For research use only. Not for therapeutic Use.
Oxacillin (Cat.No:I008519) is a narrow-spectrum beta-lactam antibiotic of the penicillin class. It is similar to methicillin, and has replaced methicillin in clinical use. Other related compounds are nafcillin, cloxacillin, dicloxacillin, and flucloxacillin. 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.
| Catalog Number | I008519 |
| CAS Number | 66-79-5 |
| Synonyms | Oxacillin, Oxacillin Sodium, Oxazocilline, Bactocill, Prostaphlin;(2S,5R,6R)-3,3-dimethyl-6-[(5-methyl-3-phenyl-1,2-oxazole-4-carbonyl)amino]-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid |
| Molecular Formula | C19H19N3O5S |
| Purity | ≥95% |
| Solubility | Soluble in DMSO, not in water |
| Storage | Store at -20°C |
| IUPAC Name | (2S,5R,6R)-3,3-dimethyl-6-[(5-methyl-3-phenyl-1,2-oxazole-4-carbonyl)amino]-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid |
| InChI | InChI=1S/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 |
| InChIKey | UWYHMGVUTGAWSP-JKIFEVAISA-N |
| SMILES | CC1=C(C(=NO1)C2=CC=CC=C2)C(=O)NC3C4N(C3=O)C(C(S4)(C)C)C(=O)O |
| Reference | </br>1:Designed positively charged cyclodextrin hosts with enhanced binding of penicillins as carriers for the delivery of antibiotics: the case of oxacillin. Agnes M, Thanassoulas A, Stavropoulos P, Nounesis G, Miliotis G, Miriagou V, Athanasiou E, Benkovics G, Malanga M, Yannakopoulou K.Int J Pharm. 2017 May 1. pii: S0378-5173(17)30391-5. doi: 10.1016/j.ijpharm.2017.04.080. [Epub ahead of print] PMID: 28473235 </br>2:Comparative Effectiveness of Cefazolin versus Nafcillin or Oxacillin for Treatment of Methicillin-Susceptible Staphylococcus aureus Infections Complicated by Bacteremia: A Nationwide Cohort Study. McDanel JS, Roghmann MC, Perencevich EN, Ohl ME, Goto M, Livorsi DJ, Jones M, Albertson JP, Nair R, O/’Shea AM, Schweizer ML.Clin Infect Dis. 2017 Mar 31. doi: 10.1093/cid/cix287. [Epub ahead of print] PMID: 28379314 </br>3:Action of antibiotic oxacillin on in vitro growth of methicillin-resistant Staphylococcus aureus (MRSA) previously treated with homeopathic medicines. Passeti TA, Bissoli LR, Macedo AP, Libame RB, Diniz S, Waisse S.Homeopathy. 2017 Feb;106(1):27-31. doi: 10.1016/j.homp.2016.10.002. Epub 2016 Dec 3. PMID: 28325220 </br>4:Oxacillin magnetically targeted for the treatment of Methicillin-Resistant S. aureus infection in rats. Carvalho JF, Azevedo ÍM, Rocha KB, Medeiros AC, Carriço AD.Acta Cir Bras. 2017 Jan;32(1):46-55. doi: 10.1590/s0102-865020170106. PMID: 28225917 Free Article</br>5:Spiroaspertrione A, a Bridged Spirocyclic Meroterpenoid, as a Potent Potentiator of Oxacillin against Methicillin-Resistant Staphylococcus aureus from Aspergillus sp. TJ23. He Y, Hu Z, Sun W, Li Q, Li XN, Zhu H, Huang J, Liu J, Wang J, Xue Y, Zhang Y.J Org Chem. 2017 Mar 17;82(6):3125-3131. doi: 10.1021/acs.joc.7b00056. Epub 2017 Feb 24. PMID: 28219242 </br>6:Multicenter Evaluation of a Modified Cefoxitin Disk Diffusion Method and PBP2a Testing To Predict mecA-Mediated Oxacillin Resistance in Atypical Staphylococcus aureus. Miller SA, Karichu J, Kohner P, Cole N, Hindler JA, Patel R, Richter S, Humphries RM.J Clin Microbiol. 2017 Feb;55(2):485-494. doi: 10.1128/JCM.02211-16. Epub 2016 Nov 30. PMID: 27903603 </br>7:Methicillin-resistant Staphylococcus aureus isolates with SCCmec type V and spa types t437 or t1081 associated to discordant susceptibility results between oxacillin and cefoxitin, Central Taiwan. Ho CM, Lin CY, Ho MW, Lin HC, Chen CJ, Lin LC, Lu JJ.Diagn Microbiol Infect Dis. 2016 Dec;86(4):405-411. doi: 10.1016/j.diagmicrobio.2016.08.025. Epub 2016 Aug 28. PMID: 27650515 </br>8:Oxacillin disk diffusion testing for the prediction of penicillin resistance in Streptococcus pneumoniae. Horna G, Molero ML, Benites L, Roman S, Carbajal L, Mercado E, Castillo ME, Zerpa R, Chaparro E, Hernandez R, Silva W, Campos F, Saenz A, Reyes I, Villalobos A, Ochoa TJ.Rev Panam Salud Publica. 2016 Aug;40(1):57-63. PMID: 27706387 Free Article</br>9:Staphylococcus aureus and the oxacillin sensitivity profile in hospitalized people with HIV/AIDS. Pio DP, Reinato LA, Lopes LP, Gir E.Rev Esc Enferm USP. 2016 Jul-Aug;50(4):617-621. doi: 10.1590/S0080-623420160000500011. English, Portuguese. PMID: 27680047 Free Article</br>10:Best Practices for Treatment of Invasive Methicillin-Susceptible Staphylococcus aureus Infections: The Case for Oxacillin. Wood JB, Thomsen IP, Creech CB, Newland JG.J Pediatric Infect Dis Soc. 2016 Dec;5(4):480-482. Epub 2016 Sep 7. No abstract available. PMID: 27609072 |
