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O8098-21 Oxacillin Sodium Salt CAS: 1173-88-2

Specifications
References
CAS Number
1173-88-2
Grade
Highly Purified
MDL Number
MFCD00082382
Molecular Formula
C19H18N3NaO5S
Molecular Weight
423.42
EU Commodity Code
38220090
Shipping Temp
RT
Storage Temp
4°C
(2S,5R,6R)-3,3-Dimethyl-6-[[(5-methyl-3-phenyl-4-isoxazolyl)carbonyl]amino]-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic Acid Sodium Salt; Penicillin P-12; Sodium Oxacillin; BRL-1400; Bactocill; Bristopen; Stapenor; Micropenin; NSC 527712; SQ16423

Oxacillin is a penicillinase-resistant β-lactam. It is similar to methicillin, and has replaced methicillin in clinical use. Another related compound is nafcillin. Since it is resistant to penicillinase enzymes, such as that produced by Staphylococcus aureus, it is widely used clinically in the US to treat penicillin-resistant Staphylococcus aureus. However, with the introduction and widespread use of both oxacillin and methicillin, antibiotic-resistant strains called oxacillin-resistant Staphylococcus aureus (MRSA/ORSA) have become increasingly prevalent worldwide. MRSA/ORSA is treated using vancomycin.

Synonyms
(2S,5R,6R)-3,3-Dimethyl-6-[[(5-methyl-3-phenyl-4-isoxazolyl)carbonyl]amino]-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic Acid Sodium Salt; Penicillin P-12; Sodium Oxacillin; BRL-1400; Bactocill; Bristopen; Stapenor; Micropenin; NSC 527712; SQ16423
CAS No
1173-88-2 Free Base: 66-79-5
Molecular Formula
C19H18N3NaO5S
Molecular Weight
423.42
Appearance
White to off-white solid
Purity
≥98%
Melting Point
>181°C (dec.)
Solubility
Methanol (Slightly), Water (Slightly)
Storage and Stability
May be stored at RT for short-term only. Long-term storage is recommended at 4°C. For maximum recovery of product, centrifuge the original vial prior to removing the cap.
References
1. Hawks, G.H. Antibiotic therapy of staphylococcal infection. Can. Med. Assoc. J. 93(16), 848-853 (1965).|2. Williamson, R., Hakenbeck, R., and Tomasz, A. In vivo interaction of β-lactam antibiotics with the penicillin-binding proteins of Streptococcus pneumoniae. Antimicrob. Agents Chemother. 18(4), 629-637 (1980).|3. Milatovic, D., Schmitz, F.J., Verhoef, J., et al. Activities of the glycylcycline tigecycline (GAR-936) against 1,924 recent European clinical bacterial isolates. Antimicrob. Agents Chemother. 47(1), 400-404 (2003).|4. Balibar, C.J., Shen, X., McGuire, D., et al. cwrA, a gene that specifically responds to cell wall damage in Staphylococcus aureus. Microbiology 156(Pt 5), 1372-1383 (2010).|5. Rodriguez, C.A., Agudelo, M., Zuluaga, A.F., et al. In vitro and in vivo comparison of the anti-staphylococcal efficacy of generic products and the innovator of oxacillin. BMC Infect. Dis. 10(153), (2010).
USBio References
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