A semisynthetic β-lactam antibiotic
Technical Support & Resources

Information provided in the product description is from published literature. Due to the nature of scientific experimentation, your results (e.g., selectivity and effective concentrations) or specific application for this product may differ. If you have questions about how this product fits your application, please contact our technical support staff.

Visit our FAQ

Contact Us

Toll Free Phone (USA and Canada Only): (888) 526-5351
Direct Phone: (734) 975-3888

Request Technical Support

Technical Support Request

To streamline the process attach the appropriate questionnaire to your inquiry.

Download IHC QuestionnaireDownload WB Questionnaire

View Our Privacy Statement for details on how we use and protect your data. In addition, this site is protected by hCaptcha and its Privacy Policy and Terms of Service apply.

Oxacillin (sodium salt)

Item No. 23954

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(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, monosodium salt
CAS Number
1173-88-2
Synonyms
  • Micropenin
  • NSC 527712
  • SQ16423
Molecular Formula
C19H18N3O5S • Na
Formula Weight
423.4
Purity
≥98%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 20 mg/mlDMSO: 16 mg/mlEthanol: 2 mg/mlPBS (pH 7.2): 10 mg/ml
SMILES
CC1(C)[C@H](C([O-])=O)N2C([C@@H](NC(C3=C(C)ON=C3C4=CC=CC=C4)=O)[C@@]2([H])S1)=O.[Na+]
InChi Code
InChI=1S/C19H19N3O5S.Na/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);/q;+1/p-1/t13-,14+,17-;/m1./s1
InChi Key
VDUVBBMAXXHEQP-SLINCCQESA-M
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
Recommended Products

Certificates of Analysis & Batch Specific Data

Provide batch numbers separated by commas to download or request available product inserts, QC sheets, certificates of analysis, data packs, and GC-MS data.

Download most recent Certificate of Analysis for this product

    1 g

    $41

    Add

    5 g

    $99

    Add

    10 g

    $178

    Add
    Cayman Chemical
    Neutrophil Biology Wall Poster

    Explore how neutrophils shape the immune response in health and disease. This poster highlights neutrophil pathogen defense mechanisms, including phagocytosis, degranulation, and NETosis, as well as neutrophil roles in inflammation and NET-associated pathologies.

    DOWNLOAD NOW
    Product Description

    Oxacillin is a semisynthetic β-lactam antibiotic.1,2 It is active against clinical isolates of methicillin-susceptible S. aureus and penicillin-susceptible S. pneumoniae, as well as group A, group B, and viridans group streptococci with MIC90 values ranging from 0.06 to 2 µg/ml in vitro.3 Oxacillin is less effective toward other bacteria with MIC90 values of greater than 16 µg/ml for S. epidermidis, S. haemolyticus, E. faecalis, E. faecium, methicillin-resistant S. aureus (MRSA), and penicillin-intermediate and -resistant S. pneumoniae. It targets the bacterial cell wall, inhibiting S. pneumoniae penicillin-binding proteins 1a, 1b, 2a, 2b, and 3 in vitro with IC50 values ranging from 0.17 to 1.75 µM.4,2 Oxacillin inhibits growth of S. aureus in a thigh model of infection in mice (ED50 = 45.19 mg/kg, s.c.).5 Formulations containing oxacillin have been used in the treatment of susceptible bacterial infections.

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description 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).