight: 401.443
• European Community (EC) Number: 200-635-5,214-636-3
• UNII: UH95VD7V76
• DSSTox Substance ID: DTXSID8023397
• Nikkaji Number: J4.514D
• Wikipedia: Oxacillin
• Wikidata: Q418725
• NCI Thesaurus Code: C62063
• RXCUI: 7773
• Metabolomics Workbench ID: 43021
• ChEMBL ID: CHEMBL819
• Mol file: 66-79-5.mol

Synonyms:Methylphenylisoxazolyl Penicillin;Oxacillin;Oxacillin Sodium;Oxacillin, Monosodium Salt, Anhydrous;Oxacillin, Monosodium Salt, Monohydrate;Oxacillin, Sodium;Oxazocilline;Penicillin, Methylphenylisoxazolyl;Prostaphlin;Sodium Oxacillin;Sodium, Oxacillin

Chemical Property of Oxacillin

Chemical Property:

• Appearance/Colour: white to off white free flowing crystalline powder
• Melting Point: 188oC
• Boiling Point: 686.8±55.0 °C(Predicted)
• PKA: pKa 2.72 (Uncertain)
• PSA: 138.04000
• Density: 1.49±0.1 g/cm3(Predicted)
• LogP: 2.22410
• Water Solubility.: 27.8 mg/L at 25 ℃
• XLogP3: 2.4
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 4
• Exact Mass: 401.10454189
• Heavy Atom Count: 28
• Complexity: 681

Purity/Quality:

98%min ^*data from raw suppliers

Safty Information:

• Pictogram(s): UN NO.
• Hazard Codes: UN NO.

MSDS Files:

SDS file from LookChem

Useful:

• Drug Classes: Penicillin (Penicillinase-Resistant)
• Canonical SMILES: CC1=C(C(=NO1)C2=CC=CC=C2)C(=O)NC3C4N(C3=O)C(C(S4)(C)C)C(=O)O
• Isomeric SMILES: CC1=C(C(=NO1)C2=CC=CC=C2)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
• Recent EU Clinical Trials: A Phase 3, Multicenter, Open-Label, Randomized, Comparator Controlled Trial of the Safety and Efficacy of Dalbavancin versus Active Comparator in Pediatric Subjects with Acute Bacterial Skin and Skin Structure Infections
• Description: Chemically this is 3-methyl-5-phenyl-4-isoxazolyl penicillin. It was synthesized in 1961 and has been extensively used in North America. It is available as an oral solution of 120 mg/5 ml. It usually comes in an injectable formulation of 1 and 2 g. A 10-g injectable formulation is also marketed.
• Indications: In terms of the spectrum of antimicrobial action, oxacillin is analogous to benzylpenicillin. However, it combines the resistance to penicillinase with durability in an acidic medium, which allows it to be used not only intramuscularly, but also orally. It is used for infections caused by penicillinase-producing staphylococci that are resistant to benzyl- and phenoxymethylpenicillins (septicemia, pneumonia, abscesses, empyemia, osteomyelitis, infected burns, infected wounds, and others). Synonyms of this drug are cryptocillin, liucipen, optocillin, totocillin, and others.
• Therapeutic Function: Antibacterial
• Clinical Use: Uses are those of group 3 penicillins

Technology Process of Oxacillin

There total 14 articles about Oxacillin 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: 84.0%

oxacillin acylated poly(N-vinylpyrrolidone-co-2-hydroxyethyl methacrylate), 31.7 wt % of oxacillin by UV spectroscopy; monomer(s): N-vinylpyrrolidone; 2-hydroxyethyl methacrylate; oxacillin → oxacillin (66-79-5,86555-25-1) + poly(N-vinylpyrrolidone-co-2-hydroxyethyl methacrylate), molecular mass 2.1E4 Da; monomer(s): N-vinylpyrrolidone; 2-hydroxyethyl methacrylate

Guidance literature:

With glycine buffer; at 37 ℃; for 24h; pH=2; Further Variations:; Reagents; pH-values; Product distribution;

DOI:10.1134/S1070427206010265

Reference yield:

6-Aminopenicillanic Acid (551-16-6) + 5-methyl-3-phenylisoxazole-4-carbonyl chloride (16883-16-2) → oxacillin (66-79-5,86555-25-1)

Guidance literature:

With sodium hydrogencarbonate; In water; acetone; at 0 - 20 ℃; for 0.166667h;

DOI:10.1021/ol502246t

Reference yield:

5-methyl-3-phenylisoxazole-4-carbonyl chloride (16883-16-2) + 6-aminopenicillanic acid → oxacillin (66-79-5,86555-25-1)

Guidance literature:

5-methyl-3-phenylisoxazole-4-carbonyl chloride; 6-aminopenicillanic acid; With triethylamine; In dichloromethane; at 20 ℃; for 0.5h;

With hydrogenchloride; In water;

DOI:10.1016/j.bmcl.2010.10.134

upstream raw materials:

6-aminopenicillanic acid trimethylsilyl ester

5-methyl-3-phenylisoxazole-4-carbonyl chloride

6-Aminopenicillanic Acid

5-methyl-3-phenylisoxazol-4-carboxylic acid

Downstream raw materials:

5-methyl-3-phenylisoxazole-4-carboxamide

3,3-dimethyl-6-{[(5-methyl-3-phenylisoxazol-4-yl)carbonyl]amino}-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid 4-oxide

6β-(5-methyl-3-phenyl-isoxazole-4-carbonylamino)-1,1-dioxo-1λ⁶-penicillanic acid

Refernces

• 1、 Dong, Kui-Yong,Qin, Hai-Tao,Bao, Xing-Xing,Liu, Feng,Zhu, Chen. "Oxime-mediated facile access to 5-methylisoxazoles and applications in the synthesis of valdecoxib and oxacillin". . p. 5266 - 5268. Retrieved 2015/01/09.
• 2、 -. "Apparatus And Methods For Delivering A Plurality Of Medicaments For Management Of Co-Morbid Diseases, Illnesses Or Conditions". . . Retrieved 2010/09/07.