MedKoo Cat#: 414659 | Name: Oxacillin Free Base

Description:

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

Oxacillin Free Base is an antibiotic similar to FLUCLOXACILLIN used in resistant staphylococci infections.

Chemical Structure

Oxacillin Free Base
Oxacillin Free Base
CAS#66-79-5 (free base)

Theoretical Analysis

MedKoo Cat#: 414659

Name: Oxacillin Free Base

CAS#: 66-79-5 (free base)

Chemical Formula: C19H19N3O5S

Exact Mass: 401.1045

Molecular Weight: 401.44

Elemental Analysis: C, 56.85; H, 4.77; N, 10.47; O, 19.93; S, 7.99

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.
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Related CAS #
1173-88-2 (sodium) 66-79-5 (free base) 7240-38-2 (sodium hydrate)
Synonym
Oxacillin Free Base; MPi-PC; MPI-penicillin; Prostaphlyn
IUPAC/Chemical Name
4-Thia-1-azabicyclo(3.2.0)heptane-2-carboxylic acid, 3,3-dimethyl-6-(((5-methyl-3-phenyl-4-isoxazolyl)carbonyl)amino)-7-oxo-, (2S-(2alpha,5alpha,6beta))-
InChi Key
UWYHMGVUTGAWSP-JKIFEVAISA-N
InChi Code
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
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
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
To be determined
Shelf Life
>2 years if stored properly
Drug Formulation
To be determined
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

Preparing Stock Solutions

The following data is based on the product molecular weight 401.44 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
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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. 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