Oxacillin sodium | CAS#66-79-5 | 1173-88-2 | antibiotics

MedKoo Cat#: 318393 | Name: Oxacillin sodium

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Description:

WARNING: This product is for research use only, not for human or veterinary use.

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

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: 401.1045

Molecular Weight: 423.42

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 450.00
5g	USD 650.00	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

Product Data

Instruction

View handling instruction

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/

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

Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

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.

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:

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.

1: Yu M, Shi H, Shen H, Chen X, Zhang L, Zhu J, Qian G, Feng B, Yu S. Simple and Rapid Discrimination of Methicillin-Resistant Staphylococcus aureus Based on Gram Staining and Machine Vision. Microbiol Spectr. 2023 Aug 17;11(4):e0528222. doi: 10.1128/spectrum.05282-22. Epub 2023 Jul 3. PMID: 37395643; PMCID: PMC10433844. 2: Gao J, Wang F, Zhang X, Zhu B, Chen X, Li P, Zhou P, Zheng J, Wang J. Separation and characterization of the polymerized impurities in oxacillin sodium by 2D HPSEC and HPLC IT-TOF MS. Rapid Commun Mass Spectrom. 2023 Apr 15;37(7):e9466. doi: 10.1002/rcm.9466. PMID: 36597914. 3: Liu J, Ma R, Bi F, Zhang F, Hu C, Venter H, Semple SJ, Ma S. Novel 5-methyl-2-phenylphenanthridium derivatives as FtsZ-targeting antibacterial agents from structural simplification of natural product sanguinarine. Bioorg Med Chem Lett. 2018 Jun 1;28(10):1825-1831. doi: 10.1016/j.bmcl.2018.04.015. Epub 2018 Apr 7. PMID: 29657101. 4: Ike B, Ugwu MC, Ikegbunam MN, Nwobodo D, Ejikeugwu C, Gugu T, Esimone CO. Prevalence, Antibiogram and Molecular Characterization of Comunity-Acquired Methicillin-Resistant Staphylococcus Aureus in AWKA, Anambra Nigeria. Open Microbiol J. 2016 Dec 30;10:211-221. doi: 10.2174/1874285801610010211. PMID: 28217194; PMCID: PMC5278563. 5: 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. PMID: 26823620; PMCID: PMC4686477. 6: Wang Y, Yan M, Ma R, Ma S. Synthesis and antibacterial activity of novel 4-bromo-1H-indazole derivatives as FtsZ inhibitors. Arch Pharm (Weinheim). 2015 Apr;348(4):266-74. doi: 10.1002/ardp.201400412. Epub 2015 Mar 13. PMID: 25773717. 7: Stan CD, Stefanache A, Drăgan M, Poiată A, Diaconu DE, Profire L. Cercetări privind îmbunătăţirea condiţiilor de acilare în cazul obţinerii penicilinelor antistafilococice [Research for the improvement of acylation conditions in antistaphylococcal penicillin synthesis]. Rev Med Chir Soc Med Nat Iasi. 2011 Jul-Sep;115(3):972-7. Romanian. PMID: 22046818. 8: Gujral RS, Haque SM, Shanker P. A novel spectrophotometric method for the determination oxacillin sodium. Int J Biomed Sci. 2009 Dec;5(4):373-9. PMID: 23675161; PMCID: PMC3614802. 9: Kirtsreesakul V, Tuntaraworasin J, Thamjarungwong B. Microbiology and antimicrobial susceptibility patterns of commensal flora in the middle nasal meatus. Ann Otol Rhinol Laryngol. 2008 Dec;117(12):914-8. doi: 10.1177/000348940811701209. PMID: 19140538. 10: Zhang Y, Trissel LA. Stability of Ampicillin Sodium, Nafcillin Sodium, And Oxacillin Sodium in AutoDose Infusion System Bags. Int J Pharm Compd. 2002 May- Jun;6(3):226-9. PMID: 23979189. 11: Stiles ML, Allen LV Jr. Stability of nafcillin sodium, oxacillin sodium, penicillin G potassium, penicillin G sodium, and tobramycin sulfate in polyvinyl chloride drug reservoirs. Am J Health Syst Pharm. 1997 May 1;54(9):1068-70. doi: 10.1093/ajhp/54.9.1068. PMID: 9143657. 12: Mishra DS, Patel SD, Marsh D, Yalkowsky SH. Low temperature solubility of antibiotics: oxacillin sodium. J Parenter Sci Technol. 1988 Nov- Dec;42(6):177-80. PMID: 3221277. 13: Thompson DF, Stiles ML, Allen LV Jr, Tu YH. Compatibility of verapamil hydrochloride with penicillin admixtures during simulated Y-site injection. Am J Hosp Pharm. 1988 Jan;45(1):142-5. PMID: 3348228. 14: Jacobs GP, Dobrilovic L, Raghavan N, Carpenter D. A note on the effect of gamma-rays on cefamandole and oxacillin. Int J Rad Appl Instrum A. 1987;38(1):71-3. doi: 10.1016/0883-2889(87)90242-5. PMID: 3030972. 15: Lundergan FS, Lombardi TP, Neilan GE, Nightingale CH. Stability of tobramycin sulfate mixed with oxacillin sodium and nafcillin sodium in human serum. Am J Hosp Pharm. 1984 Jan;41(1):144-5. PMID: 6695930. 16: Silber TJ. Apparent oral contraceptive failure associated with antibiotic administration. J Adolesc Health Care. 1983 Dec;4(4):287-9. doi: 10.1016/s0197-0070(83)80014-x. PMID: 6643209. 17: Bissell P, Glew RH, Liland JB. Parotitis associated with Eikenella corrodens in a healthy adult. Arch Otolaryngol. 1983 Nov;109(11):772-3. doi: 10.1001/archotol.1983.00800250066016. PMID: 6639449. 18: Tillman DB, Oill PA, Guze LB. Oxacillin nephritis. Arch Intern Med. 1980 Nov;140(11):1552. PMID: 7436655. 19: Tilden SJ, Craft JC, Cano R, Daum RS. Cutaneous necrosis associated with intravenous nafcillin therapy. Am J Dis Child. 1980 Nov;134(11):1046-8. doi: 10.1001/archpedi.1980.02130230026008. PMID: 7435462. 20: Holmes CJ, Ausman RK, Walter CW, Kundsin RB. Activity of antibiotic admixtures subjected to different freeze-thaw treatments. Drug Intell Clin Pharm. 1980 May;14(5):353-7. doi: 10.1177/106002808001400505. PMID: 10247478.