66-79-5

Basic information

• Product Name: OXACILLIN
• Synonyms: OXACILLIN;[2S-(2,5,6)]-3,3-dimethyl-6-(methyl-3-phenylisoxaz-4-ole-carboxamide-7-oxy-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid;(2S,5R,6R)-3,3-Dimethyl-6-[(5-methyl-3-phenylisoxazol-4-yl)carbonylamino]-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid;Bactocil;Oxazina;Penstapho;UWYHMGVUTGAWSP-JKIFEVAISA-N
• CAS NO: 66-79-5
• Molecular Formula: C₁₉H₁₉N₃O₅S
• Molecular Weight: 401.44
• EINECS: 200-635-5
• Mol File: 66-79-5.mol

Chemical Properties

• Melting Point: 188 ℃
• Boiling Point: 686.8±55.0 °C(Predicted)
• Appearance: white to off white free flowing crystalline powder
• Density: 1.49±0.1 g/cm3(Predicted)
• PKA: pKa 2.72 (Uncertain)
• Water Solubility: 27.8 mg/L at 25 ℃
• CAS DataBase Reference: OXACILLIN(CAS DataBase Reference)
• NIST Chemistry Reference: OXACILLIN(66-79-5)
• EPA Substance Registry System: OXACILLIN(66-79-5)

Safety Data

• Hazardous Substances Data: 66-79-5(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
Oxacillin is used as an antibiotic for the treatment of various bacterial infections, particularly those caused by Staphylococcus aureus and other gram-positive bacteria. Its ability to inhibit bacterial cell wall synthesis makes it a potent therapeutic agent in combating infections.
Used in Hospital Settings:
In hospitals and other healthcare facilities, Oxacillin is used as a critical component of antimicrobial therapy. It is often prescribed for skin infections, pneumonia, and other conditions caused by susceptible bacteria, helping to control and prevent the spread of infections.
Used in Research and Development:
Oxacillin also plays a significant role in research and development within the pharmaceutical and biotechnology sectors. It serves as a valuable tool for studying antibiotic resistance mechanisms and the development of new antimicrobial agents to combat resistant strains of bacteria.

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

Antimicrobial activity

There is complete cross-resistance and tolerance with other group 3 penicillins. Oxacillin is frequently used to replace methicillin for standardized susceptibility testing to detect resistant staphylococci.

Acquired resistance

In addition to methicillin-resistant strains producing the low affinity PBP 2a, rare methicillin-susceptible isolates of Staph. aureus display reduced susceptibility to oxacillin, due to incompletely defined chromosomal resistance mechanisms.

Contact allergens

Oxacillin is a semisynthetic penicillin of the group M. It is closely related to cloxacillin.

Clinical Use

Uses are those of group 3 penicillins

Side effects

There is cross-allergy with other penicillins and reactions are generally typical of the group. Abnormalities of liver function, especially elevation of transaminase levels, may occur, sometimes accompanied by fever, nausea, vomiting and eosinophilia. As with benzylpenicillin, neurotoxicity may develop on high dosage in patients with renal failure. Pseudomembranous colitis has been reported.

Synthesis

Oxacillin, [2S-(2α,5α,6β)]-3,3-dimethyl-7-oxo-6-(5-methyl-3-phenyl-4-isoxazolcarboxamido)-4-thia-1-azabicyclo[3.2.0]-heptan-2-carboxylic acid (32.1.1.10), is synthesized by reacting 5-methyl-3-phenyl-4-isoxazolcarboxylic acid chloride (32.1.1.9) with 6-APA in the presence of sodium bicarbonate. The 5-methyl-3-phenyl-4-isoxazolcarboxylic acid chloride (32.1.1.9) is synthesized by the following scheme. Reacting benzaldehyde with hydroxylamine gives benzaldoxime (32.1.1.5), which when oxidized by chlorine gives benzhydroxamic acid chloride (32.1.1.6). This is reacted with acetoacetic ester in the presence of sodium ethoxide, giving the ethyl ester of 5-methyl-3-phenyl-4-isoxazolcarboxylic acid (32.1.1.7). Alkaline hydrolysis of the resulting ester gives the corresponding acid (32.1.1.8), which is reacted with thionyl chloride to give the acid chloride necessary for acylation.

InChI:InChI=1/C19H19N3O5S/c1-9-11(12(21-27-9)10-7-5-4-6-8-10)15(23)20-13-16(24)22-14(18(25)26)19(2,3)28-17(13)22/h4-8,13-14,17H,1-3H3,(H,20,23)(H,25,26)/t13-,14+,17-/m1/s1

Upstream product

• 16883-16-2 5-methyl-3-phenylisoxazole-4-carbonyl chloride 
• 6249-80-5 1-phenylbut-3-en-1-one 
• 80735-94-0 1-Phenyl-3-buten-1-ol 
• 100-52-7 benzaldehyde 
• 2065-28-3 methyl 5-methyl-3-phenylisoxazole-4-carboxylate 
• 31295-65-5 4-bromo-5-methyl-3-phenylisoxazole 
• 1008-74-8 5-methyl-3-phenylisoxazole 
• 68843-67-4 1-phenyl-but-3-en-1-one oxime 
• 551-16-6 6-Aminopenicillanic Acid 
• 1136-45-4 5-methyl-3-phenylisoxazol-4-carboxylic acid 
• 1025-55-4 6-aminopenicillanic acid trimethylsilyl ester 

Downstream Products

• 62604-78-8 6β-(5-methyl-3-phenyl-isoxazole-4-carbonylamino)-1,1-dioxo-1λ⁶-penicillanic acid 
• 4340-44-7 5-methyl-3-phenylisoxazole-4-carboxamide 
• 36231-30-8 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 

Relevant articles and documents

Synthesis of low-molecular-weight copolymers of N-vinylpyrrolidone with 2-hydroxyethyl methacrylate and of polymeric oxacillin esters derived from them

The radical copolymerization of N-vinylpyrrolidone with 2-hydroxyethyl methacrylate in 2-propanol at 60°C, initiated by azobis(isobutyronitrile) and inhibited by mercaptoethanol or terminated after a short period, was studied. The low-molecular-weight copolymers obtained were used to prepare new polymeric forms of Oxacillin antibiotic. The chemical uniformity, composition, and antimicrobial activity of the new derivatives were studied, and the rate of their hydrolysis in saline (pH 7.3) and glycine buffer (pH 2.0) was determined. Pleiades Publishing, Inc., 2006.

Oxime-mediated facile access to 5-methylisoxazoles and applications in the synthesis of valdecoxib and oxacillin

A palladium-catalyzed efficient synthesis of 5-methylisoxazoles via oxime-mediated functionalization of unactivated olefins is described. The reaction affords a variety of 5-methylisoxazoles in moderate to good yields. To further demonstrate the utility of the method, the rapid synthesis of valdecoxib and oxacillin is reported. (Chemical Equation Presented).

Modifications of the C6-substituent of penicillin sulfones with the goal of improving inhibitor recognition and efficacy

In order to evaluate the importance of a hydrogen-bond donating substituent in the design of β-lactamase inhibitors, a series of C6-substituted penicillin sulfones, lacking a C2′ substituent, and having an sp 3 hybridized C6, was prepared and evaluated against a representative classes A and C β-lactamases. It was found that a C6 hydrogen-bond donor is necessary for good inhibitory activity, but that this feature alone is not sufficient in this series of C6β-substituted penicillin sulfones. Other factors which may impact the potency of the inhibitor include the steric bulk of the C6 substituent (e.g., methicillin sulfone) which may hinder recognition in the class A β-lactamases, and also high similarity to the natural substrates (e.g., penicillin G sulfone) which may render the prospective inhibitor a good substrate of both classes of enzyme. The best inhibitors had non-directional hydrogen-bonding substituents, such as hydroxymethyl, which may allow sufficient conformational flexibility of the acyl-enzyme for abstraction of the C6 proton by E166 (class A), thus promoting isomerization to the β-aminoacrylate as a stabilized acyl-enzyme.

Apparatus And Methods For Delivering A Plurality Of Medicaments For Management Of Co-Morbid Diseases, Illnesses Or Conditions

A method and apparatus for delivering a plurality of medicaments in a single delivery vehicle for the management of co-morbid diseases, illnesses and conditions. The present invention provides a novel delivery process for many medicaments. Medicaments may be encapsulated and stored separately within a larger capsule until the time of ingestion, consumption, or the like. Benefits of the present invention include maintaining separation of distinct ingredients within a single capsule and the capability to control the time release of multiple ingredients within the capsule.

LIQUID PHARMACEUTICAL FOR ORAL DELIVERY

A liquid pharmaceutical for oral delivery wherein at the time of use, a solid unit dosage form is added to the liquid wherein the unit dosage form is comprised of a substrate soluble in the liquid and a particulate pharmaceutically active material in a pharmaceutically effective amount. At the time of use, the unit dosage form is added to the liquid, without requiring measurement of the liquid, and the entire liquid is consumed to provide for oral delivery of the pharmaceutically effective amount of material.