Oxacillin sodium
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MedKoo CAT#: 318393

CAS#: 1173-88-2 (sodium)

Description: Oxacillin 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.


Chemical Structure

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Oxacillin sodium
CAS# 1173-88-2 (sodium)

Theoretical Analysis

MedKoo Cat#: 318393
Name: Oxacillin sodium
CAS#: 1173-88-2 (sodium)
Chemical Formula: C19H18N3NaO5S
Exact Mass: 401.10
Molecular Weight: 423.419
Elemental Analysis: C, 53.90; H, 4.29; N, 9.92; Na, 5.43; O, 18.89; S, 7.57

Price and Availability

Size Price Availability Quantity
1g USD 350
5g USD 650 2 Weeks
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Related CAS #: 1173-88-2 (sodium)   66-79-5 (free base)   7240-38-2 (sodium hydrate)    

Synonym: Oxacillin, Oxacillin Sodium, Oxazocilline, Bactocill, Prostaphlin

IUPAC/Chemical Name: sodium (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-carboxylate

InChi Key: VDUVBBMAXXHEQP-SLINCCQESA-M

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

SMILES Code: O=C([C@@H](C(C)(C)S[C@]1([H])[C@@H]2NC(C3=C(C)ON=C3C4=CC=CC=C4)=O)N1C2=O)[O-].[Na+]

Appearance: Solid powder

Purity: >98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO, not in water

Shelf Life: >2 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

More Info:

Product Data:
Biological target: Oxacillin is a narrow-spectrum beta-lactam antibiotic of the penicillin class.
In vitro activity: As oxacillin is known to increase mecA expression levels, it may be possible to attenuate the toxicity of CA-MRSA by using this antibiotic. Subinhibitory oxacillin concentrations induced PBP2a expression, repressed Agr activity, and, as a consequence, decreased phenol-soluble modulin (PSM) secretion by CA-MRSA strains. However, consistent with other studies, oxacillin also increased the expression levels of alpha-toxin and Panton-Valentine leucocidin (PVL). Reference: Antimicrob Agents Chemother. 2014;58(2):1100-7. https://pubmed.ncbi.nlm.nih.gov/24295979/
In vivo activity: Co-administration with TXA709 renders oxacillin efficacious in mouse models of both systemic and tissue infection with MRSA, with this efficacy being observed at human-equivalent doses of oxacillin well below that recommended for daily adult use. Pharmacokinetic evaluations in mice reveal that co-administration with TXA709 also increases total exposure to oxacillin. Reference: Med Chem Res. 2022 Oct;31(10):1705-1715. https://pubmed.ncbi.nlm.nih.gov/37065467/

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
Ethanol 5.0 11.81
PBS (pH 7.2) 10.0 23.62
Water 85.0 200.75

Preparing Stock Solutions

The following data is based on the product molecular weight 423.42 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol: 1. Wang J, Ma X, Li J, Shi L, Liu L, Hou X, Jiang S, Li P, Lv J, Han L, Cheng Y, Han B. The Synergistic Antimicrobial Effect and Mechanism of Nisin and Oxacillin against Methicillin-Resistant Staphylococcus aureus. Int J Mol Sci. 2023 Apr 3;24(7):6697. doi: 10.3390/ijms24076697. PMID: 37047670; PMCID: PMC10094802. 2. Rudkin JK, Laabei M, Edwards AM, Joo HS, Otto M, Lennon KL, O'Gara JP, Waterfield NR, Massey RC. Oxacillin alters the toxin expression profile of community-associated methicillin-resistant Staphylococcus aureus. Antimicrob Agents Chemother. 2014;58(2):1100-7. doi: 10.1128/AAC.01618-13. Epub 2013 Dec 2. PMID: 24295979; PMCID: PMC3910814. 3. Kaul M, Ferrer-González E, Mark L, Parhi AK, LaVoie EJ, Pilch DS. Combination with a FtsZ inhibitor potentiates the in vivo efficacy of oxacillin against methicillin-resistant Staphylococcus aureus. Med Chem Res. 2022 Oct;31(10):1705-1715. doi: 10.1007/s00044-022-02960-5. Epub 2022 Sep 5. PMID: 37065467; PMCID: PMC10104549. 4. Jiang W, Li B, Zheng X, Liu X, Cen Y, Li J, Pan X, Cao H, Zheng J, Zhou H. Artesunate in combination with oxacillin protect sepsis model mice challenged with lethal live methicillin-resistant Staphylococcus aureus (MRSA) via its inhibition on proinflammatory cytokines release and enhancement on antibacterial activity of oxacillin. Int Immunopharmacol. 2011 Aug;11(8):1065-73. doi: 10.1016/j.intimp.2011.02.028. Epub 2011 Mar 21. PMID: 21396483.
In vitro protocol: 1. Wang J, Ma X, Li J, Shi L, Liu L, Hou X, Jiang S, Li P, Lv J, Han L, Cheng Y, Han B. The Synergistic Antimicrobial Effect and Mechanism of Nisin and Oxacillin against Methicillin-Resistant Staphylococcus aureus. Int J Mol Sci. 2023 Apr 3;24(7):6697. doi: 10.3390/ijms24076697. PMID: 37047670; PMCID: PMC10094802. 2. Rudkin JK, Laabei M, Edwards AM, Joo HS, Otto M, Lennon KL, O'Gara JP, Waterfield NR, Massey RC. Oxacillin alters the toxin expression profile of community-associated methicillin-resistant Staphylococcus aureus. Antimicrob Agents Chemother. 2014;58(2):1100-7. doi: 10.1128/AAC.01618-13. Epub 2013 Dec 2. PMID: 24295979; PMCID: PMC3910814.
In vivo protocol: 1. Kaul M, Ferrer-González E, Mark L, Parhi AK, LaVoie EJ, Pilch DS. Combination with a FtsZ inhibitor potentiates the in vivo efficacy of oxacillin against methicillin-resistant Staphylococcus aureus. Med Chem Res. 2022 Oct;31(10):1705-1715. doi: 10.1007/s00044-022-02960-5. Epub 2022 Sep 5. PMID: 37065467; PMCID: PMC10104549. 2. Jiang W, Li B, Zheng X, Liu X, Cen Y, Li J, Pan X, Cao H, Zheng J, Zhou H. Artesunate in combination with oxacillin protect sepsis model mice challenged with lethal live methicillin-resistant Staphylococcus aureus (MRSA) via its inhibition on proinflammatory cytokines release and enhancement on antibacterial activity of oxacillin. Int Immunopharmacol. 2011 Aug;11(8):1065-73. doi: 10.1016/j.intimp.2011.02.028. Epub 2011 Mar 21. PMID: 21396483.

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1: Negi B, Kumar D, Kumbukgolla W, Jayaweera S, Ponnan P, Singh R, Agarwal S, Rawat DS. Anti-methicillin resistant Staphylococcus aureus activity, synergism with oxacillin and molecular docking studies of metronidazole-triazole hybrids. Eur J Med Chem. 2016 Jun 10;115:426-37. doi: 10.1016/j.ejmech.2016.03.041. Epub 2016 Mar 18. PubMed PMID: 27046397.

2: Legrand T, Vodovar D, Tournier N, Khoudour N, Hulin A. Simultaneous determination of eight β-lactam antibiotics amoxicillin, cefazolin, cefepime, cefotaxime, ceftazidime, cloxacillin, oxacillin, piperacillin in human plasma using ultra-high performance liquid chromatography with ultraviolet detection. Antimicrob Agents Chemother. 2016 May 23. pii: AAC.00176-16. [Epub ahead of print] PubMed PMID: 27216076.

3: Yoon WJ, Conley A, Herrera S, Van Dorp D, Lorelli DR. Ruptured mycotic abdominal aortic pseudoaneurysm in a patient on hemodialysis complicated with oxacillin-resistant Staphylococcus aureus bacteremia. Ann Vasc Surg. 2016 May 25. pii: S0890-5096(16)30341-7. doi: 10.1016/j.avsg.2016.01.027. [Epub ahead of print] PubMed PMID: 27236094.

4: Liu P, Xue H, Wu Z, Ma J, Zhao X. Effect of bla regulators on the susceptible phenotype and phenotypic conversion for oxacillin-susceptible mecA-positive staphylococcal isolates. J Antimicrob Chemother. 2016 May 6. pii: dkw123. [Epub ahead of print] PubMed PMID: 27154864.

5: Liu X, Zhang S, Sun B. SpoVG Regulates Cell Wall Metabolism and Oxacillin Resistance in Methicillin-Resistant Staphylococcus aureus Strain N315. Antimicrob Agents Chemother. 2016 May 23;60(6):3455-61. doi: 10.1128/AAC.00026-16. Print 2016 Jun. PubMed PMID: 27001809.

6: Viehman JA, Oleksiuk LM, Sheridan KR, Byers KE, He P, Falcione BA, Shields RK. Adverse Events Lead to Drug Discontinuation More Commonly among Patients Who Receive Nafcillin than among Those Who Receive Oxacillin. Antimicrob Agents Chemother. 2016 Apr 22;60(5):3090-5. doi: 10.1128/AAC.03122-15. Print 2016 May. PubMed PMID: 26976858.

7: Ghanwate N, Thakare P, Bhise PR, Gawande S. Colorimetric method for rapid detection of Oxacillin resistance in Staphylococcus aureus and its comparison with PCR for mec A gene. Sci Rep. 2016 Mar 10;6:23013. doi: 10.1038/srep23013. PubMed PMID: 26960268; PubMed Central PMCID: PMC4785335.

8: Wu MT, Burnham CA, Westblade LF, Dien Bard J, Lawhon SD, Wallace MA, Stanley T, Burd E, Hindler J, Humphries RM. Evaluation of Oxacillin and Cefoxitin Disk and MIC Breakpoints for Prediction of Methicillin Resistance in Human and Veterinary Isolates of Staphylococcus intermedius Group. J Clin Microbiol. 2016 Mar;54(3):535-42. doi: 10.1128/JCM.02864-15. Epub 2015 Nov 25. PubMed PMID: 26607988; PubMed Central PMCID: PMC4767974.

9: Basri DF, Sandra V. Synergistic Interaction of Methanol Extract from Canarium odontophyllum Miq. Leaf in Combination with Oxacillin against Methicillin-Resistant Staphylococcus aureus (MRSA) ATCC 33591. Int J Microbiol. 2016;2016:5249534. doi: 10.1155/2016/5249534. Epub 2016 Feb 23. PubMed PMID: 27006659; PubMed Central PMCID: PMC4781960.

10: Chovanová R, Mikulášová M, Vaverková Š. Modulation of mecA Gene Expression by Essential Oil from Salvia sclarea and Synergism with Oxacillin in Methicillin Resistant Staphylococcus epidermidis Carrying Different Types of Staphylococcal Chromosomal Cassette mec. Int J Microbiol. 2016;2016:6475837. doi: 10.1155/2016/6475837. Epub 2016 Jan 6. PubMed PMID: 26880926; PubMed Central PMCID: PMC4736799.

11: Liu X, Pai PJ, Zhang W, Hu Y, Dong X, Qian PY, Chen D, Lam H. Proteomic response of methicillin-resistant S. aureus to a synergistic antibacterial drug combination: a novel erythromycin derivative and oxacillin. Sci Rep. 2016 Jan 25;6:19841. doi: 10.1038/srep19841. PubMed PMID: 26806358; PubMed Central PMCID: PMC4726183.

12: Serna-Galvis EA, Silva-Agredo J, Giraldo AL, Flórez-Acosta OA, Torres-Palma RA. Comparative study of the effect of pharmaceutical additives on the elimination of antibiotic activity during the treatment of oxacillin in water by the photo-Fenton, TiO2-photocatalysis and electrochemical processes. Sci Total Environ. 2016 Jan 15;541:1431-8. doi: 10.1016/j.scitotenv.2015.10.029. Epub 2015 Nov 11. PubMed PMID: 26479916.

13: Kong LY, Jean A, Wong H, Semret M, Frenette C, Simor AE, Fenn S, Loo VG. Bacteremia caused by a mecA-positive oxacillin-susceptible Staphylococcus aureus strain with inducible resistance. Diagn Microbiol Infect Dis. 2015 Dec;83(4):377-8. doi: 10.1016/j.diagmicrobio.2015.09.001. Epub 2015 Sep 4. PubMed PMID: 26422086.

14: Jousselin A, Manzano C, Biette A, Reed P, Pinho MG, Rosato AE, Kelley WL, Renzoni A. The Staphylococcus aureus Chaperone PrsA Is a New Auxiliary Factor of Oxacillin Resistance Affecting Penicillin-Binding Protein 2A. Antimicrob Agents Chemother. 2015 Dec 28;60(3):1656-66. doi: 10.1128/AAC.02333-15. PubMed PMID: 26711778; PubMed Central PMCID: PMC4775990.

15: Conceição T, Coelho C, de Lencastre H, Aires-de-Sousa M. Frequent occurrence of oxacillin-susceptible mecA-positive Staphylococcus aureus (OS-MRSA) strains in two African countries. J Antimicrob Chemother. 2015 Dec;70(12):3200-4. doi: 10.1093/jac/dkv261. Epub 2015 Aug 27. PubMed PMID: 26318189.

16: Goh S, Loeffler A, Lloyd DH, Nair SP, Good L. Oxacillin sensitization of methicillin-resistant Staphylococcus aureus and methicillin-resistant Staphylococcus pseudintermedius by antisense peptide nucleic acids in vitro. BMC Microbiol. 2015 Nov 11;15:262. doi: 10.1186/s12866-015-0599-x. PubMed PMID: 26560174; PubMed Central PMCID: PMC4642645.

17: Rao SN, Rhodes NJ, Lee BJ, Scheetz MH, Hanson AP, Segreti J, Crank CW, Wang SK. Erratum for Rao et al., treatment outcomes with cefazolin versus oxacillin for deep-seated methicillin-susceptible Staphylococcus aureus bloodstream infections. Antimicrob Agents Chemother. 2015 Nov;59(11):7159. doi: 10.1128/AAC.02091-15. PubMed PMID: 26464400; PubMed Central PMCID: PMC4604403.

18: Sabat AJ, Pournaras S, Akkerboom V, Tsakris A, Grundmann H, Friedrich AW. Whole-genome analysis of an oxacillin-susceptible CC80 mecA-positive Staphylococcus aureus clinical isolate: insights into the mechanisms of cryptic methicillin resistance. J Antimicrob Chemother. 2015 Nov;70(11):2956-64. doi: 10.1093/jac/dkv210. Epub 2015 Jul 20. PubMed PMID: 26198147.

19: Tuon FF, Rocha JL, Morales HM, Sakumoto MH, Miksza KF, Pecoit-Filho R. Modulation of inflammatory mediators during treatment of cellulitis with daptomycin or vancomycin/oxacillin. Int J Antimicrob Agents. 2015 Oct;46(4):476-8. doi: 10.1016/j.ijantimicag.2015.05.018. Epub 2015 Jul 2. PubMed PMID: 26187364.

20: Teibel HM, Knoderer CA, Nichols KR. Compatibility of Vancomycin and Oxacillin During Simulated Y-Site Delivery. Hosp Pharm. 2015 Sep;50(8):710-3. doi: 10.1310/hpj5008-710. Epub 2015 Sep 16. PubMed PMID: 26823620; PubMed Central PMCID: PMC4686477.