OXACILLIN SODIUM

Base Information

• Chemical Name: OXACILLIN SODIUM
• CAS No.: 1173-88-2
• Molecular Formula: C19H18N3NaO5S
• Molecular Weight: 423.425
• Hs Code.: 2941109900
• Mol file: 1173-88-2.mol

Synonyms:Penicillin P 12;Penstapho;Penstaphocid;Prostaphlin;SQ 16423;Sodium(5-methyl-3-phenyl-2-isoxazoline-4-carboxamido)penicillanate;Sodium5-methyl-3-phenyl-4-isoxazolyl penicillin;Sodium[(3-phenyl-5-methyl-4-isoxazolyl)carbonyl]penicillin;Sodium oxacillin;Stapenor;Staphcillin V;4-Thia-1-azabicyclo[3.2.0]heptane-2-carboxylicacid, 3,3-dimethyl-6-(5-methyl-3-phenyl-4-isoxazolecarboxamido)-7-oxo-,monosodium salt (8CI);4-Thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid,3,3-dimethyl-6-[[(5-methyl-3-phenyl-4-isoxazolyl)carbonyl]amino]-7-oxo-,monosodium salt, [2S-(2a,5a,6b)]-;5-Methyl-3-phenyl-4-isoxazolyl penicillin sodiumsalt;BRL 1400;Bactocil;Bactocil sodium;Bristopen;Cryptocillin;Micropenin;Monosodium oxacillin;NSC 527712;

Chemical Property of OXACILLIN SODIUM

Chemical Property:

• Appearance/Colour: Crystalline
• Vapor Pressure: 8.32E-20mmHg at 25°C
• Melting Point: 188 °C
• Boiling Point: 686.8 °C at 760 mmHg
• Flash Point: 369.2 °C
• PSA: 140.87000
• Density: 1.49g/cm3
• LogP: 0.88940
• Storage Temp.: 2-8°C
• Solubility.: H2O: soluble50mg/mL

Purity/Quality:

USP，95% ^*data from raw suppliers

Oxacillin sodium salt monohydrate ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Safety Statements: 22-24/25

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Uses: Oxacillin sodium salt is a narrow spectrum beta-lactam antibiotic. It can be used in analytical study of combination of reversed phase liquid chromatography and zwitterion exchange-reversed phase-hydrophilic interaction mixed-mode liquid chromatography coupled with mass spectrometry for anal. of antibiotics and their impurities. Semi-synthetic antibiotic related to Penicillin. Antibacterial
• Therapeutic Function: Antibacterial
• Clinical Use: Oxacillin sodium, (5-methyl3-phenyl-4-isoxazolyl)penicillinsodium monohydrate (Prostaphlin), is the salt of a semisyntheticpenicillin that is highly resistant to inactivation bypenicillinase. Apparently, the steric effects of the 3-phenyland 5-methyl groups of the isoxazolyl ring prevent the bindingof this penicillin to the β-lactamase active site and,thereby, protect the lactam ring from degradation in muchthe same way as has been suggested for methicillin. It is alsorelatively resistant to acid hydrolysis and, therefore, may beadministered orally with good effect.Oxacillin sodium, which is available in capsule form, isreasonably well absorbed from the gastrointestinal (GI)tract, particularly in fasting patients. Effective plasma levelsof oxacillin are obtained in about 1 hour, but despite extensiveplasma protein binding, it is excreted rapidly throughthe kidneys. Oxacillin experiences some first-pass metabolismin the liver to the 5-hydroxymethyl derivative. Thismetabolite has antibacterial activity comparable to that ofoxacillin but is less avidly protein bound and more rapidlyexcreted. The halogenated analogs cloxacillin, dicloxacillin,and floxacillin experience less 5-methyl hydroxylation.The use of oxacillin and other isoxazolylpenicillinsshould be restricted to the treatment of infections causedby staphylococci resistant to penicillin G. Although theirspectrum of activity is similar to that of penicillin G, theisoxazolylpenicillins are, in general, inferior to it and thephenoxymethylpenicillins for the treatment of infectionscaused by penicillin G-sensitive bacteria. Because isoxazolylpenicillinscause allergic reactions similar to thoseproduced by other penicillins, they should be used withgreat caution in patients who are penicillin sensitive.

Technology Process of OXACILLIN SODIUM

There total 2 articles about OXACILLIN SODIUM 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:

6-Aminopenicillanic Acid (551-16-6) + 5-methyl-3-phenylisoxazole-4-carbonyl chloride (16883-16-2) → Bristopen (1173-88-2)

Guidance literature:

With ammonium hydroxide; In ethyl acetate; pH=2 - 9;

Reference yield:

→ 6β-(5-methyl-3-phenyl-isoxazole-4-carbonylamino)-penicillanic acid; sodium salt (1173-88-2,86555-26-2)

Guidance literature:

3,5-Di-tert-butyl-4-hydroxybenzyl-benzylpenicillinate (IV);

Reference yield: 85.0%

chlorhexidine diacetate (56-95-1) + Bristopen (1173-88-2) → chlorhexidine dioxacillin

Guidance literature:

In water; butan-1-ol; at 20 ℃; for 48h;

DOI:10.3390/molecules20046466

upstream raw materials:

6-Aminopenicillanic Acid

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

Downstream raw materials:

(3R)-4,4-Dimethyl-3-<(1S,5R)-3-(5-methyl-3-phenylisoxazol-4-yl)-7-oxo-4-oxa-2,6-diazabicyclo<3.2.0>hept-2-en-6-yl>thietan-2-one

5-Methyl-3-phenylisoxazol-4-ylpenicillenic acid

<(3-pyridinylcarbonyl)oxy>methyl <2S-(2α,5α,6β)>-3,3-dimethyl-6-<(5-methyl-3-phenyl-4-isoxazolyl)carboxamido>-7-oxo-4-thia-1-azabicyclo<3.2.0>heptane-2-carboxylate

<<(1,4-dihydro-1-methyl-3-pyridinyl)carbonyl>oxy>methyl <2S-(2α,5α,6β)>-3,3-dimethyl-6-<(5-methyl-3-phenyl-4-isoxazolyl)carboxamido>-7-oxo-4-thia-1-azabicyclo<3.2.0>heptane-2-carboxylate

Refernces